Skip to Content
Merck

651664

Tetrabutylammonium azide

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

SMILES string

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

InChI key

GMRIOAVKKGNMMV-UHFFFAOYSA-N

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

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

651664-BULK: + 651664-25G: + 651664-5G: + 651664-VAR:

jan

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4409
MKCP6023
MKCP6081
MKCL0899
MKCJ7544

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Synthesis of bicyclic sugar azido acids and their incorporation in cyclic peptides.
Peri F, et al.
Chemical Communications (Cambridge, England), 2303-2304 (2000)
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.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service