Tetrabutylammonium bromide

Base Information

• Chemical Name: Tetrabutylammonium bromide
• CAS No.: 1643-19-2
• Deprecated CAS: 65129-09-1,65129-13-7,1087380-97-9,1393673-93-2,65129-13-7
• Molecular Formula: C16H36BrN
• Molecular Weight: 322.373
• Hs Code.: 2923.90
• European Community (EC) Number: 216-699-2
• UNII: VJZ168I98R
• DSSTox Substance ID: DTXSID4044400
• Wikipedia: Tetrabutylammonium_bromide
• Wikidata: Q6296780
• Metabolomics Workbench ID: 58017
• ChEMBL ID: CHEMBL60696
• Mol file: 1643-19-2.mol

Synonyms:Tetrabutyl Ammonium Bromide;Tetrabutylammonium bromide（TBAB）;1-Butanaminium,N,N,N-tributyl-, bromide (9CI);Ammonium, tetrabutyl-, bromide (8CI);Tetrabutylammonium bromide (6CI,7CI);AP 6G;Actiron 43-65;Aliquat 100;Mastermix MB 4988;TBAB;Tetra-n-butylammonium bromide;Tetrabutylammonium bromide;

Chemical Property of Tetrabutylammonium bromide

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 102-106 °C(lit.)
• Refractive Index: n20/D 1.422
• Boiling Point: 102°C
• PKA: 0[at 20 ℃]
• Flash Point: 100℃
• PSA: 0.00000
• Density: 1.039 g/mL at 25 °C
• LogP: 2.00760
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: 600 g/L (20 ºC)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 321.20311
• Heavy Atom Count: 18
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

Tetrabutyl ammonium bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quaternary Amines
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[Br-]
• Chemical Composition and Structure: Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt composed of four butyl groups attached to a central nitrogen atom, with a bromide anion. Its chemical structure allows it to act as a phase transfer catalyst and as a component in deep eutectic solvents (DESs).
• Mechanism of Action: TBAB functions as a phase transfer catalyst, facilitating the transport of reactants between aqueous and organic phases. It can also act as a co-catalyst, enhancing reaction rates and product yields in various chemical processes.
• Uses: TBAB is employed as a catalyst in reactions such as alkylation, oxidation, reduction, esterification, and coupling reactions. It is also used as a zwitterionic solvent under molten conditions and as a component in DESs for green chemistry applications.; TBAB is utilized in analytical chemistry for the synthesis of DESs with various hydrogen bond donors (HBDs). These DESs have shown promise in antimicrobial activity, with different compositions exhibiting varying levels of toxicity and biocompatibility. Additionally, TBAB plays a role in cold storage systems as a hydrate-forming accelerator, improving hydrate nucleation rates and phase equilibrium.; It has been employed in reactions such as the Williamson ether synthesis experiment and has gained attention for its use in DESs, demonstrating potential applications in green chemistry.
• Production Methods: TBAB can be synthesized through chemical processes involving the reaction of butyl bromide with tetra-n-butylammonium hydroxide.

Technology Process of Tetrabutylammonium bromide

There total 33 articles about Tetrabutylammonium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.9%

1-bromo-butane (109-65-9) + tributyl-amine (102-82-9) → tetrabutylammomium bromide (1643-19-2)

Guidance literature:

In acetonitrile; at 82 ℃; for 33h; Solvent; Temperature;

Reference yield: 91.0%

tributyl-amine (102-82-9) → tetrabutylammomium bromide (1643-19-2)

Guidance literature:

With 1-bromo-butane; In acetonitrile; at 80 ℃; for 2h; under 7500.75 Torr; Temperature; Inert atmosphere;

Reference yield: 72.0%

3-bromo-3-methyl-2-trimethylsiloxy-1-pentene (138174-05-7) + tetrabutylammonium tricarbonylnitrosylferrate → (CH2C(OSi(CH3)3)C(CH3)C2H5)Fe(CO)2NO + tetrabutylammomium bromide (1643-19-2)

Guidance literature:

In dichloromethane; byproducts: CO; Stirring of mixt. at room temp. for 2 h.; Evapn. in vac., chromy. (silica gel, pentane).;

DOI:10.1246/bcsj.64.2965

upstream raw materials:

1-bromo-butane

tributyl-amine

tetrabutylammonium perchlorate

triethylamine hydrobromide

Downstream raw materials:

tetrabutylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato(2-)-C²,O><3,5-bis(trifluoromethyl)phenyl>silicate (1-)

4-Chloro-benzenesulfonatetetrabutyl-ammonium;

tetra-n-butylammonium dibenzyl phosphate

N-butyl-4-methoxyaniline

Refernces

• 1、 Jones,Foster. "". . p. 2900. Retrieved 1967.
• 2、 Turovskij, Nikolaj A.,Berestneva, Yulia V.,Raksha, Elena V.,Zubritskij, Mikhail Yu.,Grebenyuk, Serhiy A.. "NMR study of the complex formation between tert-butyl hydroperoxide and tetraalkylammonium bromides". . p. 1443 - 1448. Retrieved 2014.
• 3、 Sadek,Fuoss. "-". . p. 301,305. Retrieved 1950.
• 4、 Waddington,White. "". . p. 2701,2702. Retrieved 1963.
• 5、 Hojo, Masashi,Aoki, Sho. "Alternative mechanistic scheme for salt effects on solvolysis reactions of haloalkanes and related compounds in binary DMSO/H2O solvent mixture". . p. 1023 - 1030,8. Retrieved 2012.
• 6、 Legault, Claude Y.,Mayer, Robert J.,Mayr, Herbert,Ofial, Armin R.. "Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases". supporting information. . Retrieved 2020/03/13.
• 7、 -. "Application of ionic liquid in synthesis of propylene glycol ether and synthetic method of propylene glycol ether". Paragraph 0089; 0090. . Retrieved 2018/03/01.