rel-(1R*)-1β*,2α*-Dibromo-1,2-dihydrobenzocyclobutene

Base Information

• Chemical Name: rel-(1R*)-1β*,2α*-Dibromo-1,2-dihydrobenzocyclobutene
• CAS No.: 14420-75-8
• Molecular Formula: C₈H₆Br₂
• Molecular Weight: 261.944
• Mol file: 14420-75-8.mol

Synonyms:trans-1,2-Dibrombenzocyclobuten;1,2-dibromo-1,2-dihydrobenzocyclobutene;1,2-dibromocyclobutabenzene;trans-7,8-dibromocyclobutabenzene;trans-1,2-dibromo-1,2-dihydrobenzocyclobutene;trans-1,2-dibromobenzocyclobutene;

Chemical Property of rel-(1R*)-1β*,2α*-Dibromo-1,2-dihydrobenzocyclobutene

Chemical Property:

• Melting Point: 52-54 °C
• Boiling Point: 266.4±40.0 °C(Predicted)
• PSA: 0.00000
• Density: 2.022±0.06 g/cm3(Predicted)
• LogP: 3.57220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of rel-(1R*)-1β*,2α*-Dibromo-1,2-dihydrobenzocyclobutene

There total 7 articles about rel-(1R*)-1β*,2α*-Dibromo-1,2-dihydrobenzocyclobutene 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: 65.0%

1,2-bis(dibromomethyl)benzene (13209-15-9) → cis-dibromocyclobutabenzene (18610-18-9) + trans-1,2-dibromobenzocyclobutene (14420-75-8,18610-18-9,22250-72-2)

Guidance literature:

With nickel; In N,N-dimethyl-formamide; at 85 - 90 ℃; for 24h; Yields of byproduct given; other reagents: (Bu₃P)2Ni(COD), NaI, KI, Zn, Mg, Na-ascorbate;

DOI:10.1021/jo9516852

Reference yield:

1,2-bis(dibromomethyl)benzene (13209-15-9) → trans-1,2-dibromobenzocyclobutene (14420-75-8,18610-18-9,22250-72-2)

Guidance literature:

With ethanol; sodium iodide;

DOI:10.1021/ja01564a048

Reference yield:

α,α'-dibromo-o-xylene (91-13-4) → trans-1,2-dibromobenzocyclobutene (14420-75-8,18610-18-9,22250-72-2)

Guidance literature:

With sodium iodide;

upstream raw materials:

1,2-bis(dibromomethyl)benzene

1,3,5,7-cyclooctatetraene

α,α'-dibromo-o-xylene

Downstream raw materials:

3-p-tolyl-3a,7b-dihydro-benzo[3,4]cyclobuta[1,2-d]isoxazole

endo-2,3-bis(p-methoxyphenyl)-1,4-diphenyl-1,4,4a,8b-tetrahydro-1,4-methano-biphenylen-9-one

7b-tert-butoxy-3-(4-methoxy-phenyl)-(3ar,7bc)-3a,7b-dihydro-benzo[3,4]cyclobuta[1,2-d]isoxazole

Refernces

• 1、 Wieland,D.M.,McCarty,C.G.. "-". . p. 4285 - 4288. Retrieved 1972.
• 2、 Stanger, Amnon,Ashkenazi, Nissan,Shachter, Alona,Bl?ser, Dieter,Stellberg, Peter,Boese, Roland. "Nickel-mediated cyclobutabenzene syntheses. trans-7,8-dibromo-cyclobutabenzenes: 1 Their one-pot preparation, x-ray structure, and Diels-Alder reactions". . p. 2549 - 2552. Retrieved 2007/10/03.