tert-Butyl diazoacetate

Base Information

• Chemical Name: tert-Butyl diazoacetate
• CAS No.: 35059-50-8
• Molecular Formula: C6H10 N2 O2
• Molecular Weight: 142.158
• Hs Code.: 2927000090
• European Community (EC) Number: 628-315-4
• DSSTox Substance ID: DTXSID20408281
• Nikkaji Number: J645.201I
• Mol file: 35059-50-8.mol

Synonyms:tert-Butyl diazoacetate;35059-50-8;tert-Butyl 2-diazoacetate;t-butyl diazoacetate;tert-Butyl Diazoacetate, 85%;tert-Butyl Diazoacetate, 85per cent;tert-butyl-diazoacetate;DTXSID20408281;JBVSBLLOZVDAAZ-UHFFFAOYSA-N;Diazo-acetic acid tert-butyl ester;AMY15513;BCP32485;AKOS022185108;AS-81749;CS-0368614;FT-0664027;D87815;EN300-100815;t-Butyl diazoacetate;J-019846

Chemical Property of tert-Butyl diazoacetate

Chemical Property:

• Refractive Index: n20/D 1.453(lit.)
• Boiling Point: 51-53 °C12 mm Hg(lit.)
• Flash Point: 110 °F
• PSA: 63.69000
• Density: 1.026 g/mL at 25 °C(lit.)
• LogP: 0.70976
• Storage Temp.: Refrigerator
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 175

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-ButylDiazoacetate,85% ^*data from reagent suppliers

Safty Information:

• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C=[N+]=[N-]
• Uses: 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. New Diazoacetate Formulations An intermediate in the production of Zolpidem metabolites

Technology Process of tert-Butyl diazoacetate

There total 15 articles about tert-Butyl diazoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

tert-butyl acetoacetate (1694-31-1) → t-butyl diazoacetate (35059-50-8)

Guidance literature:

With 4-toluenesulfonyl azide; tetrabutylammomium bromide; sodium hydroxide; In water; pentane; at 0 ℃; for 12.3333h;

DOI:10.1021/acs.orglett.0c02138

Reference yield: 90.0%

tert-butyl 2-diazo-3-oxobutanoate (13298-76-5) → t-butyl diazoacetate (35059-50-8)

Guidance literature:

With potassium hydroxide; In diethyl ether; water; at 20 ℃; for 16h;

DOI:10.1021/jacs.1c11503

Reference yield: 70.0%

→ t-butylazidoacetoacetate + t-butyl diazoacetate (35059-50-8)

Guidance literature:

upstream raw materials:

tert-butyl 2-formamidoacetate

Glycine tert-butyl ester

glycine t-butyl ester acetate salt

(tert-Butoxycarbonylmethylene)triphenylphosphorane

Downstream raw materials:

4-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazole-3,5-dicarboxylic acid tert-butyl ester methyl ester

(S)-5-((1R,3R)-3-tert-Butoxycarbonyl-2,2-dimethyl-cyclopropyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

3-tert-Butyl-1H-1,2,4-diazaphosphol-5-carbonsaeure-tert-butylester

tert-butyl 3′H-cyclopropa[1,9](C₆₀-I_h)[5,6]fullerene-3′-carboxylate

Refernces

• 1、 Modak, Atanu,Alegre-Requena, Juan V.,De Lescure, Louis,Rynders, Kathryn J.,Paton, Robert S.,Race, Nicholas J.. "Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion". . p. 86 - 92. Retrieved 2021/12/27.
• 2、 Gao, Lizhu,Hwang, Geum-Sook,Ryu, Do Hyun. "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)". supporting information. p. 6021 - 6022. Retrieved 2021/05/13.