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391107

Sigma-Aldrich

trans-1-Bromo-1-propene

contains copper as stabilizer, 99%

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About This Item

Linear Formula:
CH3CH=CHBr
CAS Number:
Molecular Weight:
120.98
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.453 (lit.)

bp

64-65 °C (lit.)

density

1.408 g/mL at 25 °C (lit.)

functional group

alkyl halide
bromo

storage temp.

2-8°C

SMILES string

C\C=C\Br

InChI

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

InChI key

NNQDMQVWOWCVEM-NSCUHMNNSA-N

General description

trans-1-Bromo-1-propene is an alkenyl halide. Product contains copper as stabilizer. Its synthesis from 1,2-dibromopropane has been reported by various researchers. Its IR spectra has been investigated.

Application

trans -1-Bromo-1-propene is suitable for the synthesis of (E)-hex-4-en-2-yn-1-ol. trans -1-Bromo-1-propene ((E)-1-bromo-1-propene) may be used in the synthesis of the following:
  • (E)-1,3-dimethyl-3-(prop-1-enyl)indolin-2-one
  • 3-alkenyl-Δ3-cephems
  • (E)-1-(benzylthio)-1-propene
trans-1-Bromo-1-propene may be used as starting reagent in the synthesis of (+)-trans-isoalliin and (-)-trans-isoalliin.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

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)

5.0 °F - closed cup

Flash Point(C)

-15 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Alexander M Taylor et al.
Journal of the American Chemical Society, 131(29), 9900-9901 (2009-07-08)
The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess, and the conditions tolerate a range of
cis-trans Isomerization of 1-Bromo-1-propene and Related Compounds.
Harwell, KE and Hatch LF.
Journal of the American Chemical Society, 77(6), 1682-1684 (1955)
The Preparation of Long Chain Alkylamine Hydrochlorides1a.
Murr BL and Lester CT.
Journal of the American Chemical Society, 77(6), 1684-1685 (1955)
H Tanaka et al.
The Journal of organic chemistry, 66(2), 570-577 (2001-06-30)
Synthesis of 3-alkenyl-delta 3-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-delta 3-cephem with alkenyl halides, e.g., vinyl bromide, trans-1-bromo-1-propene, and trans-beta-bromostyrene in an Al/cat.PbBr2/cat.NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-delta 3-cephem into norcephalosporin was also achieved by a similar
Substituted Dienols from Palladium Catalyzed Coupling of Hydroaluminated Enynols with Aryl Iodides.
Crook KE, et al.
Letters in Organic Chemistry, 5(3), 158-164 (2008)

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