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311-28-4 - Tetra-n-butylammonium iodide, 98% - A15484 - Alfa Aesar

A15484 Tetra-n-butylammonium iodide, 98%

Codice CAS
311-28-4
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
50g 26,20
250g 103,00
1000g 319,00
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Tetra-n-butylammonium iodide, 98%

MDL
MFCD00011636
EINECS
206-220-5

Proprietà chimiche

Formula
[CH3(CH2)3]4NI
Peso formula
369.38
Punto di fusione
142-148°
Sensibilità
Light Sensitive & Hygroscopic
Solubilità
Soluble in water and methanol. Insoluble in benzene.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H315-H319-H335

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

Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3916152
Codice tariffe armonizzato
2923.90
TSCA
Yes
RTECS
BS5450000

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