Conditions | Yield |
---|---|
at 0℃; under 375.03 Torr; Addition; solid-gas reaction; | 100% |
Conditions | Yield |
---|---|
In acetonitrile for 4h; Ambient temperature; | 96% |
A
N,N-dimethylthiourea
B
2-mercapto-5-methylbenzimidazole
Conditions | Yield |
---|---|
In 1,4-dioxane for 2h; Heating; | A n/a B 92% |
1-methyl-3-[2-(3-methyl-thioureido)-phenyl]-thiourea
A
N,N-dimethylthiourea
B
Benzimidazol-2-thiol
Conditions | Yield |
---|---|
In 1,4-dioxane for 2h; Heating; | A n/a B 90% |
In 1,4-dioxane for 2h; Heating; Yields of byproduct given; |
A
N,N-dimethylthiourea
B
6-methoxy-1H-benzoimidazole-2-thiol
Conditions | Yield |
---|---|
In 1,4-dioxane for 2h; Heating; | A n/a B 89% |
N1,N3-dimethyl-N1-nitrosothiourea
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With acetic acid In methanol; water at 37℃; for 2.83333h; | 80% |
With acetic acid In methanol; water at 37℃; for 2.83333h; Kinetics; Thermodynamic data; Mechanism; ΔH(act.), ΔS(act.); | 80% |
N,N'-bis<(1H-benzotriazole-1-yl)methyl>thiourea
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran for 4h; Heating; | 75% |
grateloupine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
isopropyl alcohol
A
isopropyl 4-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)-butanoate
B
N,N-dimethylthiourea
C
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 70% B n/a C n/a |
methyl thioisocyanate
A
5,6-dihydro-1,3,5-trimethyl-6-methylimino-1,3,5-triazine-2,4-(1H,3H)-dithione
B
N,N-dimethylthiourea
C
1,3,5-trimethyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trithione
Conditions | Yield |
---|---|
With water; triethylamine In benzene at 40℃; under 6000480 Torr; for 20h; | A 12% B 4% C 68% |
morpholine
2-thioxo-4-thiazolidinone
N,N'-Dimethylurea
A
2-morpholin-4-yl-2-thiazole-4(5H)-one
B
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With MCM-41 mesoporous silica In ethanol; water at 80 - 90℃; for 14h; Green chemistry; | A n/a B 68% |
methanol
N-carbamoylglycine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
A
methyl (4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate
B
4,5-dimethoxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
C
N,N-dimethylthiourea
D
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 65% B n/a C n/a D n/a |
ureidoacetylaminoethanoic acid
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
isopropyl alcohol
A
isopropyl [2-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)-1-oxoethylamino]acetate
B
N,N-dimethylthiourea
C
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 65% B n/a C n/a |
N-carbamoylglycine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
isopropyl alcohol
A
2,4-imidazolidinedione
B
isopropyl (4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate
C
N,N-dimethylthiourea
D
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A n/a B 65% C n/a D n/a |
methanol
N-carbamoyl-β-alanine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
A
methyl 3-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate
B
4,5-dimethoxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
C
N,N-dimethylthiourea
D
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 59% B n/a C n/a D n/a |
N-carbamoyl-β-alanine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
isopropyl alcohol
A
isopropyl 3-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate
B
N,N-dimethylthiourea
C
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 58% B n/a C n/a |
methanol
grateloupine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
A
methyl 4-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)butanoate
B
4,5-dimethoxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
C
N,N-dimethylthiourea
D
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 51% B n/a C n/a D n/a |
N-carbamoylglycine
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
isopropyl alcohol
A
(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetic acid
B
isopropyl (4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate
C
N,N-dimethylthiourea
D
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water for 1h; Reflux; | A 39% B n/a C n/a D n/a |
methanol
ureidoacetylaminoethanoic acid
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
A
methyl [2-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)-1-oxoethylamino]acetate
B
4,5-dimethoxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
C
N,N-dimethylthiourea
D
benzil
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; | A 35% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With sulfur at 175℃; |
Conditions | Yield |
---|---|
at 110℃; |
Conditions | Yield |
---|---|
With ethanol at 100℃; |
Conditions | Yield |
---|---|
With ethanol at 100℃; |
Conditions | Yield |
---|---|
In acetic acid Equilibrium constant; |
1-Aminoethanesulfonic acid
methyl thioisocyanate
N-cyclohexyl-cyclohexanamine
A
Dicyclohexyl-amine; compound with 1-(3-methyl-thioureido)-ethanesulfonic acid
B
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With pyridine; citric acid 1.) 1.5 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In dimethylsulfoxide-d6 Equilibrium constant; |
N,N-dimethylthiourea
Conditions | Yield |
---|---|
at 100℃; |
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With ethanol |
5-(2-bromo-1-hydroxyethyl)-2-chloro-N,N-dimethylbenzenesulfonamide
B
N,N-dimethylthiourea
N,N'-dimethylaminoiminomethanesulfonic acid
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With water; hypochloric acid for 48h; pH=7.4; aq. phosphate buffer; |
Conditions | Yield |
---|---|
at 20℃; for 0.5h; Solid phase reaction; cyclocondensation; | 100% |
Conditions | Yield |
---|---|
at 20℃; for 2h; | 100% |
N,N-dimethylthiourea
methyl iodide
methyl N,N'-dimethyl-imidothiocarbamate hydroiodide
Conditions | Yield |
---|---|
In ethanol for 12h; | 100% |
N,N-dimethylthiourea
Conditions | Yield |
---|---|
In chlorobenzene for 1h; Heating; | 98% |
Conditions | Yield |
---|---|
In methanol at 25℃; for 0.5h; Cycloaddition; | 98% |
ethyl (E)-3-((E)-carbamoyldiazenyl)but-2-enoate
N,N-dimethylthiourea
Conditions | Yield |
---|---|
In methanol at 25℃; for 0.5h; Cycloaddition; | 98% |
N,N-dimethylthiourea
cadmium(II) chloride
cadmium(II) Cl2 bis(N,N'-dimetylthiourea)
Conditions | Yield |
---|---|
In ethanol mixed in hot ethanol, stirred and refluxed for 2 h; filtered hot, crystd. at room temp. for 24 h, filtered, washed twice (ethanol), dried (vac.), dried (vac.), elem. anal.; | 98% |
3-phenylcarbamoylazo-crotonic acid ethyl ester
N,N-dimethylthiourea
Conditions | Yield |
---|---|
In methanol at 25℃; for 0.5h; Cycloaddition; | 97% |
N,N-dimethylthiourea
Conditions | Yield |
---|---|
Stage #1: N,N-dimethylthiourea; tert-butyl (3-methoxy-1-methyl-3-oxoprop-1-enyl)diazenecarboxylate In methanol at 25℃; for 0.5h; Cycloaddition; Substitution; Stage #2: With sodium hydride In tetrahydrofuran; methanol at 25℃; for 1h; Cyclization; | 97% |
{(CH3)2N}(C2H5)BOB(C2H5){N(CH3)2}
N,N-dimethylthiourea
O(μ-C2H5BNCH3)2CS
Conditions | Yield |
---|---|
In toluene under inert atm., stirred mixt. of the diboroxane, (NHCH3)2CS and toluene heated for 6 h to 50-60°C (oil bath), refluxed for 16 h; evapn., distd. under vac.; elem. anal.; | 97% |
N,N-dimethylthiourea
Conditions | Yield |
---|---|
In water; acetone at 20℃; | 96% |
N,N-dimethylthiourea
Conditions | Yield |
---|---|
In chlorobenzene for 0.5h; Heating; | 95% |
N,N-dimethylthiourea
benzil
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
Conditions | Yield |
---|---|
With sodium hydroxide at 180℃; for 0.025h; Microwave irradiation; | 95% |
With sodium hydroxide In ethanol; water for 2h; Heating; | 82% |
With sodium hydroxide In ethanol for 2h; Rate constant; Mechanism; Heating; carbon-13 labelled benzil; further thioureas and benzils; | 82% |
N,N-dimethylthiourea
1-Phenylpropane-1,2-dione
4,5-dihydroxy-1,3,4-trimethyl-5-phenyltetrahydroimidazole-2-thione
Conditions | Yield |
---|---|
With trifluoroacetic acid In tetrahydrofuran; water for 48h; Ambient temperature; | 95% |
diethyl 2-dodecylmalonate
N,N-dimethylthiourea
1,3-Dimethyl-5-dodecyl-2-thioxo-4,6(1H,3H,5H)pyrimidindion
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 24h; Heating; | 95% |
Conditions | Yield |
---|---|
In methanol for 6h; Heating; | 95% |
cis-dichlorobis(triphenylphosphine)platinum(II)
N,N-dimethylthiourea
Pt(PPh3)2(N,N-dimethylthiourea)
Conditions | Yield |
---|---|
With Et3N In methanol mixt. of Pt complex, thiourea (1 equiv.) and Et3N in methanol was refluxed for 10 min; H2O added; filtered; washed (H2O, Et2O); dried (vac.); elem. anal.; | 95% |
With Ag2O In dichloromethane N2-atmosphere; refluxing Pt-complex with excess Ag2O and equimolar amt. of (MeNH)2CS for 4 h; filtration, solvent removal (reduced pressure), dissoln. in CH2Cl2, crystn. on Et2O diffusion into soln.; elem. anal.; | 75% |
4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With water; potassium hydroxide In methanol for 2h; Reflux; diastereoselective reaction; | 95% |
cyanoacetic acid
N,N-dimethylthiourea
6-amino-N1,N3-dimethyl-2-thioxopyrimidin-4-one
Conditions | Yield |
---|---|
With acetic anhydride at 70℃; for 2h; Sealed tube; Microwave irradiation; | 95% |
Stage #1: cyanoacetic acid; N,N-dimethylthiourea With acetic anhydride at 70℃; Stage #2: With water; sodium hydroxide |
Conditions | Yield |
---|---|
With Sulfonated Sulfurol supported Fe3O4 (Fe3O4(at)SiO2-Pr-Sulfurol-SO3H) In ethanol; water at 80℃; for 3.25h; | 95% |
Conditions | Yield |
---|---|
In water CuCl was added to soln. N,N'-dimethylthiourea in water; soln. was filtered and allowed to evaporate, ppt. was washed with EtOH-Et2O (1:1); | 94.3% |
benzoyl chloride
N,N-dimethylthiourea
S-benzoyl-1,3-dimethylisothiuronium chloride
Conditions | Yield |
---|---|
In acetone Heating; | 94% |
diethyl 3-(phenyl)oxirane-2,2-dicarboxylate
N,N-dimethylthiourea
Conditions | Yield |
---|---|
With ytterbium(III) triflate In 1,4-dioxane at 90℃; for 65h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
In acetonitrile CuI and N,N'-dimethylthiourea were dissolved in boiling MeCN; solvent was evapd., residue was treated with water, product was collected and washed with water; elem. anal.; | 93.6% |
N,N-dimethylthiourea
1,3-dibromo-propane
1,3-Bis-(N,N'-dimethylamidino-mercapto)-propan-dihydrobromid
Conditions | Yield |
---|---|
at 140℃; for 0.166667h; | 93% |
Conditions | Yield |
---|---|
With Sulfonated Sulfurol supported Fe3O4 (Fe3O4(at)SiO2-Pr-Sulfurol-SO3H) In ethanol; water at 80℃; for 3.3h; | 93% |
Conditions | Yield |
---|---|
In ethanol Heating; | 92% |
N-methylene-tert-butylamine
N,N-dimethylthiourea
5-tert-Butyl-1,3-dimethyl-[1,3,5]triazinane-2-thione
Conditions | Yield |
---|---|
for 4h; Heating; | 92% |
Reported in EPA TSCA Inventory.
The N,N'-Dimethylthiourea, with the CAS registry number 534-13-4, is also known as N,N′-Dimethylthiourea. It belongs to the product categories of API Intermediates; Organic Building Blocks; Sulfur Compounds; Thioureas; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 208-588-2. This chemical's molecular formula is C3H8N2S and molecular weight is 104.17. What's more, both its IUPAC name and systematic name are the same which is called 1,3-Dimethylthiourea. It should be stored in a cool, dry and well-ventilated place.
Physical properties about N,N'-Dimethylthiourea are: (1)ACD/LogP: -0.346; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.35; (4)ACD/LogD (pH 7.4): -0.35; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 15.44; (8)ACD/KOC (pH 7.4): 15.44; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 56.15 Å2; (13)Index of Refraction: 1.516; (14)Molar Refractivity: 30.427 cm3; (15)Molar Volume: 100.676 cm3; (16)Surface Tension: 40.50 dyne/cm; (17)Density: 1.035 g/cm3; (18)Flash Point: 27.319 °C; (19)Enthalpy of Vaporization: 35.962 kJ/mol; (20)Boiling Point: 121.561 °C at 760 mmHg; (21)Vapour Pressure: 14.50 mmHg at 25 °C.
Preparation of N,N'-Dimethylthiourea: this chemical can be prepared by Isothiocyanatomethane with Methylamine. This response type is addition solid-gas reaction. It needs temperature of 0 °C. The yield is 100 %.
Uses of N,N'-Dimethylthiourea: (1) it is used as intermediate in the preparation of arginine derivatives; (2) it is used to produce other chemicals. For example, it can react with Methyl-phenyl-malonyl chloride to get 1,3,5-Trimethyl-5-phenyl-2-thio-barbituric acid. The reaction occurs with reagent triethylamine and other condition of heating for 2 hours. The yield is 70 %.
When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health at low levels. It is toxic if swallowed and may cause sensitisation by skin contacting. Therefore, you should wear suitable protective clothing and gloves. In case of accident or if you feel unwell seek medical advice immediately.
You can still convert the following datas into molecular structure:
(1) SMILES: S=C(NC)NC
(2) InChI: InChI=1S/C3H8N2S/c1-4-3(6)5-2/h1-2H3,(H2,4,5,6)
(3) InChIKey: VLCDUOXHFNUCKK-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | intraperitoneal | 500mg/kg (500mg/kg) | Free Radical Biology and Medicine. Vol. 20, Pg. 421, 1996. | |
mouse | LDLo | oral | 500mg/kg (500mg/kg) | Teratology, The International Journal of Abnormal Development. Vol. 23, Pg. 335, 1981. |
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