35059-50-8

Basic information

• Product Name: TERT-BUTYL DIAZOACETATE
• Synonyms: TERT-BUTYL DIAZOACETATE;(tert-Butoxycarbonyl)diazoMethane;2-Diazo-acetic Acid 1,1-DiMethylethyl Ester;tert-butyl 2-diazoacetate;tert-ButylDiazoacetate,85%;2-Diazoacetic acid tert-butyl ester solution;tert-Butyl diazoacetate solution
• CAS NO: 35059-50-8
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16
• Product Categories: Azo/Diazo Compounds;Nitrogen Compounds;Organic Building Blocks;Intermediates
• Mol File: 35059-50-8.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 51-53 °C12 mm Hg(lit.)
• Flash Point: 110 °F
• Appearance: /
• Density: 1.026 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: Refrigerator
• CAS DataBase Reference: TERT-BUTYL DIAZOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL DIAZOACETATE(35059-50-8)
• EPA Substance Registry System: TERT-BUTYL DIAZOACETATE(35059-50-8)

Safety Data

• Hazard Codes: T,F
• Statements: 45-10-22-36/37/38-63-67-65-48/20-38-11
• Safety Statements: 53-16-23-36/37/39-45-36/37-26-62
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 35059-50-8(Hazardous Substances Data)

Usage

Description

TERT-BUTYL DIAZOACETATE is a versatile chemical compound with the chemical formula C8H12N2O2. It is a yellow oil and serves as a key starting material in various organic synthesis processes. Its unique chemical properties allow it to participate in numerous organic transformations, such as cyclopropanation, insertion, and aziridine-forming reactions.

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL DIAZOACETATE is used as a key starting material for the total synthesis of manzacidin A, a compound with potential pharmaceutical applications. Its role in this synthesis process is crucial for the development of new drugs and therapies.
Used in Chemical Synthesis:
TERT-BUTYL DIAZOACETATE is used as an intermediate in the production of Zolpidem metabolites, which are important in the pharmaceutical industry for the development of sleep aids and other related medications.
Used in Diazoacetate Formulations:
TERT-BUTYL DIAZOACETATE is used as a component in new diazoacetate formulations, which are essential for various chemical reactions and processes in the chemical industry.
Used in Stereoselective Synthesis:
TERT-BUTYL DIAZOACETATE is used as a reagent in the diasteroand enantioselective synthesis of 2-vinylcyclopropa[b]indolines from 2-vinylindoles. This application is significant in the field of organic chemistry, as it allows for the creation of specific molecular structures with desired properties.

InChI:InChI=1/C6H10N2O2/c1-6(2,3)10-5(9)4-8-7/h4H,1-3H3

Upstream product

• 51354-15-5 tert-butyl 2-formamidoacetate 
• 6456-74-2 Glycine tert-butyl ester 
• 117880-89-4 glycine t-butyl ester acetate salt 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 1694-31-1 tert-butyl acetoacetate 
• 14661-69-9 p-toluenesulfonylhydrazone glyoxylic acid chloride 
• 75-65-0 tert-butyl alcohol 
• 13298-76-5 tert-butyl 2-diazo-3-oxobutanoate 
• 6297-93-4 tert-butyl 2-(1,3-dioxoisoindolin-2-yl)acetate 
• 35000-37-4 (tert-butyloxycarbonylmethyl)triphenylphosphonium chloride 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 540-88-5 acetic acid tert-butyl ester 

Downstream Products

• 51425-03-7 4-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazole-3,5-dicarboxylic acid tert-butyl ester methyl ester 
• 16537-06-7 cyclohexyl-acetic acid tert-butyl ester 
• 92788-82-4 Phenylhydrazon des Glyoxylsaeure-tert.-butylesters 
• 50595-15-8 tert-butyl glycolate 
• 13994-40-6 tert-butyl nitrodiazoacetate 
• 6439-94-7 5-phenoxycarbonylamino-[1,2,3]thiadiazole-4-carboxylic acid tert-butyl ester 
• 5279-78-7 tert-butyl (1R,2R)-2-phenylcyclopropane-1-carboxylate 
• 131899-83-7 (1R,2S)-tert-butyl 2-phenylcyclopropane-1-carboxylate 
• 7633-38-7 di-tert-butyl fumarate 
• 105367-35-9 (1S,2R)-tert-butyl 2-phenylcyclopropane-1-carboxylate 
• 5279-78-7 t-butyl (1S,2S)-trans-2-phenyl-cyclopropane-1-carboxylate 
• 18305-60-7 di-tert-butyl maleate 
• 5279-78-7 (1R*,2R*)-tert-butyl 2-phenylcyclopropanecarboxylate 
• 5279-78-7 tert-butyl cis-2-phenylcyclopropane-1-carboxylate 

Relevant articles and documents

Dramatic influence of ester steric hindrance on the diastereoselectivity of a Michael addition towards the synthesis of the ABC tricycle of hexacyclinic acid

During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we observed an unexpected influence of the steric bulk of the ester group of the Michael acceptor in a key conjugate addition. We propose an eight-membered ring transition state to explain the formation of the undesired diastereomer in the case of unhindered esters.

Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization

Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.

Tridentate Nickel(II)-Catalyzed Chemodivergent C-H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles

A Schiff-base nickel(II)-phosphene-catalyzed chemodivergent C-H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni center facilitates the ligand dissociation, generating the electronically and coordinatively unsaturated active catalyst. The proposed mechanisms for the reported reactions are in good accord with the experimental results and theoretical calculations, providing a suitable model of stereocontrol for the cyclopropanation reaction.