537349
Ethyl acetoacetate
ReagentPlus®, 99%
동의어(들):
EAA, Ethyl 3-oxobutanoate, Acetoacetic ester
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
Linear Formula:
CH3COCH2COOC2H5
CAS 번호:
Molecular Weight:
130.14
Beilstein:
385838
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22
vapor density
4.48 (vs air)
Quality Level
vapor pressure
1 mmHg ( 28.5 °C)
제품 라인
ReagentPlus®
분석
99%
autoignition temp.
580 °F
expl. lim.
9.5 %
bp
181 °C (lit.)
mp
−43 °C (lit.)
solubility
water: soluble 130 g/L at 20 °C
density
1.029 g/mL at 20 °C (lit.)
작용기
ester
ketone
SMILES string
CCOC(=O)CC(C)=O
InChI
1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI key
XYIBRDXRRQCHLP-UHFFFAOYSA-N
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관련 카테고리
애플리케이션
Ethyl acetoacetate is a versatile reagent that can be used as a nucleophile in alkylation, conjugate addition and condensation reactions. Some of its applications are:
- Alkylation at the α-carbon of ethyl acetoacetate followed by hydrolysis and decarboxylation can afford a variety of methyl ketones.
- It also undergoes acylation at the α-carbon in the presence of MgCl2 and pyridine to give synthetically important intermediates.
- It can be used in Knoevenagel condensation with aliphatic, aromatic, and heteroaromatic aldehydes to produce α-alkylideneacetoacetates.
법적 정보
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class Code
10 - Combustible liquids
WGK
WGK 1
Flash Point (°F)
164.3 °F - closed cup
Flash Point (°C)
73.5 °C - closed cup
개인 보호 장비
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Ethyl Acetoacetate.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Synthetic Applications of Dealkoxycarbonylations of Malonate Esters, β-Keto Esters, α-Cyano Esters and Related Compounds in Dipolar Aprotic Media-Part II.
Krapcho A P
Synthesis, 1982(11), 893-914 (1982)
Knoevenagel-kondensationen mit titantetrachlorid/base?II: Alkyliden-und arylidenacet-bzw.-nitroessigester bei 0?22?.
Lehnert W
Tetrahedron, 28(3), 663-666 (1972)
Procedures for the acylation of diethyl malonate and ethyl acetoacetate with acid chlorides using tertiary amine bases and magnesium chloride.
Rathke MW and Cowan PJ.
The Journal of Organic Chemistry, 50(15), 2622-2624 (1985)
Gui-Rong Qu et al.
Organic letters, 11(8), 1745-1748 (2009-03-20)
A novel approach to the synthesis of purines bearing functionalized carbon substituents or methyl in position 6 was developed. Under different reaction conditions, 6-halopurine derivatives could react with ethyl acetoacetate efficiently to yield 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates and 6-methylpurines
문서
The Biginelli Reaction is an acid-catalyzed, three-component reaction between an aldehyde, b-ketoester, and urea that produces tetrahydropyrimidones, which have potential pharmaceutical applications.
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