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1,1,3,3-Tetramethylurea

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CAS:632-22-4
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1,1,3,3-Tetramethylurea Basic information
Product Name:1,1,3,3-Tetramethylurea
Synonyms:N,N,N',N'-TETRAMETHYLUREA;((CH3)2N)2CO;Tetramethylharnstoff;Tetramethyluree;Four Methylurea;TetraMethylurea, 99.5%;1,1,3,3-TETRAMETHYLUREA;1,1,3,3-Tetramethylurea, TMU
CAS:632-22-4
MF:C5H12N2O
MW:116.16
EINECS:211-173-9
Product Categories:Miscellaneous;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Ureas;Bioactive Small Molecules;Cell Biology;T;1;bc0001
Mol File:632-22-4.mol
1,1,3,3-Tetramethylurea Structure
1,1,3,3-Tetramethylurea Chemical Properties
Melting point −1 °C(lit.)
Boiling point 177 °C(lit.)
density 0.968 g/mL at 20 °C(lit.)
refractive index n20/D 1.451(lit.)
Fp 150 °F
storage temp. Inert atmosphere,Room Temperature
solubility Miscible with water, petroleum ether and common solvents.
form Liquid
pka2.0(at 25℃)
color Clear colorless to pale yellow
PH5-8 (25℃, 1M in H2O)
Relative polarity5
Odorfaint pleasant odor
Water Solubility H2O: 1 M at 20 °C, miscible
Merck 14,9230
BRN 773898
Dielectric constant24.460000000000001
InChIKeyAVQQQNCBBIEMEU-UHFFFAOYSA-N
CAS DataBase Reference632-22-4(CAS DataBase Reference)
NIST Chemistry ReferenceUrea, tetramethyl-(632-22-4)
EPA Substance Registry SystemTetramethylurea (632-22-4)
Safety Information
Hazard Codes Xn,T
Risk Statements 22-61
Safety Statements 53-45
RIDADR NA 1993 / PGIII
WGK Germany 3
RTECS YU2625000
3-10
TSCA Yes
HS Code 29241900
Hazardous Substances Data632-22-4(Hazardous Substances Data)
ToxicityLD50 i.v. in rats: 1.1 g/kg (Lüttringhaus, Dirksen)
MSDS Information
ProviderLanguage
1,1,3,3-Tetramethylurea English
SigmaAldrich English
ACROS English
ALFA English
1,1,3,3-Tetramethylurea Usage And Synthesis
Chemical PropertiesTetramethylurea is a clear colorless to pale yellow liquid with mild aromatic odor that is miscible with water and many organic solvents. Unusual for an urea is the liquid state of tetramethylurea in a range of > 170 °C.
UsesTetramethylurea 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.
DefinitionChEBI: 1,1,3,3-tetramethylurea is a member of the class of ureas that is urea substituted by methyl groups at positions 1, 1, 3 and 3 respectively. Metabolite observed in cancer metabolism. It has a role as a human metabolite.
PreparationThe reaction of dimethylamine with phosgene in the presence of e. g. 50 % sodium hydroxide solution and subsequent extraction with 1,2-dichloroethane yields tetramethylurea in 95% yield.
Safety ProfileModerately toxic by ingestion and intravenous routes. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. Combustible when exposed to heat, flame, and oxidizers. To fight fire, use foam, mist, spray, dry chemicals. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsDry it over BaO and distil it under nitrogen. It denatures proteins in H2O. [Elbaum & Herskovits Biochemistry 13 1268 1974, Kane Anal Biochem 53 350 1973, Beilstein 4 IV 225.]
Tag:1,1,3,3-Tetramethylurea(632-22-4) Related Product Information
4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one PIPERAZINE DIHYDROCHLORIDE 3-((4-Oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid 1-Hydroxybenzotriazole Olaparib Impurity 14 5-Bromo-2-fluorobenzonitrile Cyclopropanecarbonyl Chloride 2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile 2-Propanone, 1-[4,5-dihydro-2-(4-methyl-1-piperazinyl)-4-thioxo-3H-1,5-benzodiazepin-3-ylidene]- Olaparib Impurity 31 Olaparib Impurity 30 tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzoyl)piperazine-1-carboxylate 2,2'-Oxybis(nitrobenzene) Olaparib Impurity 25 2,2'-OXYDIANILINE Olaparib Impurity 15 tert-butyl 4-(cyclopropylcarbonyl)-1-piperazinecarboxylate tert-Butyl 1-piperazinecarboxylate