2,5-Dichloro-4,6-dimethylnicotinonitrile

Base Information

• Chemical Name: 2,5-Dichloro-4,6-dimethylnicotinonitrile
• CAS No.: 91591-63-8
• Molecular Formula: C8H6Cl2N2
• Molecular Weight: 201.055
• Hs Code.: 2933399090
• European Community (EC) Number: 639-346-8
• NSC Number: 341973
• DSSTox Substance ID: DTXSID50319215
• Wikidata: Q72466037
• Mol file: 91591-63-8.mol

Synonyms:2,5-Dichloro-4,6-dimethylnicotinonitrile;91591-63-8;2,5-dichloro-4,6-dimethylpyridine-3-carbonitrile;3-Pyridinecarbonitrile, 2,5-dichloro-4,6-dimethyl-;3-Cyano-2,5-dichloro-4,6-dimethylpyridine;2,5-Dichloro-4,6-dimethyl-3-pyridinecarbonitrile;MFCD00052631;NSC341973;2,5-dichloro-3-cyano-4,6-dimethylpyridine;SCHEMBL8471830;DTXSID50319215;BCP18750;STK724629;AKOS001751894;GS-3527;NSC 341973;NSC-341973;SY017930;2,5-dichloro-4,6-dimethyl-nicotinonitrile;AM20070269;CS-0010501;FT-0610292;2,5-dichloro-4,6-dimethyl-3-pyridyl cyanide;3-Pyridinecarbonitrile,5-dichloro-4,6-dimethyl-;A860323;AG-205/41147734;SR-01000533931;3-Pyridinecarbonitrile,2,5-dichloro-4,6-dimethyl-;J-803059;SR-01000533931-1;W-204063;2,5-Dichloro-4,6-dimethylpyridine-3-carbonitrile

Chemical Property of 2,5-Dichloro-4,6-dimethylnicotinonitrile

Chemical Property:

• Appearance/Colour: light brown solid
• Vapor Pressure: 0.000867mmHg at 25°C
• Melting Point: 82 °C
• Refractive Index: 1.564
• Boiling Point: 304.6 °C at 760 mmHg
• PKA: -2.79±0.10(Predicted)
• Flash Point: 138 °C
• PSA: 36.68000
• Density: 1.36 g/cm³
• LogP: 2.87688
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 199.9908036
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

99.9% ^*data from raw suppliers

2,5-Dichloro-4,6-dimethyl-3-pyridinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NC(=C1Cl)C)Cl)C#N
• Uses: 2,5-Dichloro-4,6-dimethyl-3-pyridinecarbonitrile, can be used for the synthesis of a selective muscarinic receptor 4 (M4) positive allosteric modulator called ML253, which is a potent and brain penetrant compound that is active in a preclinical model of schizophrenia.

Technology Process of 2,5-Dichloro-4,6-dimethylnicotinonitrile

There total 6 articles about 2,5-Dichloro-4,6-dimethylnicotinonitrile 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: 95.1%

5-chloro-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (23819-92-3) → 2,5-dichloro-4,6-dimethylpyridine-3-carbonitrile (91591-63-8)

Guidance literature:

With tetramethlyammonium chloride; trichlorophosphate; at 85 ℃; for 3h; Temperature; Reagent/catalyst;

Reference yield: 77.0%

5-chloro-2-hydroxy-4,6-dimethylnicotinonitrile (23819-92-3) → 2,5-dichloro-4,6-dimethylpyridine-3-carbonitrile (91591-63-8)

Guidance literature:

With trichlorophosphate; at 120 ℃; for 6h;

Reference yield:

3-Cyano-4,6-dimethyl-2(1H)-pyridon (769-28-8) → 2,5-dichloro-4,6-dimethylpyridine-3-carbonitrile (91591-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / sulfuryl chloride / CCl₄ / 6 h / Heating

2: 76 percent / POCl₃ / Heating

With sulfuryl dichloride; trichlorophosphate; In tetrachloromethane;

DOI:10.1023/B:COHC.0000028626.45566.67

upstream raw materials:

5-chloro-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

3-Cyano-4,6-dimethyl-2(1H)-pyridon

acetylacetone

2-hydroxy-4,6-dimethyl-3-carbonitrile

Downstream raw materials:

5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene

2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide

5-[3-(2,5-dichloro-4,6-dimethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene

Refernces

• 1、 -. "Route Of Synthesis For Opicapone". . . Retrieved 2019/01/10.
• 2、 -. "CHEMICAL COMPOUND USEFUL AS INTERMEDIATE FOR PREPARING A CATECHOL-O-METHYLTRANSFERASE INHIBITOR". Page/Page column 15-16. . Retrieved 2013/07/05.