Skip to Content
Merck
All Photos(1)

Key Documents

412708

Sigma-Aldrich

Diethyl dibromomalonate

97%

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
Br2C(CO2C2H5)2
CAS Number:
Molecular Weight:
317.96
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Reaction of diethyl dibromomalonate with methoxide: Evidence for a novel bromophilic attack.
Mebane RC, et al.
Tetrahedron Letters, 40(8), 1459-1462 (1999)
Dominik Schuch et al.
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.
Coumbarides GS, et al.
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.
Veber M, et al.
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.
van der Wolf L and Pabon HJJ.
Rec. Trav. Chim., 96(3), 72-74 (1977)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service