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A11007 Dimethyl malonate, 98+%

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

Stock No. Size Price ($) Quantity Availability
A11007-22 100g 21.50
A11007-36 500g 38.20
A11007-0E 2500g 146.00
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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
Storage & Sensitivity
Ambient temperatures.
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-H320

Combustible liquid. Causes eye irritation.

Precautionary Statements: P210-P233-P240-P241-P242-P243-P264b-P280-P305+P351+P338-P337+P313-P374-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice/attention. Fight fire with normal precautions from a reasonable distance. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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