4452-08-8

Basic information

• Product Name: NCCH=C=O
• Synonyms: NCCH=C=O;cyanoketene
• CAS NO: 4452-08-8
• Molecular Formula: C₃HNO
• Molecular Weight: 0
• Mol File: 4452-08-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 91.1°Cat760mmHg
• Flash Point: 8.9°C
• Appearance: /
• Density: 0.994g/cm³
• Vapor Pressure: 54.7mmHg at 25°C
• Refractive Index: 1.391
• CAS DataBase Reference: NCCH=C=O(CAS DataBase Reference)
• NIST Chemistry Reference: NCCH=C=O(4452-08-8)
• EPA Substance Registry System: NCCH=C=O(4452-08-8)

Safety Data

• Hazardous Substances Data: 4452-08-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C3HNO/c4-2-1-3-5/h1H

Upstream product

• 621-03-4 cyanoacetanilide 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 
• 131297-21-7 5-(Bis-tert-butylamino-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 4980-30-7 N'-[(4-chlorophenyl)methylidene]-2-cyanoacetohydrazide 
• 4974-45-2 cyano-acetic acid-(4-nitro-benzylidenehydrazide) 
• 85046-00-0 Cyanessigsaeure-(4-methoxybenzyliden)-hydrazid 
• 4974-44-1 N'-benzylidene-2-cyanoacetohydrazide 
• 22208-39-5 2-cyano-N-(4-nitrophenyl)acetamide 
• 6876-54-6 2-cyano-N-(4-methylphenyl)acetamide 
• 17722-17-7 N-(4-chlorophenyl)-2-cyanoacetamide 
• 105-56-6 ethyl 2-cyanoacetate 
• 22065-72-1 Cyanessigsaeure-o-nitrophenylester 

Relevant articles and documents

The Simplest, Isolable, Alkynyl Isocyanate HC≡CNCO: Synthesis and Characterization

Alkynyl isocyanates have been postulated as highly reactive intermediates in synthetic chemistry. Herein, the parent molecule HC≡CNCO is isolated for the first time. In sharp contrast to the previously reported short lifetime (ca. 15 s) at room temperature, we found that HC≡CNCO has a lifetime of 55 h in the gas phase (2 mbar, 300 K) with a melting point of ?79.5 °C and vaporization enthalpy (ΔHvap) of 23.1(1) kJ mol?1. Apart from the IR (gas, solid, and matrix), 1H and 13C NMR, and UV/Vis spectroscopic characterization, its photoisomerization with a acylnitrene HC≡CC(O)N and cyanoketene NCC(H)CO has been observed.

Pyrolysis of aminonitriles, cyanohydrazones, and cyanoacetamides. Part II. Elimination reactions of arylacetylhydrazone, arylcyanoacetylhydrazone, and substituted cyanoacetamides

Rates of pyrolytic reactions of arylacetyldydrazone and arylcyanoacetylhydrazone (1-4) of the general formula GCH2CONHN=CHAr (G = H,CN) have been measured. The increase in the acidity of the hydrogen atom involved in the six-centered elimination process suggested for these reactions causes a significant increase in rates and thus appears to be the limiting factor in these pyrolytic reactions. The implication of this conclusion for the pyrolytic reactions of substituted cyanoacetamides (5-8), NCCH2CONHAr are considered. The mechanism of pyrolytic reactions of compounds (5-8) appears to proceed through a 4-membered cyclic transition state.

Phosphoric anhydride in the synthesis of monosubstituted ketenes and related dimers

Monosubstituted ketenes and related condensation products, including phosphorylated, were obtained by the action of phosphoric anhydride on ethyl esters of monosubstituted acetic and malonic acids.