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480754 Sigma-Aldrich

tert-Butyl diazoacetate

  • CAS Number 35059-50-8

  • Linear Formula N2CHCO2C(CH3)3

  • Molecular Weight 142.16

  •  MDL number MFCD01318409

  •  PubChem Substance ID 24871716

  •  NACRES NA.22

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Properties

Related Categories Azo/Diazo Compounds, Building Blocks, Chemical Synthesis, Nitrogen Compounds - Organic Building Blocks, Organic Building Blocks More...
Quality Level   100
impurities   ≤15% dichloromethane
refractive index   n20/D 1.453 (lit.)
bp   51-53 °C/12 mmHg (lit.)
density   1.026 g/mL at 25 °C (lit.)
storage temp.   2-8°C
SMILES string   CC(C)(C)OC(=O)C=[N+]=[N-]
InChI   1S/C6H10N2O2/c1-6(2,3)10-5(9)4-8-7/h4H,1-3H3
InChI key   JBVSBLLOZVDAAZ-UHFFFAOYSA-N

Description

General description

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

Application

New Diazoacetate Formulations

tert-Butyl diazoacetate may be used for the preparation of tert-butyl 2-(4-chlorophenyl)cyclopropane-1-carboxylate with high enantioselectivity and trans-cis selectivity via cyclopropanation with 4-chlorostyrene in the presence of a chiral (salen)cobalt(III) bromide complex as a catalyst.

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.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Respiratory system
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
109.4 °F - closed cup
Flash Point(C) 
43 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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