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139440

Sigma-Aldrich

Diethyl 2-bromo-2-methylmalonate

98%

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About This Item

Linear Formula:
BrC(CH3)(CO2C2H5)2
CAS Number:
29263-94-3
Molecular Weight:
253.09
EC Number:
249-541-6
MDL number:
MFCD00009125
UNSPSC Code:
12352100
PubChem Substance ID:
24848412
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.449 (lit.)

density

1.325 g/mL at 25 °C (lit.)

functional group

bromo
ester

SMILES string

CCOC(=O)C(C)(Br)C(=O)OCC

InChI

1S/C8H13BrO4/c1-4-12-6(10)8(3,9)7(11)13-5-2/h4-5H2,1-3H3

InChI key

CSLQAXTUGPUBCW-UHFFFAOYSA-N

General description

Diethyl 2-bromo-2-methylmalonate acts as initiator during the atom transfer radical polymerization of methyl methacrylate.

Application

Diethyl 2-bromo-2-methylmalonate was used to investigate the 1,2,2,6,6-pentamethylpiperidine as an effective reducing agent for the radical chain conversion of primary bromoesters to the corresponding esters. It was used in the synthesis of polystyrene macroinitiator via atom transfer radical polymerization.

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)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ0967
BCCF2851
BCCB2009
BCBW3805
BCBW3806

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Organic reducing agents. Reduction of electron deficient bromides by 1, 2, 2, 6, 6-pentamethylpiperidine (PMP)/mercaptoethanol.
Amoli M, et al.
Tetrahedron Letters, 36(23), 3997-4000 (1995)
TAILOR MADE POLYMERIC SYSTEMATIC LIBRARIES VIA ATOM TRANSFER RADICAL POLYMERIZATION.
Jakubowski W, et al.
Polymer Preprints (American Chemical Society, Division of Polymer Chemistry), 49(2), 369-369 (2008)
Controlled/?living? atom transfer radical polymerization of methyl methacrylate using various initiation systems.
Matyjaszewski K, et al.
Macromolecules, 31(5), 1527-1534 (1998)

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