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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

WGK

WGK 3

Flash Point(F)

30.2 °F

Flash Point(C)

-1 °C

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)
Jing-Mei Huang et al.
Chemical communications (Cambridge, England), (26)(26), 3943-3945 (2009-08-08)
An efficient electrosynthesis of homoallylic alcohols from allylic bromides and aldehydes in aqueous ammonia is achieved in an undivided cell fitted with a pair of zinc electrodes.
Xiaoyu Yan et al.
Chemical communications (Cambridge, England), 46(41), 7801-7803 (2010-09-22)
Reaction of alkynylzirconates with allyl bromides afforded β-allyl-zirconacyclopentadienes with high selectivity in unique reaction site.
José C González-Gómez et al.
The Journal of organic chemistry, 75(18), 6308-6311 (2010-08-21)
The combination of an aldehyde, an allylic bromide, and tert-butanesulfinamide in the presence of indium metal and titanium tetraethoxide allows straightforward access to homoallylamine derivatives in high yields and stereoselectivities. Moreover, the synthetic utility of the enantioenriched homoallylamine derived from
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