1,3,5-Hexatriene

Base Information

• Chemical Name: 1,3,5-Hexatriene
• CAS No.: 2235-12-3
• Deprecated CAS: 183592-62-3
• Molecular Formula: C6H8
• Molecular Weight: 80.1295
• Hs Code.: 2901299090
• European Community (EC) Number: 218-789-7
• NSC Number: 91558
• UNII: 8C4D773AF7
• DSSTox Substance ID: DTXSID801026520
• Nikkaji Number: J1.804J,J125.201A,J2.189.510E
• Wikidata: Q27270170
• Mol file: 2235-12-3.mol

Synonyms:1,3,5-hexatriene

Chemical Property of 1,3,5-Hexatriene

Chemical Property:

• Vapor Pressure: 103mmHg at 25°C
• Melting Point: -11.7°C
• Refractive Index: n20/D 1.511(lit.)
• Boiling Point: 78.2°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.719g/cm³
• LogP: 1.91460
• Storage Temp.: −20°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 80.062600255
• Heavy Atom Count: 6
• Complexity: 58.1

Purity/Quality:

99%, ^*data from raw suppliers

(3E)-1,3,5-HEXATRIENE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 10-22-36-65
• Safety Statements: 26-36-62

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC=CC=C
• Isomeric SMILES: C=C/C=C/C=C
• Description: 1,3,5-hexatriene is the simplest conjugated triene, and its structure predicts two geometrical isomers, the cis form being the open chain analog of benzene. With a single sigma bond separating the pi bonds of 1,3,5-hexatriene it is a conjugated system and some of the pi electron density will be delocalized between each of the C-C bonds, not just those written as double bonds in the Lewis structure. There are six adjacent carbon atoms involved in the pi system and the combination of a p orbital from each of these six atoms will result in six pi molecular orbitals: ψ1, ψ2, ψ3, ψ4*, ψ5*, and ψ6* (also referred to as π1, π2, π3, π4*, π5*and π6*).

Technology Process of 1,3,5-Hexatriene

There total 48 articles about 1,3,5-Hexatriene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

cyclohexa-1,3-diene (1165952-91-9) → 1,3,5-hexatriene (2235-12-3) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With osmocene; In hexane; at 20 ℃; UV-irradiation; Inert atmosphere;

DOI:10.1016/j.inoche.2009.10.016

Reference yield: 42.0%

bicyclo[2.2.0]hex-2-ene → 1,3,5-hexatriene (2235-12-3) + [5]-ladderane + cyclohexa-1,3-diene (1165952-91-9)

Guidance literature:

With copper(I) trifluoromethanesulfonate benzene; In benzene; at -4 ℃; for 60h; Solvent; Inert atmosphere; UV-irradiation;

DOI:10.1021/jacs.6b10706

Reference yield: 17.0%

4-propenyl-1,3-dioxane (40749-83-5) → 6-methyl-3,6-dihydro-2H-pyran (55230-25-6) + 1,3,5-hexatriene (2235-12-3) + 2,4-hexadien-1-ol acetate (1516-17-2) + 3,5-hexadien-1-ol acetate (75338-23-7)

Guidance literature:

With sulfuric acid; In ethyl acetate; at 90 ℃; for 9h; Further byproducts given; metal ampul;

upstream raw materials:

phthalic anhydride

1,5-hexadiene-3-ol

hydroquinone

1,3-hexadien-5-yne

Downstream raw materials:

3-Vinyl-4-cyclohexen-1,1,2,2-tetracarbonitril

1,6-bis(p-hydroxyphenyl)-1,3,5-hexatriene

(E,E,E)-1,6-bis-(p-acetoxyphenyl)-1,3,5-hexatriene

1,10-diphenyl-1,3,5,7-decapentaene

Refernces

• 1、 Srinivasan. "". . p. 2806,2807. Retrieved 1961.
• 2、 Turczel, Gábor,Kovács, Ervin,Csizmadia, Eszter,Nagy, Tibor,Tóth, Imre,Tuba, Robert. "One-pot Synthesis of 1,3-Butadiene and 1,6-Hexanediol Derivatives from Cyclopentadiene (CPD) via Tandem Olefin Metathesis Reactions". . p. 4884 - 4891. Retrieved 2018/09/25.
• 3、 Li, Jing,Lutz, Martin,Otte, Matthias,Klein Gebbink, Robertus J. M.. "A Cptt-Based Trioxo-Rhenium Catalyst for the Deoxydehydration of Diols and Polyols". . p. 4755 - 4760. Retrieved 2018/10/02.