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437786

Sigma-Aldrich

Diethyl chloromalonate

95%

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About This Item

Linear Formula:
ClCH(CO2C2H5)2
CAS Number:
14064-10-9
Molecular Weight:
194.61
EC Number:
237-913-0
MDL number:
MFCD00009140
UNSPSC Code:
12352100
PubChem Substance ID:
24867397
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.432 (lit.)

density

1.204 g/mL at 25 °C (lit.)

functional group

chloro
ester

SMILES string

CCOC(=O)C(Cl)C(=O)OCC

InChI

1S/C7H11ClO4/c1-3-11-6(9)5(8)7(10)12-4-2/h5H,3-4H2,1-2H3

InChI key

WLWCQKMQYZFTDR-UHFFFAOYSA-N

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General description

Diethyl chloromalonate (Diethyl α-chloromalonate) is a 2-halo-1,3-dicarbonyl compound. It participates in K2CO3-catalyzed domino reactions (Michael alkylation, Mannich alkylation, and aldol alkylation) of salicylic aldehyde derivatives to afford functionalized 2,3-dihydrobenzofurans. It reacts with Cs2CO3 in the presence of elemental S8 or Sen to afford the corresponding diethyl thioxo- or selenoxomalonates, which can be trapped in situ with various 1,3-dienes.

Signal Word

Danger

Hazard Statements

H314,H335,H400

Hazard Classifications

Aquatic Acute 1 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

437786-BULK:
437786-25ML:
437786-5ML:
437786-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ5302V
MKBP8752V
03596PJ
05828HH
06420TE

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R N Henrie et al.
Journal of medicinal chemistry, 26(4), 559-563 (1983-04-01)
Reaction of diethyl chloromalonate with beta-mercapto amines, 9, gave 1,4-thiazin-3-ones, 10, which were alkylated exclusively at the lactam oxygen with triethyloxonium tetrafluoroborate and subsequently condensed with guanidine to give the first reported 5-thiapterins, 8. Oxidation of 8 with m-chloroperoxybenzoic acid
Preparation of cycloaddition chemistry of thio-and selenocarbonyls derived from reaction of elemental sulfur and selenium with stabilized a-halo anions.
Abelman MM.
Tetrahedron Letters, 32(50), 7389-7392 (1990)
Qu-Bo Li et al.
The Journal of organic chemistry, 76(17), 7222-7228 (2011-07-29)
The K(2)CO(3)-catalyzed domino reactions (Michael alkylation, Mannich alkylation, and aldol alkylation) of salicylic aldehyde derivatives (2-hydroxyaryl-α,β-unsaturated ketones, 2-hydroxyarylnitroalkenes, 2-hydroxyarylimines, and salicylic aldehydes) and 2-halo-1,3-dicarbonyl compounds (diethyl α-bromomalonate, diethyl α-chloromalonate, ethyl 2-chloroacetoacetate, and 3-chloropentane-2,4-dione) were carried out under mild conditions to

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