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108-59-8 - Dimethyl malonate, 98+% - Propanedioic acid dimethyl ester - Malonic acid dimethyl ester - A11007 - Alfa Aesar

A11007 Dimethyl malonate, 98+%

CAS Number
108-59-8
Synonyms
Propanedioic acid dimethyl ester
Malonic acid dimethyl ester

Size Price ($) Quantity Availability
100g 18.27
500g 36.26
2500g 138.02
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Dimethyl malonate, 98+%

MDL
MFCD00008460
EINECS
203-597-8

Chemical Properties

Formula
C5H8O4
Formula Weight
132.12
Melting point
-62°
Boiling Point
180-181°
Flash Point
90°(194°F)
Density
1.156
Refractive Index
1.4130
Solubility
Miscible with alcohol, ether and oils. Slightly miscible with water.

Applications

Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.

Notes

Incompatible with acids, bases, oxidizing agents and reducing agents.

Literature References

For successive C-alkylation, using NaOMe/MeOH, followed by NaH/THF, see: Org. Synth. Coll., 8, 381 (1993). For Michael addition to ɑß-unsaturated acids, catalyzed by the Li salt of L-proline, see: J. Chem. Soc., Chem. Commun., 1088 (1991). For Knoevenagel reaction with (R)-citronellal, catalyzed by piperidine/AcOH, to give the alkylidene derivative, see: Org. Synth. Coll., 9, 310 (1998).

C-Arylation with ortho-nitroaryl halides can be accomplished with NaH in DMSO. The products can be readily converted to substituted oxindoles: Synthesis, 51 (1993):

Arylation with benzene: Tetrahedron Lett., 27, 2763 (1986), and free-radical substitution with thiophene or furan at the 2-position: Heterocycles, 27, 2627 (1988), are promoted by Ce(IV) salts.

See also Diethyl­ malonate, A15468.

Zhang, J.; Shao, Y.; Wang, Y.; Li, H.; Xu, D.; Wan, X. Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP. Org. Biomol. Chem. 2015, 13 (13), 3982-3987.

Mao, J.; Liu, D.; Li, Y.; Zhao, J.; Rong, G.; Yan, H.; Zhang, G. Temperature-controlled NaI-mediated α-oxybenzoylation or oxyacylation-decarboxylation reactions of dimethyl malonate with carboxylic acids. Catal. Commun. 2015, 70, 62-65.

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6096
Beilstein
774261
Harmonized Tariff Code
2917.19
TSCA
Yes
RTECS
OO0950000

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