5-Bromo-1-pentyne

Base Information

• Chemical Name: 5-Bromo-1-pentyne
• CAS No.: 28077-72-7
• Molecular Formula: C5H7 Br
• Molecular Weight: 147.015
• Hs Code.: 2903399090
• European Community (EC) Number: 851-251-5
• DSSTox Substance ID: DTXSID70477846
• Nikkaji Number: J556.187F
• Wikidata: Q82310860
• Mol file: 28077-72-7.mol

Synonyms:5-Bromo-1-pentyne;28077-72-7;5-bromopent-1-yne;1-Bromo-4-pentyne;5-Bromopentyne;MFCD02258725;1-Pentyne, 5-bromo-;4-Pentyn-1-yl bromide;SCHEMBL40285;DTXSID70477846;KEKBNXAJNJSILY-UHFFFAOYSA-N;AKOS010651591;BS-35951;SY143808;CS-0147349;FT-0663822;E87071;EN300-122318;A848811;J-016965

Chemical Property of 5-Bromo-1-pentyne

Chemical Property:

• Boiling Point: 134 °C(Press: 763 Torr)
• PSA: 0.00000
• Density: 1.361±0.06 g/cm3(Predicted)
• LogP: 1.79470
• Solubility.: Acetone, Dichloromethane
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 145.97311
• Heavy Atom Count: 6
• Complexity: 57.6

Purity/Quality:

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

5-Bromo-1-pentyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCCBr
• Uses: 5-Bromo-1-pentyne (cas# 28077-72-7) is a useful reagent for the synthesis of spirocyclic compounds.

Technology Process of 5-Bromo-1-pentyne

There total 6 articles about 5-Bromo-1-pentyne 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: 93.0%

pent-1-yn-5-ol (5390-04-5) → 1-bromo-4-pentyne (28077-72-7)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja510081r

Reference yield: 79.0%

4-pentynyl-1-tosylate (77758-50-0) → 1-bromo-4-pentyne (28077-72-7)

Guidance literature:

With lithium bromide; In acetone; for 17h; Heating;

DOI:10.1021/jo00170a005

Reference yield:

sodium acetylide (1066-26-8) + 1,3-dibromo-propane (109-64-8) → 1-bromo-4-pentyne (28077-72-7)

Guidance literature:

In N,N-dimethyl-formamide; at 25 ℃; for 24h; Schlenk technique;

DOI:10.1055/s-0037-1611790

upstream raw materials:

pent-1-yn-5-ol

4-pentynyl-1-tosylate

pent-4-yn-1-yl methanesulfonate

Tetrahydrofurfuryl chloride

Downstream raw materials:

1-Pent-4-ynyl-cyclohexanecarboxylic acid methyl ester

2-(5-phenylpent-4-yn-1-yl)isoindoline-1,3-dione

2-methyl-3-p-tolylsulphonyloct-1-en-7-yne

4-pentynyltriphenylphosphonium bromide

Refernces

• 1、 Bielefeld, Jens,Mannhaupt, Steffen,Schmidtmann, Marc,Doye, Sven. "Hydroaminoalkylation of Allenes". supporting information. p. 967 - 971. Retrieved 2019/05/10.
• 2、 Coombs, John R.,Zhang, Liang,Morken, James P.. "Enantiomerically enriched tris(boronates): Readily accessible conjunctive reagents for asymmetric synthesis". supporting information. p. 16140 - 16143. Retrieved 2015/01/09.