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

A15484 Tetra-n-butylammonium iodide, 98%

CAS-Nummer
311-28-4
Synonyme

Größe Preis ($) Menge Verfügbarkeit
50g 26,06
250g 102,69
1000g 317,24
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Tetra-n-butylammonium iodide, 98%

MDL
MFCD00011636
EINECS
206-220-5

Chemische Eigenschaften

Formel
[CH3(CH2)3]4NI
Molmasse
369.38
Schmelzpunkt
142-148°
Sensitivität
Light Sensitive & Hygroscopic
Löslichkeit
Soluble in water and methanol. Insoluble in benzene.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302-H315-H319-H335

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

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
3916152
Harmonized Tariff Code
2923.90
TSCA
Yes
RTECS
BS5450000

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