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Methylurea

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Name

Methylurea

EINECS 209-935-0
CAS No. 598-50-5 Density 1.041 g/cm3
PSA 55.12000 LogP 0.37570
Solubility 1000 g/L (20 ºC) Melting Point ~93 °C
Formula C2H6N2O Boiling Point 114.6 °C at 760 mmHg
Molecular Weight 74.0824 Flash Point 23.1 °C
Transport Information N/A Appearance White, crystalline needles.
Safety 22-45-36/37 Risk Codes 68-37-20/21/22
Molecular Structure Molecular Structure of 598-50-5 (Methylurea) Hazard Symbols HarmfulXn
Synonyms

Urea,methyl- (6CI,8CI,9CI);1-Methylurea;Methylurea;Monomethylurea;N-Methylurea;

Article Data 93

Methylurea Synthetic route

624-83-9

methyl isocyanate

598-50-5

N-Methylurea

Conditions
ConditionsYield
With ammonium hydroxide In water at 0 - 20℃; for 3.5h;99%
With diethyl ether; ammonia
With ammonia at 45℃;
22013-97-4

N-methyl-thiocarbamic acid S-methyl ester

A

74-93-1

methylthiol

B

598-50-5

N-Methylurea

Conditions
ConditionsYield
With ammonia In water at 65℃;A n/a
B 96%
22013-97-4

N-methyl-thiocarbamic acid S-methyl ester

598-50-5

N-Methylurea

Conditions
ConditionsYield
With ammonium hydroxide In 1,4-dioxane96%
With ammonium hydroxide In 1,4-dioxane at 65℃; for 3h;
590-28-3

potassium cyanate

593-51-1

methylamine hydrochloride

598-50-5

N-Methylurea

Conditions
ConditionsYield
In water for 0.5h; Heating;90%
1142408-78-3

1,5-dimethyl-3-(3,4,5-trimethoxyphenyl)-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one

A

1142408-82-9

1-methyl-5,6-dioxo-3-(3,4,5-trimethoxyphenyl)-1,4,5,6-tetrahydro-1,2,4-triazine

B

598-50-5

N-Methylurea

Conditions
ConditionsYield
Stage #1: 1,5-dimethyl-3-(3,4,5-trimethoxyphenyl)-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one With ethanol; sodium hydroxide Reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=7; Cooling with ice;
A 89%
B n/a
598-52-7

1-(methyl)-thiourea

598-50-5

N-Methylurea

Conditions
ConditionsYield
With tetrabutylammonium periodite In dichloromethane; acetonitrile at 20℃; for 0.583333h;88%
With sodium bromate at 25℃; Rate constant; Mechanism; various stoichiometry; also in the presence of acid;
1142408-77-2

1,5-dimethyl-3-p-tolyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one

A

1142408-80-7

1-methyl-5,6-dioxo-3-p-tolyl-1,4,5,6-tetrahydro-1,2,4-triazine

B

598-50-5

N-Methylurea

Conditions
ConditionsYield
Stage #1: 1,5-dimethyl-3-p-tolyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one With ethanol; sodium hydroxide Reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=7; Cooling with ice;
A 87%
B n/a

3-(4-bromophenyl)-1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one

A

3-(4-bromophenyl)-1-methyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazine

B

598-50-5

N-Methylurea

Conditions
ConditionsYield
Stage #1: 3-(4-bromophenyl)-1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one With ethanol; sodium hydroxide Reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=7; Cooling with ice;
A 86%
B n/a
61602-19-5

1,5-dimethyl-3-phenyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one

A

1-methyl-5,6-dioxo-3-phenyl-1,4,5,6-tetrahydro-1,2,4-triazine

B

598-50-5

N-Methylurea

Conditions
ConditionsYield
Stage #1: 1,5-dimethyl-3-phenyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one With ethanol; sodium hydroxide Reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=7; Cooling with ice;
A 84%
B 16 mg
1142408-75-0

3-(4-chlorophenyl)-1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one

A

3-(4-chlorophenyl)-1-methyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazine

B

598-50-5

N-Methylurea

Conditions
ConditionsYield
Stage #1: 3-(4-chlorophenyl)-1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-one With ethanol; sodium hydroxide Reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=7; Cooling with ice;
A 83%
B 20 mg

Methylurea Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Methylurea Specification

The CAS registry number of N-Methylurea is 598-50-5. The IUPAC name is methylurea. Its EINECS registry number is 209-935-0 . In addition, the molecular formula is C2H6N2O and the molecular weight is 74.08. It is a kind of white to off-white crystalline solid and belongs to the classes of Carbonyl Compounds; Organic Building Blocks; Ureas.

Physical properties about this chemical are: (1)ACD/LogP: -1.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.23; (4)ACD/LogD (pH 7.4): -1.23; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.12; (8)ACD/KOC (pH 7.4): 5.12; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 23.55 Å2; (13)Index of Refraction: 1.432; (14)Molar Refractivity: 18.47 cm3; (15)Molar Volume: 71.1 cm3; (16)Polarizability: 7.32 ×10-24cm3; (17)Surface Tension: 35.5 dyne/cm; (18)Density: 1.041 g/cm3; (19)Flash Point: 23.1 °C; (20)Enthalpy of Vaporization: 35.3 kJ/mol; (21)Boiling Point: 114.6 °C at 760 mmHg ; (22)Vapour Pressure: 19.8 mmHg at 25°C.

Uses of N-Methylurea: it can be used in organic synthesis and pharmaceutical industry. And it can react with diethylmalonic acid diethyl ester to get 5,5-diethyl-1-methyl-pyrimidine-2,4,6-trione. This reaction will need reagents Na and EtOH. The reaction time is 4 hours at reaction temperature of 115 °C. The yield is about 68%.

N-Methylurea can react with diethylmalonic acid diethyl ester to get 5,5-diethyl-1-methyl-pyrimidine-2,4,6-trione

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. And it is irritating to the respiratory system. It has risk of irreversible effects possibly. During using it, wear suitable protective clothing and gloves and do not breathe dust. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N)NC
(2)InChI: InChI=1/C2H6N2O/c1-4-2(3)5/h1H3,(H3,3,4,5)
(3)InChIKey: XGEGHDBEHXKFPX-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo parenteral 10189mg/kg (10189mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 52, Pg. 216, 1934.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Naunyn-Schmiedebergs Archiv fuer Pharmakologie und Experimentelle Pathologie. Vol. 257, Pg. 296, 1967.
rat LDLo oral 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 47, 1953.

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