2-Cyano-5-hydroxymethylpyridine

Base Information

• Chemical Name: 2-Cyano-5-hydroxymethylpyridine
• CAS No.: 58553-48-3
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.137
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60482489
• Wikidata: Q82318863
• Mol file: 58553-48-3.mol

Synonyms:58553-48-3;2-cyano-5-hydroxymethylpyridine;5-(Hydroxymethyl)picolinonitrile;5-(HYDROXYMETHYL)PYRIDINE-2-CARBONITRILE;MFCD09029606;2-Pyridinecarbonitrile, 5-(hydroxymethyl)-;SCHEMBL453185;3-hydroxymethyl-6-cyanopyridine;DTXSID60482489;UFTHYXJJRHOQGT-UHFFFAOYSA-N;5-Hydroxymethylpyridine-2-carbonitrile;AKOS006289098;AB49273;5-hydroxymethyl-pyridine-2-carbonitrile;SY251392;TS-01731;5-(HYDROXYMETHYL)-2-PYRIDINECARBONITRILE;A856305;J-400704

Chemical Property of 2-Cyano-5-hydroxymethylpyridine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.575
• Boiling Point: 353.8°Cat760mmHg
• Flash Point: 167.8°C
• PSA: 56.91000
• Density: 1.25g/cm³
• LogP: 0.44558
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 134.048012819
• Heavy Atom Count: 10
• Complexity: 149

Purity/Quality:

98%min ^*data from raw suppliers

5-(Hydroxymethyl)pyridine-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1CO)C#N

Technology Process of 2-Cyano-5-hydroxymethylpyridine

There total 11 articles about 2-Cyano-5-hydroxymethylpyridine 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: 75.6%

zinc(II) cyanide (557-21-1) + 2-bromo-5-(hydroxymethyl)pyridine (122306-01-8) → 5-(hydroxymethyl)pyridine-2-carbonitrile (58553-48-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 30 - 120 ℃; for 12h; Inert atmosphere;

Reference yield: 73.0%

methyl 6-cyanopyridine-3-carboxylate (89809-65-4) → 5-(hydroxymethyl)pyridine-2-carbonitrile (58553-48-3)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In methanol; for 2h;

DOI:10.1021/acs.jmedchem.8b01381

Reference yield: 53.0%

3-Acetoxymethyl-6-cyanopyridine (131747-37-0) → 5-(hydroxymethyl)pyridine-2-carbonitrile (58553-48-3)

Guidance literature:

With potassium carbonate; In methanol; for 2.5h;

DOI:10.1248/cpb.38.2446

upstream raw materials:

3-Acetoxymethyl-6-cyanopyridine

3-Acetoxymethylpyridine-N-oxide

6-cyanonicotinic acid

5-methylpicolinonitrile

Downstream raw materials:

tert-bulyl N-[(6-cyanopyridin-3-yl)methyl]carbamate

5-(aminomethyl)pyridine-2-carboximidamide

5-(aminomethyl)pyridine-2-carbonitrile

(6-cyanopyridin-3-yl)methyl methanesulfonate

Refernces

• 1、 Dianati, Vahid,Navals, Pauline,Couture, Frédéric,Desjardins, Roxane,Dame, Anthony,Kwiatkowska, Anna,Day, Robert,Dory, Yves L.. "Improving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue". . p. 11250 - 11260. Retrieved 2019/01/04.
• 2、 -. "THERAPEUTIC AGENT FOR CEREBRAL INFARCTION". Page/Page column 20; 21. . Retrieved 2010/03/04.