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A29585

Sigma-Aldrich

Allyl bromide

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

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

vapor density

4.2 (vs air)

Quality Level

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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This Item
337528P51001678201
Allyl bromide ReagentPlus®, 99%, contains ≤1000 ppm propylene oxide as stabilizer

A29585

Allyl bromide

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

337528

Allyl bromide

Propargyl bromide solution 80 wt. % in toluene, contains 0.3% magnesium oxide as stabilizer

P51001

Propargyl bromide solution

Allyl methyl ether 97%

678201

Allyl methyl ether

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

-

form

liquid

form

liquid

form

-

form

-

bp

70-71 °C (lit.)

bp

70-71 °C (lit.)

bp

88-90 °C

bp

42-43 °C/760 mmHg

mp

−119 °C (lit.)

mp

−119 °C (lit.)

mp

-

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

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

signalword

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

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

30.2 °F

flash_point_c

-1 °C

ppe

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


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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)
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)
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
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)
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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