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1,1,3,3-Tetramethylurea

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Name

1,1,3,3-Tetramethylurea

EINECS 211-173-9
CAS No. 632-22-4 Density 0.9879 g/cm3
PSA 23.55000 LogP 0.22960
Solubility miscible with water Melting Point -1 °C(lit.)
Formula C5H12N2O Boiling Point 175.2 °C at 760 mmHg
Molecular Weight 116.163 Flash Point 53.9 °C
Transport Information N/A Appearance Clear colorless to pale yellow liquid
Safety 53-45 Risk Codes 22
Molecular Structure Molecular Structure of 632-22-4 (1,1,3,3-Tetramethylurea) Hazard Symbols HarmfulXn
Synonyms

Urea,1,1,3,3-tetramethyl- (6CI);Urea, tetramethyl- (8CI,9CI);NSC 91488;TMU;Temur;Tetramethylcarbamide;

Article Data 66

1,1,3,3-Tetramethylurea Synthetic route

32315-10-9

bis(trichloromethyl) carbonate

124-40-3

dimethyl amine

632-22-4

tetramethylurea

Conditions
ConditionsYield
In dichloromethane; water at 15 - 20℃; Large scale;92%
201230-82-2

carbon monoxide

506-59-2

N,N-dimethylammonium chloride

632-22-4

tetramethylurea

Conditions
ConditionsYield
With 2C7H9N4*Au(1+)*Cu(1+)*2I(1-); sodium carbonate In toluene at 60℃; Autoclave;86%
2782-91-4

1,1,3,3-tetramethyl-2-thiourea

632-22-4

tetramethylurea

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

Et3N

Et3N

A

97513-13-8

<2-<2,2-Bis(dimethylamino)-1-(diphenylphosphoryl)vinyl>-2H-tetrazol-5-yl>diphenylphosphanoxid

B

632-22-4

tetramethylurea

Conditions
ConditionsYield
In acetonitrile -20 deg C to r.t. 30 min;A 42%
B 39%

1,1,3,3-Tetramethylurea Consensus Reports

Reported in EPA TSCA Inventory.

1,1,3,3-Tetramethylurea 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.

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