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359890

Sigma-Aldrich

Dimethyl bromomalonate

technical grade, 90%

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About This Item

Linear Formula:
BrCH(COOCH3)2
CAS Number:
868-26-8
Molecular Weight:
211.01
Beilstein:
971135
EC Number:
212-775-4
MDL number:
MFCD00025865
UNSPSC Code:
12352100
PubChem Substance ID:
24862117
NACRES:
NA.22

grade

technical grade

Assay

90%

form

liquid

refractive index

n20/D 1.460 (lit.)

bp

105-108 °C/11 mmHg (lit.)

density

1.601 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C(Br)C(=O)OC

InChI

1S/C5H7BrO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3

InChI key

NEMOJKROKMMQBQ-UHFFFAOYSA-N

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General description

Dimethyl bromomalonate undergoes manganese(III)-promoted free-radical chain addition reaction with olefins, to yield dimethyl 2-bromoalkylmalonates. Organocatalyzed Michael addition of dimethyl bromomalonate to nitrostyrenes to yield synthetically useful nitrocyclopropanes has been reported. Dimethyl bromomalonate reacts readily with arylnitroso compounds to yield the corresponding N-aryl-C,C-dimethoxycarbonylnitrones.

Application

Dimethyl bromomalonate may be used in the enantioselective synthesis of nitrocyclopropanes.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Manganese (III)-promoted free-radical addition of dimethyl bromomalonate to olefins using an electrochemical regeneration procedure.
Nedelec JY and Nohair K.
Synlett, 09, 659-660 (1991)
Stereoselective synthesis of functionalised cyclopropanes from nitroalkenes via an organocatalysed Michael-initiated ring-closure approach.
Russo A and Lattanzi A.
Tetrahedron Asymmetry, 21(9), 1155-1157 (2010)
Yi-Ning Xuan et al.
Organic letters, 11(7), 1583-1586 (2009-03-06)
Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6'-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for
Synthesis and 1, 3-dipolar cycloaddition reactions of N-aryl-C, C-dimethoxycarbonylnitrones.
Tomioka Y, et al.
Journal of Heterocyclic Chemistry, 40(1), 121-128 (2003)

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