1-Bromo-3,4,4-trimethylpenta-1,2-diene

Base Information

• Chemical Name: 1-Bromo-3,4,4-trimethylpenta-1,2-diene
• CAS No.: 10575-72-1
• Molecular Formula: C8H13Br
• Molecular Weight: 189.095
• DSSTox Substance ID: DTXSID40459038
• Nikkaji Number: J573.903I,J652.998D,J2.297.265K
• Mol file: 10575-72-1.mol

Synonyms:1-bromo-3,4,4-trimethyl-1,2-pentadiene;1-bromo-3,4,4-trimethylpenta-1,2-diene;10575-72-1;1,2-Pentadiene, 1-bromo-3,4,4-trimethyl-;DTXSID40459038;(R)-1-Bromo-3,4,4-trimethyl-1,2-pentadiene;(S)-1-Bromo-3,4,4-trimethyl-1,2-pentadiene

Chemical Property of 1-Bromo-3,4,4-trimethylpenta-1,2-diene

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 188.02006
• Heavy Atom Count: 9
• Complexity: 142

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C=CBr)C(C)(C)C

Technology Process of 1-Bromo-3,4,4-trimethylpenta-1,2-diene

There total 5 articles about 1-Bromo-3,4,4-trimethylpenta-1,2-diene 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:

3,4,4-trimethylpent-1-yn-3-ol (38484-41-2,38484-42-3,104758-84-1,993-53-3) → 1-bromo-3,4,4-trimethyl-penta-1,2-diene (10575-72-1)

Guidance literature:

With hydrogen bromide; ammonium bromide; copper(I) bromide; copper;

DOI:10.1021/jo00866a020

Reference yield:

3,4,4-trimethylpent-1-yn-3-ol (38484-41-2,38484-42-3,104758-84-1,993-53-3) → 1-bromo-3,4,4-trimethyl-penta-1,2-diene (10575-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -70 °C

2: LiCu₂Br₃ / tetrahydrofuran / 0.5 h

With n-butyllithium; Li⁽¹⁺⁾*Br₃Cu₂H^(1-); In tetrahydrofuran; hexane;

DOI:10.1021/jo00083a026

Reference yield:

3,4,4-trimethylpent-1-yn-3-ol (38484-41-2,38484-42-3,104758-84-1,993-53-3) → (R)-1-bromo-3,4,4-trimethyl-1,2-pentadiene (10575-72-1) + (S)-1-bromo-3,4,4-trimethyl-1,2-pentadiene

Guidance literature:

With hydrogen bromide; copper(I) bromide; Yield given. Title compound not separated from byproducts;

upstream raw materials:

(S)-3,4,4-trimethyl-1-pentyn-3-ol

3,4,4-trimethylpent-1-yn-3-ol

(R)-3,4,4-trimethyl-pent-1-yn-3-ol

Refernces

• 1、 Landor,S.R. et al.. "-". . p. 1223 - 1226. Retrieved 1966.
• 2、 Uccello-Barretta, Gloria,Balzano, Federica,Caporusso, Anna Maria,Salvadori, Piero. "Direct Determination of the Enantiomeric Purity of Chiral Trisubstituted Allenes by Using Permethylated Cyclodextrin as a Chiral Solvating Agent". . p. 836 - 839. Retrieved 2007/10/02.