2-Bromo-4-hydroxynicotinonitrile

Base Information

• Chemical Name: 2-Bromo-4-hydroxynicotinonitrile
• CAS No.: 635731-97-4
• Molecular Formula: C₆H₃BrN₂O
• Molecular Weight: 199.007
• DSSTox Substance ID: DTXSID10383033
• Wikidata: Q82174584
• Mol file: 635731-97-4.mol

Synonyms:2-BROMO-4-HYDROXYNICOTINONITRILE;635731-97-4;2-bromo-4-oxo-1H-pyridine-3-carbonitrile;2-Bromo-4-oxo-1,4-dihydropyridine-3-carbonitrile;98645-46-6;2-Bromo-3-cyano-4-hydroxypyridine;SCHEMBL2950978;DTXSID10383033;2-bromo-4-hydroxy-nicotinonitrile;PSCVYEBXCLQANK-UHFFFAOYSA-N;MFCD09038082;AKOS006274692;SB53737;AS-61064;CS-0047472;FT-0691574;W13343;2-BROMO-4-HYDROXYPYRIDINE-3-CARBONITRILE

Chemical Property of 2-Bromo-4-hydroxynicotinonitrile

Chemical Property:

• Vapor Pressure: 0.0337mmHg at 25°C
• Refractive Index: 1.633
• Boiling Point: 242.6 °C at 760 mmHg
• Flash Point: 100.5 °C
• PSA: 56.91000
• Density: 1.84 g/cm³
• LogP: 1.42138
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 197.94288
• Heavy Atom Count: 10
• Complexity: 281

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-4-hydroxynicotinonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=C(C1=O)C#N)Br

Technology Process of 2-Bromo-4-hydroxynicotinonitrile

There total 5 articles about 2-Bromo-4-hydroxynicotinonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

2-bromo-4-methoxypyridine-3-carbonitrile (98645-42-2) → 2-Brom-3-cyan-4(1H)-pyridon (635731-97-4,98645-46-6)

Guidance literature:

With hydrogen bromide; acetic acid; for 0.75h; Heating;

DOI:10.1002/ardp.19853180602

Reference yield:

1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene (95689-38-6) → 2-Brom-3-cyan-4(1H)-pyridon (635731-97-4,98645-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / HBr / methanol / 2 h

2: 81 percent / 30 percent HBr, glacial acetic acid / 0.75 h / Heating

With hydrogen bromide; acetic acid; In methanol;

DOI:10.1002/ardp.19853180602

Reference yield:

2-chloro-3-cyano-4-methoxypyridine (98645-43-3) → 2-bromo-3-cyano-4-hydroxypyridine (635731-97-4,98645-46-6) + 2-chloro-3-cyano-4-hydroxypyridine (869802-74-4,727737-49-7)

Guidance literature:

With hydrogen bromide; In acetic acid; at 100 ℃; for 2h;

upstream raw materials:

2-bromo-4-methoxypyridine-3-carbonitrile

1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene

N,N-dimethyl-formamide dimethyl acetal

(1-ethoxyethylidene)malononitrile

Downstream raw materials:

3-amino-4-phenylaminothieno[2,3-b]pyridine-2-carboxylic acid amide

3-amino-4-(4-benzylpiperazin-1-yl)thieno[2,3-b]pyridine-2-carboxylic acid amide

3-amino-4-(4-nitrophenylamino)thieno[2,3-b]pyridine-2-carboxylic acid amide

2-bromo-3-cyano-4-(4'-methoxybenzyloxy)pyridine

Refernces

• 1、 Zheng, Guo Zhu,Bhatia, Pramila,Daanen, Jerome,Kolasa, Teodozyj,Patel, Meena,Latshaw, Steven,El Kouhen, Odile F.,Chang, Renjie,Uchic, Marie E.,Miller, Loan,Nakane, Masaki,Lehto, Sonya G.,Honore, Marie P.,Moreland, Robert B.,Brioni, Jorge D.,Stewart, Andrew O.. "Structure-activity relationship of triazafluorenone derivatives as potent and selective mGluR1 antagonists". . p. 7374 - 7388. Retrieved 2007/10/03.
• 2、 Mittelbach,Kastner,Junek. "Syntheses with nitriles LXXI: Synthesis of 4-hydroxynicotinic acid from butadienedicarbonitriles". . p. 481 - 486. Retrieved 2007/10/02.