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395315

Sigma-Aldrich

重氮基乙酰乙酸乙酯

别名:

Ethyl Α-diazoacetoacetate, Ethyl 2-diazo-3-oxobutanoate

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About This Item

线性分子式:
CH3COC(N2)CO2C2H5
CAS号:
2009-97-4
分子量:
156.14
MDL编号:
MFCD09039264
UNSPSC代码:
12352100
PubChem化学物质编号:
24864652
NACRES:
NA.22
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蒸汽压

0.36 psi ( 20 °C)

表单

liquid

存货情况

available only in USA

折射率

n20/D 1.474 (lit.)

密度

1.131 g/mL at 25 °C (lit.)

官能团

ester
ketone

SMILES字符串

CCOC(=O)C(=[N+]=[N-])C(C)=O

InChI

1S/C6H8N2O3/c1-3-11-6(10)5(8-7)4(2)9/h3H2,1-2H3

InChI key

JWTPSIXYXYNAOU-UHFFFAOYSA-N

一般描述

Ethyl diazoacetoacetate is a diazo compound. It participates in Rh2(OAc)4-catalyzed reactions with arylalkylamines and diarylamines.[1] Reaction of ethyl diazoacetoacetate with N-methyl pyrrole and pyrrole derivatives has been studied.[2]

应用

Ethyl diazoacetoacetate can be used as a reactant to synthesize:
  • 1,4-oxathiocines and thiopyran derivatives via Rh-catalyzed reaction with 2-amino-4,5-dihydro-3-thiophenecarbonitriles.[3]
  • β-keto esters via C−H insertion reaction with aromatic aldehydes using NbCl5 as a catalyst.[4]
  • Diazoacetoacetate derivatives by reacting with aldehydes via aldol condensation and subsequent and in situ oxidation reaction.[5]
  • Isoquinolone and pyridone derivatives by Rh-catalyzed C−H activation/annulation reaction with various N-methoxybenzamides.[6]

象形图

FlameExclamation mark
GHS02,GHS07

警示用语：

Danger

危险分类

Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

闪点(°F)

185.0 °F - closed cup

闪点(°C)

85 °C - closed cup

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
SHBH1120V
SHBC2445V
SHBB0043V
78696DJ
01308BJ

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Sigma-Aldrich

136441

丙二酸二甲酯

Synthesis of 1, 4-Oxathiocines and Thiopyrans by the Reaction of 2-Amino-4, 5-dihydro-3-thiophenecarbonitriles with Ethyl Diazoacetoacetate
Yamagata K, et al.
Liebigs Annalen der Chemie , 1996(5), 725-729 (1996)
Niobium (V) chloride-catalyzed C-H insertion reactions of ?-diazoesters: synthesis of β-keto esters
Yadav JS, et al.
Tetrahedron, 61(4), 875-878 (2005)
Reaction of dimethyl diazomalonate and ethyl 2-diazoacetoacetate with N-methylpyrrole.
Maryanoff BE.
The Journal of Organic Chemistry, 47(15), 3000-3002 (1982)
Niobium (V) chloride-catalyzed C-H insertion reactions of a-diazoesters: synthesis of ?-keto esters.
Yadav JS, et al.
Tetrahedron, 61(4), 875-878 (2005)
Marvis O Erhunmwunse et al.
The Journal of organic chemistry, 73(21), 8675-8677 (2008-10-09)
Diazoacetoacetate derivatives can be simply and efficiently prepared from aldehydes in a one-pot process involving initial DBU-promoted "aldol" condensation with ethyl diazoacetate followed by in situ oxidation with IBX. Aryl, alkyl, and unsaturated aldehydes are all viable substrates.
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