10420-90-3

Basic information

• Product Name: 1,3-Hexadien-5-yne.
• Synonyms: 1,3-Hexadien-5-yne.
• CAS NO: 10420-90-3
• Molecular Formula: C₆H₆
• Molecular Weight: 78.11
• Mol File: 10420-90-3.mol

Chemical Properties

• Melting Point: -81°C
• Boiling Point: 84.85°C
• Flash Point: °C
• Appearance: /
• Density: 0.7806
• Vapor Pressure: 83.9mmHg at 25°C
• Refractive Index: 1.5095
• CAS DataBase Reference: 1,3-Hexadien-5-yne.(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Hexadien-5-yne.(10420-90-3)
• EPA Substance Registry System: 1,3-Hexadien-5-yne.(10420-90-3)

Safety Data

• RIDADR: 0473
• HazardClass: 1.1A
• Hazardous Substances Data: 10420-90-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-Hexadien-5-yne is utilized as a reactive intermediate in organic synthesis for its ability to participate in various chemical reactions such as hydrogenation, halogenation, and addition reactions. Its unique structure allows for the formation of new compounds with different functional groups, making it a valuable building block in the synthesis of complex organic molecules.
Used in Production of Other Organic Compounds:
1,3-Hexadien-5-yne is also employed in the production of other organic compounds, where its reactivity and unique structure contribute to the synthesis of a wide range of chemical products. Its ability to undergo various chemical transformations makes it a useful precursor in the creation of novel organic molecules with potential applications in various industries.
Used in Natural Products:
1,3-Hexadien-5-yne can be found in some natural products, where its presence may contribute to the biological activity or chemical properties of these substances. Its occurrence in natural products highlights the importance of understanding and harnessing the reactivity of 1,3-Hexadien-5-yne. for potential applications in the development of new pharmaceuticals, fragrances, or other bioactive compounds.

InChI:InChI=1/C6H6/c1-3-5-6-4-2/h1,4-6H,2H2/b6-5+

Upstream product

• 624-65-7 2-propynyl chloride 
• 628-16-0 hexa-1,5-diyne 
• 584-12-3 2-bromofuran 
• 22037-28-1 3-bromofurane 
• 106-96-7 propargyl bromide 

Downstream Products

• 2235-12-3 1,3,5-hexatriene 
• 2957-06-4 butadienyl methyl ketone 
• 66426-78-6 (E)-1,3-decadien-5-yne 
• 56318-73-1 (Z)-3-undeca-1,3-dien-5-yne 
• 56318-81-1 (E)-3-undeca-1,3-dien-5-yne 
• 497-20-1 fulvene 
• 71-43-2 benzene 
• 139407-95-7 7-Phenylbicyclo<4.2.0>octa-1,3-diene 
• 70383-77-6 Toluene-4-sulfonic acid (E)-hepta-4,6-dien-2-ynyl ester 
• 33580-05-1 1,3-trans,5-cis-octatriene 
• 23667-67-6 (+/-)-3c-ethyl-cyclohexane-1r,2c-dicarboxylic acid 

Relevant articles and documents

The thermal decomposition of 5-membered rings: A laser pyrolysis study

The mechanisms of pyrolysis of cyclopentadiene, furan, pyrrole and thiophene have been investigated using a combination of IR laser powered homogeneous pyrolysis, chemical and physical trapping of radical intermediates, and use of precursors specifically designed to generate selected radical intermediates. The results confirm the central role played by free radicals in the cases of cyclopentadiene and thiophene, and the dominant step of 1,2-H shifts in the cases of furan and pyrrole. The experimental results may be interpreted according to the high level ab initio calculations recently reported in the literature.

Thermal Rearrangements, XXIII. - The Thermogram of a C6H6 Chemistry in the Temperature Range from 450 to 730 deg C

The thermal isomerization of 1,5-hexadiyne (1) and its 2>-labeled derivative (1a) was studied in the temperature range 450 - 730 deg C and in the presence of different carrier gases (N2, H2, D2, N2/toluene).By detailed analysis (GC, GCMS, NMR) all volatile reaction products were identified and determined quantitatively by using hexafluorobenzene as an internal standard.The experimental data show clearly that the reaction products are formed by two different routes: (i) electrocyclization leading to dimethylene cyclobutene (3) at temperatures up to about 600 deg C and (ii) radical reaction leading to benzene (4) and pentafulvene (5) at temperatures above 550 deg C.Cyclopentadienylmethyl radicals are supposed to be the essential radical intermediates. - Key Words: Isomerization, thermal / Radicals / D-Labeling / 1,5-Hexadiyne / Pentafulvene / Rearrangement, homoallyl

Formation of C6H6 Isomers by Recombination of Propynyl in the System Sodium Vapour/Propynylhalide

2-Propynyl radicals (C3H3) were generated from the respective chloride or bromide by the reaction Na + C3H3X -> C3H3 + NaX in a low-pressure flow reactor fed by multislit-diffusion burner.The temperature range was 623 to 673 K and total pressures of 300 and 600 Pa were applied.Analyses were performed by nozzle beam/mass spectrometry and by gas chromatography/mass spectrometry.The rate constants of the primary reactions were determined as k(Na + C3H3Cl) = 1.6E13 and k(Na + C3H3Br) = 7.8E13 cm3 mol-1 s-1, independent of temperature within the above range.The overall recombination rate constant of 2-propynyl was found to be 3.4E13 cm3 mol-1 s-1.The recombination products of propynyl were 1,5-hexadiyne, 1,2-hexadien-5-yne and 1,2,4,5-hexatetraene.Besides these direct products also 1,3-hexadien-5-yne and benzene were detected in relatively high yields which decreased with increasing pressure.A reaction mechanism via a propynyl-cyclopropene intermediate by which the chemically activated primary recombination products can rearrange to benzene and 1,3-hexadien-5-yne is discussed. - Keywords: Reaction kinetics / Hydrocarbon radicals / Sodium reactions / Benzene formation