Tetrabutylammonium tribromide

Base Information

• Chemical Name: Tetrabutylammonium tribromide
• CAS No.: 38932-80-8
• Molecular Formula: C16H36Br3N
• Molecular Weight: 482.181
• Hs Code.: 29211990
• DSSTox Substance ID: DTXSID801028457
• Wikipedia: Tetrabutylammonium_tribromide
• Wikidata: Q7706217
• Mol file: 38932-80-8.mol

Synonyms:trimethyl-phenyl-azanium;Tetrabutyl ammonium tribromide;tetrabutylammonium tribromide; tbabr3;1-Butanaminium,N,N,N-tributyl-,(tribromide);

Chemical Property of Tetrabutylammonium tribromide

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Melting Point: 71-76 °C(lit.)
• Refractive Index: 1.6500 (estimate)
• PSA: 0.00000
• Density: 1.5469 (rough estimate)
• LogP: 3.69880
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Acetone (Slightly), Chloroform (Slightly)
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 481.03774
• Heavy Atom Count: 20
• Complexity: 116

Purity/Quality:

98%, ^*data from raw suppliers

Tetrabutylammonium Tribromide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.Br[Br-]Br
• Uses: Tetrabutylammonium tribromide (TBATB) is a salt of the lipophilic tetrabutylammonium cation and the linear tribromide anion. It is used as a phase transfer catalyst in organic synthesis as well as a mild brominating agent. A wide range of O-isopropylidene derivatives can be prepared from the sugars and their derivatives on reaction with acetone at room temperature by employing 2 mol % of tetrabutylammonium tribromide as a catalyst. Good yields, low catalyst loading, mild reaction conditions, and a non-aqueous workup procedure are some major advantages of this protocol. Tetrabutylammonium tribromide as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds. It is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine. Tetra-n-butylammonium tribromide is useful for the preparation of vicinal dibromides from alkenes and alkynes and alfa-bromo acetals. it is utilized to generate hydrogen bromide, which is used as an efficient chemoselective reagent for acetalization of carbonyl compounds. Tetrabutylammonium Tribromide is used in the synthesis of antimicrobial agents via chalcones. Also used in the synthesis of potent tubulin polymerization inhibitors.

Technology Process of Tetrabutylammonium tribromide

There total 3 articles about Tetrabutylammonium tribromide 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: 98.0%

tetrabutylammomium bromide (1643-19-2) → tetra-N-butylammonium tribromide (38932-80-8)

Guidance literature:

With bromine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.0c12805

Reference yield: 95.0%

tetrabutylammomium bromide (1643-19-2) → tetrabuthylammonium tribromide (38932-80-8)

Guidance literature:

With sodium bromate; hydrogen bromide; In water; Ambient temperature;

DOI:10.1246/bcsj.60.1159

Reference yield:

1-bromo-butane (109-65-9) + tributyl-amine (102-82-9) → tetra-N-butylammonium tribromide (38932-80-8)

Guidance literature:

1-bromo-butane; tributyl-amine; In acetonitrile; at 20 ℃; for 24h; Inert atmosphere;

With Oxone; potassium bromide; In water; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.201900974

upstream raw materials:

tetrabutylammomium bromide

1-bromo-butane

tributyl-amine

Downstream raw materials:

(E)-3-(3-bromo-4-hydroxyphenyl)-2-cyano-N-nonyl-2-butenamide

trans-1-bromo-1,2-difluorohexene

tetrabutylammonium tetrafluoroborate

2-bromo-1-(4-(pentyloxy)phenyl)ethan-1-one

Refernces

• 1、 Sarkar, Debayan,Kuila, Puspendu,Sood, Devashish. "Controlling Stereoselectivity in Tribromide Mediated Oxidative Dearomatisations – Synthesis of Selective Spirofurano-naphthalones". . p. 5894 - 5904. Retrieved 2019.
• 2、 Kavitha, Kotthireddy,Srikrishna, Devulapally,Dubey, Pramod Kumar,Aparna, Pasula. "Tetrabutylammonium tribromide: An effective green reagent for the one-pot reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines". . p. 172 - 185. Retrieved 2018/10/26.