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Tetra-n-butylammonium iodide, 98%, Thermo Scientific Chemicals
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Catalog number A15484.18
also known as A15484-18
Price (USD)/ Each
35.65
Online exclusive
38.90 Save 3.25 (8%)
-
Quantity:
50 g
Price (USD)/ Each
35.65
Online exclusive
38.90 Save 3.25 (8%)
Tetra-n-butylammonium iodide, 98%, Thermo Scientific Chemicals
Catalog numberA15484.18
Price (USD)/ Each
35.65
Online exclusive
38.90 Save 3.25 (8%)
-
Chemical Identifiers
CAS311-28-4
IUPAC Nametetrabutylazanium iodide
Molecular FormulaC16H36IN
InChI KeyDPKBAXPHAYBPRL-UHFFFAOYSA-M
SMILES[I-].CCCC[N+](CCCC)(CCCC)CCCC
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White to cream
FormCrystals or crystalline powder or powder or flakes
Assay (Titration ex Iodide)≥97.5 to ≤102.5%
Identification (FTIR)Conforms
Melting Point (clear melt)141-150°C
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Soluble in water and methanol. Insoluble in benzene.
Notes
Light sensitive and hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
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.
Solubility
Soluble in water and methanol. Insoluble in benzene.
Notes
Light sensitive and hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General 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.