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4-Nitrobenzyl 2-diazoacetoacetate is a diazo compound characterized by the presence of a 4-nitrobenzyl group attached to a 2-diazoacetoacetate moiety. It is known for its ability to generate highly reactive carbenes, which are intermediate species in organic chemistry, and is utilized for various synthetic transformations.

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  • 82551-63-1 Structure
  • Basic information

    1. Product Name: 4-Nitrobenzyl 2-diazoacetoacetate
    2. 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
    3. CAS NO:82551-63-1
    4. Molecular Formula: C11H9N3O5
    5. Molecular Weight: 263.21
    6. EINECS: 1806241-263-5
    7. Product Categories: pharmaceutical intermediates
    8. Mol File: 82551-63-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 4-Nitrobenzyl 2-diazoacetoacetate(CAS DataBase Reference)
    10. NIST Chemistry Reference: 4-Nitrobenzyl 2-diazoacetoacetate(82551-63-1)
    11. EPA Substance Registry System: 4-Nitrobenzyl 2-diazoacetoacetate(82551-63-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 82551-63-1(Hazardous Substances Data)

82551-63-1 Usage

Uses

Used in Organic Synthesis:
4-Nitrobenzyl 2-diazoacetoacetate is used as a reagent for generating carbenes, which are highly reactive intermediates in organic chemistry. These carbenes are employed in a variety of synthetic transformations, such as cyclopropanation, insertion reactions, and C-H functionalization.
Used in the Synthesis of Complex Molecular Architectures:
4-Nitrobenzyl 2-diazoacetoacetate is used as a valuable tool for accessing complex molecular architectures due to its ability to insert into C-H bonds of various organic compounds. This property makes it a useful component in the development of novel chemical entities and pharmaceuticals.
Used in Research and Development:
In the research and development industry, 4-Nitrobenzyl 2-diazoacetoacetate is used as a key compound for exploring new chemical reactions and mechanisms, contributing to the advancement of organic chemistry and the discovery of new synthetic pathways.

Check Digit Verification of cas no

The CAS Registry Mumber 82551-63-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,5,5 and 1 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 82551-63:
(7*8)+(6*2)+(5*5)+(4*5)+(3*1)+(2*6)+(1*3)=131
131 % 10 = 1
So 82551-63-1 is a valid CAS Registry Number.
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

82551-63-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Nitrobenzyl 2-diazo-3-oxobutanoate

1.2 Other means of identification

Product number -
Other names 4-Nitrobenzyl 2-diazoacetoacetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:82551-63-1 SDS

82551-63-1Downstream Products

82551-63-1Relevant articles and documents

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

Nguyen, Thu Q.,Alqurafi, Maha,Edwards, Cash,Nguyen, Pauline,Kim, Jean,Casco, Samuel,Bennet, Maricka,Chiang, Christopher,Lohry, Maureen,Cox, Melina,Meshram, Byron,Le, Duyen,Kim, Eugene,Smriti, Snigdha,Oelschlaeger, Peter,Buynak, John D.

, p. 3330 - 3333 (2016)

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

Method for preparing 2 - diazo acetoacetic acid P-nitrobenzyl ester through microchannel reactor

-

Paragraph 0073-0106, (2021/08/25)

The invention relates to a method for preparing 2 -nitrobenzyl acetate through a microchannel reactor, which comprises the following steps: reacting a haloalkane solution of diketene, 4 - nitrobenzyl alcohol and a catalyst in a microchannel reactor A. The

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

-

Paragraph 0022, (2020/11/30)

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

Six-Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process of N-Silyloxy-3,6-dihydro-2H-1,2-oxazines

Shved, Alexander S.,Tabolin, Andrey A.,Novikov, Roman A.,Nelyubina, Yulia V.,Timofeev, Vladimir P.,Ioffe, Sema L.

supporting information, p. 5569 - 5578 (2016/11/25)

Silyl nitronates undergo rhodium-catalyzed formal [3+3]-cycloaddition with enol diazoacetates to form N-silyloxy-3,6-dihydro-2H-1,2-oxazines. The scope of the reaction and the extent of the major side process were evaluated. A mechanistic scheme was propo

Construction of enantiomerically enriched diazo compounds using diazo esters as nucleophiles: Chiral Lewis base catalysis

Mao, Haibin,Lin, Aijun,Shi, Yan,Mao, Zhijie,Zhu, Xuebin,Li, Weipeng,Hu, Hongwen,Cheng, Yixiang,Zhu, Chengjian

supporting information, p. 6288 - 6292 (2013/07/05)

Amazing diazo: The title reaction leads to highly functionalized diazo compounds in good yields with excellent enantioselectivities (see scheme; Boc=tert-butoxycarbonyl). The utility of the products was demonstrated by the rapid synthesis of a number of o

2-Diazoacetoacetic acid, an efficient and convenient reagent for the synthesis of α-diazo-β-ketoesters

Meyer, Michael E.,Ferreira, Eric M.,Stoltz, Brian M.

, p. 1316 - 1318 (2008/02/03)

The formation of various α-diazo acetoacetic esters can be obtained in a single transformation with good to excellent yields using readily available 2-diazoacetoacetic acid. The Royal Society of Chemistry 2006.

Process for the preparation of 2-diazo-3-trisubstituted silyloxy 3-butenoates

-

, (2008/06/13)

A novel process for preparing 2-diazo-3-trisubstituted silyloxy-3-butenoates, synthons useful in the conversion of 3-substituted-4-acetoxy azetidinones and penicillin to thienamycin, imipenem and other carbapenem antibiotic compounds is provided, comprisi

Process for the preparation of carbapenem intermediates

-

, (2008/06/13)

A process for the preparation of a 4-[3-carboxy-3-diazo-2-oxopropyl]azetidin-2-one of the formula STR1 comprising reacting a 4-acetoxy-2-azetininone of the formula STR2 with a compound of the formula STR3 in an inert solvent, in the presence of a base and of a silylating agent, in a one-pot process. Many of the products are new. The products are useful in the synthesis of carbapenem antibiotics.

Substituted 6-hydroxymethyl-carbapenem antibiotics

-

, (2008/06/13)

Substituted 6-hydroxymethyl-carbapenem antibiotics of the formula STR1 in which R1 is --OR4, STR2 A is a direct bond, or an alkylene and/or cycloalkylene radical, R2 is a group of the formula STR3 an aryl or heterocyclic r

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