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A29585

Sigma-Aldrich

Allyl bromide

ReagentPlus®, 99%, contains ≤1000 ppm propylene oxide as stabilizer

Synonym(s):

3-Bromo-1-propene

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About This Item

Linear Formula:
CH2=CHCH2Br
CAS Number:
106-95-6
Molecular Weight:
120.98
Beilstein:
605308
EC Number:
203-446-6
MDL number:
MFCD00000244
UNSPSC Code:
12352101
PubChem Substance ID:
24890713
NACRES:
NA.22

vapor density

4.2 (vs air)

Quality Level

200

product line

ReagentPlus®

Assay

99%

form

liquid

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 as a reagent to prepare:
  • Allyl ketones by Barbier-type allylation of various nitriles in the presence of Lewis acid.
  • Homoallylic alcohols by reacting with aldehydes or ketones using zinc dust as a catalyst.
  • 1,5-hexadiene by reductive C-C bond coupling using silver hydride cluster.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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 - closed cup

Flash Point(C)

-1 °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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Facile and efficient synthesis of homoallylic alcohols using allyl bromide and commercial zinc dust
Ranu BC, et al.
Tetrahedron Letters, 36(27), 4885-4888 (1995)
Synthesis of allyl ketone via Lewis acid promoted Barbier-type reaction
Lee Adam S-Y and Lin L-S
Tetrahedron Letters, 41(45), 8803-8806 (2000)
Jakub Wręczycki et al.
Materials (Basel, Switzerland), 13(11) (2020-06-11)
The superior ability of thiiranes (episulfides) to undergo ring-opening polymerization (ROP) in the presence of anionic initiators allows the preparation of chemically stable polysulfide homopolymers. Incorporation of elemental sulfur (S8) by copolymerization below the floor temperature of S8 permits the
Gas-phase synthesis of [Ag4H]+ and its mediation of the C-C coupling of allyl bromide
Khairallah GN and O'Hair, Richard AJ
Angewandte Chemie (International Edition in English), 44(5), 728-731 (2005)
Kiew-Ching Lee et al.
Chemical communications (Cambridge, England), (40)(40), 4209-4211 (2006-10-13)
The total synthesis of natural (4R,5R)-antillatoxin and its analog (4S,5S)-antillatoxin has been achieved; the optically pure key intermediates were prepared from indium mediated allylation of either primary or secondary allylic bromide with aldehyde in aquoues media, followed by highly selective
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