Methyl cyanoformate
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Names | |
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Preferred IUPAC name Methyl carbonocyanidate | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.037.826 ![]() |
PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C3H3NO2 |
Molar mass | 85.06 |
Appearance | colorless liquid |
Density | 1.072 g/cm3 |
Boiling point | 100 to 101 °C (212 to 214 °F; 373 to 374 K) |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
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 methoxycarbonyl group,[1] in which context it is also known as Mander's reagent. When a lithium enolate is generated in diethyl ether or methyl t-butyl ether, treatment with Mander's reagent will selectively afford the C-acylation product.[2] Thus, for enolate acylation reactions in which C- vs. O-selectivity is a concern, methyl cyanoformate is often used in place of more common acylation reagent like methyl chloroformate.
Methyl cyanoformate is also an ingredient in Zyklon A. It has lachrymatory effects.[3]
References
- ^ Simon R. Crabtree, W. L. Alex Chu, Lewis N. Mander "C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity"Synlett 1990; 1990: 169–170. doi:10.1055/s-1990-21025
- ^ Crabtree, Simon R.; Chu, W. L. Alex; Mander, Lewis N. (1990). "C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity". Synlett. 1990 (3): 169–170. doi:10.1055/s-1990-21025. ISSN 0936-5214.
- ^ Sartori, Mario (1939). The War Gases. New York: D. Von Nostrand. p. 100.
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- Agents used in chemical warfare
- incapacitation
- riot control
- Cyanogen
- Cyanogen bromide
- Cyanogen chloride (CK)
- Hydrogen cyanide (AC)
- Arsine
- Cacodyl cyanide
- Cacodyl oxide
- Hydrogen sulfide
- Phosphine
- Carbon monoxide
- Phosphorus trifluoride
- Methyl cyanoformate
- Iron pentacarbonyl
- Nickel tetracarbonyl
- 2,3,7,8-Tetrachlorodibenzodioxin
- Glycolonitrile
- Lactonitrile
- Acetone cyanohydrin
- Stibine
- Chloral cyanohydrin
Arsenicals | |
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Sulfur mustards |
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Nitrogen mustards | |
Nettle agents |
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Other |
- Anatoxin-a
- Saxitoxin (TZ)
- Bungarotoxin
- Botulinum toxin (BTX)
- Tetanospasmin (TeNT)
- Ryanodine
- Ciguatoxin (CTX)
- Guanitoxin (GTX)
- Chlorophenylsilatrane
- Palytoxin (PTX)
- Maitotoxin (MTX)
- Tetrodotoxin
- Aconitine
- Brevetoxin (PbTX)
- Strychnine
- Antillatoxin (ATX)
- Tetraethyllead
- Dimethylmercury
- HN1 hydrochloride
- HN2 hydrochloride
- HN3 hydrochloride
- A-8564
- Picrotoxin
- Sulfuryl fluoride
- Tremorine
- Oxotremorine
- Batrachotoxin
- Tetramethylenedisulfotetramine (TETS)
- Bicyclic phosphates
- Cloflubicyne
- Trimethylolpropane phosphite
- Domoic acid
choking agents
- Chlorine
- Bromine
- Phosgene (CG)
- Fluorine
- Perfluoroisobutene
- Chloropicrin (PS)
- Dimethyl(trifluoromethylthio)arsine
- Diphosgene (DP)
- Disulfur decafluoride (Z)
- Acrolein
- Ethyl bromoacetate
- Perchloromethyl mercaptan
- Phenylcarbylamine chloride
- Tetranitromethane
- Tetrachlorodinitroethane
- Chlorine trifluoride
- Perchloryl fluoride
- Cadmium oxide
- Cadmium chloride
- Mercuric chloride
- Selenium dioxide
- Selenoyl fluoride
- Trifluoronitrosomethane
- Trichloronitrosomethane
- Nitric oxide
- Nitrogen dioxide
- Dinitrogen tetroxide
- Sulfur dioxide
- Phosphorus trichloride
- Methyl isocyanate
- Ethenone
- Methyl vinyl ketone
- Trifluoroacetyl chloride
- Salcomine
- Fluomine
- Uranium hexafluoride
- Diborane
- Green Cross
agents
- BZ (CS-4030)
- Apomorphine
- Butyrophenone
- EA-4941 (CS-4640)
- Etorphine
- EA-2092
- CS-4297
- Etoxadrol
- Dimethylheptylpyran (DMHP)
- EA-2148
- EA-3167
- EA-3443
- Pethidine
- EA-3580
- Ibogaine
- EA-3834
- Kolokol-1
- LSD-25
- PAVA spray
- Psilocybin
- Sleeping gas
- Carfentanil
- JB-318
- JB-336
- CS-27349
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,668
- Benperidol
- Desflurane
- Enflurane
- Bufotenin
- Isoflurane
- Halothane
- Sevoflurane
- Pentazocine
- Procarbazine
- Fluphenazine
- Chlorpromazine
agents
- Xylyl bromide
- Pepper spray (OC)
- Mace (spray)
- CN
- CS
- CR
- CNS
- Benzyl chloride
- Benzyl bromide
- Benzyl iodide
- Bromobenzyl cyanide
- Thiophosgene
- Chloroacetone
- Bromoacetone
- Bromomethyl ethyl ketone
- Acrolein
- Phenacyl bromide
- Chloroacetophenone oxime
- Ethyl bromoacetate
- Ethyl iodoacetate
- Iodoacetone
- Allyl isothiocyanate
- Hexamethylene diisocyanate
- Crotonaldehyde
- Abrin
- Aconitine
- Cyclopiazonic acid
- Histrionicotoxins
- Aflatoxins
- Anatoxin-a
- Batrachotoxin
- Botulinum toxin
- Brevetoxin
- Ciguatoxin
- Domoic acid
- Enterotoxin type B
- Grayanotoxin
- Guanitoxin
- Maitotoxin
- Modeccin
- Palytoxin
- Ricin
- Saxitoxin
- Shiga toxin
- T-2 mycotoxin
- Tetanospasmin
- Tetrodotoxin
- Volkensin
- Veratridine
- Methyl fluoroacetate
- Napalm (variants and mixtures)
- Fluoroethyl fluoroacetate
- Depleted uranium
- post-combustion uranium oxides
- Plutonium and its compounds
- Polonium
- White phosphorus
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