1,2,4,5-Hexatetraene

Base Information

• Chemical Name: 1,2,4,5-Hexatetraene
• CAS No.: 29776-96-3
• Molecular Formula: C6H6
• Molecular Weight: 78.1136
• Nikkaji Number: J886.813A
• Mol file: 29776-96-3.mol

Synonyms:1,2,4,5-Hexatetraene;29776-96-3

Chemical Property of 1,2,4,5-Hexatetraene

Chemical Property:

• Vapor Pressure: 43.5mmHg at 25°C
• Boiling Point: 99.8°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.678g/cm³
• LogP: 1.66860
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 78.0469501914
• Heavy Atom Count: 6
• Complexity: 92

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C=CC=C=C

Technology Process of 1,2,4,5-Hexatetraene

There total 3 articles about 1,2,4,5-Hexatetraene 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:

propargyl bromide (106-96-7) → 1,3-hexadien-5-yne (10420-90-3) + 1,2-hexadiene-5-yne (33142-15-3) + 1,2,4,5-hexatetraene (29776-96-3) + hexa-1,5-diyne (628-16-0) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With sodium; In gas; at 623 ℃; under 300 Torr; Rate constant; Product distribution; Mechanism; ΔH(reaction), var. conc. of reaction partners;

Reference yield:

2-propynyl chloride (624-65-7) → 1,3-hexadien-5-yne (10420-90-3) + 1,2-hexadiene-5-yne (33142-15-3) + 1,2,4,5-hexatetraene (29776-96-3) + hexa-1,5-diyne (628-16-0) + prop-1-yne (74-99-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With sodium; In gas; at 623 ℃; under 300 Torr; Rate constant; Product distribution; Kinetics; ΔH(reaction), mechanism, further temp., var. conc. of reaction partners;

Reference yield:

propargyl bromide (106-96-7) → 1,3-hexadien-5-yne (10420-90-3) + 1,2-hexadiene-5-yne (33142-15-3) + 1,2,4,5-hexatetraene (29776-96-3) + hexa-1,5-diyne (628-16-0)

Guidance literature:

With magnesium; copper(l) chloride; Multistep reaction;

upstream raw materials:

2-propynyl chloride

propargyl bromide

Downstream raw materials:

(1S,2S)-3,6-Dimethylene-cyclohex-4-ene-1,2-dicarbonyl dichloride

4,5,12,13-tetrabenzoyl<2.2>paracyclophane

tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene-5,6,11,12-tetracarboxylic acid tetramethyl ester

4,5,12,13-Tetrakis(ethoxycarbonyl)-<2.2>paracyclophan

Refernces

UEBER EINE SAEUREKATALYSIERTE METHYLWANDERUNG IN <2.2>PARACYCLOPHANEN

10.1016/S0040-4039(00)87611-X

The research focuses on the discovery of a novel intramolecular methyl rearrangement in [2.2]paracyclophanes, where methyl substituents move from one benzene ring to another within the molecule. The purpose of the study was to explore the substitution patterns of these compounds when treated with methylenchloride and TiC14/HCl under specific conditions. The researchers observed that the treatment of the anti-configured substrate 1 in methylenchloride at 0°C for 8 hours with TiC14/HCl resulted in the formation of 4,7,12,15-tetramethyl[2.2]paracyclophan with a crossed arrangement of methyl groups, which was previously unknown in cyclophane chemistry. The proposed reaction mechanism involves an external attack of a proton on one of the aromatic systems, leading to the formation of α- and u-complexes, and subsequent deprotonation resulting in the rearranged isomer. The study concluded that the presence of vicinal methyl groups is a prerequisite for this type of methyl migration, and initial experiments confirmed this hypothesis with other [2.2]paracyclophanes. The chemicals used in the process include 1,2,4,5-hexatetraen, methylenchloride, TiC14/HCl, and other Lewis acids.