1,2-Dibromocyclopentene

Base Information

• Chemical Name: 1,2-Dibromocyclopentene
• CAS No.: 75415-78-0
• Molecular Formula: C5H6Br2
• Molecular Weight: 225.911
• Hs Code.: 29035980
• DSSTox Substance ID: DTXSID50403305
• Nikkaji Number: J880.000F
• Wikidata: Q72464080
• Mol file: 75415-78-0.mol

Synonyms:1,2-Dibromocyclopentene;75415-78-0;1,2-dibromocyclopent-1-ene;dibromocyclopentene;SCHEMBL2221444;1,2-Dibromocyclopentene, 97%;DTXSID50403305;PNWFXPGGROADNS-UHFFFAOYSA-N;1,1-Cyclohexane diacetic acid(CDA);MFCD00010246;AKOS015834957;CS-W013034;AC-18439;CS-17357;FT-0641563;EN300-102885;A838406

Chemical Property of 1,2-Dibromocyclopentene

Chemical Property:

• Appearance/Colour: Clear pale yellow liquid
• Vapor Pressure: 0.172mmHg at 25°C
• Refractive Index: n20/D 1.5558(lit.)
• Boiling Point: 219.9 °C at 760 mmHg
• Flash Point: 78.9 °C
• PSA: 0.00000
• Density: 2.116 g/cm³
• LogP: 3.17170
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 225.88158
• Heavy Atom Count: 7
• Complexity: 92.6

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dibromocyclopentene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=C(C1)Br)Br
• Uses: 1,2-Dibromocyclopentene has been used in the synthesis of cyclopentene analogs.

Technology Process of 1,2-Dibromocyclopentene

There total 6 articles about 1,2-Dibromocyclopentene 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: 67.0%

1,2-dibromo-1-chlorocyclopentane (89180-82-5) → 1,2-dibromocyclopentene (75415-78-0)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 25 ℃;

DOI:10.1021/jo00223a047

Reference yield: 30.0%

cyclopentanone (120-92-3) → 1,2-dibromocyclopentene (75415-78-0)

Guidance literature:

cyclopentanone; With phosphorus pentachloride; In toluene; for 0.5h; Inert atmosphere; Schlenk technique;

With bromine; In toluene; at -20 - 20 ℃; Inert atmosphere; Schlenk technique;

With potassium tert-butylate; In tetrahydrofuran; hexane; at -25 - 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1039/c9tc04495g

Reference yield:

1-chlorocyclopent-1-ene (930-29-0) → 1,2-dibromocyclopentene (75415-78-0)

Guidance literature:

With potassium tert-butylate; bromine; Yield given. Multistep reaction; 1.) toluene, -20 deg C, 2.) hexane, THF, from -15 deg C to RT;

DOI:10.1021/jm00022a023

upstream raw materials:

1,2-dibromo-1-chlorocyclopentane

1-chlorocyclopent-1-ene

1-Lithium-2-brom-cyclopenten-⁽¹⁾

cyclopentanone

Downstream raw materials:

{[2-(phenylethylyl)cyclopent-1-en-1-yl]ethenylyl}benzene

[(2-bromocyclopent-1-en-1-yl)ethynyl]benzene

2-phenyl-tetrahydro-cyclopenta[c]pyrrole-1,3-dione

N,N'-diphenyl-cyclopent-1-ene-1,2-dicarboxamide

Refernces

• 1、 McCullough, Richard D.,Cowan, Dwaine O.. "A Convenient Synthesis of Hexamethylenetetraselenafulvalene (HMTSF)". . p. 4646 - 4648. Retrieved 1985.
• 2、 Wang, Shangshang,Zhou, Yunyun,Zhu, Liangliang,Zhang, Junji,Zou, Qi,Zeng, Tao,Chen, Wenbo. "A photochromic prototype based on difurylperhydrocyclopentene with remarkable photoswitching behavior and: In vivo application". supporting information. p. 9570 - 9573. Retrieved 2017/09/01.