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651664

Sigma-Aldrich

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
MDL number:
MFCD00060069
UNSPSC Code:
12352116
PubChem Substance ID:
24883851
NACRES:
NA.22

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

Related Categories

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

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335,H410

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

EUH032

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synthesis of bicyclic sugar azido acids and their incorporation in cyclic peptides.
Peri F, et al.
Chemical Communications (Cambridge, England), 2303-2304 (2000)
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)
Mark Furber et al.
Journal of medicinal chemistry, 57(6), 2357-2367 (2014-03-07)
A lead generation and optimization program delivered the highly selective and potent CatC inhibitor 10 as an in vivo tool compound and potential development candidate. Structural studies were undertaken to generate SAR understanding.
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