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| CAS No.: | 632-22-4 |
|---|---|
| Name: | 1,1,3,3-Tetramethylurea |
| Article Data: | 66 |
| Molecular Structure: | |
|
|
|
| Formula: | C5H12N2O |
| Molecular Weight: | 116.163 |
| Synonyms: | Urea,1,1,3,3-tetramethyl- (6CI);Urea, tetramethyl- (8CI,9CI);NSC 91488;TMU;Temur;Tetramethylcarbamide; |
| EINECS: | 211-173-9 |
| Density: | 0.9879 g/cm3 |
| Melting Point: | -1 °C(lit.) |
| Boiling Point: | 175.2 °C at 760 mmHg |
| Flash Point: | 53.9 °C |
| Solubility: | miscible with water |
| Appearance: | Clear colorless to pale yellow liquid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 53-45 |
| PSA: | 23.55000 |
| LogP: | 0.22960 |
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| Conditions | Yield |
|---|---|
| In dichloromethane; water at 15 - 20℃; Large scale; | 92% |
| Conditions | Yield |
|---|---|
| With 2C7H9N4*Au(1+)*Cu(1+)*2I(1-); sodium carbonate In toluene at 60℃; Autoclave; | 86% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; N-nitrosopiperidine; potassium iodide In dichloromethane; water at 22℃; for 48h; | 85% |
| With manganese(IV) oxide In chloroform Ambient temperature; | 79% |
| With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 5h; Ambient temperature; | 75% |
- 138767-93-8
C16H27N3O4Si
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| In chloroform-d1 at 90℃; for 20h; | 81% |
- 78581-29-0
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
- 109-77-3
malononitrile
A
- 31774-36-4
(bis-dimethylamino-methylene)-malononitrile
B
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| With dimethylaminomethyl-polystyrene In acetonitrile at 25℃; for 24h; | A 70% B n/a |
- 18424-76-5
dimethyl malonate sodium salt
- 78581-29-0
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
A
- 31774-43-3
malonsaeure-dimethylester
B
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| In acetonitrile at 25℃; for 0.25h; | A 55% B n/a |
- 555-21-5
4-Nitrophenylacetonitrile
- 78581-29-0
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
A
- 22703-65-7
α--4-nitrophenylacetonitrile
B
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| With dimethylaminomethyl-polystyrene In acetonitrile at 81℃; for 20h; | A 52% B n/a |
- 78581-29-0
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
- 105-56-6
ethyl 2-cyanoacetate
A
- 72834-60-7
2-Cyan-3,3-bis-(dimethylamino)-acrylsaeure-ethylester
B
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| With dimethylaminomethyl-polystyrene In acetonitrile at 81℃; for 20h; | A 51% B n/a |
- 63442-64-8
bis(dimethylamino)malononitrile
- 141-52-6
sodium ethanolate
A
- 67751-11-5
N,N,N',N'-Tetramethylharnstoff-diethylacetal
B
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| In acetonitrile for 12h; | A 42% B 14 % Spectr. |
- 78581-29-0
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
- 5353-66-2
diphenylphosphorylazide
A
- 97513-13-8
<2-<2,2-Bis(dimethylamino)-1-(diphenylphosphoryl)vinyl>-2H-tetrazol-5-yl>diphenylphosphanoxid
B
- 632-22-4
tetramethylurea
| Conditions | Yield |
|---|---|
| In acetonitrile -20 deg C to r.t. 30 min; | A 42% B 39% |
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Consensus Reports
Specification
The 1,1,3,3-Tetramethylurea, also known as N,N,N',N'-Tetramethylurea, is the organic compound with the formula C5H12N2O. This chemical belongs to the product category of Miscellaneous. Its EINECS registry number is 211-173-9. With the CAS registry number 632-22-4, its IUPAC name is called 1,1,3,3-Tetramethylurea.
Physical properties of 1,1,3,3-Tetramethylurea: (1)ACD/LogP: 0.19; (2)ACD/LogD (pH 5.5): 0.19; (3)ACD/LogD (pH 7.4): 0.19; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 30.22; (7)ACD/KOC (pH 7.4): 30.22; (8)#H bond acceptors: 3; (9)Index of Refraction: 1.445; (10)Molar Refractivity: 32.68 cm3; (11)Molar Volume: 122.6 cm3; (12)Surface Tension: 30.1 dyne/cm; (13)Density: 0.946 g/cm3; (14)Flash Point: 53.9 °C; (15)Enthalpy of Vaporization: 41.15 kJ/mol; (16)Boiling Point: 175.2 °C at 760 mmHg; (17)Vapour Pressure: 1.16 mmHg at 25°C.
Preparation of 1,1,3,3-Tetramethylurea: this chemical can be prepared by diphenyl carbonate and dimethylamine. The reaction mixture is heated at 200 °C for 4 h and is cooled down. The reactant is stired after addition of NaOH. Then it will be purified by diethyl ether. Hence, decompress fractionation are chosen to separate the product. Finally, you will obtained tetramethylurea.
(C6H5)2CO+(CH3)2NH → C6H5OH+C6H5OCON(CH3)2
C6H5OCON(CH3)2 → C6H5OH+(CH3)2NCON(CH3)2
Uses of 1,1,3,3-Tetramethylurea: because of its low permittivity, this chemical is appropriate for isomerization and alkylation hydrocyanation of base catalysis. It can also be used as other condensation reaction solvent. In addition, it can be used as acetylene and polyacrylonitrile solvents.
When you are using this chemical, please be cautious about it. This chemical may cause damage to health. It is harmful if swallowed. You must avoid exposure - obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN(C)C(=O)N(C)C
(2)InChI: InChI=1S/C5H12N2O/c1-6(2)5(8)7(3)4/h1-4H3
(3)InChIKey: AVQQQNCBBIEMEU-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| monkey | LDLo | intravenous | 750mg/kg (750mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 1600, Pg. 333, 1966. | |
| mouse | LD50 | intravenous | 2230mg/kg (2230mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 160, Pg. 333, 1966. | |
| mouse | LD50 | oral | 2920mg/kg (2920mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 160, Pg. 333, 1966. | |
| mouse | LDLo | intraperitoneal | 2900mg/kg (2900mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Journal of Pharmacology and Experimental Therapeutics. Vol. 54, Pg. 188, 1935. |
| rabbit | LD50 | skin | 3160mg/kg (3160mg/kg) | BEHAVIORAL: TREMOR | National Technical Information Service. Vol. OTS0559251, |
| rat | LCLo | inhalation | 312ppm/4H (312ppm) | BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0559251, |
| rat | LD50 | intravenous | 1100mg/kg (1100mg/kg) | Angewandte Chemie, International Edition in English. Vol. 3, Pg. 260, 1964. | |
| rat | LD50 | oral | 794mg/kg (794mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | National Technical Information Service. Vol. OTS0559251, |
| rat | LD50 | unreported | 1400mg/kg (1400mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1073, 1969. |