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16940

Sigma-Aldrich

1-Bromo-2,2-dimethylpropane

purum, ≥98.0% (GC)

Synonym(s):

Neopentyl bromide

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About This Item

Linear Formula:
(CH3)3CCH2Br
CAS Number:
Molecular Weight:
151.04
Beilstein:
1730989
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

grade

purum

Assay

≥98.0% (GC)

refractive index

n20/D 1.436 (lit.)
n20/D 1.436

bp

105-106 °C/767 mmHg (lit.)

density

1.199 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)CBr

InChI

1S/C5H11Br/c1-5(2,3)4-6/h4H2,1-3H3

InChI key

CQWYAXCOVZKLHY-UHFFFAOYSA-N

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Application

1-Bromo-2,2-dimethylpropane was used in the synthesis of S-alkylated cysteine derivatives with branched alkyl chains. It was used in synthesis of secondary amines from alkyl tosylates or alkyl halides via nucleophilic substitution reaction.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

44.6 °F - closed cup

Flash Point(C)

7 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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An improved method for cysteine alkylation.
Perrey DA and Uckun FM.
Tetrahedron Letters, 42(10), 1859-1861 (2001)
Carmen E Lisowski et al.
The journal of physical chemistry. A, 114(38), 10395-10402 (2010-09-03)
The recombination of chloromethyl and t-butyl radicals at room temperature was used to generate neopentyl chloride molecules with 89 kcal mol(-1) of internal energy. The observed unimolecular reactions, which give 2-methyl-2-butene and 2-methyl-1-butene plus HCl, as products, are explained by
J Ashby et al.
Mutation research, 140(2-3), 71-74 (1984-06-01)
Neopentyl bromide and pentaerythrityl tetrachloride were shown here to be non-mutagenic to 7 strains of Salmonella typhimurium. These inactivities are reflected in the inability of either compound to produce a colour reaction in the chemical alkylation test of Epstein (4-nitrobenzylpyridine
Direct mono-N-alkylation of amines in ionic liquids: chemoselectivity and reactivity.
Chiappe C and Pieraccini D.
Green Chemistry, 5(2), 193-197 (2003)

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