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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
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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.[1]

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[2]
  • to form an N-protected halodienamide which provided four- and five-membered lactams in the presence of copper (I) and a tertiary amine[3]
  • in preparation of polycaprolactone macroinitiator via reaction with oligomeric caprolactone diol[4] and mesoporous silica nanoparticles with ATRP initiator anchored on the exterior surface[5]

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
MKCW9569
0000308606
SHBL0471
SHBG9238V
STBD8431V

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Sigma-Aldrich

733350

Bis[2-(2-bromoisobutyryloxy)undecyl] disulfide

2-Bromo-2-methylpropionyl Bromide
Winter CH
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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
Sikai Chen et al.
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
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
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
View All Related Papers

Protocols

ARGET ATRP: Procedure for PMMA Polymer Brush Growth

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

ARGET ATRP: Procedure for PMMA Polymer Brush Growth

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

ARGET ATRP: Procedure for PMMA Polymer Brush Growth

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

ARGET ATRP: Procedure for PMMA Polymer Brush Growth

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

See All

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Does this come packaged in a SureSeal bottle

    1 answer

    1. This product is not packaged in SureSeal containers. The 100G package size is in 50mL amber glass bottles with PTFE-lined polypropylene caps. The 500G package size is the same with the exception of a 500ml bottle volume. Both package sizes are shipping in an overpack protective can.

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