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651664

Sigma-Aldrich

Tetrabutylammonium azide

Synonym(s):
N,N,N-Tributyl-1-butanaminium azide, Tetrabutylammonium nitride
Empirical Formula (Hill Notation):
C16H36N4
CAS Number:
Molecular Weight:
284.48
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

form

solid

reaction suitability

reaction type: click chemistry

mp

84-88 °C (lit.)

storage temp.

2-8°C

SMILES string

[N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.N3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1

InChI key

GMRIOAVKKGNMMV-UHFFFAOYSA-N

Application

Tetrabutylammonium azide can be used as a reagent for the synthesis of:
  • Heteroarylannulated bicyclic morpholines
  • Cyanimide-based inhibitors of cathepsin C
  • Trimethylene carbonate
  • Aerobic oxidative transformation of primary azides to nitriles
  • Substitution reactions at tetracoordinate boron


It is also used as a catalyst for cyclic carbonate formation.
Reagent for synthesis of:
  • Heteroarylannulated bicyclic morpholines
  • Cyanimide-based inhibitors of cathepsin C
  • Trimethylene carbonate

Reagent for:
  • Aerobic oxidative transformation of primary azides to nitriles
  • Substitution reactions at tetracoordinate boron

Catalyst for syslic carbonate formation

Packaging

5, 25 g in glass bottle

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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