3-Methylisonicotinonitrile

Base Information

• Chemical Name: 3-Methylisonicotinonitrile
• CAS No.: 7584-05-6
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 2933399090
• European Community (EC) Number: 231-491-1
• DSSTox Substance ID: DTXSID50226733
• Nikkaji Number: J307.889B
• Wikidata: Q72489621
• Mol file: 7584-05-6.mol

Synonyms:3-Methylisonicotinonitrile;7584-05-6;4-Cyano-3-methylpyridine;3-methylpyridine-4-carbonitrile;3-METHYL-ISONICOTINONITRILE;3-Methyl-4-pyridinecarbonitrile;3-METHYL-4-CYANOPYRIDINE;4-PYRIDINECARBONITRILE, 3-METHYL-;4-Pyridinecarbonitrile,3-methyl-;SCHEMBL342957;DTXSID50226733;EINECS 231-491-1;MFCD09261048;AKOS015842250;GS-5496;PB23623;AM804327;CS-0037320;FT-0696005;EN300-39351;W-204311;F8881-5702;Z382716050

Chemical Property of 3-Methylisonicotinonitrile

Chemical Property:

• Vapor Pressure: 0.101mmHg at 25°C
• Melting Point: 51-52oC
• Refractive Index: 1.531
• Boiling Point: 222.59 °C at 760 mmHg
• PKA: 2.17±0.18(Predicted)
• Flash Point: 89.795 °C
• PSA: 36.68000
• Density: 1.084 g/cm³
• LogP: 1.26168
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 133

Purity/Quality:

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

4-Cyano-3-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CN=C1)C#N
• Uses: 4-Cyano-3-methylpyridine is an intermediate used to synthesis of azaindenoisoquinoline as topoisomerase I inhibitors and potential anticancer agents.

Technology Process of 3-Methylisonicotinonitrile

There total 25 articles about 3-Methylisonicotinonitrile 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: 75.0%

3-methyl-4-nicotinicamide (251101-36-7) → 3-methyl-4-cyanopyridine (7584-05-6)

Guidance literature:

With trichlorophosphate; for 20h; Reflux;

DOI:10.1002/chem.201600308

Reference yield: 60.0%

3-Methylpyridine (108-99-6) + trimethylsilyl cyanide (7677-24-9) → 3-methyl-4-cyanopyridine (7584-05-6) + 2-cyano-3-methylpyridine (20970-75-6)

Guidance literature:

3-Methylpyridine; With trifluoromethylsulfonic anhydride; In chloroform; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

trimethylsilyl cyanide; In chloroform; at 60 ℃; for 3h; Inert atmosphere; Sealed tube;

With 4-methyl-morpholine; In chloroform; at 60 ℃; for 17h; Overall yield = 64 %; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703931

Reference yield: 49.0%

3-picoline-N-oxide (1003-73-2) + potassium cyanide → 3-methyl-4-cyanopyridine (7584-05-6)

Guidance literature:

3-picoline-N-oxide; With ethyl iodide; In acetonitrile; at 20 ℃;

potassium cyanide; In water; acetonitrile; at 20 - 55 ℃;

upstream raw materials:

3-picoline-N-oxide

dimethyl sulfate

methyl iodide

4-chloro-3-methylpyridine

Downstream raw materials:

(E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile

9-aza-5,6-dihydro-2,3-dimethoxy-5-oxo-11H-indeno[1,2-c]-isoquinoline

2-chloro-3-methylisonicotinonitrile

3-methylisonicotinimidamide

Refernces

• 1、 Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.. "Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source". supporting information. p. 7683 - 7689. Retrieved 2020/04/22.
• 2、 Qin, Li-Huai,Wang, Zhi-Long,Xie, Xin,Long, Ya-Qiu. "Discovery and synthesis of 6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one-based novel chemotype CCR2 antagonists via scaffold hopping strategy". . p. 3559 - 3572. Retrieved 2018/05/28.