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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 번호
108-59-8
동의어
Propanedioic acid dimethyl ester
Malonic acid dimethyl ester

사이즈 가격 ($) 수량 재고 여부
100g 20.50
500g 36.40
2500g 139.00
장바구니에 추가 대량 견적에 추가 항목 보기

Dimethyl malonate, 98+%

MDL
MFCD00008460
EINECS
203-597-8

화학적 특성

화학식
C5H8O4
화학 식량
132.12
융점
-62°
비등점
180-181°
인화점
90°(194°F)
밀도
1.156
굴절률
1.4130
용해도
Miscible with alcohol, ether and oils. Slightly miscible with water.

용도

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.

참고

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

참조 문헌

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 해저드 및 주의 설명서

해저드 설명서 (EU): H227

Combustible liquid.

주의 설명서: P210u-P280a-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/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.

기타 참조

Merck
14,6096
바일슈타인
774261
통합 관세 코드
2917.19
TSCA(독성물질규제법)"
Yes
RTECS(화학물질 독성 등록)
OO0950000

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