395315
重氮基乙酰乙酸乙酯
别名:
Ethyl Α-diazoacetoacetate, Ethyl 2-diazo-3-oxobutanoate
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关于此项目
线性分子式:
CH3COC(N2)CO2C2H5
化学文摘社编号:
分子量:
156.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Form:
liquid
InChI
1S/C6H8N2O3/c1-3-11-6(10)5(8-7)4(2)9/h3H2,1-2H3
SMILES string
CCOC(=O)C(=[N+]=[N-])C(C)=O
InChI key
JWTPSIXYXYNAOU-UHFFFAOYSA-N
vapor pressure
0.36 psi ( 20 °C)
form
liquid
availability
available only in USA
refractive index
n20/D 1.474 (lit.)
density
1.131 g/mL at 25 °C (lit.)
functional group
ester
ketone
Application
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.
- β-keto esters via C−H insertion reaction with aromatic aldehydes using NbCl5 as a catalyst.
- Diazoacetoacetate derivatives by reacting with aldehydes via aldol condensation and subsequent and in situ oxidation reaction.
- Isoquinolone and pyridone derivatives by Rh-catalyzed C−H activation/annulation reaction with various N-methoxybenzamides.
General description
Ethyl diazoacetoacetate is a diazo compound. It participates in Rh2(OAc)4-catalyzed reactions with arylalkylamines and diarylamines. Reaction of ethyl diazoacetoacetate with N-methyl pyrrole and pyrrole derivatives has been studied.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
5.2 - Organic peroxides and self-reacting hazardous materials
wgk
WGK 3
flash_point_f
185.0 °F - closed cup
flash_point_c
85 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
法规信息
新产品
此项目有
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)
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)
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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