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139440

Sigma-Aldrich

Diethyl 2-bromo-2-methylmalonate

98%

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Linear Formula:
BrC(CH3)(CO2C2H5)2
CAS Number:
Molecular Weight:
253.09
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.449 (lit.)

density

1.325 g/mL at 25 °C (lit.)

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Controlled/?living? atom transfer radical polymerization of methyl methacrylate using various initiation systems.
Matyjaszewski K, et al.
Macromolecules, 31(5), 1527-1534 (1998)
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)

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