1-Bromo-6,6-dimethyl-2-hepten-4-yne

Base Information

• Chemical Name: 1-Bromo-6,6-dimethyl-2-hepten-4-yne
• CAS No.: 78629-21-7
• Molecular Formula: C9H13Br
• Molecular Weight: 201.106
• DSSTox Substance ID: DTXSID401276614
• Mol file: 78629-21-7.mol

Synonyms:1-Bromo-6,6-dimethyl-2-hepten-4-yne;126764-15-6;78629-21-7;(E)-1-bromo-6,6-dimethylhept-2-en-4-yne;(E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne;2-Hepten-4-yne, 1-bromo-6,6-dimethyl-;2-Hepten-4-yne,1-bromo-6,6-dimethyl-, (2E)-;starbld0014608;SCHEMBL5167079;OOLYZFSILFGXCC-GQCTYLIASA-N;DTXSID401276614;MFCD00190231;AKOS015912091;1-bromo-6,6-dimethyl-2-hepten-4-ine;?1-Bromo-6,6-dimethyl-2-hepten-4-yne;(E)-6,6-dimethyl-2-hepten-4-ynyl bromide;CS-0237570;(E)-1-bromo-6,6-di-methyl-2-hepten-4-ine;(2E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne;EN300-18547004

Chemical Property of 1-Bromo-6,6-dimethyl-2-hepten-4-yne

Chemical Property:

• Refractive Index: 1.503
• Boiling Point: 222.59 °C at 760 mmHg
• Flash Point: 87.96 °C
• PSA: 0.00000
• Density: 1.202 g/cm³
• LogP: 2.98700
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 200.02006
• Heavy Atom Count: 10
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C#CC=CCBr
• Isomeric SMILES: CC(C)(C)C#C/C=C/CBr

Technology Process of 1-Bromo-6,6-dimethyl-2-hepten-4-yne

There total 5 articles about 1-Bromo-6,6-dimethyl-2-hepten-4-yne 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-hydroxy-6,6-dimethylhept-1-ene-4-yne (78629-20-6) → (E)-6,6-dimethyl-2-hepten-4-ynyl bromide (78629-21-7)

Guidance literature:

With hydrogen bromide; phosphorus tribromide;

Reference yield:

3-hydroxy-6,6-dimethylhept-1-ene-4-yne (78629-20-6) → cis-1-bromo-6,6-dimethyl-2-hepten-4-yne (78629-19-3) + (E)-6,6-dimethyl-2-hepten-4-ynyl bromide (78629-21-7)

Guidance literature:

With hydrogen bromide; phosphorus tribromide; In ethanol; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jm00378a003

Reference yield:

3,3-Dimethylbut-1-yne (917-92-0) → (E)-6,6-dimethyl-2-hepten-4-ynyl bromide (78629-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -15 to -20 deg C, 2.) THF, hexane, RT, overnight

2: aq. HBr, PBr₃ / ethanol

With n-butyllithium; hydrogen bromide; phosphorus tribromide; In ethanol;

DOI:10.1021/jm00378a003

upstream raw materials:

acetic anhydride

safflomin-A

3-hydroxy-6,6-dimethylhept-1-ene-4-yne

3,3-Dimethylbut-1-yne

Downstream raw materials:

Trans-3'-[N-cyclopropyl-N-(6,6-dimethyl-2-hepten-4-ynyl)aminomethyl]acetophenone

trans-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-(3-bromo-5-methylbenzyl)amine

trans-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-(3-bromo-4-fluorobenzyl)amine

Refernces

• 1、 Chou, Shan-Yen,Tseng, Chin-Lu,Chen, Shyh-Fong. "A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: A key intermediate for terbinafine". . p. 3895 - 3898. Retrieved 2007/10/03.
• 2、 Stuetz, Anton,Petranyi, Gabor. "Synthesis and Antifungal Activity of (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine (SF 86-327) and Related Allylamine Derivatives with Enhanced Oral Activity". . p. 1539 - 1543. Retrieved 2007/10/02.