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:
Molecular Weight:
166.56
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
249-275-0
Beilstein/REAXYS Number:
1768415
MDL number:
Assay:
94%
Form:
liquid
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.)
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
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.
signalword
Danger
hcodes
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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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 374539-25G | 04061831834727 |
| 374539-100G | 04061836692124 |