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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:
1768415
EC Number:
249-275-0
MDL number:
MFCD00042837
UNSPSC Code:
12352100
PubChem Substance ID:
24863315
NACRES:
NA.22

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

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)

224.6 °F - closed cup

Flash Point(C)

107 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0992
BCCD6418
BCBZ3642
BCBT3542
BCBS2849V

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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)
An Efficient and Practical Synthesis of Dimethyl 2-chloromalonate.
Babu GR, et al.
Der Pharma Chemica, 3(6) (2011)
New one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.
Yavari I and Baharfar R.
Tetrahedron Letters, 39(9), 1051-1054 (1998)
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)
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