[ CAS No. 624-28-2 ] {[proInfo.proName]}

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Quality Control of [ 624-28-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 624-28-2 ]

SDS Specification

Alternatived Products of [ 624-28-2 ]

Product Citations

Wireless Detection of Trace Ammonia: A Chronic Kidney Disease Biomarker

Shao-Xiong Lennon Luo ; Timothy M. Swager ; ACS Nano,2024,18(1):364-372. DOI: 10.1021/acsnano.3c07325

Abstract: Elevated levels of ammonia in breath can be linked to medical complications, such as chronic kidney disease (CKD), that disturb the urea balance in the body. However, early stage CKD is usually asymptomatic, and mass screening is hindered by high instrumentation and operation requirements and accessible and reliable detection methods for CKD biomarkers, such as trace ammonia in breath. Enabling methods would have significance in population screening for early stage CKD patients. We herein report a method to effectively immobilize transition metal selectors in close proximity to a single-walled carbon nanotube (SWCNT) surface using pentiptycene polymers containing metal-chelating backbone structures. The robust and modular nature of the pentiptycene metallopolymer/SWCNT complexes creates a platform that accelerates sensor discovery and optimization. Using these methods, we have identified sensitive, selective, and robust copper-based chemiresistive ammonia sensors that display low parts per billion detection limits. We have added these hybrid materials to the resonant radio frequency circuits of commercial near-field communication (NFC) tags to achieve robust wireless detection of ammonia at physiologically relevant levels. The integrated devices offer a noninvasive and cost-effective approach for early detection and monitoring of CKD.

Keywords: ammonia sensing ; chronic kidney disease ; carbon nanotubes ; conjugated polymers ; wireless sensing

Purchased from AmBeed: 100125-12-0 ; 15862-18-7 ; 624-28-2 ; 400859-09-8

Product Details of [ 624-28-2 ]

CAS No. :	624-28-2	MDL No. :	MFCD00006221
Formula :	C₅H₃Br₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZHXUWDPHUQHFOV-UHFFFAOYSA-N
M.W :	236.89	Pubchem ID :	69353
Synonyms :

Calculated chemistry of [ 624-28-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.64
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	2.57
Log Po/w (WLOGP) :	2.61
Log Po/w (MLOGP) :	2.01
Log Po/w (SILICOS-IT) :	2.8
Consensus Log Po/w :	2.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0779 mg/ml ; 0.000329 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.769 mg/ml ; 0.00325 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0435 mg/ml ; 0.000184 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 624-28-2 ]

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

Application In Synthesis of [ 624-28-2 ]

* 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 [ 624-28-2 ]
Downstream synthetic route of [ 624-28-2 ]

[ 624-28-2 ] Synthesis Path-Upstream 1~3

1
[ 624-28-2 ]
[ 23719-80-4 ]
[ 579475-29-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: With zinc(II) chloride In tetrahydrofuran at 20℃; for 2 h; Stage #2: at 20℃;	2-Cyclopropyl-5-('4,4,5,5-tetramethyl-L3.2-dioxaborolan-2-vDpyridine0.5M Zinc chloride in THF (5.5 mL, 2.8 mmol) was added to a solution of 0.5M cyclopropylmagnesium bromide in THF (5.5 mL, 2.8 mmol) under argon. The solution was stirred at RT for 2 h at which time a slurry had formed. To this slurry was added in one portion 2,5-dibromopyridine (0.65 g, 2.8 mmol) and PdCl₂ x dppf (0.041 g, 0.050 mmol). After a few minutes an exotherm was seen and the slurry became thicker, the exotherm subsided and the slurry was stirred at RT overnight. The reaction mixture was poured into saturated sodium bicarbonate solution and extracted with ether. The ether phase was dried, filtered and concentrated, then re-dissolved in DCM and applied to a short plug of silica gel. The gel was washed with DCM and the washings were concentrated. The residue was taken up in ether and washed with 1.0M hydrochloric acid. The acidic water phase was made basic with 2.0M sodium hydroxide and the product was extracted back into ether. The combined ether phases were washed with brine, dried, filtered and concentrated to give 0.28 g (50percent) of 5-bromo-2-cyclopropylpyridine as a yellow oil. LC-MS mlz 197.9/199.9 (M+l); ¹H-NMR(CDCl₃) δ 8.48 (d, IH), 7.63 (dd, IH), 7.04 (d, IH), 1.99 (m, IH), 1.03-0.98 (m, 4H) ppm

Reference： [1] Patent: WO2006/65215, 2006, A1, . Location in patent: Page/Page column 28
[2] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2777 - 2782

2
[ 624-28-2 ]
[ 203861-73-8 ]
[ 579475-29-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 70℃; for 3 h;	To a solution 2,5-dibromopyridine[CAS 624-28-2, commercially available](5 g, 21 mmol) and Pd(PPh₃)₄(244 mg, 1 mol percent) in THF (25 mL) was added cycloropylzinc chloride (0.4M in THF, 53 mL, 26 mmol), and the mixture was stirred under argon atmosphere at 70° C. for 3 h. Cooled to 23° C., poured into sat. NaHCO₃-solution, extracted with ether, washed with brine, dried over Na₂SO₄. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel chromatography with heptane-EtOAc (9:1) to give the title compound as a colorless liquid (4.3 g, 103percent). MS (EI) 197 [(M)⁺] and 199 [(M+2)⁺].

Reference： [1] Patent: US2006/217387, 2006, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2005/14002, 2005, A1, . Location in patent: Page/Page column 39

3
[ 624-28-2 ]
[ 856866-72-3 ]

Reference： [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039

[ 624-28-2 ] Synthesis Path-Downstream 1~11

1
[ 624-28-2 ]
[ 127842-54-0 ]
[ 303165-20-0 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2413 - 2426
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 741 - 744

2
[ 624-28-2 ]
[ 124-40-3 ]
[ 26163-07-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water;Reflux;	(A) 5-bromo-/V,/V-di methyl pyridi n-2-ami ne[095] A solution of 2,5-dibromopyridine (10 g, 42.3 mmol) in aqueousdimethylamine (50 mL) was refluxed overnight. The volatiles were removed in vacuo, and the residue was treated with EtOAc/PE. The precipitates were collected by filtration and dried to give the title compound. MS (m/z): 201 (M+H)+, 203 (M+H)+.
	In water;Reflux;	A solution of 2,5-dibromopyridine (10 g, 42.3 mmol) in aqueous dimethylamine (50 mL) was refluxed overnight. The volatiles were removed in vacuo, and the residue was treated with EtOAc/PE. The precipitates were collected by filtration and dried to give the title compound. MS (m/z): 201 (M+H)+, 203 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 374 - 378
[3]Patent: WO2012/167423,2012,A1 .Location in patent: Page/Page column 36
[4]Patent: US2014/121200,2014,A1 .Location in patent: Paragraph 0168; 0169

3
[ 624-28-2 ]
[ 26163-07-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dimethyl amine; In tetrahydrofuran;	A. 5-Bromo-2-(dimethylamino)pyridine A solution of 2,5-dibromopyridine (11.84 g, 50.0 mmol) in 2.0 M solution of dimethylamine in tetrahydrofuran (100 mL) in a sealed tube was heated at 120 C. for 12 hours. The reaction was quenched with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 10-15% ethyl acetate/hexane) to provide the title compound (8.67 g, 86% yield): 1H NMR (CDCl3) 8.16 (d, 1H), 7.49 (dd, 1H), 6.41 (d, 1H), 3.05 (s, 6H); ES-MS m/z 201 [M+H]+.

Reference： [1]Patent: US6593322,2003,B1

4
[ 850568-54-6 ]
[ 624-28-2 ]
[ 1258878-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; toluene; at 120℃; for 0.333333h;Microwave irradiation;	Preparation of Intermediate E - Tert-butyl 4-(S-bromopgammaridiit-2-gammaI) benzoate (E-I)A mixture of 2,5-dibromopyridine (12.6 mmol), [4-(tert-butoxycarbonyl) phenyl] boronic acid (13.93 mmol), 2 N sodium carbonate (9.5 ml), methanol (20.0 ml), toluene (40.0 ml) and Tetrakis (0.63 mmol) was irradiated in the Advancer Biotage Microwave Reactor for 20 min at 120 0C. The solvent was evaporated under reduced pressure and the resulting solid diluted with methylene chloride and water. The layers were separated and the aqueous layer washed with methylene chloride. The combined organic layers was dried (MgSCU) and filtered through celite. Silica gel chromatography purification, eluting with 0 to 10 percent ethyl acetate / hexane afforded the title compound E-1. 1H NMR(CDCB): delta = 8.79 (d, J= 2.2 Hz, 1H), 8.109 (d, J= 12 Hz5 2H), 8.043 (d, J- 11.9 Hz5 2H), 7.92 (d, J= 10.9 Hz, 1H), 7.690 (d, J= 8.4 Hz, 1H), 1.651 (s, 9H).

Reference： [1]Patent: WO2010/147776,2010,A1 .Location in patent: Page/Page column 68-69

5
[ 624-28-2 ]
[ 67442-07-3 ]
[ 1260759-84-9 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2642 - 2650

6
[ 624-28-2 ]
[ 635712-99-1 ]

Reference： [1]Polyhedron,2013,vol. 52,p. 755 - 760

7
[ 624-28-2 ]
[ 6414-69-3 ]
[ 1427371-57-0 ]

Yield	Reaction Conditions	Operation in experiment
		B. A solution of Zn metal (18 g, 0.27 mol) in DMF (5 mL) was purged with N2. BrCH2CH2Br (2.0 g, 10 mmol) was added, followed by TMSCl (0.92 g, 8.5 mmol). The resulting mixture was stirred at 90 C. for 30 min, and allowed to cool to rt. A solution of compound 57a (50 g, 0.22 mol) in DMF (150 mL) was added, and the resulting mixture was stirred overnight at rt. Pd(PPh3)2Cl2 (7.4 g, 10 mmol) was added, followed by 2,5-dibromopyridine (50 g, 0.21 mol). The resulting mixture was stirred at 68 C. for 2 h. The reaction was quenched by the addition of saturated NaHCO3 solution (300 mL). The resulting solution was extracted with EtOAc (2*100 mL), and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:2 v/v)) to obtain compound 57b as a yellow oil. Mass Spectrum (LCMS, ESI pos.): Calcd. for C10H12BrNO2: 258.0 (M+H). Found: 258.2.

Reference： [1]Patent: US2014/364413,2014,A1 .Location in patent: Paragraph 0867; 0868

8
[ 624-28-2 ]
[ 6414-69-3 ]
(E)-ethyl 3-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)propanoate [ No CAS ]

Reference： [1]Patent: US2014/364413,2014,A1

9
[ 624-28-2 ]
[ 76350-90-8 ]
5-bromo-2-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,4,7,10,13,20-Hexaoxa<13.1>(1,2)benzenophan; potassium hydroxide; In toluene; for 1.5h;Reflux; Dean-Stark;	A mixture of 2,5-dibromopyridine (5 g, 21.11 mmol), (2-methyl-[l,l'-biphenyl]-3- yl)methanol (5.44 g, 27.4 mmol), dibenzo-18-crown-6 (0.380 g, 1.055 mmol), potassium hydroxide (2.84 g, 50.7 mmol) and toluene (50 mL) was stirred at reflux with a Dean- Stark trap ( pre-filled with toluene). After 1.5 hours, the heat was removed. TLC analysis showed that starting material was consumed. LC/MS consistent with crude desired product. The solvents were removed under reduced pressure by rotary evaporation. Water (50 mL) was added and the product extracted into dichloroethane (3x50 mL). The combined organic portion was dried over magnesium sulfate and filtered. The solvents were removed under reduced pressure by rotary evaporation to give 9.7 grams of a yellow oil. LC/MS was consistent with crude desired product. The yellow oil became an off- white solid on standing. Chromatographed on a 330g silica gel column with 0-20% ethyl acetate in hexanes to give the product (6.3g, 84%). 1H NMR (400MHz, DMSO-d6) delta 8.34 (dd, J=2.8, 0.5 Hz, 1H), 7.95 (dd, J=8.8, 2.5 Hz, 1H), 7.50 - 7.43 (m, 3H), 7.42 - 7.37 (m, 1H), 7.34 - 7.31 (m, 2H), 7.28 (t, J=7.5 Hz, 1H), 7.23 - 7.18 (m, 1H), 6.95 (dd, J=8.8, 0.5 Hz, 1H), 5.41 (s, 2H), 2.20 (s, 3H).

Reference： [1]Patent: WO2015/34820,2015,A1 .Location in patent: Page/Page column 72-73

10
[ 624-28-2 ]
[ 23687-26-5 ]
C₁₄H₁₀BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; at 100℃; for 16h;Inert atmosphere;	K3PO4 (1.70 g, 7.99 mmol), Pd2(dba)3 (0.152 g, 0.166 mmol) and Xantphos (0.161 mg, 0.277 mmol) were added to a solution of 2,5-dibromopyridine (0.738 g, 3.052 mmol, CAS 624-28-2) in dry THF (20 mL) while nitrogen was bubbling through the mixture. After 10 min, <strong>[23687-26-5]6-aminoisoquinoline</strong> (0.400 g, 2.774 mmol, CAS 23687-26-5) was added and the mixture was stirred at rt for 10 min. Then, the mixture was heated at 100 °C for 16 h. After cooling to rt, the mixture was washed with aq. sat. NaHC03 and extracted with EtOAc. The organic layer was dried over MgS04, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 75/25). The desired fractions were collected and concentrated in vacuo providing intermediate 17 (0.680 g, 80percent pure, 65percent yield).

Reference： [1]Patent: WO2018/15307,2018,A1 .Location in patent: Page/Page column 26

11
[ 624-28-2 ]
[ 68-12-2 ]
[ 26163-07-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium t-butanolate; In water; at 140℃; for 6h;Sealed tube;	2,5-dibromopyridine (1.0 mmol), DMF (1 mmol),Sodium tert-butoxide (0.5-4.0 mmol) and 2 mL of water were successively added to a 10 mL sealed tube, and the mixture was heated and stirred for 6 hours in an oil bath at 140 C, and quenched with dichloromethane.When the reaction is over,The yield of the product can be determined by GC and GC-MS by adding the internal standard to the crude product.When the sodium tert-butoxide was 0.5 mmol, 1.0 mmol, 2.0 mmol, 3.0 mmol, and 4.0 mmol, the isolated yields of the products were 55%, 66%, 72%, 80%, and 82%, respectively.

Reference： [1]Patent: CN108689923,2018,A .Location in patent: Paragraph 0016-0029

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Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

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[ 624-28-2 ]

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[ 624-28-2 ]

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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. 624-28-2 ] {[proInfo.proName]}

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[ 624-28-2 ] Synthesis Path-Upstream 1~3

[ 624-28-2 ] Synthesis Path-Downstream 1~11

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Bromides

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Pyridines

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