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437786

Diethyl chloromalonate

Name: Diethyl chloromalonate
Brand: ALDRICH

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About This Item

Linear Formula:

ClCH(CO₂C₂H₅)₂

CAS Number:

14064-10-9

Molecular Weight:

194.61

NACRES:

NA.22

PubChem Substance ID:

24867397

UNSPSC Code:

12352100

EC Number:

237-913-0

MDL number:

MFCD00009140

Assay:

95%

Form:

liquid

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Properties

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

Description

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 Se_n to afford the corresponding diethyl thioxo- or selenoxomalonates, which can be trapped in situ with various 1,3-dienes.

pictograms

GHS05,GHS07,GHS09

signalword

Danger

hcodes

H314,H335,H400

pcodes

P261 - P271 - P273 - P280 - P303 + P361 + P353 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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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)

Preparation of 2-amino-4(3H)-oxopyrimido[5,4-b] [1,4]thiazines (5-thiapterins) and their evaluation as cofactors for phenylalanine hydroxylase.

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

K2CO3-promoted domino reactions: construction of functionalized 2,3-dihydrobenzofurans and clofibrate analogues.

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

Global Trade Item Number

SKU	GTIN
437786-5ML	04061836677657
437786-25ML	04061832120560