2-Chloro-6-phenylnicotinonitrile

Base Information

• Chemical Name: 2-Chloro-6-phenylnicotinonitrile
• CAS No.: 43083-14-3
• Molecular Formula: C12H7ClN2
• Molecular Weight: 214.654
• Hs Code.: 2933399090
• NSC Number: 363888
• DSSTox Substance ID: DTXSID60320731
• Nikkaji Number: J1.018.167D
• Wikidata: Q72457256
• Mol file: 43083-14-3.mol

Synonyms:2-chloro-6-phenylnicotinonitrile;43083-14-3;2-chloro-6-phenylpyridine-3-carbonitrile;2-Chloro-3-cyano-6-phenylpyridine;3-Pyridinecarbonitrile, 2-chloro-6-phenyl-;MFCD01316320;NSC363888;SCHEMBL1904903;DTXSID60320731;BBL029232;STL311953;AKOS000345176;AC-3581;CS-W002757;NSC 363888;NSC-363888;10H-428S;SY007417;A6974;AM20070202;FT-0679917;J-508987;W-205926

Chemical Property of 2-Chloro-6-phenylnicotinonitrile

Chemical Property:

• Vapor Pressure: 3.3E-06mmHg at 25°C
• Melting Point: 155-159 °C
• Refractive Index: 1.632
• Boiling Point: 376.4 °C at 760mmHg
• PKA: -3.62±0.10(Predicted)
• Flash Point: 181.4 °C
• PSA: 36.68000
• Density: 1.3 g/cm³
• LogP: 3.27368
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 214.0297759
• Heavy Atom Count: 15
• Complexity: 252

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-6-phenylnicotinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC(=C(C=C2)C#N)Cl

Technology Process of 2-Chloro-6-phenylnicotinonitrile

There total 10 articles about 2-Chloro-6-phenylnicotinonitrile 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: 93.8%

3-cyano-2-hydroxy-6-phenylpyridine (43083-13-2) → 2-chloro-3-cyano-6-phenylpyridine (43083-14-3)

Guidance literature:

With phosphorus pentachloride; trichlorophosphate; at 150 ℃; for 1h;

DOI:10.1248/cpb.30.4314

Reference yield: 72.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + acetophenone (98-86-2) + malononitrile (109-77-3) → 2-chloro-3-cyano-6-phenylpyridine (43083-14-3)

Guidance literature:

N,N-dimethyl-formamide; With bis(trichloromethyl) carbonate; In 1,2-dichloro-ethane; at 0 - 20 ℃;

acetophenone; In 1,2-dichloro-ethane; at 20 - 60 ℃;

malononitrile; In 1,2-dichloro-ethane; at 60 ℃; Reflux;

DOI:10.1080/00304940903324531

Reference yield: 63.4%

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + 2,6-dichloro-3-pyridinecarbonitrile (40381-90-6) → 2-chloro-3-cyano-6-phenylpyridine (43083-14-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 90 ℃; for 6h; Inert atmosphere;

upstream raw materials:

3-cyano-2-hydroxy-6-phenylpyridine

1,2-dihydro-2-oxo-6-phenylpyridine-3-carbonitrile

N,N-dimethyl-formamide

acetophenone

Downstream raw materials:

6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile

3-Amino-6-phenyl-thieno<2,3-b>pyridin-2-carbonitril

methyl 3-amino-6-phenylthieno[2,3-b]pyridine-2-carboxylate

2-(2-chlorophenoxy)-6-phenylnicotinonitrile

Refernces

• 1、 -. "Pyrazolo [3,4 - the b] pyridine and [...] composition preparation method and use of (by machine translation)". Paragraph 0164; 0165; 0166; 0167. . Retrieved 2017/07/22.
• 2、 Li,Hong,Su. "A convenient method for the synthesis of 3,5,6-trisubstituted-2- chloropyridines with bis-(trichloromethyl) carbonate". experimental part. p. 533 - 538. Retrieved 2010/04/02.