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Quality Control of [ 16867-03-1 ]

COA NMR CNMR HPLC LC-MS

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Product Citations Expand+

Synthesis, Characterization, and Application of pH-Sensitive Monoazo Heterocyclic Disperse Dyes: A Study of Solvatochromism, DFT Analysis, and Biological Activity

Salman, Muhammad ; Jabbar, Abdul ; Farooq, Salma , et al. Fibers Polym.,2025. DOI: 10.1007/s12221-024-00797-w

Abstract: In the present work, fve monoazo heterocyclic disperse dyes PY₁–PY₅ were synthesized in good yield. A 2-amino-3-hydroxypyridine was used as a coupling component with fve distinct heterocyclic diazonium salts. All the dyes are new except the dye PY₄. The obtained colorants were characterized by melting point, ¹ H-NMR, FT-IR, UV–Vis, FAB-LRMS, and FABHRMS. The main skeletons of the dyes PY₁, PY₃, and PY₄ were further confrmed by ¹³C-NMR (BB), ¹ H–¹ H COSY, ¹ H–¹³C HSQC, and ¹ H–¹³C HMBC. The efect of pH variation on the λ_max of these colorants was assessed in methanol and DMSO. Their solvatochromism analyses were performed in various organic solvents, e.g., acetic acid, methanol, acetone, acetonitrile, dimethyl sulfoxide, and dimethyl formamide. The geometries of the dyes were optimized at the B3LYP/6-311G (d,p) level, and their electronic excitation properties were determined using time-dependent density functional theory. The computed data were in good agreement with the experimental data. These colorants were applied to polyester fabric as disperse dyes and evaluated for build-up study along with complete observation of their fastness to water, washing, sublimation, rubbing, perspiration, and light. The antimicrobial exploration of these dyes was performed in detail against human pathogenic fungi including Aspergillus fumigatus, Candida glabrata, Candida albicans and Trichophyton rubrum. The dye PY₅ was found to have promising inhibition against all the human pathogenic fungi used.

Keywords: Azo disperse dyes ; pH sensitivity ; Antifungal activity ; Solvent efect ; DFT ; Global reactivity parameters

Purchased from AmBeed: 16867-03-1

Product Details of [ 16867-03-1 ]

CAS No. :	16867-03-1	MDL No. :	MFCD00006317
Formula :	C₅H₆N₂O	Boiling Point :	-
Linear Structure Formula :	C₅H₃N(NH₂)(OH)	InChI Key :	BMTSZVZQNMNPCT-UHFFFAOYSA-N
M.W :	110.11	Pubchem ID :	28114
Synonyms :

Calculated chemistry of [ 16867-03-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	30.66
TPSA :	59.14 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.7
Log Po/w (XLOGP3) :	0.15
Log Po/w (WLOGP) :	0.38
Log Po/w (MLOGP) :	-0.45
Log Po/w (SILICOS-IT) :	0.25
Consensus Log Po/w :	0.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.17
Solubility :	7.41 mg/ml ; 0.0673 mol/l
Class :	Very soluble
Log S (Ali) :	-0.95
Solubility :	12.4 mg/ml ; 0.113 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.03
Solubility :	10.3 mg/ml ; 0.0938 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.31

Safety of [ 16867-03-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 16867-03-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 16867-03-1 ]
Downstream synthetic route of [ 16867-03-1 ]

[ 16867-03-1 ] Synthesis Path-Upstream 1~8

1
[ 16867-03-1 ]
[ 78-39-7 ]
[ 86467-39-2 ]

Yield	Reaction Conditions	Operation in experiment
65.8%	Stage #1: at 120℃; for 4 h; Stage #2: Cooling	80 mL of ethyl orthoacetate was added to 15 g (136 mmol) of 2-amino-3-hydroxypyridine, followed by addition of p-toluenesulfonic acid in a catalytic amount, and the mixture was reacted at 120° C. for 4 hours. After the reaction solution was cooled, triethylamine was added to the solution, to neutralize p-toluenesulfonic acid. Then, the solution was subjected to distillation under reduced pressure by using an evaporator, and then purified by silica gel column chromatography.Amount of the product: 12.0 g, Yield: 65.8percent.

Reference： [1] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 87 - 91
[2] Heterocycles, 1995, vol. 41, # 3, p. 477 - 486
[3] Monatshefte fur Chemie, 2007, vol. 138, # 7, p. 663 - 667
[4] Patent: US2009/247736, 2009, A1, . Location in patent: Page/Page column 13
[5] Tetrahedron Letters, 1990, vol. 31, # 8, p. 1155 - 1156
[6] Synthetic Communications, 1992, vol. 22, # 20, p. 2891 - 2901

2
[ 16867-03-1 ]
[ 123-54-6 ]
[ 86467-39-2 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 13, p. 6310 - 6314

3
[ 16867-03-1 ]
[ 64-19-7 ]
[ 86467-39-2 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 13, p. 2295 - 2298

4
[ 16867-03-1 ]
[ 32894-07-8 ]
[ 86467-39-2 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 8, p. 1155 - 1156

5
[ 16867-03-1 ]
[ 75-36-5 ]
[ 31354-48-0 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 10, p. 2405 - 2412
[2] Tetrahedron Letters, 2004, vol. 45, # 7, p. 1465 - 1468

6
[ 16867-03-1 ]
[ 108-24-7 ]
[ 31354-48-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3730 - 3742

7
[ 16867-03-1 ]
[ 877399-47-8 ]

Reference： [1] Patent: CN108341802, 2018, A,

8
[ 16867-03-1 ]
[ 24424-99-5 ]
[ 902835-93-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With guanidine hydrochloride In ethanol at 35 - 40℃; for 2.5 h;	General procedure: Amine (1 mmol) was added to a magnetically stirred solution of guanidine hydrochloride (15 molpercent) and di-tert-butyl dicarbonate (1.2 mmol) in EtOH (1 mL), at 35-40°C and stirred for appropriate time (Table 1). After completion of the reaction (followed by TLC or GC), EtOH was evaporated under vacuum and the residue either was washed with water to remove the catalyst or was dissolved in CH₂Cl₂ (or EtOAc) and filtered off to separate out the catalyst. Evaporation of the organic solvent (if used in work up) gives almost a pure product. In the cases of using an excess (Boc)₂O the product was washed with petroleum ether or hexane to recover the residual (Boc)₂O. If necessary, the product was further purified either by crystallization (hexane and dichloromethane, or diethyl ether and petroleum ether) or silica gel column chromatography using EtOAc-hexane (1: 6) as eluent.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264

[ 16867-03-1 ] Synthesis Path-Downstream 1~16

1
[ 16867-03-1 ]
[ 2991-28-8 ]
[ 52333-66-1 ]

Reference： [1]Journal of Medicinal Chemistry,1978,vol. 21,p. 1158 - 1162

2
[ 16867-03-1 ]
[ 140-89-6 ]
[ 53052-06-5 ]

Yield	Reaction Conditions	Operation in experiment
86.95%	With pyridine; at 110.0℃;	Step 1: Preparation of oxazolo[4,5-b]pyridine-2-thiol A solution of 2-aminopyridin-3-ol (5.0g, 45.45 mmol) and potassium ethyl xanthate (8.0g, 49.99 mmol) in pyridine (50mL) was heated at 110C overnight. The reaction mixture was cooled to 0C, added ice water and acidified with Cone. HCl. The solid was filtered and dried under vacuum to afford the title compound (6.0g, 86.95%). 1HNMR (DMSO-d6, 300MHz): delta 8.24-8.22 (d, 1H), 7.90-7.87 (d, 1H), 7.30-7.26 (m, 1H). LCMS: m/z: 153.0 (M+l) +.
86.95%	With pyridine; at 110.0℃;	A solution of 2-aminopyridin-3-ol (5.0 g, 45.45 mmol) and potassium ethyl xanthate (8.0 g, 49.99 mmol) in pyridine (50 mL) was heated at 1100 C. overnight. The reaction mixture was cooled to 00 C., added ice water and acidified with Conc. HC1. The solid was filtered and dried under vacuum to afford the title compound (6.0 g, 86.95%). 10206] ?HNMR (DMSO-d5, 300 MHz): oe 8.24-8.22 (d, 1H), 7.90-7.87 (d, 1H), 7.30-7.26 (m, 1H). LCMS: mlz:153.0 (M+1).
74%	In ethanol; for 24h;Reflux;	A mixture of 2-amino-pyridin-3-ol (1) (2.00 g, 18.16 mmol) and potassium ethyl xanthate (2.91 g, 18.16 mmol) in ethanol (40 mL) was heated under reflux for 24 h. The solvent was removed in vacuo and water (30 mL) was added. The mixture was acidified with AcOH to pH 5. The resultant precipitate was filtered, washed with water (20 mL) and dried to give oxazolo[4,5-b]pyridine-2-thiol (2) (2.05 g, 74% yield). 300 MHz 1H-NMR (DMSO-d6, ppm): 8.21 (dd, J=5.2, 1.3 Hz, 1H) 7.85 (dd, J=8.1, 1.3 Hz, 1H) 7.25 (dd, J=8.1, 5.2 Hz, 1H).

With hydrogenchloride; In pyridine; water;

(1) 2-Amino-3-hydroxypyridine (5.51 g) was dissolved in pyridine (100 mL), and potassium ethylxanthate (8.82 g) was added thereto. The mixture was refluxed for 2 hr. Iced water (400 mL) was added to the reaction mixture, and concentrated hydrochloric acid (40 mL) was added thereto. The mixture was extracted with chloroform and the extract was washed with brine and concentrated under reduced pressure to give 1,3-oxazolo[4,5-b]pyridine-2-thiol (5.13 g) as a pale-brown powder.

Reference： [1]Patent: WO2015/104688,2015,A1 .Location in patent: Page/Page column 36
[2]Patent: US2016/340366,2016,A1 .Location in patent: Paragraph 0205; 0206
[3]Monatshefte fur Chemie,2011,vol. 142,p. 895 - 899
[4]Patent: US2019/367499,2019,A1 .Location in patent: Paragraph 0166
[5]Journal of Organic Chemistry,1995,vol. 60,p. 5721 - 5725
[6]European Journal of Medicinal Chemistry,2005,vol. 40,p. 15 - 23
[7]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 114 - 125
[8]Patent: EP1308439,2003,A1

3
[ 16867-03-1 ]
[ 33142-21-1 ]
ethyl 8-hydroxyimidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8145 - 8152

4
[ 16867-03-1 ]
[ 20348-09-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1081 - 1086
[2]Patent: US2016/145268,2016,A1

5
[ 16867-03-1 ]
[ 122-51-0 ]
[ 273-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; at 140℃; for 8h;	Reference H Synthesis of 2 [(S)-(TERT-BUTOXYCARBONYL) AMINO-L-(OXAZOLO] [4, [5-B] PYRIDIN-2-YL) BUTAN-1-OL] Step 1 A mixture of 2-amino-3-hydroxypyridine (11 g, 100 mmol), triethylorthoformate (80 mL) and p-toluenesulfonic acid (61 mg) was heated at [140 C] for 8 h. Excess triethylorthoformate was removed under vacuum and oxazolo [4, [5-B]] pyridine was crystalized from ethyl acetate (9 g). Step 2 In a clean roundbottom flask equipped with stir bar was placed oxazolo [4,5- [B]] pyridine (600 mg, 5 mmol) in THF (30 mL) and the reaction mixture was cooled to [0 C] under N2 atomosphere. Isopropylmagnesium chloride (2 M in THF, 2.5 mL, 5 mmol) was added. After stirring for 1 h at 0 [C,] [(USD)-2-(TERT-BUTOXYCARBONYL)] aminobutyraldehyde (573 mg, 3 mmol) in THF (20 mL) was added. The ice bath was removed and the reaction mixture was allowed to warm to room temperature. After 2 h, the reaction mixture was quenched with saturated ammonium chloride solution and concentrated to dryness. The residue was extracted with EtOAc, then washed with brine, dried with anhyd. [MGS04,] filtered and concentrated. The crude product was purified by chromatograph to yield 383 mg of the desired compound.

Reference： [1]Patent: WO2004/838,2003,A1 .Location in patent: Page 66-67

6
[ 16867-03-1 ]
[ 85482-13-9 ]
2-amino-3-(2,5-dichlorobenzyloxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydroxide; dichloromethane; water;	(a) 2-Amino- 3-(2,5-dichlorobenzyloxy)pyridine A mixture of <strong>[85482-13-9]2,5-dichlorobenzyl bromide</strong> (14.8 g, 75.9 mmol) and 2-amino-3hydroxypyridine (7.7 g, 69.7 mmol) in 40% aqueous sodium hydroxide solution (52 ml) and dichloromethane (52 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. More water was added and the product extracted into dichloromethane, dried, and the solvent evaporated to obtain the product after trituration with ether (8.6 g, 46%), m.p. 103-104 C.

Reference： [1]Patent: US5409943,1995,A

7
[ 16867-03-1 ]
[ 4761-00-6 ]
[ 151411-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane;	(a) 2-Amino- 3-(2,4,6-trimethylbenzyloxy)pyridine A mixture of 2-amino-3-hydroxy pyridine (29.6 g, 0.269 mol), dichloromethane (200 ml) and 40% aqueous sodium hydroxide solution (200 ml) was stirred for five minutes, then 2,4,6-trimethylbenzyl bromide (50 g, 0.296 mol) and Adogen 464 (5 ml) were added and stirring continued for 16 hours. The mixture was diluted with water and extracted with dichloromethane. Drying and evaporation of the organic extracts, and trituration with ether gave the desired product. Yield 29.6 g (41%), m.p. 160-166 C.

Reference： [1]Patent: US5409943,1995,A

8
[ 16867-03-1 ]
MeOCS₂ K [ No CAS ]
[ 53052-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon disulfide; potassium hydroxide; In methanol; water;	EXAMPLE 15 6,7-Dimethoxy-2-[4-(oxazolo[4,5-b]pyridin-2-yl)-1-piperazinyl]-4-quinazolinamine (Ia: R3 =oxazolo[4,5-b]pyridin-2-yl; R4, R5, R6 and R9 =H; R7 and R8 =OMe; and n=1) A mixture of 2-amino-3-hydroxypyridine and MeOCS2 K [prepared from potassium hydroxide (6.2 g), methanol (96 ml), water (17.4 ml) and carbon disulfide (7.1 g)] was refluxed for 20 hr and filtered. The filtrate was neutralized with acetic acid and the resulting precipitate was collected, washed with water and dried to give 2-mercapto-oxazolo[4,5-b]pyridine (8.2 g).

Reference： [1]Patent: US4351832,1982,A

9
[ 16867-03-1 ]
[ 39903-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In ethanol;	B. The 2-amino-5-bromo-3-pyridinol is prepared by dissolving 110.0 g of 2-amino-3-pyridinol in 250 ml of 95percent ethanol. The solution is cooled to about 5° C. and at that temperature is treated with 160 g of liquid bromine during 2 hours. The mixture is stirred for 1 hour after the addition is completed and then concentrated to give 170.6 g of 2-amino-5-bromo-3-pyridinol.

Reference： [1]Archiv der Pharmazie,2011,vol. 344,p. 158 - 164
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 828 - 835
[3]Tetrahedron Letters,2014,vol. 55,p. 1528 - 1531
[4]Patent: WO2016/97918,2016,A1
[5]Patent: US4022897,1977,A

10
[ 16867-03-1 ]
[ 79-11-8 ]
[ 20348-09-8 ]

Yield	Reaction Conditions	Operation in experiment
		In Scheme 90c, the oxazine (24) can be prepared from compound (22) using a similar strategy previously used for (21). Base catalyzed addition of (22) to [CHLOROACETIC] acid followed by cyclization affords intermediate (22). Compound (22) can undergo halogenation using bromine in an aprotic solvent such as DMF to give compound (24).

Reference： [1]Patent: WO2004/14384,2004,A2 .Location in patent: Page/Page column 256; 262

11
[ 16867-03-1 ]
[ 105-36-2 ]
[ 20348-09-8 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 1852 - 1855

12
[ 16867-03-1 ]
[ 24424-99-5 ]
[ 902835-93-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With guanidine hydrochloride; In ethanol; at 35 - 40℃; for 2.5h;	General procedure: Amine (1 mmol) was added to a magnetically stirred solution of guanidine hydrochloride (15 mol%) and di-tert-butyl dicarbonate (1.2 mmol) in EtOH (1 mL), at 35-40C and stirred for appropriate time (Table 1). After completion of the reaction (followed by TLC or GC), EtOH was evaporated under vacuum and the residue either was washed with water to remove the catalyst or was dissolved in CH2Cl2 (or EtOAc) and filtered off to separate out the catalyst. Evaporation of the organic solvent (if used in work up) gives almost a pure product. In the cases of using an excess (Boc)2O the product was washed with petroleum ether or hexane to recover the residual (Boc)2O. If necessary, the product was further purified either by crystallization (hexane and dichloromethane, or diethyl ether and petroleum ether) or silica gel column chromatography using EtOAc-hexane (1: 6) as eluent.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1260 - 1264
[2]Monatshefte fur Chemie,2011,vol. 142,p. 1035 - 1043

13
[ 75-15-0 ]
[ 16867-03-1 ]
[ 53052-06-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium hydroxide; In ethanol; at 90.0℃; for 2h;	A solution of 2-aminopyri din-3 -ol (3.00 g, 27.24 mmol), carbon disulfide (41.45 g, 544.8 mmol), and potassium hydroxide (5.40 g, 96.24 mmol) in ethanol (50 mL) was stirred for 2 h at 90 C. The reaction was then quenched by the addition of 150 mL of water. The resulting solution was extracted with 3x150 mL of ethyl acetate. The pH value of the combined aqueous layers was adjusted to 6 with 6 M aqueous HC1 solution and then extracted with 3x150 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, filtered, and concentrated to give oxazolo[4,5-b]pyridine-2-thiol (3.0 g, 71%) as a red solid. MS: (ESI, m/z): 153[M+H]+.
67%	With potassium hydroxide; In ethanol; for 10h;Reflux;	In a 100 ml round bottom flask was placed 2- amino-3-hydroxy pyridine (2.20g, 20 mmol) and 40 ml of absoluteethanol was added and the mixture was stirred for 15minutes. In the meanwhile, 2.0g (29 mmol) KOH pelletswere powdered and transferred into the flask followed by theaddition of 15 ml of carbon disulfide. The resulting mixturewas refluxed over an oil bath for 8 hours when a yellowprecipitate appeared. The contents of the flask were cooledto room temperature. The solvent was rotary evaporated andthe residue was transferred in to a beaker and 75 ml of waterwas added followed by neutralization with acetic acid. Theprecipitated product was filtered under vacuum and washedwith 3x50 ml of water and dried under vacuum over night toyield 2.1g of light yellow solid product (yield, 65%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2075 - 2078
[2]Patent: WO2019/204550,2019,A1 .Location in patent: Paragraph 00149
[3]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1837 - 1843
[4]Letters in Organic Chemistry,2010,vol. 7,p. 519 - 527
[5]Archiv der Pharmazie,2017,vol. 350

14
[ 16867-03-1 ]
[ 894852-01-8 ]

Reference： [1]Patent: WO2015/71780,2015,A1

15
[ 16867-03-1 ]
[ 152628-03-0 ]
2-propyl-4-methyl-6-(oxazolo[4,5-b]pyridine-2-yl)benzimidazole [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 26401 - 26410

16
[ 16867-03-1 ]
[ 137-26-8 ]
[ 53052-06-5 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 5591 - 5598

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Technical Information

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P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 16867-03-1 ] {[proInfo.proName]}

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[ 16867-03-1 ] Synthesis Path-Upstream 1~8

[ 16867-03-1 ] Synthesis Path-Downstream 1~16

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