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102-07-8 Usage

Chemical Properties

solid

Definition

ChEBI: A member of the class of ureas that is urea in which one of the hydrogens of both amino groups is replaced by a phenyl group. It is present in coconut milk (Cocos nucifera).

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 29, p. 3075, 1981Chemistry Letters, 14, p. 603, 1985Tetrahedron Letters, 15, p. 1191, 1974 DOI: 10.1016/S0040-4039(01)82442-4

General Description

1,3-Diphenylurea is a cytokinin compound present in fruit and vegetables.

Biochem/physiol Actions

1,3-Diphenylurea is metabolized by a moderate halophilic Marinobacter sp. isolated from a contaminated ephemeral desert stream bed in Negev desert.

Check Digit Verification of cas no

The CAS Registry Mumber 102-07-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 102-07:
(5*1)+(4*0)+(3*2)+(2*0)+(1*7)=18
18 % 10 = 8
So 102-07-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H12N2O/c14-13(16)15(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,14,16)

102-07-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0031)  1,3-Diphenylurea  >98.0%(HPLC)(N)

  • 102-07-8

  • 25g

  • 260.00CNY

  • Detail
  • TCI America

  • (C0031)  1,3-Diphenylurea  >98.0%(HPLC)(N)

  • 102-07-8

  • 100g

  • 650.00CNY

  • Detail
  • TCI America

  • (C0031)  1,3-Diphenylurea  >98.0%(HPLC)(N)

  • 102-07-8

  • 500g

  • 1,710.00CNY

  • Detail
  • Alfa Aesar

  • (A18720)  N,N'-Diphenylurea, 98%   

  • 102-07-8

  • 25g

  • 162.0CNY

  • Detail
  • Alfa Aesar

  • (A18720)  N,N'-Diphenylurea, 98%   

  • 102-07-8

  • 100g

  • 497.0CNY

  • Detail
  • Aldrich

  • (142158)  1,3-Diphenylurea  98%

  • 102-07-8

  • 142158-25G

  • 290.16CNY

  • Detail
  • Aldrich

  • (142158)  1,3-Diphenylurea  98%

  • 102-07-8

  • 142158-100G

  • 1,297.53CNY

  • Detail
  • Vetec

  • (V900531)  1,3-Diphenylurea  Vetec reagent grade, 98%

  • 102-07-8

  • V900531-500G

  • 392.86CNY

  • Detail

102-07-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-diphenylurea

1.2 Other means of identification

Product number -
Other names Urea, N,N‘-diphenyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:102-07-8 SDS

102-07-8Synthetic route

phenyl isocyanate
103-71-9

phenyl isocyanate

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In acetic acid for 0.0833333h;98%
In hexane95%
N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With sodium hydroxide; copper(l) chloride In water; acetonitrile at 25℃; for 0.333333h;100%
With quinolinium monofluorochromate(VI) In acetonitrile for 3.5h; Heating;98%
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; water; potassium hydroxide In acetonitrile at 20℃; for 0.0166667h;98%
Benzohydroxamic acid
495-18-1

Benzohydroxamic acid

bis(trimethylsilyl)benzohydroxamic acid
77219-88-6

bis(trimethylsilyl)benzohydroxamic acid

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
at 100℃; for 1.5h;100%
1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
Ambient temperature; prolonged holding in air;100%
With air (H2O)100%
With hydrogenchloride In dichloromethane at 0℃; for 0.5h; Yield given;
With water
phenyl isocyanate
103-71-9

phenyl isocyanate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With C24H28N8PrS4(1-)*Li(1+) In acetonitrile at 60℃; for 12h; Inert atmosphere;99%
With water; triethylamine In 1,4-dioxane at 20℃; for 0.05h;98%
at 20 - 50℃; Product distribution / selectivity;95%
carbon dioxide
124-38-9

carbon dioxide

N-trimethylsilylaniline
3768-55-6

N-trimethylsilylaniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With pyridine at 120℃; under 3800.26 Torr; for 18h;99%
With pyridine; C14H34Cl2InNO2Si2 In toluene at 110℃; under 2280.15 Torr; for 24h; Catalytic behavior; Pressure;70%
dodecacarbonyl-triangulo-triruthenium at 150℃; under 10343 Torr; for 20h;48%
carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With 1-butyl-3-methyl-1H-imidazole-2(3H)-selenone; oxygen at 90℃; under 9750.98 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Ionic liquid; Autoclave;99%
With palladium; oxygen; potassium iodide In 1,4-dioxane at 130℃; under 30003 Torr; for 24h; Autoclave; Green chemistry;99%
With potassium tetraiodopalladate(II) at 90℃; under 37503.8 Torr; for 24h; Neat (no solvent); Autoclave;96%
Benzohydroxamic acid
495-18-1

Benzohydroxamic acid

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
Stage #1: Benzohydroxamic acid With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine In dichloroethane at 0℃; for 1.5h; Lossen rearrangement; Inert atmosphere;
Stage #2: aniline In dichloroethane at 0 - 84℃; for 15h; Lossen rearrangement; Inert atmosphere;
99%
Stage #1: Benzohydroxamic acid With ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 1.5h; Lossen Rearrangement;
Stage #2: aniline In tetrahydrofuran at 20℃; for 4h; Lossen Rearrangement;
83%
Stage #1: Benzohydroxamic acid With ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.25h; Green chemistry;
Stage #2: aniline In dichloromethane for 6h; Lossen Rearrangement; Green chemistry; chemoselective reaction;
82%
Stage #1: Benzohydroxamic acid With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 15h; Rearrangement;
Stage #2: aniline In dichloromethane at 20℃; for 4h; Addition;
66%
1-tert-butyl-1-ethyl-3-phenylurea
1202047-15-1

1-tert-butyl-1-ethyl-3-phenylurea

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With water In toluene at 70℃; for 1h;99%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; aniline In acetonitrile at 0 - 5℃; for 1h;
Stage #2: With ETS-10 molecular sieve catalyst In acetonitrile at 80℃; for 4h; Solvent; Temperature;
99%
In acetonitrile at 20℃; for 4h; Sealed tube;38 %Chromat.
aniline
62-53-3

aniline

3-phenyl-5H-1,4,2-dioxazol-5-one
19226-36-9

3-phenyl-5H-1,4,2-dioxazol-5-one

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With sodium acetate In methanol at 60℃; for 2h; Solvent; Reagent/catalyst; Temperature; Concentration;99%
1-benzoyl-1H-benzotriazole
4231-62-3

1-benzoyl-1H-benzotriazole

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With trimethylsilylazide; triethylamine In toluene at 110℃; for 1h; Sealed tube;99%
With diphenyl phosphoryl azide; triethylamine In toluene at 110℃; Curtius Rearrangement; Sealed tube;96%
aniline
62-53-3

aniline

urea
57-13-6

urea

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With iodine at 90 - 95℃; for 0.0833333h;98%
With zinc(II) chloride at 80 - 85℃; for 0.0833333h; Neat (no solvent);98%
With PEG-400; cerium(III) chloride; potassium iodide In water for 0.266667h; microwave irradiation;97%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

A

N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With oxygen; sodium iodide; Pd-Se/Al2)3 at 170℃; under 49505 Torr; for 3h; Product distribution; Further Variations:; Catalysts;A 97%
B n/a
With oxygen; tertamethylammonium iodide; silica gel; palladium at 160 - 170℃; further catalyst systems;A 94%
B 0.5%
With selenium; oxygen; triethylamine at 180℃; under 15001.5 Torr; for 6h; Autoclave;A 85%
B 8%
With selenium; oxygen; triethylamine at 120℃; under 15001.5 Torr; for 6h; Autoclave;A 35%
B 46%
With oxygen; palladium on activated charcoal; tertamethylammonium iodide at 160 - 170℃; further catalyst systems;A 42%
B 11%
2-tert-butoxy-6-hydroxy-N-phenylpiperidine-1-carboxamide
1274701-95-9

2-tert-butoxy-6-hydroxy-N-phenylpiperidine-1-carboxamide

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With water at 80℃;97%
phenyl carbamate
64-10-8

phenyl carbamate

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With benzoic acid In para-xylene at 130℃; for 8h; Inert atmosphere; Schlenk technique;96%
With graphene oxide In neat (no solvent) at 80℃; for 4h; Sealed tube;94%
With sulfated polyborate at 120℃; for 1h;93%
1-nitropentane
628-05-7

1-nitropentane

5-allyl-3-isobutoxy-2-methyl-4-<7-(α-tetrahydropyranyl)oxyheptyl>-2-cyclopenten-1-one

5-allyl-3-isobutoxy-2-methyl-4-<7-(α-tetrahydropyranyl)oxyheptyl>-2-cyclopenten-1-one

3-isobutoxy-2-methyl-5-(3-butyl-4,5-dihydroisoxazolin-5-yl)methyl-4-<7-(α-tetrahydropyranyl)oxyheptyl>-2-cyclopenten-1-one

3-isobutoxy-2-methyl-5-(3-butyl-4,5-dihydroisoxazolin-5-yl)methyl-4-<7-(α-tetrahydropyranyl)oxyheptyl>-2-cyclopenten-1-one

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With phenyl isocyanate; triethylamine In benzeneA 96%
B n/a
carbon dioxide
124-38-9

carbon dioxide

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With iron(III) chloride; phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In tetrahydrofuran at 110℃; under 760.051 - 3040.2 Torr; for 24h; Sealed tube;96%
With diethylene glycol dimethyl ether; cesium fluoride at 100℃; for 20h; Schlenk technique; Glovebox;96%
With iron(III) chloride; phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In tetrahydrofuran at 110℃; under 760.051 Torr; for 24h; Reagent/catalyst; Solvent; Temperature; Sealed tube;92%
1-benzoyl-4-phenylsemicarbazide
1152-32-5

1-benzoyl-4-phenylsemicarbazide

aniline
62-53-3

aniline

A

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
In various solvent(s) at 150℃; for 1h;A 94%
B 96%
aniline
62-53-3

aniline

benzoic acid
65-85-0

benzoic acid

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 0.0166667h; Curtius Rearrangement; Microwave irradiation;96%
With phenyl N-phenylphosphoramidoazidate; triethylamine In acetonitrile for 1.5h; Heating;94%
Stage #1: benzoic acid With sodium azide; phenyl chloroformate; sodium t-butanolate In 1,2-dimethoxyethane at 25℃; for 8h;
Stage #2: aniline In 1,2-dimethoxyethane at 75℃; for 16h;
89%
aniline
62-53-3

aniline

3,3'-carbonylbis<5-phenyl-1,3,4-oxadiazole-2(3H)-thione>
122350-19-0

3,3'-carbonylbis<5-phenyl-1,3,4-oxadiazole-2(3H)-thione>

A

5-phenyl-1,3,4-oxadiazole-2(3H)-thione
3004-42-0

5-phenyl-1,3,4-oxadiazole-2(3H)-thione

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
In various solvent(s) for 1h; Ambient temperature;A n/a
B 96%
phenylcarbamoyl azide
940-38-5

phenylcarbamoyl azide

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With sodium acetate In acetonitrile at 80℃; for 12h; Inert atmosphere;96%
With sodium acetate In acetonitrile at 80℃; under 760.051 Torr; for 12h; Schlenk technique; Inert atmosphere;95%
With sodium acetate In ethyl acetate at 75℃; for 24h;95%
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; N-t-butylbenzamide In 1,2-dichloro-ethane at 90℃; for 24h; Curtius Rearrangement;35%
N-trimethylsilylaniline
3768-55-6

N-trimethylsilylaniline

phenyl isocyanate
103-71-9

phenyl isocyanate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium at 100℃; under 15514.4 Torr; for 20h;95%
iodobenzene
591-50-4

iodobenzene

phenyl carbamate
64-10-8

phenyl carbamate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 85℃; for 24h;95%
With potassium phosphate In N,N-dimethyl-formamide at 20 - 120℃; for 1h; Microwave irradiation; Sealed tube; Inert atmosphere;94%
With copper(I) oxide; potassium phosphate monohydrate at 120℃; for 0.666667h; Microwave irradiation; Inert atmosphere; Neat (no solvent);90%
benzoyl chloride
98-88-4

benzoyl chloride

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
Stage #1: benzoyl chloride With pyridine; trimethylsilylazide In N,N-dimethyl-formamide at 20℃; Curtius rearrangement; Microflow reaction; Inert atmosphere;
Stage #2: aniline With acetic acid In N,N-dimethyl-formamide at 110℃; Microflow reaction; Inert atmosphere;
95%
Stage #1: benzoyl chloride With N-ethyl-N,N-diisopropylamine; hydroxylamine-O-sulfonic acid In dichloromethane Lossen Rearrangement; Inert atmosphere; Green chemistry;
Stage #2: aniline In dichloromethane at 100℃; for 0.0833333h; Solvent; Reagent/catalyst; Microwave irradiation; Inert atmosphere; Green chemistry;
80%
N-phenylcarbamic acid
501-82-6

N-phenylcarbamic acid

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With trichloroisocyanuric acid; triphenylphosphine In 1,4-dioxane at 80℃; for 4h;95%
N-(pivaloyloxy)benzamide
61650-22-4

N-(pivaloyloxy)benzamide

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With [RhCl2(p-cymene)]2; silver(I) acetate In 1,4-dioxane at 80℃; for 12h; Catalytic behavior;95%
N-benzoyl-O-acetylhydroxylamine
21251-12-7

N-benzoyl-O-acetylhydroxylamine

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With [RhCl2(p-cymene)]2; silver(I) acetate In 1,4-dioxane at 80℃; for 12h;94%
With potassium carbonate
O-Phenylcarbamyl benzohydroxamic acid
2963-12-4

O-Phenylcarbamyl benzohydroxamic acid

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
triethylamine In dichloromethane for 0.5h; Heating;94%
N-methylene-tert-butylamine
13987-61-6

N-methylene-tert-butylamine

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

5-tert-Butyl-1,3-diphenyl-[1,3,5]triazinan-2-one
140367-33-5

5-tert-Butyl-1,3-diphenyl-[1,3,5]triazinan-2-one

Conditions
ConditionsYield
for 4h; Heating;100%
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

3a,8a-dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione
58137-72-7

3a,8a-dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione

Conditions
ConditionsYield
In acetic acid for 0.25h; Heating;100%
In water at 50 - 60℃;64%
In benzene Reflux; regioselective reaction;
bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

Conditions
ConditionsYield
100%
98%
With iodine; triethylamine98%
oxalyl dichloride
79-37-8

oxalyl dichloride

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

diphenylparabanic acid
6488-59-1

diphenylparabanic acid

Conditions
ConditionsYield
In dichloromethane for 1.5h; Reflux;99%
In toluene at 50 - 85℃; for 2h; Temperature;91%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

Conditions
ConditionsYield
With isocyanate de chlorosulfonyle; oxygen; palladium at 160 - 170℃;98%
With oxygen; rhodium contaminated with carbon at 160 - 170℃; under 63253.7 Torr; for 3h;
bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

Conditions
ConditionsYield
With iron(II) acetylacetonate; phenylsilane; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; Glovebox; Schlenk technique;98%
Stage #1: bis(diphenyl)urea With phenylsilane; tris(2-diphenylphosphinoethyl)phosphine; iron(II) diacetylacetonate In tetrahydrofuran at 100℃; for 24h;
Stage #2: With water at 20℃; Reagent/catalyst; Solvent;
98 %Chromat.
nitrobenzene
98-95-3

nitrobenzene

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

p-nitrosodiphenylamine
156-10-5

p-nitrosodiphenylamine

Conditions
ConditionsYield
With oxygen; sodium hydroxide In dimethyl sulfoxide at 60℃; for 4h; Reagent/catalyst;97.3%
diethyl sulfate
64-67-5

diethyl sulfate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

ethyl centralite
85-98-3

ethyl centralite

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In toluene for 3h; Alkylation; Heating;97%
bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

N,N'-diphenyl-N-nitroso-urea
60285-31-6

N,N'-diphenyl-N-nitroso-urea

Conditions
ConditionsYield
With nitrosylchloride In N,N-dimethyl-formamide at 0℃; for 2h;96%
With cis-nitrous acid; acetic acid

102-07-8Relevant articles and documents

Desulfurization of N,N'-Diarylthioureas by Lead Tetraacetate Oxidation

Debroy, Abhijit,Nandy Mazumdar, Sujit,Barua, Parag D.,Mahajan, Mahinder P.

, p. 315 - 316 (1984)

Lead tetraacetae oxidation of N,N'-diarylthioureas in refluxing dichloromethane and pyridine gave the corresponding N,N'-diarylureas.Sulfur was isolated during each oxidation reaction.

-

Wakeshima,Kijima

, p. 953 (1975)

-

CeO2-catalyzed direct synthesis of dialkylureas from CO2 and amines

Tamura, Masazumi,Ito, Kazuki,Nakagawa, Yoshinao,Tomishige, Keiichi

, p. 75 - 85 (2016)

CeO2 showed higher activity for the direct synthesis of 1,3-dibutylurea (DBU) from CO2 and n-butylamine than the metal oxides tested. The solvent largely influenced the reaction over CeO2, and N-methylpyrrolidone (NMP) was preferable among various solvents tested from the viewpoints of activity and selectivity. The catalyst system composed of CeO2 catalyst and NMP solvent (CeO2 in NMP) was applicable to the reactions of various amines such as linear primary alkylamines or branched primary alkylamines, although tert-butylamine afforded low conversion. In contrast, secondary amines and aniline provided no yield of the ureas. The combination of 2-cyanopyridine with CeO2 in NMP (CeO2 in NMP with 2-cyanopyridine) promoted the transformation of the unreactive amines, showing that tert-butylamine and aniline were converted to the corresponding ureas in 82% and 80% yields, respectively. These yields are much higher than those reported in the previous literatures, indicating that CeO2 in NMP with 2-cyanopyridine drastically promoted transformation of amines with low reactivity.

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Haruki,E. et al.

, p. 1361 - 1367 (1968)

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Annulation Reactions of In-Situ-Generated N-(Het)aroyldiazenes with Isothiocyanates Leading to 2-Imino-1,3,4-oxadiazolines

Zhao, Qiongli,Ren, Linning,Hou, Jiao,Yu, Wenquan,Chang, Junbiao

, p. 210 - 213 (2019)

A novel annulation reaction of N-(het)aroyldiazenes and isothiocyanates has been established. This transformation involves a sequential cyclization and desulfurization/intramolecular rearrangement to produce 2-imino-1,3,4-oxadiazolines. The less-stable N-(het)aroyldiazenes can be conveniently generated in situ by I2-mediated oxidation of hydrazides, which allows a one-pot synthesis of the products directly from readily accessible hydrazide and isothiocyanate substrates. This operationally simple synthetic process requires no use of malodorous isocyanides and can be conveniently conducted on a gram scale.

A convenient and inexpensive method for conversion of thiocarbonyl compounds to their oxo derivatives using oxone under solvent-free conditions

Mohammadpoor-Baltork, Iraj,Sadeghi, Majid M.,Esmayilpour, Karim

, p. 953 - 959 (2003)

A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.

N-heterocyclic carbene - Palladium complexes as efficient catalysts for the oxidative carbonylation of amines to ureas

Zheng, Shuzhan,Peng, Xingao,Liu, Jianming,Sun, Wei,Xia, Chungu

, p. 1471 - 1476 (2007)

A highly efficient oxidative carbonylation reaction of amines to ureas was developed making use of carbene-palladium complexes in the absence of any promoter. Both aliphatic amines and aromatic amines were transformed in good to excellent yields to the expected ureas.

Novel Route from Thiocarbamate to Isocyanate: 2,2,2-Trinitroethyl Isocyanate

Sitzmann, Michael E.,Gilligan, William H.

, p. 5879 - 5881 (1985)

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Synthesis of symmetrical ureas by (Diacetoxyiodo)benzene-induced hofmann rearrangement

Landsberg, Dirk,Kalesse, Markus

, p. 1104 - 1106 (2010)

Amides undergo Hofmann rearrangement by treatment with (diacetoxyiodo) benzene (DAIB) to provide symmetrical ureas in a simple and robust transformation. Georg Thieme Verlag Stuttgart - New York.

Photochemical molecular storage of Cl2, HCl, and COCl 2: Synthesis of organochlorine compounds, salts, ureas, and polycarbonate with photodecomposed chloroform

Kuwahara, Yuki,Zhang, Ailing,Soma, Haruka,Tsuda, Akihiko

, p. 3376 - 3379 (2012)

Chloroform is available as not only an organic solvent but also photochemical molecular storage for synthetically important chemicals such as Cl2, HCl, and COCl2. We have succeeded in synthesizing organochlorine compounds, hydrochloric salt of amines, ureas, organic carbonates, and polycarbonate in practical high yields with photodecomposed chloroform.

Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides

Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong

, p. 2820 - 2826 (2021)

A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.

Copper-catalyzed arylation of phenylurea using KF/Al2O3

Hosseinzadeh, Rahman,Sarrafi, Yaghoub,Mohadjerani, Maryam,Mohammadpourmir, Fatemeh

, p. 840 - 843 (2008)

A mild and efficient method for the copper-catalyzed arylation of phenylurea is described. The coupling reaction of phenylurea with different functionalized aryl iodides in the presence of air stable CuI, N,N′-dibenzylethylenediamine as a ligand, and KF/Al2O3 as a base gives symmetrical and unsymmetrical diarylureas in relatively high yields.

Silica gel confined ionic liquid + metal complexes for oxygen-free carbonylation of amines and nitrobenzene to ureas

Shi, Feng,Zhang, Qinghua,Gu, Yanlong,Deng, Youquan

, p. 225 - 230 (2005)

A new kind of silica gel confined ionic liquid containing a metal complex as heterogenized catalysts was prepared for the carbonylation of amines and nitrobenzene without molecular oxygen to afford the corresponding ureas with greatly enhanced catalytic activity (TOF exceeded 11000 mol·mol -1· h-1), with a much lower amount of ionic liquids being needed, with easy catalyst separation and possible reusability, and avoidance of the using of explosive CO + O2 gas mixtures. Such an enhancement in catalytic activity may be derived from the effect of a high concentration of ionic liquid containing a metal complex due to the confinement into the nanopores or cavities of the silica gel matrix.

Oxidative carbonylation of aniline with new cobalt catalytic systems

Orejon, Aranzazu,Castellanos, Aida,Salagre, Pilar,Castillon, Sergio,Claver, Carmen

, p. 764 - 768 (2005)

New neutral cobalt(II) complexes containing 2,9-bis(2-hydroxyphenyl)-1,10- phenanthroline and 2,9-bis(2-hydroxyphenyl)-2,2′-bipyridine ligands have been synthesized. These complexes are active catalysts in the oxidative carbonylation of aniline in 1-butanol and NaI as a promoter. The principal products obtained are N,N′-diphenylurea and 1-butyl-N-phenylcarbamate.

Squaramides as potent transmembrane anion transporters

Busschaert, Nathalie,Kirby, Isabelle L.,Young, Sarah,Coles, Simon J.,Horton, Peter N.,Light, Mark E.,Gale, Philip A.

, p. 4426 - 4430 (2012)

Square peg in a round ball: Squaramides are shown to be potent transmembrane anion transporters for both chloride and bicarbonate, performing better than the thiourea and urea analogues. Studies into the nature of this transport point to a mobile carrier mechanism, where the squaramide delivers the anion cargo across the lipid bilayer (see scheme, green sphere=anion). These drug-like molecules provide a platform for the development of a new generation of anion-transport systems. Copyright

Ionic liquids/ZnO nanoparticles as recyclable catalyst for polycarbonate depolymerization

Iannone, Francesco,Casiello, Michele,Monopoli, Antonio,Cotugno, Pietro,Sportelli, Maria Chiara,Picca, Rosaria Anna,Cioffi, Nicola,Dell'Anna, Maria M.,Nacci, Angelo

, p. 107 - 116 (2017)

A useful protocol for waste bis-phenol A-polycarbonates (BPA-PC) chemical recycling is proposed based on a bifunctional acid/basic catalyst composed by nanostructured zinc oxide and tetrabutylammonium chloride (ZnO-NPs/NBu4Cl) in quality of Lewis acid and base, respectively. Retro-polymerization reaction proved to be of general application for several nucleophiles, including water, alcohols, amines, polyols, aminols and polyamines, leading to the complete recovery of BPA monomer and enabling the PC polymer to function as a green carbonylating agent (green phosgene alternative) for preparing carbonates, urethanes and ureas. A complete depolymerization can be obtained in seven hours at 100 °C and ZnO nanocatalyst can be recycled several times without sensible loss of activity. Remarkably, when polycarbonate is reacted with glycerol, it is possible to realize in a single process the conversion of two industrial wastes (BPA-PC and glycerol) into two valuable chemicals like BPA monomer and glycerol carbonate (the latter being a useful industrial solvent and fuel additive).

Cragg, R. H.,Greenwood, N. N.

, (1967)

Synthesis of high-performance polyurethanes with rigid 5-6-5-fused ring system in the main chain from naturally occurring myo-inositol

Sudo, Atsushi,Shibata, Yoshiya,Miyamoto, Ayano

, p. 3956 - 3963 (2013)

A bisketal of myo-inositol was used as a diol-type monomer for synthesis of polyurethanes. The monomer was obtained by treatment of myo-inositol with 1,1-dimethoxycyclohexane in the presence of p-toluenesulfonic acid as a catalyst. The ketalization resulted in the formation of a 5-6-5-fused ring system, which endowed the diol-type monomer with high rigidity. The diol readily reacted with diisocyanate to give the corresponding polyurethane, which exhibited excellent heat resistance due to the rigid 5-6-5 system in the main chain. Copyright

-

Kondo et al.

, p. 307 (1972)

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Conversion of thioamides into their corresponding oxygen analogues using silver carbonate supported on celite

Movassagh,Lakouraj,Gholami

, p. 1507 - 1511 (2003)

Silver carbonate supported on celite (Ag2CO3/Celite) is used as a mild heterogeneous reagent for conversion of a variety of thioamides into their corresponding amides in acetonitrile at room temperature.

PLATINUM COMPLEX CATALYZED SYNTHESIS OF UREA DERIVATIVES FROM NITROARENES AND AMINES UNDER CARBON MONOXIDE

Tsuji, Yasushi,Takeuchi, Ryo,Watanabe, Yoshihisa

, p. 249 - 256 (1985)

N,N'-Diarylureas were obtained in good yields from nitroarenes and aminoarenes at 140 deg C under carbon monoxide (initial 60 kg cm-2) in the presence of a catalytic amount of dichlorobis(triphenylphosphine)platinum(II), the yields of N,N'-diphenylurea, N,N'-bis(4-methylphenyl)urea, and N,N'-bis(4-chlorophenyl)urea were 65, 67 and 61percent, respectively.Benzimidazole derivatives were obtained by the intramolecular cyclization reaction.An attempted synthesis of unsymmetric ureas resulted in the formation of a mixture of symmetric and unsymmetric products.

Microwave assisted, ligand free, copper catalyzed reaction of aryl halides with phenyl urea

Gavade, Sandip N.,Balaskar, Ravi S.,Mane, Madhav S.,Pabrekar, Pramod N.,Shingare, Murlidhar S.,Mane, Dhananjay V.

, p. 292 - 295 (2011)

The ligand free coupling reaction of phenyl urea with different functionalized aryl halides in the presence of air stable Cu2O and t-BuOK as a base gives symmetrical and unsymmetrical diarylureas in relatively high yields. This method is milder than the palladium catalyzed arylation and avoids the use of toxic phosphine ligand.

Mo-ZrO2 solid acid catalyst for synthesis of substituted diphenylureas

Reddy, Benjaram M.,Reddy, Vangala R.

, p. 2789 - 2794 (1999)

Synthesis of substituted diphenylureas from substituted anilines and β- ketoester by using an efficient eco-friendly Mo-ZrO2 solid acid catalyst is described.

Alternatives to phosgene and carbon monoxide: Synthesis of symmetric urea derivatives with carbon dioxide in ionic liquids

Shi, Feng,Deng, Youquan,SiMa, Tianlong,Peng, Jiajian,Gu, Yanlong,Qiao, Botao

, p. 3257 - 3260 (2003)

Simple, clean, safe, reproducible, and practical describes the synthesis of disubstituted urea derivatives, which are effectively synthesized from amines and carbon dioxide with a CsOH/ionic-liquid catalyst system. The products are easily separated and the catalytic system can be reused without deactivation (see picture).

Efficient synthesis of N,N′-disubstituted ureas/thioureas catalyzed by iodine

Pasha,Jayashankara

, p. 1787 - 1793 (2006)

Iodine is an efficient catalyst for the synthesis of symmetrically N,N′-disubstituted ureas/thioureas by heating respective amines or phenyl hydrazine and urea/thiourea on a preheated hot plate at 90-95°C, under solvent-free conditions. The yields are excellent, and the reactions go to complete within 5-10 min. Copyright Taylor & Francis Group, LLC.

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: Chemoselective Non-Metal-Catalyzed Carboxamidation of Indoles

Vala, Anand,Parmar, Deepa,Rayani, Rahul,Kusurkar, Rakesh,Guduru, Ramakrishna,Kaneriya, Uttam,Gondaliya, Uday,Parmar, Nirali,Soni, Jigar Y.

, (2022/02/21)

1,4,2-Dioxazol-5-ones are known to undergo decarboxylation under thermal conditions followed by Lossen s rearrangement to give isocyanates. Described herein is the in situ trapping of the isocyanates by indoles to give indole-3-carboxamides in good to exc

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides

Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna

, p. 2080 - 2084 (2021/10/07)

Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.

Chromium-catalyzed ligand-free amidation of esters with anilines

Chen, Changpeng,Ling, Liang,Luo, Meiming,Zeng, Xiaoming

supporting information, p. 762 - 766 (2021/04/14)

Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.

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