Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

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

A11007 Dimethyl malonate, 98+%

CAS-Nummer
108-59-8
Synonyme
Propanedioic acid dimethyl ester
Malonic acid dimethyl ester

Größe Preis ($) Menge Verfügbarkeit
100g 18,27
500g 36,26
2500g 138,02
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Dimethyl malonate, 98+%

MDL
MFCD00008460
EINECS
203-597-8

Chemische Eigenschaften

Formel
C5H8O4
Molmasse
132.12
Schmelzpunkt
-62°
Siedepunkt
180-181°
Flammpunkt
90°(194°F)
Dichte
1.156
Brechungsindex
1.4130
Löslichkeit
Miscible with alcohol, ether and oils. Slightly miscible with water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H227

Combustible liquid.

Sicherheitshinweise: 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.

Weitere Referenzen

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

Empfohlen

Kürzlich angesehen

Chemikalien

Life science

Metalle und Stoffe

Katalysatoren

Forschungs- und Laborbedarf