82551-63-1

Basic information

• Product Name: 4-Nitrobenzyl 2-diazoacetoacetate
• Synonyms: p-Nitrobenzyl 2-diazoacetoacetate;p-Nitrobenzyl-diazoacetoacetate;4-Nitrobenzyl 2-diazoacetoacetate;2-diazo-5-(4-nitrophenyl)-3-oxopentanoate;Butanoic acid,2-diazo-3-oxo-, (4-nitrophenyl)Methyl ester;4-nitrobenzyl 2-diazo-3-oxobutanoate;p-Nitrobenzyl -diazoacetoacetate: p-Nitrobenzyl 2-diazoacetoacetate
• CAS NO: 82551-63-1
• Molecular Formula: C₁₁H₉N₃O₅
• Molecular Weight: 263.21
• EINECS: 1806241-263-5
• Product Categories: pharmaceutical intermediates
• Mol File: 82551-63-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Nitrobenzyl 2-diazoacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrobenzyl 2-diazoacetoacetate(82551-63-1)
• EPA Substance Registry System: 4-Nitrobenzyl 2-diazoacetoacetate(82551-63-1)

Safety Data

• Hazardous Substances Data: 82551-63-1(Hazardous Substances Data)

Usage

General Description

4-Nitrobenzyl 2-diazoacetoacetate is a compound consisting of a 4-nitrobenzyl group attached to a 2-diazoacetoacetate moiety. It is a diazo compound, which means it contains a N=N double bond. This chemical compound is often used in organic synthesis as a reagent for generating carbenes, which are highly reactive intermediate species in organic chemistry. Carbenes are useful for a variety of synthetic transformations, such as cyclopropanation, insertion reactions, and C-H functionalization. 4-Nitrobenzyl 2-diazoacetoacetate is known for its ability to insert into C-H bonds of various organic compounds, making it a valuable tool for accessing complex molecular architectures. However, its high reactivity and potential hazards associated with diazo compounds require careful handling and proper precautions when working with this compound.

InChI:InChI=1/C11H9N3O5/c1-7(15)10(13-12)11(16)19-6-8-2-4-9(5-3-8)14(17)18/h2-5H,6H2,1H3

Upstream product

• 619-73-8 4-nitrobenzyl chloride 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 941-55-9 4-toluenesulfonyl azide 
• 61312-84-3 4-nitrobenzyl 3-oxobutanoate 
• 79791-38-1 4-dodecylbenzenesulphonyl azide 
• 105-45-3 acetoacetic acid methyl ester 
• 134973-72-1 2-diazoacetoacetic acid 

Downstream Products

• 86269-29-6 (Z)-(2S,8R,9S)-3,3,6-Trimethyl-10-oxo-9-(2-phenoxy-acetylamino)-7-oxa-4-thia-1-aza-bicyclo[6.2.0]dec-5-ene-2,5-dicarboxylic acid 2-benzyl ester 5-(4-nitro-benzyl) ester 
• 86288-03-1 (Z)-2-[(2R,3R)-1-((R)-1-Benzyloxycarbonyl-2-methyl-allyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-ylsulfanyl]-3-hydroxy-but-2-enoic acid 4-nitro-benzyl ester 
• 100163-31-3 secopenicillin 
• 86269-28-5 (Z)-(2S,8R,9S)-3,3,6-Trimethyl-10-oxo-9-phenylacetylamino-7-oxa-4-thia-1-aza-bicyclo[6.2.0]dec-5-ene-2,5-dicarboxylic acid 2-methyl ester 5-(4-nitro-benzyl) ester 
• 81946-79-4 4-[3-(p-nitrobenzyloxycarbonyl)-3-diazo-2-oxopropyl]-azetidin-2-one 
• 87726-17-8 panipenem 
• 1206197-77-4 C₂₅H₂₅N₃O₇ 
• 1206197-85-4 C₂₆H₂₇N₃O₆ 
• 1206197-92-3 C₂₅H₂₅N₃O₆ 

Relevant articles and documents

Functionalizing the γ-position of α-diazo-β-ketoesters

Although α-diazo-β-ketoesters are synthetically versatile intermediates, methodology for introducing this functionality into complex molecules is still limited, most frequently involving a carboxylic acid precursor, which is then activated and transformed

Atypical Carbapenem Antibiotics with Improved Activity Against Carbapenemase-Producing Acinetobacter baumannii

The following invention deals with the design, preparation, evaluation, and use of carbapenem antibiotics with improved activity, relative to current commercially available carbapenem antibiotics, against infections involving multidrug resistant, carbapen