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427292

Sigma-Aldrich

1-Bromo-2-butyne

≥98%

Synonym(s):

1-(Bromomethyl)-2-methylacetylene, 2-Butyn-1-yl bromide, 2-Butynyl bromide, 4-Bromobut-2-yne

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About This Item

Linear Formula:
CH3C≡CCH2Br
CAS Number:
3355-28-0
Molecular Weight:
132.99
Beilstein:
605306
MDL number:
MFCD00190233
UNSPSC Code:
12352100
PubChem Substance ID:
24866752
NACRES:
NA.22

Assay

≥98%

form

liquid

refractive index

n20/D 1.508 (lit.)

bp

40-41 °C/20 mmHg (lit.)

density

1.519 g/mL at 25 °C (lit.)

SMILES string

CC#CCBr

InChI

1S/C4H5Br/c1-2-3-4-5/h4H2,1H3

InChI key

LNNXOEHOXSYWLD-UHFFFAOYSA-N

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General description

1-Bromo-2-butyne is a propargyl bromide derivative. It is one of the constitutional isomer of bromo butyne. Its Br-loss threshold photoionization breakdown diagram has been analyzed to derive dissociative photoionization thresholds to C4H5+ production. It participates in the preparation of linagliptin.

Application

1-Bromo-2-butyne was used in the alkylation of L-tryptophan methyl ester. It was used as a source to generate CH3CCCH2 radicals to investigate the reaction kinetics of these radicals with NO and NO2.
It may be used in the synthesis of the following:
  • 4-butynyloxybenzene sulfonyl chloride
  • mono-propargylated diene derivative
  • isopropylbut-2-ynylamine
  • allenylcyclobutanol derivatives
  • allyl-[4-(but-2-ynyloxy)phenyl]sulfane
  • allenylindium
  • alkynyl alcohols
  • axially chiral teranyl compounds
Exploited in the synthesis of axially chiral teranyl compounds.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

96.8 °F - closed cup

Flash Point(C)

36 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates.
Levin JI, et al.
Bioorganic & Medicinal Chemistry Letters, 13(16), 2799-2803 (2003)
Kinetics of resonance stabilized CH3CCCH2 radical reactions with NO and NO2.
Rissanen MP, et al.
Chemical Physics Letters, 543, 28-33 (2012)
Imaging breakdown diagrams for bromobutyne isomers with photoelectron-photoion coincidence.
Bodi A and Hemberger P.
Physical Chemistry Chemical Physics, 16(2), 505-515 (2014)
Takanori Shibata et al.
Journal of the American Chemical Society, 126(27), 8382-8383 (2004-07-09)
An asymmetric [2+2+2] cycloaddition of an alpha,omega-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5)
Stereoselective synthesis of a-disubstituted cyclopentanones by palladium-catalyzed rearrangement of allenylcyclobutanols with aryl halides.
Yoshida M, et al.
Tetrahedron, 58(39), 7839-7846 (2002)
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