Bicyclo[4.1.0]hepta-1,3,5-triene

Base Information

• Chemical Name: Bicyclo[4.1.0]hepta-1,3,5-triene
• CAS No.: 4646-69-9
• Molecular Formula: C7H6
• Molecular Weight: 90.1246
• Hs Code.: 2902199090
• DSSTox Substance ID: DTXSID50196846
• Nikkaji Number: J356.296D
• Wikidata: Q83069855
• Mol file: 4646-69-9.mol

Synonyms:Bicyclo[4.1.0]hepta-1,3,5-triene;1,3,5-Norcaratriene;4646-69-9;Benzocyclopropene;Bicyclo(4.1.0)hepta-1,3,5-triene;Cyclopropabenzene;C7H6;DTXSID50196846;AMSMVCOBCOZLEE-UHFFFAOYSA-N;CHEBI:189198;AKOS015917178;bicyclo[4.1.0]hepta-1,3,5-trien;Bicyclo[4.1.0]hepta-1,3,5-triene #;FT-0654664;EN300-1695756;A827049;InChI=1/C7H6/c1-2-4-7-5-6(7)3-1/h1-4H,5H

Chemical Property of Bicyclo[4.1.0]hepta-1,3,5-triene

Chemical Property:

• Vapor Pressure: 4.79mmHg at 25°C
• Boiling Point: 150.9°Cat760mmHg
• Flash Point: 30.1°C
• PSA: 0.00000
• Density: 1.085g/cm³
• LogP: 1.59080
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 90.0469501914
• Heavy Atom Count: 7
• Complexity: 66.1

Purity/Quality:

99% ^*data from raw suppliers

BICYCLO[4.1.0]HEPTA-1,3,5-TRIENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2=CC=CC=C21

Technology Process of Bicyclo[4.1.0]hepta-1,3,5-triene

There total 3 articles about Bicyclo[4.1.0]hepta-1,3,5-triene 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: 50.0%

1-bromo-6-chlorocyclohepta-1,3,5-triene → benzocyclopropene (4646-69-9) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 2h;

DOI:10.1002/hlca.19890720721

Reference yield: 24.0%

pyrographite (7440-44-0) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → benzocyclopropene (4646-69-9) + Diphenylmethane (101-81-5) + heptafulvalene (531-45-3) + 7-phenylcycloheptatriene (1541-11-3) + Cyclohepta-1,3,5-triene (544-25-2) + toluene (108-88-3,15644-74-3,16713-13-6)

Guidance literature:

Product distribution; Mechanism; arc generated carbon; labelled benzene was investigated; C-H insertion reaction is exothermic by over 100 kcal/mol;

DOI:10.1021/ja00526a062

Reference yield:

benzocyclobutenone (3469-06-5) → benzocyclopropene (4646-69-9) + ethenylidenecyclopentadiene (27041-32-3) + 1-ethynylcyclopenta-1,3-diene

Guidance literature:

Heating;

DOI:10.1016/S0040-4039(98)00133-6

upstream raw materials:

benzocyclobutenone

pyrographite

benzene

Downstream raw materials:

1,6-diiodo-1,3,5-cycloheptatriene

2-iodobenzyliodide

1-(1-phenylethylidene)bicyclo<4.1.0>hepta-1,3,5-triene

2-Methyl-3-benzyl-butadien-(1.3)

Refernces

• 1、 Mueller, Paul,Schaller, Jean-Pierre. "Synthesis of Cycloproparenes via Aromatization of 7-Oxanorbornenes with Low-Valent Titanium". . p. 1608 - 1617. Retrieved 2007/10/02.