412708
Diethyl dibromomalonate
97%
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About This Item
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Quality Level
assay
97%
form
liquid
refractive index
n20/D 1.484 (lit.)
bp
140-143 °C/18 mmHg (lit.)
density
1.68 g/mL at 25 °C (lit.)
functional group
bromo
ester
SMILES string
CCOC(=O)C(Br)(Br)C(=O)OCC
InChI
1S/C7H10Br2O4/c1-3-12-5(10)7(8,9)6(11)13-4-2/h3-4H2,1-2H3
InChI key
PFZYFZRUPFUEOB-UHFFFAOYSA-N
General description
Diethyl dibromomalonate reacts with sodium methoxide in cyclohexene to afford dibromonorcarane. It also reacts with allyl(pyridine)cobaloximes to afford the corresponding allyl-substituted esters.
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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Reaction of diethyl dibromomalonate with methoxide: Evidence for a novel bromophilic attack.
Tetrahedron Letters, 40(8), 1459-1462 (1999)
Journal of the American Chemical Society, 131(36), 12918-12920 (2009-08-22)
Tetrahydrofur-2-ylmethyl radicals were stereoselectively generated from substituted pent-4-en-1-ols in aerobic cobalt(II)-catalyzed oxidations. Intermediates were trapped with cyclohexa-1,4-diene, gamma-terpinene, BrCCl(3), diethyl dibromomalonate, or electron-deficient olefins such as acrylonitrile or dimethyl fumarate to afford functionalized tetrahydrofurans in synthetically useful yields.
Investigations into the Bromination of Substituted Phenols using Diethyl Bromomalonate and Diethyl Dibromomalonate.
Bulletin of the Chemical Society of Japan, 74(1), 179-180 (2001)
Reactions of organocobalt complexes with bromoesters: regiospecific synthesis of allyl-and cyclopropylmethyl-substituted malonic and acetoacetic esters.
Journal of Organometallic Chemistry, 209(3), 393-399 (1981)
A novel bromination for an unsaturated a-anion ester. Synthesis of 2-bromo-cis-8, cis-11, cis-14-eicosatrienoic acid.
Rec. Trav. Chim., 96(3), 72-74 (1977)
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