Tetramethylammonium bromide

Base Information

• Chemical Name: Tetramethylammonium bromide
• CAS No.: 64-20-0
• Molecular Formula: C4H12BrN
• Molecular Weight: 154.05
• Hs Code.: 2923.90
• European Community (EC) Number: 200-581-2
• NSC Number: 148344
• UNII: 6L9NE9609P
• DSSTox Substance ID: DTXSID80883212
• Wikidata: Q3645284
• Mol file: 64-20-0.mol

Synonyms:tetraamethylammonium acetate;tetramethylammonium;tetramethylammonium bromide;tetramethylammonium chloride;tetramethylammonium fluoride;tetramethylammonium hydrogen dichloride;tetramethylammonium hydroxide;tetramethylammonium hydroxide pentahydrate;tetramethylammonium iodide;tetramethylammonium nitrate;tetramethylammonium perchlorate;tetramethylammonium sulfate (2:1);tetramethylammonium tribromide;tetramethylammonium triiodide;trimethylaminomethane

Chemical Property of Tetramethylammonium bromide

Chemical Property:

• Appearance/Colour: slightly grey crystalline powder
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.4379 (estimate)
• Boiling Point: >360°C
• Flash Point: NotoConsidered to be a fire hazard
• PSA: 0.00000
• Density: 1.56 g/cm³
• LogP: -2.67360
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 153.01531
• Heavy Atom Count: 6
• Complexity: 19.1

Purity/Quality:

99% ^*data from raw suppliers

Tetramethylammonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-28-36-45-37/39-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quaternary Amines
• Canonical SMILES: C[N+](C)(C)C.[Br-]
• Uses: Tetramethylammonium bromide acts as an ion pair reagent. It is used as a surface-active agent and an active ingredient for conditioners. Further, it is used as a softner for textiles and paper products. It is also employed as a disinfection agent, sanitizer, antimicrobial and antistatic agent. In addition to this, it plays in important role as a phase transfer catalyst in synthetic chemistry. Tetrabutylammonium bromide (TBAB) may be used in the molten state in the following processes:Synthesis of (2S)-5-(3-phenyl-2-phthalimidylpropanoylamino)isophthalic acid.Synthesis of alkyl-substituted pyrroles in the absence of catalyst and organic solvent.Synthesis of dithioacetals from acetals by transthioacetalisation in a solvent free environment.Synthesis of polyamides (PAs) by the polymerization of terephthalic acid and diisocyanates.Catalyze the addition of thiols to conjugated alkenes.Dehydrochlorination of poly(vinyl chloride).

Technology Process of Tetramethylammonium bromide

There total 24 articles about Tetramethylammonium 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: 96.5%

carbonic acid dimethyl ester (616-38-6) → tetramethylammonium bromide (64-20-0)

Guidance literature:

With ammonium bromide; at 169.84 ℃; for 8h;

DOI:10.1039/b601343k

Reference yield: 88.6%

methyl bromide (74-83-9) + Neopentyl N,N,N',N'-tetramethylphosphorodiamidite (105334-48-3) → tetramethylammonium bromide (64-20-0) + Neopentyl N,N-dimethylphosphoramidobromidite + bisdimethylamino(methyl)neopentyloxyphosphonium bromide

Guidance literature:

In diethyl ether; Ambient temperature;

Reference yield:

2-pyrrolidinon (616-45-5) + methanol (67-56-1) → 4-butanolide (96-48-0) + 1-methyl-pyrrolidin-2-one (872-50-4,26138-58-9) + 4-hydroxybutanoic acid (591-81-1) + methyl 4-hydroxybutanoate (925-57-5) + tetramethylammonium bromide (64-20-0) + trimethylamine (75-50-3)

Guidance literature:

With ammonium bromide; at 250 ℃; for 5.33333h; under 3750.38 Torr; Inert atmosphere; Autoclave;

DOI:10.1039/c0gc00061b

upstream raw materials:

acetonyl-trimethyl-ammonium; bromide

(1-formyl-hexyl)-trimethyl-ammonium; bromide

ethanol

cis+trans-dibromoethylene

Downstream raw materials:

tetramethyl ammoniumhydroxide

tetramethylammonium tribromide

(β-hydroxy-phenethyl)-trimethyl-ammonium; bromide

tetramethylammonium (5-oxo-5H-dibenzo{a,d}cyclohepten-10-yl)triphenylborate

Refernces

Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B

10.1016/j.tet.2016.07.018

The study presents a novel and efficient copper-catalyzed vinylic Finkelstein reaction for the synthesis of various halogenated alkenes, which are important structural elements in pharmaceuticals, agrochemicals, and natural products. The researchers developed a method to convert alkenyl iodides and bromides into their chlorinated and brominated counterparts with high yields and full retention of double bond geometry. This method's broad applicability and mild reaction conditions make it suitable for a range of functionalized substrates. The study demonstrates the potential of this reaction in total synthesis and medicinal chemistry by using it to synthesize the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The researchers also explored the extension of this halogen exchange to acetylenic and allenic Finkelstein reactions.