84555-18-0

Basic information

• Product Name: 2-Pyridinecarboxylicacid,cyanomethylester(9CI)
• Synonyms: 2-Pyridinecarboxylicacid,cyanomethylester(9CI);Cyanomethyl picolinate
• CAS NO: 84555-18-0
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• Product Categories: GLYCINESCAFFOLD
• Mol File: 84555-18-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Pyridinecarboxylicacid,cyanomethylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinecarboxylicacid,cyanomethylester(9CI)(84555-18-0)
• EPA Substance Registry System: 2-Pyridinecarboxylicacid,cyanomethylester(9CI)(84555-18-0)

Safety Data

• Hazardous Substances Data: 84555-18-0(Hazardous Substances Data)

Upstream product

• 98-98-6 2-Picolinic acid 
• 107-14-2 chloroacetonitrile 
• 119165-69-4 2-[4,5-dihydro-1,3-oxazol-2-yl]pyridine 
• 75-05-8 acetonitrile 

Downstream Products

• 4923-12-0 (2-picoloylcarbonyl)thiosemicarbazone 
• 1452-77-3 pyridine-2-carboxylic acid amide 

Relevant articles and documents

Fe(III)-catalyzed oxidative coupling of alkylnitriles with aromatic carboxylic acids: Facile access to cyanomethyl esters

The first oxidative coupling of alkylnitriles with aromatic carboxylic acids using di-tert-butyl peroxide (DTBP) as oxidant was achieved under the catalysis of ionic Fe(III) complexes bearing an imidazolinium cation. This protocol features nontoxic iron catalysis, direct α-C(sp3)–H bond oxidative esterification of alkylnitriles, non-prefunctionalized starting materials, and a broad substrate scope with outstanding steric hindrance tolerance, providing a novel, straightforward, and green approach toward cyanomethyl ester synthesis.

Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation

The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright