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249904

Sigma-Aldrich

3,3-Dimethylallyl bromide

technical grade, ~90%

Synonym(s):

1-Bromo-3-methyl-2-butene, Prenyl bromide

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About This Item

Linear Formula:
(CH3)2C=CHCH2Br
CAS Number:
870-63-3
Molecular Weight:
149.03
Beilstein/REAXYS Number:
1420778
EC Number:
212-799-5
MDL number:
MFCD00000242
UNSPSC Code:
12352100
PubChem Substance ID:
24855022
NACRES:
NA.22

grade

technical grade

assay

~90%

form

liquid

contains

silver wool as stabilizer

refractive index

n20/D 1.489 (lit.)

bp

82-83 °C/150 mmHg (lit.)

density

1.29 g/mL at 20 °C (lit.)

functional group

alkyl halide
bromo

storage temp.

2-8°C

SMILES string

C\C(C)=C\CBr

InChI

1S/C5H9Br/c1-5(2)3-4-6/h3H,4H2,1-2H3

InChI key

LOYZVRIHVZEDMW-UHFFFAOYSA-N

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Application

3,3-Dimethylallyl bromide has been used in the preparation of:
  • (±)-eldanolide
  • 1-(3,3-dimethylallyl)-L-tryptophan
  • (±)-fumagillin, antibiotic isolated from Aspergillus fumigattus

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

104.0 °F - closed cup

flash_point_c

40 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK2172
BCCB3019
BCBL9481V
BCBC2733
BCBC2733V

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A direct synthesis of (?)-eldanolide via the highly regioselective prenylation of 2-trimethylsiloxyfuran.
Jefford CW, et al.
Tetrahedron Letters, 28(9), 949-950 (1987)
A total synthesis of ( )-fumagillin.
E J Corey et al.
Journal of the American Chemical Society, 94(7), 2549-2550 (1972-04-05)
Biosynthesis of aromatic isoprenoids. Part 5. The preparation of 1-(3, 3-dimethylallyl)-L-tryptophan and cyclo-L-aianyl-1-(3, 3-dimethylallyl)-L-tryptophan and their non-incorporation into echinulin.
Grundon MF, et al.
Journal of the Chemical Society. Perkin Transactions 1, 1294-1298 (1980)

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