5-Cyanopyridine-2-carboxylic acid

Base Information

• Chemical Name: 5-Cyanopyridine-2-carboxylic acid
• CAS No.: 53234-55-2
• Molecular Formula: C7H4N2O2
• Molecular Weight: 148.121
• Hs Code.: 2933399990
• European Community (EC) Number: 684-461-9
• DSSTox Substance ID: DTXSID20496466
• Nikkaji Number: J3.355.917H
• Wikidata: Q72459100
• Mol file: 53234-55-2.mol

Synonyms:53234-55-2;5-cyanopyridine-2-carboxylic acid;5-cyanopicolinic acid;5-cyano-2-pyridinecarboxylic acid;5-cyano-pyridine-2-carboxylic acid;MFCD09152775;2-PYRIDINECARBOXYLIC ACID, 5-CYANO-;5-cyanopicolinicacid;5-cyano-picolinic acid;5-cyano-2-picolinic acid;SCHEMBL287315;AMY6290;DTXSID20496466;HRLVPHGCEGTVLK-UHFFFAOYSA-N;5-cyano-2-pyridine carboxylic acid;BCP08290;CK2603;AKOS005071871;AB49711;BB-0611;CS-W016339;5-Cyanopyridine-2-carboxylic acid, 97%;SY032223;A7745;FT-0665303;EN300-72520;J-517440;Z1148282290

Chemical Property of 5-Cyanopyridine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.77E-06mmHg at 25°C
• Melting Point: 212-214℃
• Refractive Index: 1.596
• Boiling Point: 370.7 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 178 °C
• PSA: 73.98000
• Density: 1.42g/cm³
• LogP: 0.65148
• Storage Temp.: 2-8°C
• Water Solubility.: Sparingly soluble in water.(0.26 g/L) (25°C),
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 148.027277375
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

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

5-CyanopicolinicAcid ^*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=CC(=NC=C1C#N)C(=O)O
• Uses: 5-Cyanopicolinic Acid is a substituted picolinic acid tested for inhibition of DBM (Dopamine β-monooxygenase) from bovine adrenal medulla. It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Technology Process of 5-Cyanopyridine-2-carboxylic acid

There total 3 articles about 5-Cyanopyridine-2-carboxylic acid 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: 74.0%

→ (S)-N-(3-(2-amino-5,5-difluoro-4-(fluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide (1415914-91-8) + 5-cyano-pyridine-2-carboxylic acid (53234-55-2)

Guidance literature:

Reference yield:

6-chloronicotinonitrile (33252-28-7) + carbon monoxide (201230-82-2) → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + 5-cyano-pyridine-2-carboxylic acid (53234-55-2)

Guidance literature:

With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); triethylamine; In water; tert-butyl alcohol; at 60 ℃; for 16h; under 11251.1 Torr; Reagent/catalyst; Solvent; Temperature; Pressure; Overall yield = 92 %; Autoclave; Inert atmosphere;

Reference yield:

methyl 5-bromopicolinate (29682-15-3) → 5-cyano-pyridine-2-carboxylic acid (53234-55-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-methyl-pyrrolidin-2-one / 1.5 h / 170 °C

2: sodium hydroxide / ethanol / 0.17 h / 20 °C

With sodium hydroxide; In 1-methyl-pyrrolidin-2-one; ethanol;

upstream raw materials:

methyl 5-bromopicolinate

6-chloronicotinonitrile

carbon monoxide

Downstream raw materials:

(2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide

(2R,3R)-N-[3-(5-amino-3-cyclopropyl-2-fluoro-3,6-dihydro-2H-1,4-oxazin-3-yl)phenyl]-5-cyanopyridine-2-carboxamide

(2R,3R)-N-{3-[5-amino-3-cyclopropyl-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-cyanopyridine-2-carboxamide

(S)-N-(3-(2-amino-4-(difluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

Refernces

• 1、 -. "SYNTHESIS OF BACE1 INHIBITORS". Page/Page column 15; 16. . Retrieved 2014/11/13.
• 2、 -. "FUSED AMINODIHYDROTHIAZINE DERIVATIVES USEFUL AS BACE INHIBITORS". . . Retrieved 2012/08/07.