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Tetramethylharnstoff
TMU · TETRAMETHYLUREA · N,N,N',N'-TETRAMETHYLUREA · Urea, tetramethyl- · Temur · tetramethyl-ure · Olaparib Impurity 38 · 1,1,3,3-tetramethyl-ure
Identifikatoren & physikalische Daten
| CAS No. | 632-22-4 |
|---|---|
| Summenformel | C5H12N2O |
| Durchschnittliche Molmasse | 116,16 g/mol |
| Monoisotopische Masse | 116,094963 g/mol |
| SMILES | CN(C)C(=O)N(C)C |
| InChIKey | AVQQQNCBBIEMEU-UHFFFAOYSA-N |
| PubChem CID | 12437 |
| ChEMBL | CHEMBL11949 |
| ChEBI | CHEBI:84278 |
| EC No. | 211-173-9 |
| DTXSID | DTXSID1060893 |
| Lokaler Name | Tetramethylharnstoff |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 23,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 78,4 |
| Stoffklassen | Nitrogen Compounds -> Urea Compounds |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (Verteilungskoeffizient) | log Kow = 0.19 |
| Geruch | FAINT, PLEASANT |
| Dichte | 0.9687 @ 20 °C/4 °C0.968 g/mL at 20 °C(lit.) |
| Color/Form | LIQUID |
| Löslichkeit | MISCIBLE WITH WATER, PETROLEUM ETHER, ALL COMMON SOLVENTSSLIGHTLY SOL IN ALCOHOLwater solubility = 1X10+6 mg/lMiscible with water, petroleum ether and common solvents.H2O: 1 M at 20 °C, miscible |
| Flammpunkt | ABOUT 75 °C150 °F |
| Siedepunkt | 176.5 °C177 °C(lit.) |
| Schmelzpunkt | -1.2 °C−1 °C(lit.) |
| Dampfdruck | vaopr pressure = 13.9 mm Hg @ 71 °C |
| Brechungsindex | INDEX OF REFRACTION: 1.4493 @ 25 °C/Dn20/D 1.451(lit.) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 2.0(at 25℃) |
| Farbe | Clear colorless to pale yellow |
| pH | 5-8 (25℃, 1M in H2O) |
| Geruch | faint pleasant odor |
| Merck | 14,9230 |
| BRN | 773898 |
| Dielektrizitätskonstante | 24.460000000000001 |
| InChI | 1S/C5H12N2O/c1-6(2)5(8)7(3)4/h1-4H3 |
| InChIKey | AVQQQNCBBIEMEU-UHFFFAOYSA-N |
| SMILES | CN(C)C(=O)N(C)C |
| CAS Datenbank | 632-22-4(CAS DataBase Reference) |
| NIST chemische Informationen | Urea, tetramethyl-(632-22-4) |
| EPA chemische Informationen | Tetramethylurea (632-22-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 116 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Urea, tetramethyl-Tetramethylurea: Does not have an individual approval but may be used under an appropriate group standard |
| Brandpotenzial | FIRE HAZARD: MODERATE, VIA HEAT, FLAME & OXIDIZERS. |
| Gefahrenübersicht | Teratogenic effects observed in mice dosed by SC injectionIV doses of 150 mg/kg daily for five days produced weight loss in dogs, monkeys, and mice[HSDB] A strong skin irritant, but not a sensitizer in guinea pigsTemporary kidney injury and possible liver injury observed in two week feeding study of male rats at 450 mg/kg[EPA] Causes general anesthesia and somnolence in IP lethal-dose study of mice[RTECS] Teratogenic effects and fetal loss observed in studies of rodentsNo human data on reproductive or lactation effects[REPROTOX] An irritant[Alfa Aesar MSDS] |
| Special Reports | REVIEW OF PREPN, MFR, PROPERTIES AND USE AS SOLVENT AND AS REAGENT: LUTTRINGHAUS, DIRKSEN, AGNEW CHEM INT ED 3, 260 (1964).[The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 1190] |
| Hazard Classes and Categories | Acute Tox. 4 (97.4%)Flammable liquids - Category 4 |
| Brandbekämpfungsverfahren | FOAM, MIST, SPRAY, DRY CHEMICALS. |
| Wechselwirkungen | MIXING TETRAMETHYLUREA WITH MINERAL OIL INCREASED MATERNAL TMU TOXICITY WHEN APPLIED TO SKIN OF RATS.TETRAMETHYL UREA WAS CAPABLE OF ENHANCING THE TOXICITY OF MORPHINE AND CHLORPROMAZINE IN DOGS, MONKEYS, AND MICE. |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
The 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.