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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

Quality Level

100

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.)

functional group

acyl bromide
bromo

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000308606
SHBL0471
SHBG9238V
STBD8431V
SHBD0695V

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Sigma-Aldrich

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International journal of biological macromolecules, 153, 364-372 (2020-02-29)
Poultry chicken feather keratin was extracted and then modified for the fabrication of keratin-graft-PNIPAM copolymers. The keratin was well extracted from feather fiber and powdered. Subsequently, it underwent the surficial functionalization process with initiator groups. After the study conducted full
Andrew J Clark et al.
The Journal of organic chemistry, 72(15), 5923-5926 (2007-07-03)
Reaction of 2-substituted dienamides with catalytic amounts of copper halide/tripyridylamine (TPA) furnishes either 5-exo or 6-endo products with the outcome dependent upon the radical initiating unit. Reaction of 3-substituted dienamides produces beta-lactams via a 4-exo cyclization with termination of the
Sarah Atzet et al.
Biomacromolecules, 9(12), 3370-3377 (2008-12-09)
Biodegradable poly(2-hydroxyethyl methacrylate)(pHEMA) hydrogels for engineered tissue constructs were developed by the use of atom transfer radical polymerization (ATRP), a degradable cross-linker, and a macroinitiator. Hydrogels are appropriate materials for tissue engineering scaffolds because of their tissue-like mechanical compliance and
Preparation and characterization of hyperbranched polymer grafted mesoporous silica nanoparticles via self-condensing atom transfer radical vinyl polymerization.
Li X, et al.
Polymer, 51(1), 92-99 (2010)
Ya'nan Deng et al.
Mikrochimica acta, 185(8), 370-370 (2018-07-11)
Poly(2-naphthyl acrylate) was first grafted onto silica-coated magnetic nanoparticles by surface-initiated atom transfer radical polymerization to prepare a reversed-phase magnetic adsorbent. The resulting polymer brush displays enhanced extraction efficiency by offering active sites on the surfaces of adsorbent. It was
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Polymerizing via ATRP

Polymerization via ATRP procedures demonstrated by Prof. Dave Haddleton's research group at the University of Warwick.

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