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Merck
CN

374539

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863315
EC Number:
249-275-0
Beilstein/REAXYS Number:
1768415
MDL number:
MFCD00042837
Assay:
94%
Form:
liquid

Key Documents

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InChI key

LNBQBURECUEBKZ-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

94%

form

liquid

impurities

4-5% dimethyl dichloromalonate

Quality Level

200

bp

105-106 °C/19 mmHg (lit.)

density

1.305 g/mL at 25 °C (lit.)

functional group

chloro, ester

Related Categories

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

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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A preparative method for Synthesis of 4, 5, 6-trichloropyrimidine.
Ostrowski S, et al.
ARKIVOC (Gainesville, FL, United States), 6, 905-908 (2000)
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
New one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.
Yavari I and Baharfar R.
Tetrahedron Letters, 39(9), 1051-1054 (1998)
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)
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