16668-67-0

Basic information

• Product Name: (3Z)-hex-3-ene-1,5-diyne
• Synonyms: 3-Hexene-1,5-diyne, (Z)-
• CAS NO: 16668-67-0
• Molecular Formula: C₆H₄
• Molecular Weight: 76.096
• Mol File: 16668-67-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 52°C at 760 mmHg
• Density: 0.857g/cm³
• Vapor Pressure: 283mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: (3Z)-hex-3-ene-1,5-diyne(CAS DataBase Reference)
• NIST Chemistry Reference: (3Z)-hex-3-ene-1,5-diyne(16668-67-0)
• EPA Substance Registry System: (3Z)-hex-3-ene-1,5-diyne(16668-67-0)

Safety Data

• Hazardous Substances Data: 16668-67-0(Hazardous Substances Data)

Upstream product

• 17761-23-8 diazopropyne 
• 536-74-3 phenylacetylene 
• 18350-25-9 Diacetylterephthaloyl diperoxide 
• 3355-34-8 polyparaphenylene 
• 343968-69-4 3-(toluene-4-sulfonyloxy)-hexa-1,5-diyne 
• 54572-77-9 1,1,2,5,6,6-hexabromo-hexa-2,4-diene 

Downstream Products

• 16668-68-1 trans-hexa-1,3-diyn-2-ene 
• 30047-26-8 (1Z,7Z,13Z,19Z)-cyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne 
• 16668-69-2 1,3,7,9,13,15-Hexadehydro<18>annulen 
• 3355-34-8 polyparaphenylene 
• 160283-70-5 cis-1,6-bis(4-methoxyphenyl)-hex-1,5-diyne-3-ene 
• 120017-12-1 α-3(Z)-hexene-1,5-diynylbenzenemethanol 
• 120017-11-0 1,8-diphenyl-4-octene-2,6-diyne-1,8-diol 
• 120017-10-9 α-3(Z)-hexene-1,5-diynyl-α-phenylbenzenemethanol 
• 120017-14-3 1-<3(Z)-hexene-1,5-diynyl>cyclohexanol 
• 120017-13-2 1,1'-<3(Z)-hexene-1,5-diyne-1,6-diyl>biscyclohexanol 

Relevant articles and documents

The ultraviolet photochemistry of phenylacetylene and the enthalpy of formation of 1,3,5-hexatriyne

The ultraviolet photochemistry of phenylacetylene was studied in a molecular beam at 193 nm. The only primary photofragments observed were HCCH (acetylene) and C6H4. Some of the C6H4 molecules were found to decompose to 1,3,5-hexatriyne and molecular hydrogen. An enthalpy of formation of ΔHf ≤ 160 ± 4 kcal mol-1 was determined for 1,3,5=hexatriyne from the energetic threshold for this process. This experimentally determined value agrees well with our ab initio calculations performed at the G2 level of theory. Angular distribution measurements for the HCCH + C6H4 channel yielded an i sotropic distribution and were attributed to a long-lived intermediate and ground-state dissociation. An exhaustive search yielded no evidence for the phenyl + ethynyl or, the atomic hydrogen elimination channels even though these were observed in the pyrolytic studies of phenylacetylene.

Reaction of diazoalkanes with unsaturated compounds: 13. A new method of preparation and [1+2]- and [3+2]-cycloaddition reactions of diazopropyne

A THF solution of diazopropyne was obtained in 60% yield by the reaction of a 30% aqueous solution of methylamine with N,N′-dinitroso-N,N′-dipropargylterephthalodiamide. The reactions of diazopropyne with methyl acrylate and methyl methacrylate giving var

The Energy Well of Diradicals, V. - 1,3,5-Cyclohexatriene-1,4-diyl and 2,4-Cyclohexadiene-1,4-diyl

The energy profile of the Bergman rearrangement of (Z)-3-hexene-1,5-diyne (4) has been established from the NO and oxygen dependance of the trapping rate of the intermediate diradical 1 which leads to a heat of formation for 1,4-didehydrobenzene (1) of ΔH0f = 138.0 +/- 1.0 kcal * mol-1.By the same technique the heat of formation of 1,2,4-cyclohexatriene (2), generated by thermolysis of (Z)-1,3-hexadien-5-yne (10), gives ΔH0f = 105.1 +/- 1.0 kcal * mol-1 which indicates a high diradical character for 2. - Key Words: Diradicals / NO and O2 trapping / Heat of formation / Energy well / Rearrangements / Bergman cyclisation