1-Bromo-2-butyne

Base Information

• Chemical Name: 1-Bromo-2-butyne
• CAS No.: 3355-28-0
• Molecular Formula: C4H5Br
• Molecular Weight: 132.988
• Hs Code.: 29033990
• DSSTox Substance ID: DTXSID10373595
• Nikkaji Number: J277.515H
• Wikidata: Q72452215
• Mol file: 3355-28-0.mol

Synonyms:1-Bromo-2-butyne;3355-28-0;1-bromobut-2-yne;2-Butyne, 1-bromo-;2-Butynyl Bromide;MFCD00190233;C4H5Br;bromo-2-butyne;1-bromo2-butyne;but-2-ynylbromide;l-bromo-2-butine;1-bromo-2-butine;4-bromo-2-butyne;but-2-ynyl bromide;1-bromo-but-2-yne;SCHEMBL41298;?1-BROMO-2-BUTYNE;1-Bromo-2-butyne, 99%;AMY1227;DTXSID10373595;LNNXOEHOXSYWLD-UHFFFAOYSA-N;BCP17711;BBL103446;STL557256;AKOS005256637;AB91641;AS-20130;B2190;FT-0634801;EN300-61875;A821831;J-504388;F0001-0987

Chemical Property of 1-Bromo-2-butyne

Chemical Property:

• Appearance/Colour: Clear pale yellow-greenish liquid
• Vapor Pressure: 15.2mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• Boiling Point: 124.7 °C at 760 mmHg
• Flash Point: 36.3 °C
• PSA: 0.00000
• Density: 1.46 g/cm³
• LogP: 1.40460
• Storage Temp.: Flammables area
• Solubility.: Miscible with acetonitrile.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 131.95746
• Heavy Atom Count: 5
• Complexity: 62.2

Purity/Quality:

99%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 16-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CCBr
• Uses: 1-Bromo-2-butyne is used in the preparation of six to eight annulated ring compounds in reaction with indoles and pseudopterane (+/-)-Kallolide B, which is a marine natural product. Further, it acts as a precursor in the preparation of axially chiral teranyl compounds, alkylation of L-tryptophan methyl ester, 4-butynyloxybenzene sulfonyl chloride and mono-propargylated diene derivative. In addition to this, it is also used in the synthesis of isopropylbut-2-ynylamine, allenylcyclobutanol derivatives, allyl-[4-(but-2-ynyloxy)phenyl]sulfane, allenylindium and axially chiral teranyl compounds.

Technology Process of 1-Bromo-2-butyne

There total 9 articles about 1-Bromo-2-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: 100.0%

methyl propargyl alcohol (764-01-2) → 1-Bromo-2-butyne (3355-28-0)

Guidance literature:

With bromine; triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/acs.orglett.9b02124

Reference yield: 58.0%

2-But-2-ynyl-1,3-diisopropyl-isourea (113984-38-6) → 1,3-diisopropylurea (4128-37-4) + 1-Bromo-2-butyne (3355-28-0)

Guidance literature:

With trifluorormethanesulfonic acid; tetrabutylammomium bromide; In dichloromethane; at 40 ℃; for 15h;

DOI:10.1016/S0040-4039(00)96534-1

Reference yield: 54.0%

→ 1-Bromo-2-butyne (3355-28-0)

Guidance literature:

upstream raw materials:

methyl propargyl alcohol

4-methoxy-but-2-yne

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

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

Downstream raw materials:

2-Hexyne

octa-2,6-diyne

1-(phenylseleno)-2-butyne

2-methyl-4-hexynoic acid methyl ester

Refernces

• 1、 Ogiwara, Yohei,Suzuki, Yui,Sato, Kazuya,Sakai, Norio. "Construction of N-Heterocyclic Systems Containing a Fully Substituted Allylic Carbon by Palladium/Phosphine Catalysis". . p. 6965 - 6969. Retrieved 2018.
• 2、 Biletskyi, Bohdan,Tenaglia, Alphonse,Clavier, Hervé. "Cobalt-catalyzed versus uncatalyzed intramolecular Diels-Alder cycloadditions". supporting information. p. 103 - 107. Retrieved 2017/12/28.