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B78203

Sigma-Aldrich

1-Bromo-1-propene (cis and trans)

98%

Synonym(s):

1-Propenyl bromide

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About This Item

Linear Formula:
CH3CH=CHBr
CAS Number:
590-14-7
Molecular Weight:
120.98
Beilstein:
1719096
EC Number:
209-671-6
MDL number:
MFCD00000186
UNSPSC Code:
12352100
PubChem Substance ID:
24892021
NACRES:
NA.22

Assay

98%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.4538 (lit.)

bp

58-63 °C (lit.)

mp

−116 °C (lit.)

density

1.413 g/mL at 25 °C (lit.)

SMILES string

C\C=C\Br

InChI

1S/C3H5Br/c1-2-3-4/h2-3H,1H3/b3-2+

InChI key

NNQDMQVWOWCVEM-NSCUHMNNSA-N

Related Categories

Application

1-Bromo-1-propene upon n-BuLi treatment generates the propynyllithium anion, in situ, which later undergoes nucleophilic addition reactions. Some of its other applications are:
  • Synthesis of organic reagents such as methyl but-2-ynoate and 1-iodopropyne.
  • Preparation o f intermediates in the total synthesis of (+)-aphanamol I and skyllamycins A-C.
  • Synthesis of allylated pyrazoles, aryl alkynyl sulfides and allenamides.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °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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Gold (I)?Catalyzed Intermolecular [2+ 2] Cycloadditions between Allenamides and Alkenes.
Faustino H, et al.
Advanced Synthesis & Catalysis, 354(9), 1658-1664 (2012)
Synthesis of 1?Iodopropyne.
Bartko S G, et al.
Organic Syntheses, 93, 245-262 (2003)
Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5+ 2] cycloaddition of allenes and vinylcyclopropanes.
Wender P A and Zhang L
Organic Letters, 2(15), 2323-2326 (2000)
Synthetic scope, computational chemistry and mechanism of a base induced 5-endo cyclization of benzyl alkynyl sulfides.
Motto J M, et al.
Tetrahedron, 67(5), 1002-1010 (2011)
Facile multi-decagram synthesis of methyl but-2-ynoate.
Darses B, et al.
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 1(1), 117-119 (2014)
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