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

Chemical Properties

Yellow Oil

Uses

Different sources of media describe the Uses of 35059-50-8 differently. You can refer to the following data:
1. It is a key starting material in the total synthesis of manzacidin A. It can also be used in the synthesis of diastero- and enantioselective synthesis of 2-vinylcyclopropa[b]indolines from 2-vinylindoles.
2. New Diazoacetate Formulations
3. An intermediate in the production of Zolpidem metabolites

General Description

tert-Butyl diazoacetate can be used for numerous organic transformations, including cyclopropanation, insertion, and aziridine-forming reactions.

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 
• 540-88-5 acetic acid tert-butyl ester 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 27532-96-3 glycine tert-butyl ester hydrochloride 

Downstream Products

• 130994-95-5 (2R,5R,7R,8R)-3-Methylene-9-oxo-8-(2-phenoxy-acetylamino)-6-thia-1-aza-bicyclo[5.2.0]nonane-2,5-dicarboxylic acid 5-tert-butyl ester 2-(4-nitro-benzyl) ester 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 131899-83-7 (1R,2S)-tert-butyl 2-phenylcyclopropane-1-carboxylate 
• 105367-35-9 (1S,2R)-tert-butyl 2-phenylcyclopropane-1-carboxylate 
• 5279-78-7 t-butyl (1S,2S)-trans-2-phenyl-cyclopropane-1-carboxylate 
• 7633-38-7 di-tert-butyl fumarate 
• 18305-60-7 di-tert-butyl maleate 
• 5279-78-7 tert-butyl (1R,2R)-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.

Erratum: Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers (J. Am. Chem. Soc. (2011) 133:51 (20708?20711) DOI: 10.1021/ja209270e)

Pages 20709 and 20710. In the published version of the paper, the trans:cis ratios of 2w and 2x were reversed. The revised results were confirmed by NOE experiments and comparison of the optical rotation data with reported values after transformation. The

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.