66723-45-3

Basic information

• Product Name: isocyanoacetylene
• Synonyms: isocyanoacetylene
• CAS NO: 66723-45-3
• Molecular Formula: C3HN
• Molecular Weight: 0
• Mol File: 66723-45-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: isocyanoacetylene(CAS DataBase Reference)
• NIST Chemistry Reference: isocyanoacetylene(66723-45-3)
• EPA Substance Registry System: isocyanoacetylene(66723-45-3)

Safety Data

• Hazardous Substances Data: 66723-45-3(Hazardous Substances Data)

Upstream product

• 354-23-4 1,2-dichloro-1,2,2-trifluoroethane 
• 1070-71-9 propiolonitrile 

Relevant articles and documents

Syntheses and 1H-, 13C- and 15N-NMR spectra of ethynyl isocyanide, H-C≡C-N≡C, D-C≡C-N≡C and prop-1-ynyl isocyanide, H3C-C≡C-N≡C, D3C-C≡C-N≡C: High resolution infrared spectrum of prop-1-ynyl isocyanide

Ethynyl isocyanide, H-C≡C-N≡C (1a), deuteroethynyl isocyanide, D-C≡C-N≡C (1b), prop-1-ynyl isocyanide, H3C-C≡C-N≡C (1c), and trideuteroprop-1-ynyl isocyanide, D3C-C≡C-N≡C (1d) are synthesized by flash vacuum pyrolysis of suitable organometallic precursor molecules (CO)5Cr(CN-CCl=CClH) (5a), (CO)5Cr(CN-CCl=CClD) (5b), (CO)5Cr(CN-CCl?CCl-CH3) (5c) and (CO)5Cr(CN-CCl=CCl-CD3) (5d), respectively. Compounds 5a-d are formed in two steps by radical alkylation of tetraethylammonium pentacarbonyl(cyano)chro mate, NEt4[Cr(CO)5(CN)] (2) by 1,1,2,2,-tetrachloroethane (3a), 1,1,2,2-tetrachloro-1,2-dideuteroethane (3b), 1,1,2,2,-tetrachloropropane (3c), and 1,1,2,2-tetrachloro-1,3,3,3-tetradeuteropropane (3d) yielding [(CO)5Cr(CN-CCl2-CCl2-H)] (4a), [(CO)5Cr(CN-CCl2-CCl2D)] (4b), [(CO)5Cr(CN-CCl2-CCl2-CH3)] (4c), and [(CO)5Cr(CN-CCl2-CCl2-CD3)] (4d). Dehalo genation of 4a-d using zinc in diethylether/acetic acid gives 5a-d, respectively. A multinuclear NMR study revealed the 1H-, 13C- and 15N-NMR data of 1a and 1c. Molecular spectroscopic data of 1c were determined by high resolution infrared spectroscopy. The by-products of the pyrolysis are the E and Z isomers of the halogenated ethenyl isocyanides H(Cl)C=CCl-NC (6a) and H3C(Cl)C=CCl-NC (6c) which have been characterized by IR, MS and NMR spectroscopy.

Syntheses of halogenated ethenyl isocyanide chromium complexes as organometallic precursor molecules for ethenyl and ethynyl isocyanides

The radical alkylation of tetraethylammonium pentacarbonyl(cyano) chromate 1 yielded the halogenated ethyl isocyanide complexes [(CO)5Cr-(CN-CCIX-CCIYF)] 3 (a. X=Cl, Y= F; b. X=F. Y=F and c. X=Y=Cl). Dehalogenation of 3 using zinc in diethyl ether gave [(CO)5Cr(CN-CX=CFY)] 4. The compounds 4a, b reacted with various nucleophiles exclusively at the difluoromethylene group. The unstable phosphorane 5, which is formed on reaction of 4b with trimethylphosphane, decomposed thermally and on hydrolysis yielding pentacarbonyl(1,2-difluoroethenyl isocyanide)chromium (6). The cyano substituent can be introduced in the β position of the isocyanide function by reaction of 4a. b with potassium cyanide, leading to the formation of [(CO)5Cr(CN-CX=CF-CN)] (7). Reactions of 4a, b with organolithium or organomagnesium compounds yielded [(CO)5Cr(CN-CX=CF-R)] (8) and [(CO)5Cr(CN-CF=CF-C≡C-CF=CF-NC)Cr(CO)5] (10). The trimethylsilyl group in 8a, b, d could be removed by a solution of potassium carbonate in methanol leading to [(CO)5Cr(CN-CX=CF-Cn-H)] (11) (n=2, 4). Octacarbonyldicobalt reacted with 8e under coordination of the C-C triple bond to the hexacarbonyldicobalt fragment, resulting in the cluster compound 12. The crystal and molecular structure of 8i, 11a, b, and 12 were elucidated by X-ray crystallography. The alkenyl and alkynyl isocyanides CN-CCl=CF2 (13a). CN-CF=CF2 (13b). CN-CCl=CCIF (13c), CN-CF=CFH (14), CN-CC-H (15), CN-CC-CN (16), and CN-CCl=CF-CN (17) were obtained by flash vacuum pyrolysis of 4a, 4b, 4c, 6, and 7a, respectively.

Synthese und Struktur von Ethinylisocyanid

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