[A15484] CAS 311-28-4 | Tetra-n-butylammonium iodide, 98%

CAS : 311-28-4
MDL : MFCD00011636
EINECS : 206-220-5

Chemical Properties

Formula : [CH3(CH2)3]4NI
Formula weight : 369.38
Melting Point : 142-148°
Sensitivity : Hygroscopic. Light Sensitive. Ambient temperatures.
Form : Crystalline powder
Solubility : Soluble in water and methanol. Insoluble in benzene.

Literature References

Catalyst for the high-yield methylation of alcohols with dimethyl sulfate: Angew. Chem., 85, 868; Angew. Chem. Int. Ed., 12, 846 (1973), or the benzylation of alcohols with benzyl bromide in organic solvents: Org. Synth. Coll., 8, 34 (1993); 9, 52 (1998). Useful source of I- for nucleophilic displacements, e.g. in the formation of neopentyl iodides from the triflates: J. Org. Chem., 45, 4387 (1980). Aliphatic and aromatic sulfonic acids are reduced to thiols in the presence of trifluoroacetic anhydride, followed by hydrolysis of the resulting trifluoroacetates: Tetrahedron Lett., 21, 1235 (1980). In combination with Boron trifluoride diethyl­ etherate, A15275, has been used in a mild, versatile cleavage of ethers: Synthesis, 274 (1985).

Applications

Tetra-n-butylammonium iodide is used as a catalyst for methylation and benzylation of alcohols with dimethyl sulfate and benzyl bromide respectively. It is a useful source of iodide anion and involved in the preparation of neopentyl iodides from the triflates. It is also used in the preparation of novel quaternary amines, which serve as an antibacterial agent in the rise of drug-resistant bacteria. It acts as a phosphonium reversible inhibitors of cholinesterases. It is associated with boron trifluoride diethyl¬ etherate and used in the cleavage of ethers.

Grade Specifications

GHS Hazard and Precautionary Statements

Hazard Statements : H301-H315-H319-H335Toxic if swallowed.Causes skin irritation.Causes serious eye irritation.May cause respiratory irritation.
Precautionary Statements : P261-P301+P310-P305+P351+P338-P302+P352-P405-P501aAvoid breathing dust/fume/gas/mist/vapours/spray.IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.IF ON SKIN: Wash with plenty of soap and water.Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.Other References:Beilstein: 3916152