Methyl cyanoformate

Base Information

• Chemical Name: Methyl cyanoformate
• CAS No.: 17640-15-2
• Molecular Formula: C3H3 N O2
• Molecular Weight: 85.0623
• Hs Code.: 2926909090
• European Community (EC) Number: 241-626-6
• UNII: 7S9M7F9JLT
• DSSTox Substance ID: DTXSID1066235
• Nikkaji Number: J47.920I
• Wikipedia: Methyl_cyanoformate
• Wikidata: Q415666
• Mol file: 17640-15-2.mol

Synonyms:Methyl cyanoformate;17640-15-2;Carbonocyanidic acid, methyl ester;methyl carbonocyanidate;Cyanoformate methyl ester;Cyklon A [Czech];Cyklon A;FORMIC ACID, CYANO-, METHYL ESTER;EINECS 241-626-6;2-methoxy-2-oxoacetonitrile;BRN 1742994;7S9M7F9JLT;Methylester kyseliny kyanmravenci [Czech];Methylester kyseliny kyanmravenci;3-02-00-01587 (Beilstein Handbook Reference);methylcyanoformat;Mander's reagent;methyl-cyanoformate;MeOCOCN;NCCOOMe;Cyanoformic acid methyl;CH3OC(O)CN;Methyl cyanoformate, 99%;UNII-7S9M7F9JLT;[(Cyanocarbonyl)oxy]methane;DTXSID1066235;BCP23823;MFCD00013420;AKOS015900076;AT37626;LS-69682;FT-0628718;EN300-66501;Q415666

Chemical Property of Methyl cyanoformate

Chemical Property:

• Vapor Pressure: 36.6mmHg at 25°C
• Melting Point: 185-186 °C
• Refractive Index: n20/D 1.374(lit.)
• Boiling Point: 100.5°Cat760mmHg
• Flash Point: 26.1°C
• PSA: 50.09000
• Density: 1.135g/cm³
• LogP: -0.31702
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 85.016378338
• Heavy Atom Count: 6
• Complexity: 98.6

Purity/Quality:

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

Methyl Cyanoformate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 10-26/27/28-36/38-36/37/38
• Safety Statements: 26-28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C#N
• Description: Methyl cyanoformate is the organic compound with the formula CH3OC(O)CN. It is used as a reagent in organic synthesis as a source of the methoxy carbonyl group , in which context it is also known as Mander's reagent. It was also the active ingredient in the pesticide product Zyklon A.
• Uses: Selective acylating reagent. Organic synthesis.

Technology Process of Methyl cyanoformate

There total 27 articles about Methyl cyanoformate 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: 63.0%

1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester (2166-14-5) + 2,2-dimethylpropylidynephosphine (78129-68-7) → methyl cyanoformate (17640-15-2) + 4-tert-Butyl-1-(2,4,5-tri-tert-butyl-[1,3]diphosphol-1-yl)-1H-[1,2,3]azadiphosphole-5-carboxylic acid methyl ester (122747-89-1)

Guidance literature:

In toluene; at 110 ℃; for 24h; sealed tube;

DOI:10.1016/S0040-4039(00)82211-X

Reference yield: 55.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl cyanoformate (17640-15-2) + triphenylphosphine oxide-nitric acid complex (18365-29-2)

Guidance literature:

With Nitrogen dioxide; In dichloromethane; Yields of byproduct given; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199901)1999:1<251::AID-EJOC251>3.0.CO;2-M

Reference yield:

potassium cyanide (151-50-8) + methyl chloroformate (79-22-1) → methyl cyanoformate (17640-15-2)

Guidance literature:

With 18-crown-6 ether; In dichloromethane;

DOI:10.1021/jo00883a041

upstream raw materials:

2-methoxyacetonitrile

methyl 2-amino-2-oxoacetate

sodium cyanide

methyl chloroformate

Downstream raw materials:

dimethyl isopropylidenemalonate

6-Chloro-3-phenyl-s-triazolo<4,3-b>pyridazine

5-[(toluene-4-sulfonyl)-trimethylsilanylethynyl-amino]-pent-2-ynoic acid methyl ester

(R)-1-((E)-4-Benzoyloxy-but-2-enyl)-2-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-3-oxo-piperidine-4-carboxylic acid methyl ester

Refernces

• 1、 Lidy,Sundermeyer. "-". . p. 1449. Retrieved 1973.
• 2、 Sugimoto, Hiromichi,Nakamura, Satoshi,Ohwada, Tomohiko. "Retro-Diels-Alder reaction of 4H-1,2-benzoxazines to generate o-quinone methides: Involvement of highly polarized transition states". . p. 10088 - 10095. Retrieved 2008/04/12.
• 3、 -. "Process for producing cyanoformate esters". . . Retrieved 2008/06/13.