Conditions | Yield |
---|---|
In water at 60℃; for 2h; | 97% |
1,3-Dimethyl-5-(1-phenyl-ethyl)-[1,3,5]triazinan-2-one
A
N,N'-Dimethylurea
B
rac-methylbenzylamine
Conditions | Yield |
---|---|
With ammonium chloride at 70℃; for 3h; other hexahydro-2-oxo-1,3,5-triazines; | A n/a B 90% |
sodium methylate
1,3-Dimethyl-1-(1H-pyrazole-4-carbonyl)-urea
A
methyl pyrazole-4-carboxylate
B
N,N'-Dimethylurea
Conditions | Yield |
---|---|
In methanol for 2h; Heating; | A 79% B 83% |
1,3-Dimethyl-1-(1H-pyrazole-4-carbonyl)-urea
A
methyl pyrazole-4-carboxylate
B
N,N'-Dimethylurea
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Heating; | A 79% B 83% |
Conditions | Yield |
---|---|
With ytterbium(III) triflate In 1,4-dioxane at 90℃; for 8h; Schlenk technique; Inert atmosphere; Sealed tube; | A n/a B 8% C 80% |
1,3-dimethyl-4-thiouracil
6-Amino-1,3-dimethylbarbituric acid
A
N,N'-Dimethylurea
B
1,3-dimethyl-7-mercaptopyrido<2,3-d>pyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol | A n/a B 78% |
L-cysteine ethyl ester hydrochloride
A
N,N'-Dimethylurea
B
ethyl (R)-4,5-dihydrothiazole-4-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Heating; | A n/a B 78% |
N,N-dimethylthiourea
benzil
A
N,N'-Dimethylurea
B
1,3,4,6-Tetramethyl-3a,6a-diphenyl-5-thioxo-hexahydro-imidazo[4,5-d]imidazol-2-one
C
1,3-dimethyl-4,5-diphenyl-5-imidazoline-2-thioneN,N-dimethyl-4-oxo-4H-chromene-2-carboxamide
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 4h; Mechanism; Heating; other substrates; | A n/a B n/a C 71% |
With hydrogenchloride In ethanol for 4h; Heating; | A n/a B n/a C 71% |
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
1-phenylbutan-1,3-dione
A
N,N'-Dimethylurea
Conditions | Yield |
---|---|
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃; | A 6% B 70% |
6-Amino-1,3-dimethylbarbituric acid
5-(1,3-Dimethyl-2,4-dioxopyrimidil)methyl ketone
A
N,N'-Dimethylurea
B
6-Acetyl-1,3-dimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 9h; Heating; | A n/a B 65% |
6-amino-1,3-diethyluracil
1,3-dimethyl-5-cyanouracil
A
N,N'-Dimethylurea
B
1,3-Diethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 1h; Heating; | A n/a B 65% |
di(succinimido) carbonate
methylamine
A
2,5-dioxopyrrolidin-1-yl methylcarbamate
B
N,N'-Dimethylurea
Conditions | Yield |
---|---|
In acetonitrile Ambient temperature; | A 63.1% B n/a |
6-Amino-1,3-dimethylbarbituric acid
1,3-dimethyl-5-cyanouracil
A
N,N'-Dimethylurea
B
6-cyano-1,3-dimethylpyrido<2,3-d>pyrimidine-2,4,7-(1H,3H,8H)-trione
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 4h; Heating; | A n/a B 63% |
6-amino-1,3-dipropyluracil
1,3-dimethyl-5-cyanouracil
A
N,N'-Dimethylurea
B
2,4,7-Trioxo-1,3-dipropyl-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 2h; Heating; | A n/a B 63% |
N1,N3-dimethyl-N1-nitrosothiourea
N,N'-Dimethylurea
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether for 0.5h; | 62% |
With hydrogenchloride; water 1) ether, 2) ether; Yield given. Multistep reaction; |
sodium ethanolate
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
acetylacetone
A
N,N'-Dimethylurea
B
ethyl 3-acetyl-4-hydroxybenzoate
Conditions | Yield |
---|---|
In ethanol for 2h; Mechanism; Heating; other 1,3-ambident nucleophiles. Object of study: a novel ring transformation; | A n/a B 55% |
In ethanol for 2h; Heating; | A n/a B 55% |
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
acetylacetone
A
N,N'-Dimethylurea
B
ethyl 3-acetyl-4-hydroxybenzoate
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 2h; Heating; Yield given; | A n/a B 55% |
With sodium ethanolate In ethanol for 2h; Heating; Yield given; |
6-Amino-1,3-dimethylbarbituric acid
1,3-dimethyl-5-nitrouracil
A
N,N'-Dimethylurea
B
6-nitropyridopyrimidine
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 3h; Heating; | A n/a B 50% |
Conditions | Yield |
---|---|
In ethanol; water at 80℃; for 12h; Green chemistry; | A n/a B 50% |
Conditions | Yield |
---|---|
In dichloromethane at 23℃; for 2h; | A n/a B 48% |
1,8-bis(1,3-dimethyluracil-6-yl)-cyclam
A
N,N'-Dimethylurea
Conditions | Yield |
---|---|
With zinc(II) perchlorate In dimethyl sulfoxide at 120℃; for 1h; | A n/a B 44.2% |
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
acetylacetone
A
N,N'-Dimethylurea
Conditions | Yield |
---|---|
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃; | A 4% B 15% C 36% D 14% |
ethyl acetoacetate
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
A
N,N'-Dimethylurea
B
3-(Ethoxycarbonyl)-4-hydroxy-N-methylbenzamide
Conditions | Yield |
---|---|
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃; | A 9% B 20% C 34% |
1,3-dimethyluracil
6-Amino-1,3-dimethylbarbituric acid
A
N,N'-Dimethylurea
B
1,3-dimethylpyrido<2,3-d>pyrimidine-2,4,7(1H,3H,8H)-trione
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 95h; Heating; | A n/a B 33% |
Conditions | Yield |
---|---|
With iron(III) chloride In methanol; N,N-dimethyl-formamide at 75℃; under 4137.29 Torr; for 6h; Catalytic behavior; Autoclave; | 32% |
Stage #1: nitromethane; methylamine In methanol; N,N-dimethyl-formamide for 0.166667h; Stage #2: carbon monoxide With iron(III) chloride In methanol; N,N-dimethyl-formamide at 90℃; under 3040.2 Torr; for 5h; Autoclave; | 28% |
Conditions | Yield |
---|---|
With hydrogenchloride; amalgamated zinc |
Conditions | Yield |
---|---|
With nickel at 100℃; under 51485.6 - 102971 Torr; Hydrogenation; |
methylammonium N-methylcarbamate
N,N'-Dimethylurea
Conditions | Yield |
---|---|
at 170℃; |
Conditions | Yield |
---|---|
With water | |
With water at 100℃; |
N,N'-Dimethylurea
indan-1,2,3-trione hydrate
3a,8a-dihydroxy-1,3-dimethyl-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione
Conditions | Yield |
---|---|
at 20℃; for 2h; | 100% |
In water at 50 - 60℃; | 82% |
N,N'-Dimethylurea
N-chloro-N,N'-dimethylurea
Conditions | Yield |
---|---|
With sodium hypochlorite In water Product distribution / selectivity; | 100% |
With water; sodium chloride at 20℃; for 0.5h; Reagent/catalyst; pH-value; Concentration; Electrolysis; | 89% |
N,N'-Dimethylurea
Glyoxilic acid
5-hydroxy-1,3-dimethylimidazolidine-2,4-dione
Conditions | Yield |
---|---|
In ethyl acetate Solvent; | 100% |
N,N'-Dimethylurea
N,N'-dimethyl-N,N'-dinitrourea
Conditions | Yield |
---|---|
With dinitrogen pentoxide In carbon dioxide at 0 - 5℃; under 45004.5 - 60006 Torr; for 0.5h; Time; liquid CO2; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide In 1,2-dichloro-ethane Product distribution; 1.) r.t., 15 min; 2.) 70-80 deg C; effect of oleum concentration in different solvents, influence of the temperature of dissolution of sulfuric acid, influence of reaction temperature on the yield; | 98% |
With sulfuric acid; sulfur trioxide In 1,2-dichloro-ethane 1.) 15 min, r.t.; 2.) 70-80 deg C, 6-8 h; | 98% |
With sulfuric acid; sulfur trioxide |
N,N'-Dimethylurea
Diphenylamino-phosphordichlorid
1,3-dimethyl-2-diphenylamino-1,3-diaza-2λ3-phosphetidin-4-on
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 12h; Ambient temperature; | 98% |
N,N'-Dimethylurea
1,3 dimethyl 1 nitrosourea
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; | 98% |
With sulfuric acid; sodium nitrite In water cooling; | 58% |
With cis-nitrous acid In 1,4-dioxane; water Rate constant; variation of H2O/dioxane ratio, addition of acids or salts; |
formaldehyd
N,N'-Dimethylurea
rac-methylbenzylamine
1,3-Dimethyl-5-(1-phenyl-ethyl)-[1,3,5]triazinan-2-one
Conditions | Yield |
---|---|
In water at 70 - 110℃; | 98% |
Conditions | Yield |
---|---|
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; palladium diacetate In 1,4-dioxane at 100℃; for 2h; | 98% |
N,N'-Dimethylurea
tert-butylisonitrile
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With D-glucose In water at -5 - 20℃; | 98% |
triphenylboroxine
N,N'-Dimethylurea
Bis-(dimethylamino)-phenylboran
O(μ-C6H5BNCH3)2CO
Conditions | Yield |
---|---|
In toluene byproducts: (CH3)2NH; under inert atm., mixt. of (C6H5BO)3 and ((CH3)2N)2BC6H5 heated for 90 min to 125°C, cooled to room temp., addn. of toluene and (NHCH3)2CO, stirred mixt. heated to reflux for 4 days; evapn., distd. under vac., sublimation, slowly crystn. on standing; elem. anal.; | 98% |
Conditions | Yield |
---|---|
With zirconyl chloride octahydrate for 0.05h; Irradiation; | 98% |
With 1H-imidazole In octane at 130℃; for 24h; |
Conditions | Yield |
---|---|
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction; | 98% |
N-methylene-tert-butylamine
N,N'-Dimethylurea
5-tert-Butyl-1,3-dimethyl-[1,3,5]triazinan-2-one
Conditions | Yield |
---|---|
for 4h; Heating; | 97% |
Conditions | Yield |
---|---|
With 3 A molecular sieve In 1,4-dioxane at 70℃; for 168h; Substitution; | 97% |
N,N'-Dimethylurea
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 4h; | 97% |
N,N'-Dimethylurea
[Cr(CO)5(C4HN2O(C6H5)(CH3)2)]
Conditions | Yield |
---|---|
In tetrahydrofuran heating of (CO)5Cr(C(CCPh)OCH2CH3) and HNMeCONHMe (2 equiv.) at 60°C in THF with stirring (Organometallics 17 (1998) 2135); cooling to room temp.; evapn. of solvent in vac., flash chromy.; | 97% |
In tetrahydrofuran Ar-atmosphere; room temp. (48 h); | 70% |
Conditions | Yield |
---|---|
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction; | 97% |
N,N'-Dimethylurea
ethyl acetoacetate
benzaldehyde
1,3,6-trimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In neat (no solvent) at 80℃; for 0.025h; Catalytic behavior; Reagent/catalyst; Solvent; Microwave irradiation; | 96% |
With chloro-trimethyl-silane In N,N-dimethyl-formamide | 79% |
With hafnium tetrakis(trifluoromethanesulfonate) In neat (no solvent) at 80℃; Biginelli Pyrimidone Synthesis; | 68% |
Dowex-50W at 130℃; Biginelli condensation; | 59% |
Conditions | Yield |
---|---|
In ethanol | 96% |
N,N'-Dimethylurea
acetic anhydride
cyanoacetic acid
6-Amino-1,3-dimethylbarbituric acid
Conditions | Yield |
---|---|
at 60℃; for 3h; | 96% |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 3h; | 96% |
Conditions | Yield |
---|---|
With magnesium(II) nitrate hexahydrate In octane at 130℃; for 24h; Reagent/catalyst; | 96% |
N,N'-Dimethylurea
sodium p-toluenesulfonamide
A
N-Methyl-N'-toluene-p-sulfonylurea
B
methylamine
Conditions | Yield |
---|---|
at 160℃; for 3h; Product distribution; Rate constant; Equilibrium constant; Other temperature, other time, other ratio of reactants, activation energy, ΔH, ΔS;; | A 95.5% B n/a |
at 160℃; for 3h; | A 95.5% B n/a |
formaldehyd
N,N'-Dimethylurea
(1R,2R)-2-aminocyclohexanol
5-((1R,2R)-2-Hydroxy-cyclohexyl)-1,3-dimethyl-[1,3,5]triazinan-2-one
Conditions | Yield |
---|---|
In water at 70 - 110℃; | 95% |
N,N'-Dimethylurea
3-trifluoromethylnitrobenzene
N-methyl-4-nitro-2-trifluoromethylaniline
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide | 95% |
N,N'-Dimethylurea
2,4-dichloro-5-(chlorosulfonyl)benzoic acid
2,4-dichloro-5-chlorosulfonylbenzoic acid N-methylamide
Conditions | Yield |
---|---|
at 90℃; | 95% |
4-Methoxyphenylacetic acid
N,N'-Dimethylurea
2-(4-methoxyphenyl)-N-methylacetamide
Conditions | Yield |
---|---|
With 1H-imidazole In octane at 130℃; for 24h; Reagent/catalyst; | 95% |
4-chlorophenylacetic Acid
N,N'-Dimethylurea
2-(4-chlorophenyl)-N-methylacetamide
Conditions | Yield |
---|---|
With magnesium(II) nitrate hexahydrate In octane at 130℃; for 24h; Reagent/catalyst; | 95% |
1,3-Dimethylurea (CAS NO.96-31-1) is reported in EPA TSCA Inventory.
The 1,3-Dimethylurea, with CAS number of 96-31-1, can be called N,N'-Dimethylharnstoff ; N,N'-Dimethylurea ; Symmetric dimethylurea ; sym-Dimethylurea . It is a white crystal, 1,3-Dimethylurea (CAS NO.96-31-1) is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Properties of 1,3-Dimethylurea:
(1)H bond acceptors: 3; (2)H bond donors: 2; (3)Freely Rotating Bonds: 0; (4)Index of Refraction: 1.413; (5)Molar Refractivity: 23.16 cm3; (6)Molar Volume: 92.8 cm3; (7)Surface Tension: 27.4 dyne/cm; (8)Density: 0.949 g/cm3; (9)Flash Point: 124.3 °C; (10)Enthalpy of Vaporization: 50.71 kJ/mol; (11)Boiling Point: 269 °C at 760 mmHg; (12)Vapour Pressure: 0.00744 mmHg at 25°C; (13)EINECS: 202-498-7; (14)Melting point: 101-104 °C(lit.); (15)Storage temp: Store at RT. ; (16)Water Solubility: 765 g/L (21.5 oC); (17)BRN: 1740672; (18)Polar Surface Area: 23.55 Å2
Structure Descriptors of 1,3-Dimethylurea:
(1)SMILES:O=C(NC)NC;
(2)Std. InChI:InChI=1S/C3H8N2O/c1-4-3(6)5-2/h1-2H3,(H2,4,5,6);
(3)Std. InChIKey:MGJKQDOBUOMPEZ-UHFFFAOYSA-N.
Toxicity of 1,3-Dimethylurea:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source mouse LDLo intraperitoneal 4962mg/kg (4962mg/kg) BEHAVIORAL: TREMOR
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
LUNGS, THORAX, OR RESPIRATION: CYANOSISJournal of Pharmacology and Experimental Therapeutics. Vol. 54, Pg. 188, 1935. rat LD50 unreported > 2gm/kg (2000mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1073, 1969.
Use of 1,3-Dimethylurea:
1,3-Dimethylurea is used for synthesis of caffeine, theophylline, pharmachemicals, textile aids, herbicides and others. In the textile processing industry 1,3-dimethylurea is used as intermediate for the production of formaldehyde-free easy-care finishing agents for textiles. The estimated world production of DMU is estimated to be less than 25,000 tons.
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