3-Bromo-4-cyanopyridine

Base Information

• Chemical Name: 3-Bromo-4-cyanopyridine
• CAS No.: 13958-98-0
• Molecular Formula: C6H3BrN2
• Molecular Weight: 183.007
• Hs Code.: 2933399990
• European Community (EC) Number: 678-792-8
• DSSTox Substance ID: DTXSID20454223
• Nikkaji Number: J2.121.239C
• Wikidata: Q69755202
• Mol file: 13958-98-0.mol

Synonyms:3-Bromo-4-cyanopyridine;13958-98-0;3-Bromoisonicotinonitrile;3-bromopyridine-4-carbonitrile;4-Pyridinecarbonitrile, 3-bromo-;MFCD00234143;5-bromoisonicotinonitrile;3-bromo-isonicotinonitrile;SCHEMBL526349;3-bromo-4-pyridinecarbonitrile;DTXSID20454223;VPDIXJCBBUZNPO-UHFFFAOYSA-N;BCP25595;BBL102302;STL556101;3-Bromo-4-cyanopyridine, AldrichCPR;AKOS005199114;AB05148;BS-2009;CS-W002552;AC-33368;SY013185;AM20050808;B5215;FT-0646909;EN300-122211;A807565;J-512109;ETHYL2-(5-BROMO-1H-INDOL-3-YL)-2-OXOACETATE;Z1201619912

Chemical Property of 3-Bromo-4-cyanopyridine

Chemical Property:

• Melting Point: 129-131°C(lit.)
• Boiling Point: 267.48 °C at 760 mmHg
• PKA: -0.48±0.18(Predicted)
• Flash Point: 115.568 °C
• PSA: 36.68000
• Density: 1.726 g/cm³
• LogP: 1.71578
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 181.94796
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-4-cyanopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC(=C1C#N)Br
• Uses: 3-Bromo-4-cyanopyridine is used in the synthesis of nicotinic receptor ligands which have application towards diseases such as nicotinic addiction,, neurodegenerative and cognitive disorders. It is al so used in the synthesis of orally bioavailable cannabinoid receptor 2 agonists for use as analgesic and anti-inflammatory agents.

Technology Process of 3-Bromo-4-cyanopyridine

There total 11 articles about 3-Bromo-4-cyanopyridine 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: 96.0%

3-bromopyridine-4-carboxamide (13958-99-1) → 3-bromo-4-cyanopyridine (13958-98-0)

Guidance literature:

With trichlorophosphate; for 2.5h; Heating;

DOI:10.1080/00304949709355235

Reference yield: 87.0%

3-bromoisonicotinaldehyde oxime (1610416-94-8) → 3-bromo-4-cyanopyridine (13958-98-0)

Guidance literature:

With triethylamine; trichlorophosphate; In tetrahydrofuran; for 3h; Inert atmosphere; Cooling with ice;

Reference yield: 84.0%

(Z)-3-bromoisonicotinaldehyde oxime (927806-21-1) → 3-bromo-4-cyanopyridine (13958-98-0)

Guidance literature:

With triethylamine; trichlorophosphate; In tetrahydrofuran; at 0 ℃; for 2.5h;

upstream raw materials:

3-Bromo-4-methylpyridin

3-bromopyridine-4-carboxamide

pyridine-4-carbonitrile

3-bromoisonicotinic acid

Downstream raw materials:

1H-pyrazolo[3,4-c]pyridin-3-amine

C₁₃H₇BrF₂N₂O

3-(4-methylphenyl)-2,6-naphthyridin-1-one

4-cyano-3-(4-methylphenylethynyl)pyridine

Refernces

• 1、 Dunn. "A facile synthesis of 3-amino-1(2)H-pyrazolo[3,4-c]pyridine". . p. 577 - 579. Retrieved 1997.
• 2、 Kumpan, Katerina,Nathubhai, Amit,Zhang, Chenlu,Wood, Pauline J.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Lehti?, Lari,Threadgill, Michael D.. "Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases". supporting information. p. 3013 - 3032. Retrieved 2015/08/03.
• 3、 -. "N-(ARYLALKYL)-N'-PYRAZOLYL-UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS". Paragraph 00873. . Retrieved 2014/06/11.