1-Bromo-2-octyne

Base Information

• Chemical Name: 1-Bromo-2-octyne
• CAS No.: 18495-27-7
• Molecular Formula: C8H13Br
• Molecular Weight: 189.095
• Hs Code.: 2903399090
• DSSTox Substance ID: DTXSID20373728
• Nikkaji Number: J1.287.179A
• Wikidata: Q82162042
• Mol file: 18495-27-7.mol

Synonyms:1-Bromo-2-octyne;18495-27-7;1-bromooct-2-yne;2-Octyne, 1-bromo-;2-octynyl bromide;1-Brom-2-octin;2-Octyne,1-bromo-;SCHEMBL1873508;DTXSID20373728;QKPBYOBXEXNWOA-UHFFFAOYSA-N;MFCD00190196;AKOS006343944;FS-4715;CS-0152339;FT-0637705;D94830;EN300-7606135;A812902

Chemical Property of 1-Bromo-2-octyne

Chemical Property:

• Refractive Index: 1.4883
• Boiling Point: 195.9 °C at 760 mmHg
• Flash Point: 72.5 °C
• PSA: 0.00000
• Density: 1.203 g/cm³
• LogP: 2.96500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 188.02006
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Bromo-2-octyne ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC#CCBr
• Uses: 1-Bromo-2-octyne, is an intermediate in the synthesis of pinolenic acid. This compound is also used in preparation of substituted indoles though Rh-catalyzed amino-Claisen rearrangement.

Technology Process of 1-Bromo-2-octyne

There total 21 articles about 1-Bromo-2-octyne 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: 100.0%

2-octyn-1-ol (20739-58-6) → 1-bromooct-2-yne (18495-27-7)

Guidance literature:

With carbon tetrabromide; triphenylphosphine;

DOI:10.1016/j.tetlet.2005.05.027

Reference yield: 95.0%

1-(p-tolylsulfonyloxy)oct-2-yne (57342-29-7) → 1-bromooct-2-yne (18495-27-7)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; sodium bromide; In dichloromethane; water; for 6h; Ambient temperature;

Reference yield: 87.0%

2-(oct-2-yn-1-yloxy)tetrahydro-2H-pyran (36602-98-9) → 1-bromooct-2-yne (18495-27-7)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; 0 deg C to room temp. overnight;

DOI:10.1016/S0040-4039(00)95252-3

upstream raw materials:

2-octyn-1-ol

tetra-N-methyl-phosphorodiamidic acid oct-2-ynyl ester

n-butyl magnesium bromide

1,4-dibromobut-2-yne

Downstream raw materials:

non-3-ynoic acid

((3Z,6Z)-dodeca-3,6-dien-1-yl)triphenylphosphonium bromide

tert-Butyl-diphenyl-[(R)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-3-ynyloxy]-silane

16-chlorohexadeca-6,9-diyne

Refernces

• 1、 Rosenberger,Newkom,Aig. "Total synthesis of leukotriene E4, a member of the SRS-A family". . p. 3656 - 3661. Retrieved 1983.
• 2、 Place et al.. "". . p. 3801. Retrieved 1978.
• 3、 Suzuki, Shunsuke,Shibata, Yu,Tanaka, Ken. "Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Racemic Secondary Allylic Alcohols through Kinetic Resolution". supporting information. p. 3698 - 3702. Retrieved 2020/03/03.
• 4、 Yan, Mei,Jin, Tienan,Ishikawa, Yoshifumi,Fujita, Takeshi,Chen, Lu-Yang,Asao, Naoki,Chen, Ming-Wei,Yamamoto, Yoshinori,Minato, Taketoshi,Bao, Ming. "Nanoporous gold catalyst for highly selective semihydrogenation of alkynes: Remarkable effect of amine additives". supporting information. p. 17536 - 17542,7. Retrieved 2020/09/16.