[ CAS No. 601-89-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 601-89-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 601-89-8 ]

SDS Specification

Alternatived Products of [ 601-89-8 ]

Product Details of [ 601-89-8 ]

CAS No. :	601-89-8	MDL No. :	MFCD00007124
Formula :	C₆H₅NO₄	Boiling Point :	No data available
Linear Structure Formula :	C₆H₃(OH)₂NO₂	InChI Key :	ZLCPKMIJYMHZMJ-UHFFFAOYSA-N
M.W :	155.11	Pubchem ID :	11760
Synonyms :

Calculated chemistry of [ 601-89-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	39.31
TPSA :	86.28 ?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 :	Yes
Log Kp (skin permeation) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	1.56
Log Po/w (WLOGP) :	1.01
Log Po/w (MLOGP) :	-0.3
Log Po/w (SILICOS-IT) :	-1.25
Consensus Log Po/w :	0.45

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.12
Solubility :	1.17 mg/ml ; 0.00755 mol/l
Class :	Soluble
Log S (Ali) :	-2.98
Solubility :	0.162 mg/ml ; 0.00104 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.61
Solubility :	37.7 mg/ml ; 0.243 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 601-89-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 601-89-8 ]

* 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.

Downstream synthetic route of [ 601-89-8 ]

[ 601-89-8 ] Synthesis Path-Downstream 1~9

1
[ 6665-97-0 ]
[ 107-06-2 ]
[ 601-89-8 ]

Reference： [1]Journal of Organic Chemistry,1951,vol. 16,p. 586,606

2
[ 601-89-8 ]
[ 77-78-1 ]
[ 3114-61-2 ]
[ 6665-97-0 ]

Reference： [1]Patent: US2385282,1942,A

3
[ 601-89-8 ]
[ 77-78-1 ]
[ 6665-97-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In acetone; for 1.0h;Inert atmosphere; Reflux;	To a solution of 2-nitroresorcinol 49 (4.80 g, 30.9 mmol) in acetone (30 mL) was added K2CO3 (21.39 g, 155 mmol) under nitrogen atmosphere. Dimethylsulfate (8.80 mL, 92.8 mmol) was then added and the mixture obtained was heated to reflux for 1 h. After cooling to room temperature, the solvent was removed in vacuo. The solid obtained was washed with triethylamine and water, then filtered and dried (MgSO4) to give pure compound 5055 (5.6 g, 99%) as a white solid; TLC Rf (EtOAc) = 0.73; 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.88 (s, 6H, 2OCH3), 6.63 (d, J = 8.6 Hz, 2H, ArH), 7.33 (t, J = 8.6 Hz, 1H, ArH).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6042 - 6054
[2]Tetrahedron Letters,2009,vol. 50,p. 4087 - 4091
[3]Chemistry - A European Journal,2018,vol. 24,p. 14933 - 14937
[4]Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 17
[5]Chemische Berichte,1906,vol. 39,p. 2725
[6]Justus Liebigs Annalen der Chemie,1910,vol. 372,p. 139
[7]Journal of the American Chemical Society,1933,vol. 55,p. 4225,4227

4
[ 601-89-8 ]
[ 74-88-4 ]
[ 6665-97-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In acetone; at 60 - 70℃;	MeI (3.0 mL, 48.3 mmol) was added to mixture of 77 (2.50 g, 16.1 mmol) and K2CO3 (4.46 g, 325 mesh, 32.3 mmol) in acetone (250 mL). The reaction mixture was heated to 60-70 C. (bath temperature) over night under N2. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to yield 78 as a yellow solid (2.87 g, 97%) which was used in the next step without further purification.
	With potassium carbonate; In acetone;Heating; Inert atmosphere;	1,3-Dimethoxy-2-nitro-benzene (78) MeI (3.0 mL, 48.3 mmol) was added to mixture of 77 (2.50 g, 16.1 mmol) and K2CO3 (4.46 g, 325 mesh, 32.3 mmol) in acetone (250 mL). The reaction mixture was heated to 6070 C. (bath temperature) over night under N2. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to yield 78 as a yellow solid (2.87 g, 97%) which was used in the next step without further purification.

Reference： [1]Patent: US2007/179164,2007,A1 .Location in patent: Page/Page column 56
[2]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2929 - 2934
[3]Organic Letters,2011,vol. 13,p. 4320 - 4323
[4]Patent: US9486455,2016,B2 .Location in patent: Page/Page column 155

5
[ 601-89-8 ]
[ 3114-61-2 ]

Reference： [1]Patent: US2385282,1942,A

6
[ 601-89-8 ]
[ 2734-70-5 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 4225,4227
[2]Chemische Berichte,1907,vol. 40,p. 4006
[3]Justus Liebigs Annalen der Chemie,1910,vol. 372,p. 139
[4]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6042 - 6054
[5]Chemistry - A European Journal,2018,vol. 24,p. 14933 - 14937

7
[ 601-89-8 ]
[ 77-78-1 ]
[ 3114-61-2 ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydroxide; In water; at 40℃; for 0.25h;	Dimethylsulfate (2.7 mL, 0.058 mmol) was added carefully to 2-nitrobenzene-1,3-diol (2.5 g, 0.232 mmol) and the mixture was stirred vigorously while 10% NaOH solution (21 mL) was added and the temperature was kept below 40 C. After about 15 min, the mixture was cooled and then filtered. The filtrate was collected and acidified with 10% HCl, and extracted with ether (3×25 mL). The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. Chromatography (10-30% EtOAc/hexanes) provided 9A10 (1 g, 37%).

Reference： [1]Patent: US2007/93477,2007,A1 .Location in patent: Page/Page column 27

8
[ 601-89-8 ]
[ 74-88-4 ]
[ 3114-61-2 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 7.0h;	To a stirred solution of 28 (25.0 g, 161 mmol) in DMF (500 mL) were added K2CO3 (6.80 g, 49.2 mmol) and MeI (11.0 mL, 177 mmol). After stirring for 7 h at room temperature, the reaction mixture was concentrated in vacuo and diluted with water. The resulting mixture was washed with EtOAc; the aqueous layer was acidified with 1 mol/L HCl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane-EtOAc = 2:1) to give 29 (8.78 g, 51.9 mmol, 32%) as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ 3.95 (3H, s), 6.54 (1H, dd, J = 8.6, 1.2 Hz), 6.71 (1H, dd, J = 8.6, 1.2 Hz), 7.40 (1H, t, J = 8.6 Hz), 10.22 (1H, s).
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 7.0h;	3-Methoxy-2-nitrophenol To a solution of 2-nitroresoreinol (25.0 g) in DMF (500 mL) were added potassium carbonate (6.8 g) and methyl iodide (11.0 mL), followed by stirring at room temperature for 7 hours. The solvent was evaporated under reduced pressure, and then to the residue was added water, followed by washing with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extracted layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the desired product (8.78 g) as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ 3.95 (3H, s), 6.54 (1H, dd, J=8.6, 1.2 Hz), 6.71 (1H, dd, J=8.6, 1.2 Hz), 7.40 (1H, t, J=8.6 Hz), 10.22 (1H, s).
1.6 g	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h;	5 g of 2-nitrobenzene-1,3-diol was dissolved in N,N-dimethylformamide (75 mL), and then potassium carbonate (1.3 g, 0.3 equivalent) and methyl iodide (2.23 mL, 1.1 equivalents) were added thereto at 0 C., followed by stirring at room temperature for 30 minutes. The formation of the product was confirmed by TLC, and then distilled water was added to stop the reaction, followed by extraction using ethyl acetate. The organic phase was washed by 2 M hydrochloric acid (20 mL) and then dried over anhydrous magnesium sulfate, followed by filtration, and thus obtaining 1.6 g of the title compound by purification of the residue obtained by vacuum concentration of the filtrate through silica gel column chromatography (hexane:ethyl acetate=85:15).MS (ESI) m/z: 168 (M-H)-

1.6 g

In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h;

5 g of 2-nitrobenzene-1,3-diol was dissolved in N,N-dimethylformamide (75 mL), and then potassium carbonate(1.3 g, 0.3 equivalent) and methyl iodide (2.23 mL, 1.1 equivalents) were added thereto at 0C, followed by stirring atroom temperature for 30 minutes. The formation of the product was confirmed by TLC, and then distilled water wasadded to stop the reaction, followed by extraction using ethyl acetate. The organic phase was washed by 2 M hydrochloricacid (20 mL) and then dried over anhydrous magnesium sulfate, followed by filtration, and thus obtaining 1.6 g of thetitle compound by purification of the residue obtained by vacuum concentration of the filtrate through silica gel columnchromatography (hexane:ethyl acetate = 85:15).MS (ESI) m/z: 168 (M-H)-

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 1644 - 1658
[2]Patent: EP2168959,2010,A1 .Location in patent: Page/Page column 122
[3]Patent: US2019/322686,2019,A1 .Location in patent: Paragraph 1156; 1157
[4]Patent: EP3815687,2021,A1 .Location in patent: Paragraph 0139

9
[ 601-89-8 ]
[ 1035229-32-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700
[2]Patent: US2016/31838,2016,A1
[3]Patent: WO2009/154557,2009,A1

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Technical Information

? Acidity of Phenols ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? Halogenation of Phenols ? Hydrogenolysis of Benzyl Ether ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Reimer-Tiemann Reaction ? Vilsmeier-Haack Reaction

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