Methyl cyanoformate: Difference between revisions

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 {{chembox
+| Watchedfields = changed
-| verifiedrevid = 434624587
+| verifiedrevid = 472646918
-| ImageFile = MeCNformate.png
+| ImageFile = Methyl cyanoformate Structural Formulae V.1.svg
 | ImageSize =
-| IUPACName = Methyl cyanoformate
+| PIN = Methyl carbonocyanidate
 | OtherNames =
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
+| CASNo_Ref = {{cascite|correct|??}}
-|   CASNo =  17640-15-2
-|  PubChem = 28660
+| CASNo = 17640-15-2
+| UNII_Ref = {{fdacite|correct|FDA}}
-|  ChemSpiderID = 26657
-|  SMILES = N#CC(=O)OC
+| UNII = 7S9M7F9JLT
+| PubChem = 28660
-|  InChI = 1/C3H3NO2/c1-6-3(5)2-4/h1H3
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-|  InChIKey = OBWFJXLKRAFEDI-UHFFFAOYAH
+| ChemSpiderID = 26657
-|  StdInChI = 1S/C3H3NO2/c1-6-3(5)2-4/h1H3
+| SMILES = N#CC(=O)OC
-|  StdInChIKey = OBWFJXLKRAFEDI-UHFFFAOYSA-N
+| InChI = 1/C3H3NO2/c1-6-3(5)2-4/h1H3
+| InChIKey = OBWFJXLKRAFEDI-UHFFFAOYAH
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C3H3NO2/c1-6-3(5)2-4/h1H3
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = OBWFJXLKRAFEDI-UHFFFAOYSA-N
   }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
 | C=3 | H=3 | N=1 | O=2
-|   MolarMass = 85.06
+| MolarMass = 85.06
-|   Appearance = colorless liquid
+| Appearance = colorless liquid
-|   Density = 1.072 g/cm<sup>3</sup>
+| Density = 1.072 g/cm<sup>3</sup>
-|   MeltingPt =
+| MeltingPt =
-|   BoilingPt = 100-101 °C
+| BoilingPtC = 100 to 101
-|   Solubility =
+| BoilingPt_notes =
+| Solubility =
-  }}
-| Section3 = {{Chembox Hazards
-|   MainHazards = toxic
-|   FlashPt =
-|   Autoignition =
   }}
+|Section3={{Chembox Hazards
+| MainHazards = toxic
+| FlashPt =
+| AutoignitionPt =
+ }}
 }}
-'''Methyl cyanoformate''' is the [[organic compound]] with the [[Chemical formula|formula]] CH<sub>3</sub>OC(O)CN.  This colorless liquid is used as a [[reagent]] in [[organic synthesis]] as a source of the methoxycarbonyl group.<ref>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}}</ref>
+'''Methyl cyanoformate''' is the [[organic compound]] with the [[Chemical formula|formula]] CH<sub>3</sub>OC(O)CN.  It is used as a [[reagent]] in [[organic synthesis]] as a source of the methoxycarbonyl group,<ref name=Crabtree>{{cite journal | doi = 10.1055/s-1990-21025 | title = C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity | date = 1990 | last1 = Crabtree | first1 = Simon R. | last2 = Chu | first2 = W. L. Alex | last3 = Mander | first3 = Lewis N. | journal = Synlett | issue = 3 | pages = 169–170 }}</ref> in which context it is also known as [[Lew Mander|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.<ref name=Crabtree/>  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]].
-It was also the active ingredient in the pesticide product Zyklon A.
+Methyl cyanoformate is also an ingredient in [[Zyklon A]]. It has [[Lachrymatory agent|lachrymatory]] effects.<ref>{{cite book |last1=Sartori |first1=Mario |title=The War Gases |date=1939 |page=100|publisher=D. Von Nostrand|location=New York}}</ref>
-It is also known as [[Lew Mander|Mander's]] reagent.
-==See also==
-* [[Zyklon B]]
 ==References==
 <references/>
+{{Chemical agents}}
 [[Category:Methyl esters]]
@@ Line 45: / Line 51: @@
 [[Category:Reagents for organic chemistry]]
 [[Category:Nitriles]]
+[[Category:Fumigants]]
+[[Category:Blood agents]]
+[[Category:Lachrymatory agents]]
 {{ester-stub}}
-[[de:Cyanameisensäuremethylester]]
-[[it:Cianoformiato di metile]]
-[[nl:Methylcyanoformaat]]
-[[zh:氰基甲酸甲酯]]