140775

Tetrabutylammonium iodide

reagent grade, 98%

• Synonym(s): TBAI
• Linear Formula: (CH₃CH₂CH₂CH₂)₄N(I)
• CAS Number: 311-28-4
• Molecular Weight: 369.37
• Beilstein/REAXYS Number: 3916152
• EC Number: 206-220-5
• MDL number: MFCD00011636
• UNSPSC Code: 12352107
• PubChem Substance ID: 24848477
• NACRES: NA.22

Properties

• grade: reagent grade
• assay: 98%
• form: solid
• mp: 141-143 °C (lit.)
• SMILES string: [I-].CCCC[N+](CCCC)(CCCC)CCCC
• InChI: 1S/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
• InChI key: DPKBAXPHAYBPRL-UHFFFAOYSA-M

Description

Application

Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:

• Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.
• Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.
• Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.

Other reactions where TBAI can be used as a catalyst:

• TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.
• Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.
• Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H315,H319
• pcodes: P264 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P332 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves