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252271

Sigma-Aldrich

α-Bromoisobutyryl bromide

98%

Synonym(s):

2-Bromo-2-methylpropionyl bromide, BIBB

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About This Item

Linear Formula:
(CH3)2CBrCOBr
CAS Number:
20769-85-1
Molecular Weight:
229.90
Beilstein:
1746128
EC Number:
244-017-3
MDL number:
MFCD00000122
UNSPSC Code:
12352100
PubChem Substance ID:
24855196
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.507 (lit.)

bp

162-164 °C (lit.)

density

1.86 g/mL at 25 °C (lit.)

SMILES string

CC(C)(Br)C(Br)=O

InChI

1S/C4H6Br2O/c1-4(2,6)3(5)7/h1-2H3

InChI key

YOCIJWAHRAJQFT-UHFFFAOYSA-N

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General description

BIBB is an important reagent in the synthesis of amides, macrocyclic amides, ketenes, and alkynic ketones.

Application

α-Bromoisobutyryl bromide has been used:
  • as atom transfer radical polymerization (ATRP) initiator for functionalization of hydroxyl groups present on the surface of graphene oxide
  • to form an N-protected halodienamide which provided four- and five-membered lactams in the presence of copper (I) and a tertiary amine
  • in preparation of polycaprolactone macroinitiator via reaction with oligomeric caprolactone diol and mesoporous silica nanoparticles with ATRP initiator anchored on the exterior surface

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °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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eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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ARGET ATRP procedure facilitates PMMA polymer brush growth with surface cleaning and initiator monolayer deposition.

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