Tetramethylammonium iodide

Base Information

• Chemical Name: Tetramethylammonium iodide
• CAS No.: 75-58-1
• Deprecated CAS: 2084121-45-7
• Molecular Formula: C4H12IN
• Molecular Weight: 201.05
• Hs Code.: 29239000
• European Community (EC) Number: 200-881-3
• NSC Number: 4856
• UNII: L493Z502W3
• DSSTox Substance ID: DTXSID60883235
• Wikidata: Q26840810
• ChEMBL ID: CHEMBL2288325
• Mol file: 75-58-1.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 iodide

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: >300 °C(lit.)
• PSA: 0.00000
• Density: 1.84 g/cm3 (20oC)
• LogP: -2.67360
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive & Hygroscopic
• Water Solubility.: sparingly soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 201.00145
• Heavy Atom Count: 6
• Complexity: 19.1

Purity/Quality:

99% ^*data from raw suppliers

Tetramethylammonium iodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Quaternary Amines
• Canonical SMILES: C[N+](C)(C)C.[I-]
• Uses: Emergency disinfection of drinking water. Required dosage: 8 ppm of iodine. Facile iodination of aromatic compounds including anilines, acids and alcohols.

Technology Process of Tetramethylammonium iodide

There total 56 articles about Tetramethylammonium iodide 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: 96.0%

N,N-dimethylmethane sulfenamide (33696-21-8) + methyl iodide (74-88-4) → Dimethyldisulphide (624-92-0) + tertamethylammonium iodide (75-58-1)

Guidance literature:

In chloroform; Product distribution; Ambient temperature; var. amino thioethers, var. electrophiles;

DOI:10.1021/jo00268a039

Reference yield: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (5-Acetylamino-2-hydroxy-benzyl)-trimethyl-ammonium; iodide (81926-15-0) → tertamethylammonium iodide (75-58-1) + 5-acetamido-2,3-dihydrobenzo<1,2-b>furan (81926-25-2)

Guidance literature:

In methanol; dichloromethane; N,N-dimethyl-formamide; at 3 ℃; for 24h;

Reference yield: 70.0%

1-dimethylaminomethyl-naphthalen-2-ol (5419-02-3) + methyl iodide (74-88-4) → bis(2-hydroxy-1-naphthyl)methane (1096-84-0) + tertamethylammonium iodide (75-58-1) + (2-hydroxy-[1]naphthylmethyl)-trimethyl-ammonium; iodide (62019-32-3)

Guidance literature:

In benzene; for 48h; Ambient temperature;

upstream raw materials:

2,6-dimethyl-1H-pyrimidin-4-one

methyl iodide

3-(Dimethylaminomethyl)indole

1,5-bis(p-toluenesulphonyl)-1,5-diazacyclooctane

Downstream raw materials:

methyl thiocyanate

methyl thioisocyanate

trimethylamine

tetramethyl ammoniumhydroxide

Refernces

• 1、 Chen, Nanjun,Fan, Jiantao,Hu, Chuan,Jin, Yiqi,Lee, Young Moo,Li, Hui,Liu, Haijun,Wu, Bo,Xu, Shaoyi. "Insight into the Alkaline Stability of N-Heterocyclic Ammonium Groups for Anion-Exchange Polyelectrolytes". supporting information. p. 19272 - 19280. Retrieved 2021/07/25.
• 2、 Kantlehner, Willi,Hauber, Michael,Haug, Erwin,Schallenmueller, Claus,Regele, Claudia. "Orthoamides. LIV. Contributions to the chemistry of azavinylogous orthoformic acid amide derivatives". . p. 682 - 699. Retrieved 2007/10/03.