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%min ^*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
• General Description: 1,1,3,3-Tetramethylurea (TMU) is a versatile organic compound used as an acid scavenger in glycosylation reactions and as a reagent in the synthesis of optically active perfluorinated compounds. It facilitates reactions by neutralizing acidic byproducts, as seen in thermal glycosidation, and serves as a key component in the anionic dimerization of perfluoroepoxides to produce chiral intermediates. Its stability and lack of interfering protons also make it suitable for applications in NMR spectroscopy and enantiomer analysis.

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:

1-(2-Hydroxy-2-phenyl-propyl)-1,3,3-trimethyl-urea

2-(4-fluorophenyl)-1,1,3,3-tetramethylguanidine

Tetrakis(dimethylamino)ethylen

Tris(dimethylamino)methoxy-ethylen

Refernces

α-Selective thermal glycosidation of rhamnosyl and mannosyl chlorides

10.1016/S0040-4039(00)97381-7

The research documented in the literature focuses on the selective thermal glycosylation of various alcohols using 2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl chloride and 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl chloride to produce α-glycosides with high selectivity. The study builds on previous work involving thermal glycosidation with glucosyl or xylosyl chlorides but introduces a significant improvement in stereoselectivity, particularly with sterically hindered alcohols. The key chemicals involved in this research include the rhamnosyl and mannosyl chlorides as glycosyl donors, various alcohols such as cholesterol, cholestanol, dihydrolanosterol, and others as acceptors, and in some experiments, N,N,N',N'-tetramethylurea (TMU) as an acid scavenger. The process is notable for its simplicity, safety, and economy, as it does not require hazardous metal salts or solvents, making it a practical and environmentally friendly method for glycosylation.

OPTICALLY ACTIVE PERFLUORO-2-PROPOXYPROPIONIC ACID

10.1246/cl.1980.843

The research focuses on the synthesis and characterization of optically active perfluoro-2-propoxypropionic acid. The key chemicals involved include perfluoro-2-propoxypropionyl fluoride, which was prepared by the anionic dimerization of perfluoro-1,2-epoxypropane using tetramethylurea in diglyme. This fluoride reacted with (-)-1-phenylethylamine to form a mixture of diastereomeric amides. These amides were separated chromatographically, and their subsequent hydrolysis yielded the enantiomers of perfluoro-2-propoxypropionic acid, marking the first example of optically active organic perfluoro compounds. The study highlights the potential of these compounds as reagents for analyzing enantiomers and as solvents for 1H NMR analysis of chiral molecules, given their stability and lack of hydrogen atoms.