Basic information
- Standard SMILES
CN(C)C(=O)N(C)C- InChIKey
AVQQQNCBBIEMEU-UHFFFAOYSA-N- Molecular formula
- C5H12N2O
- Average molar mass
- 116.16 g/mol
- Monoisotopic mass
- 116.094963
Overview
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.
Names & identifiers
- Preferred name
- Tetramethylurea
- IUPAC
- 1,1,3,3-tetramethylurea
- English name
- 1,1,3,3-Tetramethylurea
- Molecular formula
- C5H12N2O
- Molecular weight
- 116.16
Names & synonyms
1,1,3,3-TetramethylureaTETRAMETHYLUREA632-22-4TemurUrea, tetramethyl-N,N,N',N'-TetramethylureaTetramethylureeUrea, 1,1,3,3-tetramethyl-NSC-914882O1EJ64031DTXSID1060893CHEBI:84278
Show more names
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
Database identifiers
- CAS
632-22-4- PubChem CID
- 12437
- DTXSID
DTXSID1060893- ChEMBL
CHEMBL11949- ChEBI
CHEBI:84278- UNII
- 2O1EJ64031
- EC Number
- 211-173-9
- Nikkaji
- J6.897G
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 23.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 78.4
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Urea Compounds
SpringerMaterials PropertiesSchoenflies notation
LogP
log Kow = 0.19
0.19
OdorFAINT, PLEASANT
Density0.9687 @ 20 °C/4 °C
Color/FormLIQUID
Solubility
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 Pressurevaopr pressure = 13.9 mm Hg @ 71 °C
Refractive IndexINDEX OF REFRACTION: 1.4493 @ 25 °C/D
Physicochemical properties
- Melting point
- 1 °C · −1 °C(lit.)
- Boiling point
- 177 °C · 177 °C(lit.)
- Density
- 0.968 g/mL · 0.968 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.451(lit.)
- Flash point
- 150 °F · 150 °F
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Miscible with water, petroleum ether and common solvents.
- form
- Liquid
- pka
- 2 · 2.0(at 25℃)
- color
- Clear colorless to pale yellow
- PH
- 5 · 5-8 (25℃, 1M in H2O)
- Relative polarity
- 5 · 5
- Odor
- faint pleasant odor
- Water Solubility
- 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 DataBase Reference
- 632 · 632-22-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 O1EJ64031 · 2O1EJ64031
- NIST Chemistry Reference
- Urea, tetramethyl-(632-22-4)
- EPA Substance Registry System
- Tetramethylurea (632-22-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H318-H360D
- Precautionary statements
- 202 · P202-P280-P301+P312-P302+P352-P305+P351+P338-P308+P313
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,T
- Risk Statements
- 22 · 22-61
- Safety Statements
- 53 · 53-45
- RIDADR
- 1993 · NA 1993 / PGIII
- WGK Germany
- 3 · 3
- RTECS
- 2625000 · YU2625000
- F
- 3 · 3-10
- TSCA
- TSCA listed
- HazardClass
- CBL
- HS Code
- 29241900 · 29241900
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Repr. 1BSkin Irrit. 2
- Hazardous Substances Data
- 632 · 632-22-4(Hazardous Substances Data)
- Toxicity
- 50 i.v · LD50 i.v. in rats: 1.1 g/kg (Lüttringhaus, Dirksen)
- Excepted Quantities
- Non-Hazardous
Safety & regulation
GHS classification
GHS Classification
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]
Hazard information
Regulatory Information
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
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
Acute Tox. 4 (97.4%)
Flammable liquids - Category 4
Safety & protection
Fire Fighting ProceduresFOAM, MIST, SPRAY, DRY CHEMICALS.
Toxicology
Interactions
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
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
Safety data
- F
- 3-10
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YU2625000
- ridadr
- NA 1993 / PGIII
- hs_code
- 29241900
- Toxicity
- LD50 i.v. in rats: 1.1 g/kg (Lüttringhaus, Dirksen)
- risk_code
- 22-61
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS08
- hazard_code
- Xn,T
- safety_code
- 53-45
- hazard_class
- CBL
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302-H315-H318-H360D
- Excepted Quantities
- Non-Hazardous
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Repr. 1BSkin Irrit. 2
- Precautionary statements
- P202-P280-P301+P312-P302+P352-P305+P351+P338-P308+P313
- Hazardous Substances Data
- 632-22-4(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as solvent and reagent; [Merck Index]
SOLVENT & REAGENT
U.S. Exports
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production
(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
Applications
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.
Preparation methods
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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
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.
Related reactions
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