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374539

Sigma-Aldrich

Dimethyl chloromalonate

94%

Synonym(s):

1,3-Dimethyl 2-chloropropanedioate, 2-Chloro-malonic acid dimethyl ester, Chloropropanedioic acid dimethyl ester, Dimethyl α-chloromalonate, Dimethyl 2-chloromalonate, Dimethyl 2-chloropropanedioate

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About This Item

Linear Formula:
ClCH(COOCH3)2
CAS Number:
28868-76-0
Molecular Weight:
166.56
Beilstein/REAXYS Number:
1768415
EC Number:
249-275-0
MDL number:
MFCD00042837
UNSPSC Code:
12352100
PubChem Substance ID:
24863315
NACRES:
NA.22

Quality Level

200

assay

94%

form

liquid

impurities

4-5% dimethyl dichloromalonate

refractive index

n20/D 1.437 (lit.)

bp

105-106 °C/19 mmHg (lit.)

density

1.305 g/mL at 25 °C (lit.)

functional group

chloro
ester

SMILES string

COC(=O)C(Cl)C(=O)OC

InChI

1S/C5H7ClO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3

InChI key

LNBQBURECUEBKZ-UHFFFAOYSA-N

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General description

Dimethyl chloromalonate (dimethyl 2-chloromalonate) is a dialkyl 2-substituted malonate. Carbanions of dimethyl chloromalonate are reported to react with naphthoquinone derivatives, via vicarious nucleophilic substitution or oxidative nucleophilic substitution of hydrogen processes. Dimethyl chloromalonate is reported to react with hydroquinone and monosubstituted hydroquinones to afford 2-oxido-benzo[b]furan derivatives. Synthesis of dimethyl 2-chloromalonate, via chlorination of dimethyl malonate has been reported.

Application

Dimethyl chloromalonate is suitable for use in the synthesis of 4,5,6-trichloropyrimidine. It may be used in the stereoselective synthesis of highly functionalized nitrocyclopropanes. It may be used in one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

224.6 °F - closed cup

flash_point_c

107 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0992
BCCD6418
BCBZ3642
BCBT3542
BCBS2849V

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Séamus H McCooey et al.
The Journal of organic chemistry, 71(19), 7494-7497 (2006-09-09)
A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported. The addition of dimethyl chloromalonate to a variety of nitroolefins catalyzed by tertiary amines leads to a Michael adduct which cyclizes to form
A preparative method for Synthesis of 4, 5, 6-trichloropyrimidine.
Ostrowski S, et al.
ARKIVOC (Gainesville, FL, United States), 6, 905-908 (2000)
Vicarious nucleophilic substitution of hydrogen (VNS) in 1, 4-naphthoquinone derivatives-competition between VNS and vinylic nucleophilic substitution (SN V).
Ma?kosza M and Nizamov S.
Tetrahedron, 57(47), 9615-9621 (2001)
The reaction of hydroquinone and monosubstituted hydroquinones with dimethyl chloromalonate.
Renfrew AH, et al.
Journal of the Chemical Society. Perkin Transactions 1, 2382-2386 (1979)
An Efficient and Practical Synthesis of Dimethyl 2-chloromalonate.
Babu GR, et al.
Der Pharma Chemica, 3(6) (2011)
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