374539
氯丙二酸二甲酯
94%
别名:
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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关于此项目
线性分子式:
ClCH(COOCH3)2
化学文摘社编号:
分子量:
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
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
bp
105-106 °C/19 mmHg (lit.)
density
1.305 g/mL at 25 °C (lit.)
functional group
chloro, ester
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
存储类别
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
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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