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Merck

252271

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24855196
EC Number:
244-017-3
Beilstein/REAXYS Number:
1746128
MDL number:
MFCD00000122
Assay:
98%
Form:
liquid

Key Documents

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InChI key

YOCIJWAHRAJQFT-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

98%

form

liquid

Quality Level

100

bp

162-164 °C (lit.)

density

1.86 g/mL at 25 °C (lit.)

functional group

acyl bromide, bromo

Related Categories

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

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 3 petroleums + Hazardous rank III + Water insoluble liquid

fsl

252271-5G: + 252271-BULK: + 252271-100G: + 252271-VAR: + 252271-500G:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL0471
SHBG9238V
STBD8431V
SHBD0695V
STBC7019V

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Shih-Jer Huang et al.
International journal of nanomedicine, 8, 2011-2027 (2013-06-08)
Cationic polymers are one of the major nonviral gene delivery vectors investigated in the past decade. In this study, we synthesized several cationic copolymers using atom transfer radical polymerization (ATRP) for gene delivery vectors: pluronic F127-poly(dimethylaminoethyl methacrylate) (PF127-pDMAEMA), pluronic F127-poly
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
Nicklas N Poulsen et al.
Journal of separation science, 40(3), 779-788 (2016-11-22)
Many bioanalytical methods rely on electrophoretic separation of structurally labile and surface active biomolecules such as proteins and peptides. Often poor separation efficiency is due to surface adsorption processes leading to protein denaturation and surface fouling in the separation channel.
Sun Hwa Lee et al.
Macromolecular rapid communications, 31(3), 281-288 (2010-02-02)
A method for growing polymers directly from the surface of graphene oxide is demonstrated. The technique involves the covalent attachment of an initiator followed by the polymerization of styrene, methyl methacrylate, or butyl acrylate using atom transfer radical polymerization (ATRP).
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
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Protocols

ARGET ATRP: Procedure for PMMA Polymer Brush Growth

ARGET ATRP procedure facilitates PMMA polymer brush growth with surface cleaning and initiator monolayer deposition.

Polymerizing via ATRP

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

ATRPによる重合

ウォーリック大学のProf. Dave Haddletonの研究グループによって実証された、ATRPによる重合。

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