• Chemical structure of TBAI (tetrabutylammonium iodide), CAS 311-28-4, ≥97% — quaternary ammonium iodide (C16H36IN) whose four butyl chains make the cation lipophilic enough to carry iodide into organic phases, where the poorly solvated anion is strongly nucleophilic. Used as a phase-transfer catalyst, as an iodide source for nucleophilic displacement and halide exchange, with TBHP for oxidative C-H functionalisation, and as a supporting electrolyte in non-aqueous electrochemistry. Supplied by NorrChemica
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NorrChemica™

TBAI (Tetrabutylammonium Iodide)

CAS 311-28-4 ≥97%

TBAI (Tetrabutylammonium Iodide) | CAS 311-28-4 | ≥97%

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Technical Specifications

CAS Number 311-28-4
EC / EINECS Number 206-220-5
MDL Number MFCD00011636
SMILES CCCC[N+](CCCC)(CCCC)CCCC.[I-]
InChI 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
InChIKey DPKBAXPHAYBPRL-UHFFFAOYSA-M
PubChem CID 67553
Molecular Formula C₁₆H₃₆IN
Molecular Weight 369.37 g/mol
Melting Point 144–149 °C
Solubility Soluble in water, ethanol and acetone, acetonitrile. Slightly soluble in chloroform and benzene.
Purity ≥97%
Physical Form White to almost white powder to crystal
HS Code 2923.90
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store at room temperature in a tightly sealed container, protected from light

Product Description & Scientific Applications

Tetrabutylammonium iodide, TBAI (C16H36IN, 369.37 g/mol), is a quaternary ammonium iodide salt with two distinct roles that follow from the same structure.

As an iodide source it is non-basic and nucleophilic, which decouples nucleophilicity from basicity. As a phase-transfer catalyst its lipophilic cation carries anions into the organic phase, for example in a biphasic dichloromethane/aqueous sodium hydroxide system.

Under tert-butyl hydroperoxide it becomes something else again: the iodide is oxidised to a hypoiodite species that abstracts a hydrogen atom to generate a carbon radical. That is the basis of most recent TBAI chemistry.

Applications and Reactions

  • Oxidative ketone coupling: with tert-butyl hydroperoxide it couples benzyl ketones to 1,4-diketones, optimally at 30 mol% for 94% yield.
  • Control experiments: both components are required. Without TBAI no reaction occurs; without the peroxide the yield falls to 17%.
  • Radical iodination: an inexpensive, readily available iodine source for trapping carbon radicals as alkyl iodides.
  • Halide exchange: refluxing an acetate with it exchanges the leaving group for iodide in about 73% yield.
  • Asymmetric catalysis: added to a reaction in dichloromethane at −78 °C it improved both yield and enantioselectivity over the additive-free run.
  • Electrosynthesis: an electrocatalytic mediator at 25 mol% in an undivided cell.
  • Storage: room temperature in a tightly sealed container, protected from light.

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Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class Not classified as dangerous goods
Transport Category Not dangerous goods (ADR/IATA/IMDG)
H-Statements H302 - H315 - H319
P-Statements P264 - P280 - P301+P312 - P302+P352 - P305+P351+P338 - P332+P313
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