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% |
C16H27N3O4Si
tetramethylurea
Conditions | Yield |
---|---|
In chloroform-d1 at 90℃; for 20h; | 81% |
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
malononitrile
A
(bis-dimethylamino-methylene)-malononitrile
B
tetramethylurea
Conditions | Yield |
---|---|
With dimethylaminomethyl-polystyrene In acetonitrile at 25℃; for 24h; | A 70% B n/a |
dimethyl malonate sodium salt
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
A
malonsaeure-dimethylester
B
tetramethylurea
Conditions | Yield |
---|---|
In acetonitrile at 25℃; for 0.25h; | A 55% B n/a |
4-Nitrophenylacetonitrile
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
A
α--4-nitrophenylacetonitrile
B
tetramethylurea
Conditions | Yield |
---|---|
With dimethylaminomethyl-polystyrene In acetonitrile at 81℃; for 20h; | A 52% B n/a |
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
ethyl 2-cyanoacetate
A
2-Cyan-3,3-bis-(dimethylamino)-acrylsaeure-ethylester
B
tetramethylurea
Conditions | Yield |
---|---|
With dimethylaminomethyl-polystyrene In acetonitrile at 81℃; for 20h; | A 51% B n/a |
bis(dimethylamino)malononitrile
sodium ethanolate
A
N,N,N',N'-Tetramethylharnstoff-diethylacetal
B
tetramethylurea
Conditions | Yield |
---|---|
In acetonitrile for 12h; | A 42% B 14 % Spectr. |
Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat)
diphenylphosphorylazide
A
<2-<2,2-Bis(dimethylamino)-1-(diphenylphosphoryl)vinyl>-2H-tetrazol-5-yl>diphenylphosphanoxid
B
tetramethylurea
Conditions | Yield |
---|---|
In acetonitrile -20 deg C to r.t. 30 min; | A 42% B 39% |
Conditions | Yield |
---|---|
With 4-methylmorpholine N-oxide; sodium hydroxide In water at 50℃; for 1h; | 40% |
Conditions | Yield |
---|---|
tetraphosphorus decasulfide; triphenyl antimony oxide In benzene at 120℃; under 36752.9 Torr; for 3h; | 33% |
potassium cyanide
A
2,2-Bis(dimethylamino)-2-ethoxyacetonitril
B
tetramethylurea
Conditions | Yield |
---|---|
With sodium cyanide In acetonitrile for 40h; Ambient temperature; | A 30.2% B n/a |
N-Methoxy-N-chloro-N',N'-dimethylurea
dimethyl amine
A
bis-(dimethylamino)methane
B
tetramethylurea
Conditions | Yield |
---|---|
at 0℃; for 1h; | A 26.4% B 9.1% |
N-Methoxy-N-chloro-N',N'-dimethylurea
A
1,2-bis(N,N-dimethylcarbamoyl)hydrazine
B
N-methoxy-N′,N′-dimethylurea
C
tetramethylurea
Conditions | Yield |
---|---|
With triethylamine In benzene at 7℃; | A 17.4% B 7.2% C 22.7% |
N-(n-butyl)-N',N'-dimethyl-N-nitrourea
A
N-(n-butyl)-N',N'-dimethylurea
B
1-butyl N,N-dimethylcarbamate
C
tetramethylurea
Conditions | Yield |
---|---|
In tetrachloromethane at 110℃; Mechanism; | A 10% B 7% C 19% |
In tetrachloromethane at 110℃; | A 10 % Spectr. B 7 % Spectr. C 19 % Spectr. |
dimethylchloroamine
potassium cyanide
A
NCNMe2
B
tetramethylurea
Conditions | Yield |
---|---|
With ethanol |
1,μ-dithio-dicarbonic acid bis-dimethylamide
A
carbon oxide sulfide
B
tetramethylurea
Conditions | Yield |
---|---|
at 25℃; | |
at 210℃; |
dimethyl amine
N,N-Dimethylcarbamoyl chloride
benzene
tetramethylurea
Conditions | Yield |
---|---|
je nach Bedingungen; |
N-(1-norbornyl)-N',N'-dimethyl-N-nitrosourea
A
N-(n-butyl)-N',N'-dimethylurea
B
1-butyl N,N-dimethylcarbamate
C
tetramethylurea
Conditions | Yield |
---|---|
In tetrachloromethane at 110℃; | A 10 % Spectr. B 7 % Spectr. C 19 % Spectr. |
Conditions | Yield |
---|---|
With dibenzoyl peroxide In chlorobenzene at 100℃; for 3h; | 25 % Turnov. |
With dibenzoyl peroxide In chlorobenzene at 100℃; for 3h; Product distribution; Kinetics; | 25 % Turnov. |
N-(n-butyl)-N',N'-dimethyl-N-nitrosourea
A
1-butyl N,N-dimethylcarbamate
C
tetramethylurea
Conditions | Yield |
---|---|
In tetrachloromethane at 60℃; | A 37 % Spectr. B 12 % Spectr. C 26 % Spectr. |
at 83℃; | A 45 % Spectr. B 32 % Spectr. C 23 % Spectr. |
In tetrachloromethane at 60℃; for 163h; Product distribution; Mechanism; other temperature; without solvent; other reaction time; |
N,N,N,N-tetramethyldiamino methoxycarbonium methylsulfonate
A
N-Nitrosodimethylamine
B
tetramethylurea
Conditions | Yield |
---|---|
With sodium nitrite In water at 69.9℃; for 2h; | A 20 % Spectr. B 80 % Spectr. |
Conditions | Yield |
---|---|
With iodine; potassium carbonate; palladium diacetate In acetonitrile at 95℃; under 2052 Torr; for 3h; | 40 % Chromat. |
With oxygen |
Conditions | Yield |
---|---|
With tetrachloromethane for 48h; |
1,1,3,3-tetramethyl-2-thiourea
Hexafluoroacetone
A
2,2,4,4-Tetrakis(trifluoromethyl)-1,3-dithietane
B
tetramethylurea
Conditions | Yield |
---|---|
In acetonitrile 1) 24h, r.t., 2) 24h, 40 deg C; Yield given. Yields of byproduct given; | |
In acetonitrile for 24h; Ambient temperature; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
at 20℃; Rate constant; pH=11; |
Conditions | Yield |
---|---|
at 20℃; Rate constant; pH=11; |
tetramethylurea
N,N,N',N'-tetramethylchlorformamidinium chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In chloroform at 105℃; for 18h; Inert atmosphere; Schlenk technique; | 100% |
With oxalyl dichloride In chloroform at 85℃; for 16h; Inert atmosphere; | 99.5% |
With COCl2 | 98% |
tetramethylurea
Conditions | Yield |
---|---|
Stage #1: tetramethylurea With phosgene In toluene at 20 - 60℃; for 0.416667h; Stage #2: With ammonium hexafluorophosphate In dichloromethane; water at 20℃; | 100% |
Stage #1: tetramethylurea With oxalyl dichloride In toluene at 20℃; for 18h; Cooling with ice; Stage #2: With potassium hexafluorophosphate In water at 20℃; | 76% |
With potassium hexafluorophosphate 1) toluene, 0 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
at 20 - 25℃; for 21h; | 100% |
In pentane at 0 - 20℃; for 0.666667h; | 98.1% |
methyl ester of bis(pentafluoroethyl)phosphinic acid
tetramethylurea
Conditions | Yield |
---|---|
at 0 - 20℃; for 22.5h; | 100% |
Conditions | Yield |
---|---|
In pentane at 0 - 20℃; for 0.666667h; | 99.8% |
tetramethylurea
bis(cyclopentadienyl)bis(1,1,3,3-tetramethylurea)ytterbium(II)
Conditions | Yield |
---|---|
In hexane addn. of tetramethylurea to soln. of complex; suspn. decantation, solid washing (hexane), drying (vac.); elem. anal.; | 97% |
samarium diiodide bis(tetrahydrofuran)
tetramethylurea
[SmI2(tetrahydrofuran)2(tetramethylurea)2]
Conditions | Yield |
---|---|
In tetrahydrofuran ligand added to equimolecular amt. of Sm complex in THF at room temp. under Ar; left to stand for 2 h; filtered through a frit, evapd.; elem. anal.; X-ray detn.; | 96% |
phosgene
tetramethylurea
N,N,N',N'-tetramethylchlorformamidinium chloride
Conditions | Yield |
---|---|
In toluene at 0 - 20℃; for 26h; | 95% |
Tosyl isocyanate
tetramethylurea
N-bis(dimethylamino)methylene-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Reflux; | 93.6% |
In toluene for 48h; Reflux; | 93.6% |
Conditions | Yield |
---|---|
In acetonitrile for 24h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ruthenium(III) chloride trihydrate In decane at 110℃; for 0.166667h; Microwave irradiation; | 93% |
tetramethylurea
recorcinol
Tetramethyl-urea; compound with benzene-1,3-diol
Conditions | Yield |
---|---|
92% |
Conditions | Yield |
---|---|
Stage #1: tetramethylurea With oxalyl dichloride In dichloromethane at 60℃; for 18h; Stage #2: n-Octylamine In acetonitrile at 60℃; for 4h; Stage #3: With potassium carbonate; sodium hydroxide In diethyl ether; water at 0℃; | 92% |
With oxalyl dichloride 1.) DME, 60 deg C, 12 h, 2.) MeCN, reflux, 24 h; Multistep reaction; |
tetramethylurea
Conditions | Yield |
---|---|
In acetonitrile for 24h; Heating; | 92% |
Conditions | Yield |
---|---|
In toluene (N2); stirring (0°C); ppt. washing (CHCl3, Et2O), drying (vac.); elem. anal.; | 92% |
Conditions | Yield |
---|---|
With [Ir(3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl)2(4,4'-bis(trifluoromethyl)bipyridine)]PF6; C16H14N4O In 1,2-dichloro-ethane at 25℃; Irradiation; | 92% |
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane for 5h; Heating / reflux; | 91.9% |
2,3-naphthalenediol
tetramethylurea
Naphthalene-2,3-diol; compound with tetramethyl-urea
Conditions | Yield |
---|---|
91% |
tetramethylurea
Conditions | Yield |
---|---|
In ethanol; water a mixture of MoO2(acac)2 and tetramethylurea in 96% ethanol stirred for 45 min at room temp.; concentrated under vacuum; diethyl ether added and the precipitate collected by filtration, washed with diethyl ether three times and dried under vacuum; elem. anal.; | 91% |
1-ethyl-2-methylindole
tetramethylurea
bis(1-ethyl-2-methyl-1H-indol-3-yl)methane
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ruthenium(III) chloride trihydrate In decane at 110℃; for 0.166667h; Microwave irradiation; | 91% |
2,4-Dinitrophenol
tetramethylurea
2,4-Dinitro-phenol; compound with tetramethyl-urea
Conditions | Yield |
---|---|
90% |
tetramethylurea
Conditions | Yield |
---|---|
With Oxalyl bromide In chloroform at 65℃; Ionic liquid; Schlenk technique; | 90% |
Pentachlorophenol
tetramethylurea
2,3,4,5,6-Pentachloro-phenol; compound with tetramethyl-urea
Conditions | Yield |
---|---|
In diethyl ether; hexane | 89% |
tetramethylurea
Conditions | Yield |
---|---|
In neat (no solvent) mixed, gently heated, stirred for 1 h at room temp.; crystd.(diethyl ether), filtered, dried (vac.), recrystd.(diethyl ether-1,2-dichloroethane), elem. anal.; | 89% |
Conditions | Yield |
---|---|
In toluene (N2); stirring (0°C); ppt. washing (CHCl3, Et2O), drying (vac.); elem. anal.; | 89% |
Conditions | Yield |
---|---|
With 2C6H15N*ClH*Cl2HOPS In chloroform for 10h; Reflux; | 89% |
Conditions | Yield |
---|---|
With 4,4'-Dichlorobenzophenone at 30℃; for 35h; Irradiation; | 89% |
2-<<1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl>thio>-4-(trifluoromethyl)-4,5,5,5-tetrafluoro-1-pentene-1,3-dione
tetramethylurea
Dimethyl-carbamic acid 1-[1-dimethylcarbamoyl-1-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethylsulfanyl)-meth-(E)-ylidene]-2,3,3,3-tetrafluoro-2-trifluoromethyl-propyl ester
Conditions | Yield |
---|---|
Ambient temperature; | 88% |
1,2-dimethylindole
tetramethylurea
bis(1,2-dimethyl-1H-indol-3-yl)methane
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ruthenium(III) chloride trihydrate In decane at 110℃; for 0.166667h; Microwave irradiation; | 88% |
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. |
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