3,5-Dibromostyrene

Base Information

• Chemical Name: 3,5-Dibromostyrene
• CAS No.: 120359-56-0
• Molecular Formula: C8H6Br2
• Molecular Weight: 261.944
• UNII: 224BN365J3
• DSSTox Substance ID: DTXSID90595612
• Nikkaji Number: J455.490F
• Wikidata: Q82490671
• Mol file: 120359-56-0.mol

Synonyms:3,5-dibromostyrene;120359-56-0;1,3-Dibromo-5-ethenylbenzene;Benzene, 1,3-dibromo-5-ethenyl-;1,3-Dibromo-5-vinylbenzene;224BN365J3;J455.490F;1,3-Dibromo-5-vinyl-benzene;SCHEMBL353448;UNII-224BN365J3;DTXSID90595612;OITDEAXLQUVPQW-UHFFFAOYSA-N;AKOS030255523;DB-314890;F87637

Chemical Property of 3,5-Dibromostyrene

Chemical Property:

• Boiling Point: 271.1±33.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.772±0.06 g/cm3(Predicted)
• LogP: 3.85460
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Dichloromethane
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 261.88158
• Heavy Atom Count: 10
• Complexity: 112

Purity/Quality:

98% ^*data from raw suppliers

3,5-Dibromostyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=CC(=CC(=C1)Br)Br
• Uses: 3,5-DibroMostyrene is a styrene derivative used in the preparation of bisphosphane ligand and phenanthroline-based functionalized macrocycles and catenanes.

Technology Process of 3,5-Dibromostyrene

There total 4 articles about 3,5-Dibromostyrene 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: 70.0%

3,5-dibromobenzaldehyde (56990-02-4) → 3,5-dibromostyrene (120359-56-0)

Guidance literature:

With potassium tert-butylate; Methyltriphenylphosphonium bromide; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.10.027

Reference yield: 45.0%

3,5-dibromobenzaldehyde (56990-02-4) + Methyltriphenylphosphonium bromide (1779-49-3) → 3,5-dibromostyrene (120359-56-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

3,5-dibromobenzaldehyde; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

Reference yield:

1,3,5-trisbromobenzene (626-39-1) → 3,5-dibromostyrene (120359-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BuLi / 1.) Et₂O, -78 deg C, 45 min, 2.) Et₂O, -78 deg C, 1 h

2: 1.) BuLi / 1.) THF, 0 deg C, 15 min and 3 h, 25 deg C, 2.) THF, reflux, 12 h

With n-butyllithium;

DOI:10.1071/C96180

upstream raw materials:

3,5-dibromobenzaldehyde

methyl-triphenylphosphonium iodide

1,3,5-trisbromobenzene

Methyltriphenylphosphonium bromide

Downstream raw materials:

3,5-diazidostyrene

(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol

(4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide

(2R,3R)-1-(ethoxycarbonyl)-2,3-bis(3',5'-dibromophenyl)cyclopropane-1-carboxylic acid