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651664

Tetrabutylammonium azide

Synonym(s):

N,N,N-Tributyl-1-butanaminium azide, Tetrabutylammonium nitride

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About This Item

Empirical Formula (Hill Notation):
C16H36N4
CAS Number:
993-22-6
Molecular Weight:
284.48
NACRES:
NA.22
PubChem Substance ID:
24883851
UNSPSC Code:
12352116
MDL number:
MFCD00060069
Form:
solid
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form

solid

Quality Level

200

reaction suitability

core: ammonium, reaction type: click chemistry

mp

84-88 °C (lit.)

functional group

amine, azide

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

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
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.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

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

supp_hazards

EUH032

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKAA4541
MKAA2641
70996MJ
71296MJ
83097LJ

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A facile catalytic synthesis of trimethylene carbonate from trimethylene oxide and carbon dioxide.
Darensbourg DJ, et al.
Green Chemistry, 12(8), 1376-1379 (2010)
Substitution Reactions at Tetracoordinate Boron: Synthesis of N-Heterocyclic Carbene Boranes with Boron- Heteroatom Bonds.
Solovyev A, et al.
Journal of the American Chemical Society, 132(42), 15072-15080 (2010)
Aerobic oxidative transformation of primary azides to nitriles by ruthenium hydroxide catalyst.
He J, et al.
The Journal of Organic Chemistry, 76(11), 4606-4610 (2011)
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