(1R,3S)-1,3-Bis(bromomethyl)cyclohexane

Base Information

• Chemical Name: (1R,3S)-1,3-Bis(bromomethyl)cyclohexane
• CAS No.: 57702-85-9
• Molecular Formula: C8H14Br2
• Molecular Weight: 270.00500
• DSSTox Substance ID: DTXSID20521363
• Wikidata: Q82385789
• Mol file: 57702-85-9.mol

Synonyms:(1R,3S)-1,3-Bis(bromomethyl)cyclohexane;57702-85-9;SCHEMBL26655398;DTXSID20521363

Chemical Property of (1R,3S)-1,3-Bis(bromomethyl)cyclohexane

Chemical Property:

• Boiling Point: 93-96 °C(Press: 0.4 Torr)
• PSA: 0.00000
• Density: 1.6095 g/cm3
• LogP: 3.58260
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 269.94418
• Heavy Atom Count: 10
• Complexity: 83.3

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC(C1)CBr)CBr
• Isomeric SMILES: C1C[C@H](C[C@H](C1)CBr)CBr

Technology Process of (1R,3S)-1,3-Bis(bromomethyl)cyclohexane

There total 5 articles about (1R,3S)-1,3-Bis(bromomethyl)cyclohexane 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%

cis-/trans-1,3-Bis(hydroxymethyl)cyclohexane (3971-28-6) → 1,3-bis-bromomethyl-cyclohexane (57702-85-9)

Guidance literature:

With pyridine; phosphorus tribromide; In benzene; at 4.84 - 20 ℃; Inert atmosphere;

DOI:10.1107/S0108270113015060

Reference yield:

cis-3-Oxabicyclo<3.3.1>nonan → 1,3-bis-bromomethyl-cyclohexane (57702-85-9)

Guidance literature:

With hydrogen bromide; phosphorus tribromide; at 150 ℃;

DOI:10.1007/BF00951712

Reference yield:

cyclohexane-1,3-dicarboxylic acid (3971-31-1) → 1,3-bis-bromomethyl-cyclohexane (57702-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 24 h / Reflux

2: lithium aluminium tetrahydride / diethyl ether / 20 °C / Inert atmosphere; Cooling with ice

3: phosphorus tribromide; pyridine / benzene / 4.84 - 20 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; sulfuric acid; phosphorus tribromide; In diethyl ether; benzene;

DOI:10.1107/S0108270113015060

upstream raw materials:

3-oxabicyclo<3.3.1>nonane

cyclohexane-1,3-dicarboxylic acid

dimethyl cyclohexane-1,3-dicarboxylate

cis-/trans-1,3-Bis(hydroxymethyl)cyclohexane