Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A15484 Tetra-n-butylammonium iodide, 98%

CAS Number
311-28-4
Synonyms

Stock No. Size Price ($) Quantity Availability
A15484-18 50g 27.50
A15484-30 250g 107.00
A15484-0B 1000g 332.00
Add to Cart Bulk/Specialty Print Quote View Item

Tetra-n-butylammonium iodide, 98%

MDL
MFCD00011636
EINECS
206-220-5

Chemical Properties

Formula
[CH3(CH2)3]4NI
Formula Weight
369.38
Melting point
142-148°
Storage & Sensitivity
Hygroscopic. Light Sensitive. Ambient temperatures.
Solubility
Soluble in water and methanol. Insoluble in benzene.

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.

Notes

Light sensitive and hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

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).

Liu, J. B.; Xu, X. H.; Chen, Z. H.; Qing, F. L. Direct Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra-n-butylammonium Iodide. Angew. Chem. Int. Ed. 2015, 54 (3), 897-900.

Adonin, S. A.; Sokolov, M. N.; Fedin, V. P. Mono-and binuclear Bi(III) iodide complexes containing 2, 2'-bipyridyl and 1, 10-phenanthroline: Synthesis and structure. J. Struct. Chem. 2015, 56 (4), 708-713.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3916152
Harmonized Tariff Code
2923.90
TSCA
Yes
RTECS
BS5450000

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware