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337528

Sigma-Aldrich

Allyl bromide

reagent grade, 97%, contains ≤1000 ppm propylene oxide as stabilizer

Synonym(s):
3-Bromo-1-propene
Linear Formula:
CH2=CHCH2Br
CAS Number:
Molecular Weight:
120.98
Beilstein:
605308
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

reagent grade

vapor density

4.2 (vs air)

assay

97%

autoignition temp.

554 °F

contains

≤1000 ppm propylene oxide as stabilizer

expl. lim.

7.3 %

refractive index

n20/D 1.469 (lit.)

bp

70-71 °C (lit.)

mp

−119 °C (lit.)

density

1.398 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

BrCC=C

InChI

1S/C3H5Br/c1-2-3-4/h2H,1,3H2

InChI key

BHELZAPQIKSEDF-UHFFFAOYSA-N

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Application

Allyl bromide can be used:
  • For the synthesis of stereodefined allylated arenes via Suzuki-type coupling reaction.
  • In Barbier-type allylation reactions of aldehydes and ketones.{17]
  • To synthesize a monomer, 1-1-(allyloxy)-4-nitrobenzene while synthesizing nanostructured molecularly imprinted polymer for selective tryptophan assay in biological and pharmaceutical samples.

Packaging

1 L in glass bottle
250 mL in glass bottle

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Carc. 1B - Eye Dam. 1 - Flam. Liq. 2 - Muta. 1B - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

30.2 °F

Flash Point(C)

-1 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

A tryptophan assay based on the glassy carbon electrode modified with a nano-sized tryptophan-imprinted polymer and multi-walled carbon nanotubes
Alizadeh T and Amjadi S
New. J. Chem., 41(11), 4493-4502 (2017)
Catalyst-Free Suzuki-Type Coupling of Allylic Bromides with Arylboronic Acids
Scrivanti A, et al.
European Journal of Organic Chemistry, 2012(2), 264-268 (2012)
Marcel S F Lie Ken Jie et al.
Lipids, 38(12), 1293-1297 (2004-02-12)
A methylene-interrupted C18 keto-acetylenic fatty ester (methyl 12-oxo-9-octadecynoate) was obtained from methyl ricinoleate by bromination-dehydrobromination followed by oxidation. Reaction of methyl 12-oxo-9-octadecynoate with bis(benzonitrile) palladium(II) chloride, allyl bromide, or methyl-allyl bromide furnished methyl 8-[5-hexyl-3-allyl-furan-2-yl]-octanoate (1, 56%) or methyl 8-15-hexyl-3-(2-methyl-allyl)-furan-2-yl]-octanoate (2...
Terra D Haddad et al.
The Journal of organic chemistry, 75(3), 642-649 (2009-12-24)
We report a simple, efficient, and general method for the indium-mediated enantioselective allylation of aromatic and aliphatic aldehydes and ketones under Barbier-type conditions in a one-pot synthesis affording the corresponding chiral alcohol products in very good yield (up to 99%)...
Design and synthesis of modular oxazoline ligands for the enantioselective chromium-catalyzed addition of allyl bromide to ketones.
Jeremie J Miller et al.
Journal of the American Chemical Society, 129(10), 2752-2753 (2007-02-21)

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