1,1,3,3-Tetramethylurea

Base Information

• Chemical Name: 1,1,3,3-Tetramethylurea
• CAS No.: 632-22-4
• Molecular Formula: C5H12N2O
• Molecular Weight: 116.163
• Hs Code.: 29241900
• European Community (EC) Number: 211-173-9
• NSC Number: 91488
• UNII: 2O1EJ64031
• DSSTox Substance ID: DTXSID1060893
• Nikkaji Number: J6.897G
• Wikipedia: Tetramethylurea
• Wikidata: Q26699773
• ChEMBL ID: CHEMBL11949
• Mol file: 632-22-4.mol

Synonyms:Urea,1,1,3,3-tetramethyl- (6CI);Urea, tetramethyl- (8CI,9CI);NSC 91488;TMU;Temur;Tetramethylcarbamide;

Chemical Property of 1,1,3,3-Tetramethylurea

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Melting Point: -1 °C(lit.)
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 175.2 °C at 760 mmHg
• PKA: 2.0(at 25℃)
• Flash Point: 53.9 °C
• PSA: 23.55000
• Density: 0.9879 g/cm³
• LogP: 0.22960
• Storage Temp.: Store below +30°C.
• Solubility.: H2O: 1 M at 20 °C, miscible
• Water Solubility.: miscible
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 116.094963011
• Heavy Atom Count: 8
• Complexity: 78.4

Purity/Quality:

99% ^*data from raw suppliers

Tetramethylurea ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 22-61
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Urea Compounds
• Canonical SMILES: CN(C)C(=O)N(C)C
• Uses: Tetramethylurea is used as a solvent in dyestuff industries, in condensation reaction and intermediates in surfactant. It is utilized for base catalyzed isomerization and alkylation hydrocyanation due to its low permittivity. It reacts with oxalyl chloride to prepare tetramethyl chloroformamidinium chloride, which is used for the conversion of carboxylic acids and dialkyl phosphates to anhydrides and pyrophosphates respectively.

Technology Process of 1,1,3,3-Tetramethylurea

There total 95 articles about 1,1,3,3-Tetramethylurea 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: 92.0%

bis(trichloromethyl) carbonate (32315-10-9) + dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

Guidance literature:

In dichloromethane; water; at 15 - 20 ℃; Large scale;

Reference yield: 86.0%

carbon monoxide (201230-82-2) + N,N-dimethylammonium chloride (506-59-2) → tetramethylurea (632-22-4)

Guidance literature:

With 2C₇H₉N₄*Au⁽¹⁺⁾*Cu⁽¹⁺⁾*2I^(1-); sodium carbonate; In toluene; at 60 ℃; Autoclave;

DOI:10.1002/anie.201914089

Reference yield: 85.0%

1,1,3,3-tetramethyl-2-thiourea (2782-91-4) → tetramethylurea (632-22-4)

Guidance literature:

With hydrogenchloride; N-nitrosopiperidine; potassium iodide; In dichloromethane; water; at 22 ℃; for 48h;

DOI:10.1016/S0040-4020(01)88548-3

upstream raw materials:

dimethylchloroamine

potassium cyanide

1,μ-dithio-dicarbonic acid bis-dimethylamide

dimethyl amine

Downstream raw materials:

2-N-(4-acetophenyl)tetramethylguanidine

2-isopropyl-1,1,3,3-tetramethylguanidine

N,N,N′,N′-tetramethyl-N″-tert-butylguanidine

N,N,N',N'-tetramethyl-N-phenylguanidine

Refernces

• 1、 Dereven’kov, Ilia A.,Ivlev, Pavel A.,Salnikov, Denis S.,Bischin, Cristina,Attia, Amr A. A.,Silaghi-Dumitrescu, Radu,Makarov, Sergei V.. "Studies of reaction of tetramethylthiourea with hydrogen peroxide: evidence of formation of tetramethylthiourea monoxide as a key intermediate of the reaction". . p. 496 - 509. Retrieved 2017.
• 2、 Tabushi et al.. "-". . p. 5581. Retrieved 1968.
• 3、 Cao, Yanwei,Yang, Jian-Gong,Deng, Yi,Wang, Shengchun,Liu, Qi,Shen, Chaoren,Lu, Wei,Che, Chi-Ming,Chen, Yong,He, Lin. "Amine-Responsive Disassembly of AuI–CuI Double Salts for Oxidative Carbonylation". supporting information. p. 2080 - 2084. Retrieved 2019/12/24.
• 4、 -. "Tetramethylurea and preparation method thereof". Paragraph 0052-0054; 0057; 0058; 006; 0062; 0065; 0066. . Retrieved 2018/10/19.