All Photos(1)
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
Linear Formula:
ClCH(COOCH3)2
CAS Number:
Molecular Weight:
166.56
Beilstein:
1768415
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.)
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
WGK
WGK 3
Flash Point(F)
224.6 °F
Flash Point(C)
107 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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)
New one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.
Yavari I and Baharfar R.
Tetrahedron Letters, 39(9), 1051-1054 (1998)
An Efficient and Practical Synthesis of Dimethyl 2-chloromalonate.
Babu GR, et al.
Der Pharma Chemica, 3(6) (2011)
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)
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