359890
Dimethyl bromomalonate
technical grade, 90%
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About This Item
Linear Formula:
BrCH(COOCH3)2
CAS Number:
Molecular Weight:
211.01
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-775-4
Beilstein/REAXYS Number:
971135
MDL number:
Assay:
90%
Form:
liquid
InChI key
NEMOJKROKMMQBQ-UHFFFAOYSA-N
InChI
1S/C5H7BrO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3
SMILES string
COC(=O)C(Br)C(=O)OC
grade
technical grade
assay
90%
form
liquid
Quality Level
bp
105-108 °C/11 mmHg (lit.)
density
1.601 g/mL at 25 °C (lit.)
functional group
bromo, ester
Related Categories
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.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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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)
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)
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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