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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+%

Numéro CAS
108-59-8
Synonymes
Propanedioic acid dimethyl ester
Malonic acid dimethyl ester

Dimensions Prix ($) Quantité Disponibilité
100g 18,27
500g 36,26
2500g 138,02
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Dimethyl malonate, 98+%

MDL
MFCD00008460
EINECS
203-597-8

Propriétés chimiques

Formule
C5H8O4
Poids formulaire
132.12
Point de fusion
-62°
Point d'ébullition
180-181°
Point d'éclair
90°(194°F)
Densité
1.156
Indice de réfraction
1.4130
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227

Combustible liquid.

Mentions de prudence: 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.

Autres références

Merck
14,6096
Beilstein
774261
Code tarifaire harmonisé
2917.19
TSCA
Yes
RTECS
OO0950000

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