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Merck
CN

05870

Allyl bromide

purum, ≥98.0% (GC)

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
EC Number:
203-446-6
UNSPSC Code:
12352101
PubChem Substance ID:
329748182
Beilstein/REAXYS Number:
605308
MDL number:
MFCD00000244

Key Documents

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InChI key

BHELZAPQIKSEDF-UHFFFAOYSA-N

InChI

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

SMILES string

BrCC=C

vapor density

4.2 (vs air)

grade

purum

assay

≥98.0% (GC)

autoignition temp.

554 °F

contains

silverwool as stabilizer

expl. lim.

7.3 %

refractive index

n20/D 1.469 (lit.), n20/D 1.469

bp

70-71 °C (lit.)

mp

−119 °C (lit.)

density

1.398 g/mL at 25 °C (lit.)

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Application

Allyl bromide can be used:
  • As a starting material to prepare allylaluminum and allylgallium sesquibromides.
  • As a precursor in the synthesis of allyl ketones by reacting with substituted nitriles under Barbier-type reaction conditions.
  • As a starting material in the synthesis of 2-allyl-1(E),3(E)-dienyl sulfoxides by reacting with 1,2-allenylic sulfoxides using Pd catalyst.
  • In the indium catalyzed addition reactions of N-tert-butylsulfinyl aldimines to yield N-tert-butylsulfinylamine chiral building blocks.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

30.2 °F - closed cup

flash_point_c

-1 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Indium-catalyzed reduction of allyl bromide with gallium or aluminum. Formation of allylgallium and allylaluminum sesquibromides
Takai K and Ikawa Y
Organic Letters, 4(10), 1727-1729 (2002)
Indium-mediated diastereoselective addition of allyl bromides to enantiomerically pure N-tert-butylsulfinyl aldimines
Foubelo F and Yus M
Tetrahedron Asymmetry, 15(24), 3823-3825 (2004)
Highly regio-and stereoselective PdCl2(MeCN) 2-catalyzed cross coupling of 1, 2-allenylic sulfoxides with allyl bromide
Ma S, et al.
Tetrahedron Letters, 45(17), 3517-3520 (2004)
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)
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
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