632-22-4

Basic information

• Product Name: 1,1,3,3-Tetramethylurea
• Synonyms: TETRAMETHYLUREA;N,N,N',N'-TETRAMETHYLUREA;TMU;1,1,3,3-TETRAMETHYLUREA;((CH3)2N)2CO;1,1,3,3-tetramethyl-ure;Temur;Tetramethylharnstoff
• CAS NO: 632-22-4
• Molecular Formula: C₅H₁₂N₂O
• Molecular Weight: 116.16
• EINECS: 211-173-9
• Product Categories: Miscellaneous;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Ureas;Bioactive Small Molecules;Cell Biology;T
• Mol File: 632-22-4.mol
• Article Data: 44

Chemical Properties

• Melting Point: −1 °C(lit.)
• Boiling Point: 177 °C(lit.)
• Flash Point: 150 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.968 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 1 M at 20 °C, miscible
• PKA: 2.0(at 25℃)
• Water Solubility: miscible
• Merck: 14,9230
• BRN: 773898
• CAS DataBase Reference: 1,1,3,3-Tetramethylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,3,3-Tetramethylurea(632-22-4)
• EPA Substance Registry System: 1,1,3,3-Tetramethylurea(632-22-4)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-61
• Safety Statements: 53-45
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: YU2625000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 632-22-4(Hazardous Substances Data)

Usage

Chemical Properties

Tetramethylurea is a clear colorless to pale yellow liquid with mild aromatic odor that is miscible with water and many organic solvents. Unusual for an urea is the liquid state of tetramethylurea in a range of > 170 °C.

Uses

Tetramethylurea is used as a solvent in dyestuff industries, in condensation reaction and intermediates in surfactant. It is utilized for base catalyzed isomerization and alkylation hydrocyanation due to its low permittivity. It reacts with oxalyl chloride to prepare tetramethyl chloroformamidinium chloride, which is used for the conversion of carboxylic acids and dialkyl phosphates to anhydrides and pyrophosphates respectively.

Definition

ChEBI: 1,1,3,3-tetramethylurea is a member of the class of ureas that is urea substituted by methyl groups at positions 1, 1, 3 and 3 respectively. Metabolite observed in cancer metabolism. It has a role as a human metabolite.

Preparation

The reaction of dimethylamine with phosgene in the presence of e. g. 50 % sodium hydroxide solution and subsequent extraction with 1,2-dichloroethane yields tetramethylurea in 95% yield.

Safety Profile

Moderately toxic by ingestion and intravenous routes. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. Combustible when exposed to heat, flame, and oxidizers. To fight fire, use foam, mist, spray, dry chemicals. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Dry it over BaO and distil it under nitrogen. It denatures proteins in H2O. [Elbaum & Herskovits Biochemistry 13 1268 1974, Kane Anal Biochem 53 350 1973, Beilstein 4 IV 225.]

InChI:InChI=1/C5H12N2O/c1-6(2)5(8)7(3)4/h1-4H3

Synthetic route

bis(trichloromethyl) carbonate (32315-10-9) + dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

Conditions	Yield
In dichloromethane; water at 15 - 20℃; Large scale;	92%

carbon monoxide (201230-82-2) + N,N-dimethylammonium chloride (506-59-2) → tetramethylurea (632-22-4)

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

1,1,3,3-tetramethyl-2-thiourea (2782-91-4) → tetramethylurea (632-22-4)

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 (138767-93-8) → tetramethylurea (632-22-4)

Conditions	Yield
In chloroform-d1 at 90℃; for 20h;	81%

Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat) (78581-29-0) + malononitrile (109-77-3) → (bis-dimethylamino-methylene)-malononitrile (31774-36-4) + tetramethylurea (632-22-4)

Conditions	Yield
With dimethylaminomethyl-polystyrene In acetonitrile at 25℃; for 24h;	A 70% B n/a

dimethyl malonate sodium salt (18424-76-5) + Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat) (78581-29-0) → malonsaeure-dimethylester (31774-43-3) + tetramethylurea (632-22-4)

Conditions	Yield
In acetonitrile at 25℃; for 0.25h;	A 55% B n/a

4-Nitrophenylacetonitrile (555-21-5) + Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat) (78581-29-0) → α--4-nitrophenylacetonitrile (22703-65-7) + tetramethylurea (632-22-4)

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) (78581-29-0) + ethyl 2-cyanoacetate (105-56-6) → 2-Cyan-3,3-bis-(dimethylamino)-acrylsaeure-ethylester (72834-60-7) + tetramethylurea (632-22-4)

Conditions	Yield
With dimethylaminomethyl-polystyrene In acetonitrile at 81℃; for 20h;	A 51% B n/a

bis(dimethylamino)malononitrile (63442-64-8) + sodium ethanolate (141-52-6) → N,N,N',N'-Tetramethylharnstoff-diethylacetal (67751-11-5) + tetramethylurea (632-22-4)

Conditions	Yield
In acetonitrile for 12h;	A 42% B 14 % Spectr.

Bis(N,N,N',N'-tetramethylformamidinium)ether-bis(trifluormethansulfonat) (78581-29-0) + diphenylphosphorylazide (5353-66-2) + Et3N → <2-<2,2-Bis(dimethylamino)-1-(diphenylphosphoryl)vinyl>-2H-tetrazol-5-yl>diphenylphosphanoxid (97513-13-8) + tetramethylurea (632-22-4)

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

chloroform (67-66-3) + dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

Conditions	Yield
With 4-methylmorpholine N-oxide; sodium hydroxide In water at 50℃; for 1h;	40%

carbon dioxide (124-38-9) + dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

Conditions	Yield
tetraphosphorus decasulfide; triphenyl antimony oxide In benzene at 120℃; under 36752.9 Torr; for 3h;	33%

potassium cyanide (151-50-8) + N,N,N,N-tetramethyldiamino ethoxycarbonium tetrafluoroborate → 2,2-Bis(dimethylamino)-2-ethoxyacetonitril (71023-22-8) + tetramethylurea (632-22-4)

Conditions	Yield
With sodium cyanide In acetonitrile for 40h; Ambient temperature;	A 30.2% B n/a

N-Methoxy-N-chloro-N',N'-dimethylurea (88470-22-8) + dimethyl amine (124-40-3) → bis-(dimethylamino)methane (51-80-9) + tetramethylurea (632-22-4)

Conditions	Yield
at 0℃; for 1h;	A 26.4% B 9.1%

N-Methoxy-N-chloro-N',N'-dimethylurea (88470-22-8) → 1,2-bis(N,N-dimethylcarbamoyl)hydrazine (17696-89-8) + N-methoxy-N′,N′-dimethylurea (68692-39-7) + tetramethylurea (632-22-4)

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 (93280-56-9) → N-(n-butyl)-N',N'-dimethylurea (52696-91-0) + 1-butyl N,N-dimethylcarbamate (7304-97-4) + tetramethylurea (632-22-4)

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 (1585-74-6) + potassium cyanide (151-50-8) → NCNMe2 (1467-79-4) + tetramethylurea (632-22-4)

Conditions	Yield
With ethanol

1,μ-dithio-dicarbonic acid bis-dimethylamide (56387-81-6) → carbon oxide sulfide (463-58-1) + tetramethylurea (632-22-4)

Conditions	Yield
at 25℃;
at 210℃;

dimethyl amine (124-40-3) + N,N-Dimethylcarbamoyl chloride (79-44-7) + benzene (71-43-2) → tetramethylurea (632-22-4)

phosgene (75-44-5) + dimethyl amine (124-40-3) + benzene (71-43-2) → tetramethylurea (632-22-4)

Conditions	Yield
je nach Bedingungen;

N-(1-norbornyl)-N',N'-dimethyl-N-nitrosourea (36284-91-0) → N-(n-butyl)-N',N'-dimethylurea (52696-91-0) + 1-butyl N,N-dimethylcarbamate (7304-97-4) + tetramethylurea (632-22-4)

Conditions	Yield
In tetrachloromethane at 110℃;	A 10 % Spectr. B 7 % Spectr. C 19 % Spectr.

bis(dimethylamino)methoxymethane (1186-70-5) → tetramethylurea (632-22-4)

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 (56654-53-6) → 1-butyl N,N-dimethylcarbamate (7304-97-4) + n-butyl 2-(dimethylamino)pentanoate + tetramethylurea (632-22-4)

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 (63812-19-1) → N-Nitrosodimethylamine (62-75-9) + tetramethylurea (632-22-4)

Conditions	Yield
With sodium nitrite In water at 69.9℃; for 2h;	A 20 % Spectr. B 80 % Spectr.

tetrachloromethane (56-23-5) + dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

carbon monoxide (201230-82-2) + dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

Conditions	Yield
With iodine; potassium carbonate; palladium diacetate In acetonitrile at 95℃; under 2052 Torr; for 3h;	40 % Chromat.
With oxygen

dimethyl amine (124-40-3) → tetramethylurea (632-22-4)

Conditions	Yield
With tetrachloromethane for 48h;

1,1,3,3-tetramethyl-2-thiourea (2782-91-4) + Hexafluoroacetone (684-16-2) → 2,2,4,4-Tetrakis(trifluoromethyl)-1,3-dithietane (791-50-4) + tetramethylurea (632-22-4)

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;

(Dimethylamino-m-tolylsulfanyl-methylene)-dimethyl-ammonium; iodide → toluene-3-thiol (108-40-7) + tetramethylurea (632-22-4)

Conditions	Yield
at 20℃; Rate constant; pH=11;

(Dimethylamino-p-tolylsulfanyl-methylene)-dimethyl-ammonium; iodide → para-thiocresol (106-45-6) + tetramethylurea (632-22-4)

Conditions	Yield
at 20℃; Rate constant; pH=11;

tetramethylurea (632-22-4) → N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9, 13829-06-6)

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 (632-22-4) → N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate

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;

tetramethylurea (632-22-4) + methyl trifluoromethanesulfonate (333-27-7) → N,N,N',N'-tetramethyl-O-methylisouronium trifluoromethanesulfonate

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 (852616-02-5) + tetramethylurea (632-22-4) → N,N,N’,N’,O-pentamethylisouroniumbis(pentafluoro-ethyl)phosphinate

Conditions	Yield
at 0 - 20℃; for 22.5h;	100%

trifluoromethanesulfonic acid ethyl ester (425-75-2) + tetramethylurea (632-22-4) → O-ethyl-N,N,N',N'-tetramethylisouronium trifluoromethanesulfonate

Conditions	Yield
In pentane at 0 - 20℃; for 0.666667h;	99.8%

(bicyclopentadienyl)Yb*(tetrahydrofuran)2 + tetramethylurea (632-22-4) → bis(cyclopentadienyl)bis(1,1,3,3-tetramethylurea)ytterbium(II) (170168-69-1)

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) (94138-28-0) + tetramethylurea (632-22-4) → [SmI2(tetrahydrofuran)2(tetramethylurea)2] (237735-22-7)

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 (75-44-5) + tetramethylurea (632-22-4) → N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9, 13829-06-6)

Conditions	Yield
In toluene at 0 - 20℃; for 26h;	95%

Tosyl isocyanate (4083-64-1) + tetramethylurea (632-22-4) → N-bis(dimethylamino)methylene-4-methylbenzenesulfonamide (1823-69-4)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Reflux;	93.6%
In toluene for 48h; Reflux;	93.6%

benzyldiphenylsulfonium tetrafluoroborate + tetramethylurea (632-22-4) → C12H19N2O(1+)*BF4(1-)

Conditions	Yield
In acetonitrile for 24h; Ambient temperature;	93%

N-Ethylindole (10604-59-8) + tetramethylurea (632-22-4) → bis(1-ethyl-1H-indol-3-yl)methane

Conditions	Yield
With tert.-butylhydroperoxide; ruthenium(III) chloride trihydrate In decane at 110℃; for 0.166667h; Microwave irradiation;	93%

tetramethylurea (632-22-4) + recorcinol (108-46-3) → Tetramethyl-urea; compound with benzene-1,3-diol (87448-51-9)

Conditions	Yield
	92%

n-Octylamine (111-86-4) + tetramethylurea (632-22-4) → 1,1,3,3-tetramethyl-2-(1-octyl)guanidine (89610-36-6)

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 (632-22-4) + Trifluoro-methanesulfonatetriphenyl-trifluoromethanesulfonyloxymethyl-arsonium; → Oxo(bis(dimethylamino)carbenio)(triphenylarsonio)methan-bis(trifluormethansulfonat)

Conditions	Yield
In acetonitrile for 24h; Heating;	92%

phosgene (75-44-5) + yttrium(III) chloride (10361-92-9) + tetramethylurea (632-22-4) → (N(CH3)2)2CCl(1+)*YCl4(1-) = [(N(CH3)2)2CCl](YCl4)

Conditions	Yield
In toluene (N2); stirring (0°C); ppt. washing (CHCl3, Et2O), drying (vac.); elem. anal.;	92%

Benzylidenemalononitrile (2700-22-3) + tetramethylurea (632-22-4) → C15H18N4O

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%

methanol (67-56-1) + tris(pentafluoroethyl)phosphine oxide (58431-32-6) + tetramethylurea (632-22-4) → 2-methyl-1,1,3,3-tetramethylisouronium bis(pentafluoroethyl)phosphinate

Conditions	Yield
In 1,2-dimethoxyethane for 5h; Heating / reflux;	91.9%

2,3-naphthalenediol (92-44-4) + tetramethylurea (632-22-4) → Naphthalene-2,3-diol; compound with tetramethyl-urea (87448-53-1)

Conditions	Yield
	91%

bis(acetylacetonato)dioxidomolybdenum(VI) + tetramethylurea (632-22-4) → [Mo2O5(acetylacetonate)2(tetramethylurea)2]

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 (40876-94-6) + tetramethylurea (632-22-4) → bis(1-ethyl-2-methyl-1H-indol-3-yl)methane (36798-54-6)

Conditions	Yield
With tert.-butylhydroperoxide; ruthenium(III) chloride trihydrate In decane at 110℃; for 0.166667h; Microwave irradiation;	91%

2,4-Dinitrophenol (51-28-5) + tetramethylurea (632-22-4) → 2,4-Dinitro-phenol; compound with tetramethyl-urea (87448-56-4)

Conditions	Yield
	90%

tetramethylurea (632-22-4) → tetramethylbromoamidinium tribromide

Conditions	Yield
With Oxalyl bromide In chloroform at 65℃; Ionic liquid; Schlenk technique;	90%

Pentachlorophenol (87-86-5) + tetramethylurea (632-22-4) → 2,3,4,5,6-Pentachloro-phenol; compound with tetramethyl-urea (87448-58-6)

Conditions	Yield
In diethyl ether; hexane	89%

[tetrakis(μ-acetate)diaquadiruthenium(II,III)] hexafluorophosphate + tetramethylurea (632-22-4) → Ru2(μ-O2CCH3)4[(CH3)4N2CO]2(PF6)

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%

phosgene (75-44-5) + tetramethylurea (632-22-4) + copper dichloride → bis(dimethylamino)chlorocarbenium tetrachlorocuprate

Conditions	Yield
In toluene (N2); stirring (0°C); ppt. washing (CHCl3, Et2O), drying (vac.); elem. anal.;	89%

tetramethylurea (632-22-4) → 1,1,3,3-tetramethyl-2-thiourea (2782-91-4)

Conditions	Yield
With 2C6H15N*ClH*Cl2HOPS In chloroform for 10h; Reflux;	89%

phenyl styryl sulfone (16212-06-9) + tetramethylurea (632-22-4) → 1-cinnamyl-1,3,3-trimethylurea

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 (75790-42-0) + tetramethylurea (632-22-4) → 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 (75782-18-2)

Conditions	Yield
Ambient temperature;	88%

1,2-dimethylindole (875-79-6) + tetramethylurea (632-22-4) → bis(1,2-dimethyl-1H-indol-3-yl)methane (102660-41-3)

Conditions	Yield
With tert.-butylhydroperoxide; ruthenium(III) chloride trihydrate In decane at 110℃; for 0.166667h; Microwave irradiation;	88%

Upstream product

• 1585-74-6 dimethylchloroamine 
• 151-50-8 potassium cyanide 
• 56387-81-6 1,μ-dithio-dicarbonic acid bis-dimethylamide 
• 124-40-3 dimethyl amine 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 71-43-2 benzene 
• 75-44-5 phosgene 
• 2782-91-4 1,1,3,3-tetramethyl-2-thiourea 
• 36284-91-0 N-(1-norbornyl)-N',N'-dimethyl-N-nitrosourea 
• 63442-64-8 bis(dimethylamino)malononitrile 
• 141-52-6 sodium ethanolate 
• 1186-70-5 bis(dimethylamino)methoxymethane 
• 56654-53-6 N-(n-butyl)-N',N'-dimethyl-N-nitrosourea 
• 18424-76-5 dimethyl malonate sodium salt 

Downstream Products

• 14075-46-8 [2-(1-benzyl-5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine 
• 110147-46-1 (1-benzyl-5-methoxy-2-methyl-indol-3-yl)-acetic acid dimethylamide 
• 62432-71-7 (2-hydroxy-2-phenyl-ethyl)-trimethyl-urea 
• 20815-36-5 2-(4'-methylphenyl)-1,1,3,3-tetramethylguanidine 
• 20815-38-7 2-(4'-chlorophenyl)-1,1,3,3-tetramethylguanidine 
• 20815-41-2 2-N-(4-acetophenyl)tetramethylguanidine 
• 20815-35-4 2-(4'-methoxyphenyl)-1,1,3,3-tetramethylguanidine 
• 20815-34-3 N,N,N',N'-tetramethylguanidino-N,N-dimethyl-p-phenylenediamine 
• 17951-14-3 2-(4'-nitrophenyl)-1,1,3,3-tetramethylguanidine 
• 29166-71-0 2-isopropyl-1,1,3,3-tetramethylguanidine 
• 29166-72-1 N,N,N′,N′-tetramethyl-N″-tert-butylguanidine 
• 2556-43-6 N,N,N',N'-tetramethyl-N-phenylguanidine 
• 62432-70-6 1-(2-Hydroxy-2-phenyl-propyl)-1,3,3-trimethyl-urea 
• 26953-01-5 2-(2',4'-dimethylphenyl)-1,1,3,3-tetramethylguanidine 

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A versatile peroxido complex: The rhodium peroxido complex 1, which can be prepared from 2 and dioxygen, participates in mono-oxygenation of a phosphine and dioxygenation of tetrakis(dimethylamino)ethylene to give, respectively, phosphine oxide and a urea derivative, while peroxygenation of 9,10-dimethylanthracene to yield the anthracene endoperoxide takes place in the presence of dioxygen and substoichiometric amounts of 1 (see scheme). Copyright

On the exchange reaction,, using hexafluoroacetone

The reaction of λ3-phospha-diazetidin-thione, 1 with hexafluoroacetone (HFA) furnished not only the expected addition product, the λ5P-perfluoropinacolyl phosphorane, 2. In addition, HFA was observed to cause {A figure is presented} exchange in 2, and exclusive formation of a urea derivative, 3, was noted upon prolonged interaction of HFA with 2. Likewise, N,N,N′,N′,-tetramethylthiourea, 1, was found to be converted to N,N,N′,N′-tetrarmethylurea, 5, by HFA. The reactions were followed by 1H-, 13C-, 19F- and 31P-n.m.r. spectroscopy.

Copper(II) chloride-catalyzed oxidative carbonylation of glycerol to glycerol carbonate

A systematic study on copper(II) as catalyst for the synthesis of glycerol carbonate via oxidative carbonylation is here reported for the first time. Copper(II) chloride has been found to efficiently promote the process under homogeneous conditions treating glycerol with CO:O2 (Ptot = 4 MPa; P(O2) = 0.7 MPa), in DMA at 130 C and in the presence of pyridine as co-catalyst. Excellent conversions (>92%) and selectivities (>93%) are obtained in relatively short reaction times (3-4 h) also with copper(II) complexes. The catalyst overall TON is evaluated and new experimental evidences are provided allowing significant advancements in the mechanism comprehension.

Tetramethylurea and preparation method thereof

The invention provides tetramethylurea and a preparation method thereof. The preparation method comprises the following steps that S1, dimethylamine and triphosgene are provided; S2, the dimethylamineand the triphosgene react to generate the tetramethylurea. According to the preparation method of the tetramethylurea, the dimethylamine and the triphosgene are used as raw materials, the dimethylamine can be a dimethylamine water solution or dimethylamine gas, and the triphosgene can be triphosgene itself or an organic triphosgene solution. The preparation method is simple in operation, high inproduct yield, low in cost and suitable for industrial production.

Metal-free direct thiocarbamation of imidazopyridines with carbamoyl chloride and elemental sulfur

The combination of elemental sulfur and carbamoyl chloride was found to act as a carbamothioyl group surrogate for direct thiocarbamation of imidazopyridines in the absence of a metal catalyst.