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Tetramethylharnstoff

Tetramethylurea

HCID 12437
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Grundinformationen

CAS
632-22-4
Standard-SMILES
CN(C)C(=O)N(C)C
InChIKey
AVQQQNCBBIEMEU-UHFFFAOYSA-N
Summenformel
C5H12N2O
Durchschnittliche Molmasse
116,16 g/mol
Monoisotopische Masse
116,094963

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Tetramethylurea
IUPAC
1,1,3,3-tetramethylurea
Lokaler Name
Tetramethylharnstoff
Englischer Name
1,1,3,3-Tetramethylurea
Summenformel
C5H12N2O
Molmasse
116.16

Namen und Synonyme

1,1,3,3-TetramethylureaTETRAMETHYLUREA632-22-4TemurUrea, tetramethyl-N,N,N',N'-TetramethylureaTetramethylureeUrea, 1,1,3,3-tetramethyl-NSC-914882O1EJ64031DTXSID1060893CHEBI:84278
Weitere Namen anzeigen
tetramethyl-ureOlaparib Impurity 381,1,3,3-tetramethyl-ure((CH3)2N)2CO
RefChem:188798DTXCID1043750211-173-9TMUurea, N,N,N',N'-tetramethyl-Tetramethyl UreaNSC 91488BRN 0773898

Datenbank-Bezeichner

CAS
632-22-4
PubChem CID
12437
DTXSID
DTXSID1060893
ChEMBL
CHEMBL11949
ChEBI
CHEBI:84278
UNII
2O1EJ64031
EC Number
211-173-9
Nikkaji
J6.897G

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,2
Polarare Oberfläche (TPSA)
23,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
8
Formalladung
0
Komplexität
78,4

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Urea Compounds
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 Einträge

log Kow = 0.19

0.19

OdorFAINT, PLEASANT
Density0.9687 @ 20 °C/4 °C
Color/FormLIQUID
Solubility · 3 Einträge

MISCIBLE WITH WATER, PETROLEUM ETHER, ALL COMMON SOLVENTS

SLIGHTLY SOL IN ALCOHOL

water solubility = 1X10+6 mg/l

Flash PointABOUT 75 °C
Boiling Point176.5 °C
Melting Point-1.2 °C
Vapor Pressure

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302 (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.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Urea, tetramethyl-

Tetramethylurea: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFIRE HAZARD: MODERATE, VIA HEAT, FLAME & OXIDIZERS.
Hazards Summary · 1 Eintrag

Teratogenic effects observed in mice dosed by SC injection; IV 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 pigs; Temporary 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 rodents; No human data on reproductive or lactation effects; [REPROTOX] An irritant; [Alfa Aesar MSDS]

Special ReportsREVIEW 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 · 2 Einträge

Chemie und Industrie

Verwendung und Herstellung

Uses · 2 Einträge

Used as solvent and reagent; [Merck Index]

SOLVENT & REAGENT

U.S. Exports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Imports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Production · 2 Einträge

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

Methods of ManufacturingPREPN: LAWSON, CROOM, J ORG CHEM, 28, 232 (1963).
General Manufacturing InformationUrea, N,N,N',N'-tetramethyl-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenTetramethylurea 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.

Darstellung

synthetischeThe 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Zugehörige Reaktionen

56
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1705
HRID 1705als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 7199
HRID 7199als Eduktuspto-grants-2006_08
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HRID 49885als Eduktuspto-grants-2004_03
Reaktionsgleichung von HRID 191842
HRID 191842als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 192386
HRID 192386als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 281478
HRID 281478als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 306830
HRID 306830als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 408790
HRID 408790als Produktuspto-grants-2014_06
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vaopr pressure = 13.9 mm Hg @ 71 °C
Refractive IndexINDEX OF REFRACTION: 1.4493 @ 25 °C/D

Physikochemische Eigenschaften

Schmelzpunkt
1.2 °C · −1.2 °C (29.8 °F; 271.9 K)
Siedepunkt
176.5 °C · 176.5 °C (349.7 °F; 449.6 K)
Dichte
0.968 g/mL · 0.968 g/mL
Brechungsindex
1.45 · 1.45
Flammpunkt
75 °C · 75 °C
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
Miscible with water, petroleum ether and common solvents.
pka
2 · 2.0(at 25℃)
Aggregatzustand
liquid
Farbe
Colorless
PH
5 · 5-8 (25℃, 1M in H2O)
Geruch (Odor)
faint pleasant odor
Wasserlöslichkeit
2 O: · H2O: 1 M at 20 °C, miscible
Merck
14 · 14,9230
BRN
773898 · 773898
Dielectric constant
24.46 · 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 · 632-22-4(CAS DataBase Reference)
NIST chemische Informationen
Urea, tetramethyl-(632-22-4)
EPA chemische Informationen
Tetramethylurea (632-22-4)

Acute Tox. 4 (97.4%)

Flammable liquids - Category 4

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresFOAM, MIST, SPRAY, DRY CHEMICALS.

Toxikologische Informationen

Interactions · 3 Einträge

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.

TETRAMETHYLUREA LOWERED YIELDS AND/OR INCIDENCES OF TUMORS PROMOTED BY RETINYL ACETATE OR CROTON OIL AFTER INITIATION BY 7,12-DIMETHYLBENZ(A)ANTHRACENE. TOPICAL APPLICATION OF INDUCERS MIGHT HAVE THERAPEUTIC POTENTIAL IN EPIDERMAL CARCINOMA.

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Non-Human Toxicity Excerpts · 3 Einträge

ONE SC INJECTION OF 5.6 OR 8.6 MMOL TETRAMETHYLUREA/KG OR REPEATED DAILY ADMIN OF 0.9 AND 1.7 MMOL/KG TO PREGNANT MICE HAD A TERATOGENIC EFFECT ON EMBRYOS. GREATEST EFFECT WAS BY SINGLE DOSES ON 8TH OR 11TH DAY OF GESTATION. WHEN GIVEN ON 8TH DAY IT PRODUCED MOSTLY CRANIAL EFFECTS & ON 22ND DAY PAW MALFORMATIONS.

TETRAMETHYLUREA WAS APPLIED TO SKIN OF RATS & RABBITS DURING ORGANOGENESIS. SLIGHT TERATOGENIC EFFECTS WERE DEMONSTRATED.

TETRAMETHYLUREA 150 MG/KG IV ACUTELY OR DAILY FOR 5 DAYS WAS NOT LETHAL & CAUSED ONLY WEIGHT LOSS IN DOGS, MONKEYS, & MICE. DOSES HIGHER THAN 100 MG/KG CAUSED HYPOTENSION IN DOGS.

Toxicity DataLCLo (rat) = 312 ppm/4h

Sicherheitsdaten

F
3-10
wgk
3
tsca
TSCA listed
ridadr
NA 1993 / PGIII
hs_code
2924199090
RTECS-Nr.
YU2625000
risk_code
22-61
Toxizität
LD50 i.v. in rats: 1.1 g/kg (Lüttringhaus, Dirksen)
hazard_code
Xn,T
safety_code
53-45
hazard_class
CBL
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
632-22-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Repr. 1BSkin Irrit. 2
Tetramethylthioharnstoff
1,2-Dichlorethan
Carbonylchlorid
N-Methylmethanamin, gasförmig

Nachgelagerte Produkte

Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate2-Bromothiophenol(bis-dimethylamino-methylene)-malononitrileMethyl 4-Mercaptobenzoate2-Chlorothiophenol

Ergänzende Hinweise

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.