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Sigma-Aldrich

Dimethyl aminomalonate hydrochloride

97%

Synonym(s):

Aminomalonic acid dimethyl ester hydrochloride

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About This Item

Linear Formula:
NH2CH(COOCH3)2 · HCl
CAS Number:
16115-80-3
Molecular Weight:
183.59
Beilstein/REAXYS Number:
3696467
EC Number:
240-284-5
MDL number:
MFCD00038880
UNSPSC Code:
12352100
PubChem Substance ID:
24864387
NACRES:
NA.22

Quality Level

200

assay

97%

form

crystals

mp

160 °C (dec.) (lit.)

solubility

water: soluble 25 mg/mL, clear, colorless to faintly yellow

SMILES string

Cl[H].COC(=O)C(N)C(=O)OC

InChI

1S/C5H9NO4.ClH/c1-9-4(7)3(6)5(8)10-2;/h3H,6H2,1-2H3;1H

InChI key

QWNDKNJSEWOEDM-UHFFFAOYSA-N

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General description

Dimethyl aminomalonate hydrochloride is a hydrochloride salt of a dialkyl aminomalonate.

Application

Dimethyl aminomalonate hydrochloride (aminomalonic acid dimethyl ester hydrochloride) may be used in synthesis of methyl 3-phenyl-5-hydantoincarboxylate and Boc-Leu-Ama(OMe)2(Boc= tert-butyloxycarbonyl, Leu= leucine, Ama= aminomalonic acid). It may be used as starting reagent in the synthesis of the following:
  • (R,S)-2-phenethylcysteine hydrochloride
  • dimethyl 2,2,2-polynitroalkylnitroaminonitromalonate
  • spirotryprostatin B

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of Nitro Compounds Starting with Dialkyl Aminomalonates.
Ishchenko MA, et al.
Russ. J. Org. Chem., 37(2), 194-197 (2001)
D Krumme et al.
FEBS letters, 436(2), 209-212 (1998-10-22)
Novel peptides containing the sequence -Pro-Leu-Ama(NHOH)- were synthesized and characterized by spectroscopic techniques. Their inhibitory properties towards the activated form of native human gelatinase B (MMP-9) and the catalytic domain of neutrophil collagenase (cdMMP-8) were determined. The most effective inhibitor
Alpha-alkylcysteines as inhibitors for carboxypeptidase A. Synthesis, evaluation, and implication for inhibitor design strategy.
Lee HS and Kim DH.
Bull. Korean Chem. Soc., 23(4), 593-598 (2002)
Heterocyclizations, XIV. 1,3,5,7,-Tetraoxoperhydroimidazo[1,5-c]imidazole, a Novel Bridgehead Nitrogen Ureide
Capuano L, et al.
Chemische Berichte, 107(10), 3237-3245 (1974)
Oxindole as starting material in organic synthesis.
Ziarani GM, et al.
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