4-Bromo-1-butyne

Base Information

• Chemical Name: 4-Bromo-1-butyne
• CAS No.: 38771-21-0
• Molecular Formula: C4H5 Br
• Molecular Weight: 132.988
• Hs Code.: 29039990
• European Community (EC) Number: 629-361-8
• DSSTox Substance ID: DTXSID10454136
• Nikkaji Number: J556.186H
• Wikidata: Q72452211
• Mol file: 38771-21-0.mol

Synonyms:4-Bromo-1-butyne;38771-21-0;4-bromobut-1-yne;1-Bromo-3-butyne;1-Butyne, 4-bromo-;4-bromobutyne;3-Butynyl Bromide;4-bromo-but-1-yne;4-Bromo-1-butyne, 97%;SCHEMBL932665;AMY1272;DTXSID10454136;XLYOGWXIKVUXCL-UHFFFAOYSA-N;BBL103378;STL557188;AKOS015836189;AS-47016;A6541;B3242;CS-0147245;FT-0690002;EN300-109730;F11435

Chemical Property of 4-Bromo-1-butyne

Chemical Property:

• Vapor Pressure: 20.004mmHg at 25°C
• Refractive Index: 1.481
• Boiling Point: 110 °C
• Flash Point: 24 ºC
• PSA: 0.00000
• Density: 1.417
• LogP: 1.40460
• Storage Temp.: Refrigerator
• Water Solubility.: Immiscible with water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 131.95746
• Heavy Atom Count: 5
• Complexity: 47.9

Purity/Quality:

98% ^*data from raw suppliers

4-Bromo-1-butyne ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 10-25-43
• Safety Statements: 36/37-45

MSDS Files:

Useful:

• Canonical SMILES: C#CCCBr
• Uses: 4-Bromo-1-butyne is used for pharmaceutical intermediates. 4-Bromo-1-butyne is used as a reactant in the synthesis of:Macrocycles by cobalt-mediated [2+2+2] co-cyclotrimerization.2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.Intramolecular 1,3-dipolar cycloaddition to synthesize 1,3,4-oxadiazoles.Lactones bearing alkynes for reductive cyclization in the preparation of azulene derivatives.Substituted α-pyrones by gold-catalyzed coupling reactions.

Technology Process of 4-Bromo-1-butyne

There total 2 articles about 4-Bromo-1-butyne 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: 27.0%

3-Butyn-1-ol (927-74-2) → 4-bromobut-1-yne (38771-21-0)

Guidance literature:

With phosphorus tribromide;

Reference yield:

3-butyn-1-yl p-toluenesulfonate (23418-85-1) → 4-bromobut-1-yne (38771-21-0)

Guidance literature:

With ethoxyethoxyethanol; calcium bromide;

DOI:10.1039/jr9500003650

Reference yield: 98.0%

4-bromobut-1-yne (38771-21-0) + 4-fluorobenzyl azide (159979-96-1) → C11H11BrFN3 (1251392-43-4)

Guidance literature:

With copper(II) loaded mesoporous SBA-15; In dichloromethane; at 20 ℃; regioselective reaction;

DOI:10.1016/j.molcata.2014.06.003

upstream raw materials:

3-butyn-1-yl p-toluenesulfonate

3-Butyn-1-ol

Downstream raw materials:

ethyl 2-(ethoxycarbonyl)-5-hexynoate

(E)-1-oct-3-enyl bromide

but-1-yn-4-yl phenyl sulfide

2-<4-<(tert-butyloxycarbonyl)amino>phenyl>-5-hexynoic acid

Refernces

• 1、 Spinella,Caruso,Martino,Sessa. "Synthesis of aplyolide A, ichthyotoxic macrolide isolated from the skin of the marine mollusk Aplysia depilans". . p. 1971 - 1973. Retrieved 2007/10/03.
• 2、 -. "METHOD OF SELECTIVELY INHIBITING CALCIUM-INDEPENDENT MYOCARDIAL PHOSPHOLIPASE A2". . . Retrieved 2008/06/13.