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122-37-2 Usage

Uses

4-Hydroxydiphenylamine is used as a reactant in the preparation of iron methylisopropylglyoxime dimethylpyridine/dimethylaminopyridine/phenylaminophenol/imidazolidone complexes.

Definition

Gray solid leaflets. Insoluble in water; soluble in alcohol, ether, acetone, chloroform, alkali, and benzene.

Hazard

Irritant.

Safety Profile

Poison by intravenous route.Moderately toxic by ingestion. A severe eye irritant. Seealso AROMATIC AMINES. When heated todecomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise the amine from chlorobenzene/pet ether, pentane (m 72o) or *C6H6/pet ether (m 70o). [Beilstein 13 III 1019, 13 IV 1052.]

Check Digit Verification of cas no

The CAS Registry Mumber 122-37-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 122-37:
(5*1)+(4*2)+(3*2)+(2*3)+(1*7)=32
32 % 10 = 2
So 122-37-2 is a valid CAS Registry Number.

122-37-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (L18945)  4-Hydroxydiphenylamine, 98%   

  • 122-37-2

  • 10g

  • 424.0CNY

  • Detail
  • Alfa Aesar

  • (L18945)  4-Hydroxydiphenylamine, 98%   

  • 122-37-2

  • 50g

  • 1761.0CNY

  • Detail

122-37-2SDS

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 4-Hydroxydiphenylamine

1.2 Other means of identification

Product number -
Other names 4-anilinophenol

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:122-37-2 SDS

122-37-2Synthetic route

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

4-amino-phenol
123-30-8

4-amino-phenol

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With SingaCycle-A1; sodium t-butanolate In tetrahydrofuran at 60℃; for 6h; Inert atmosphere; regioselective reaction;98%
4-nitro-phenol
100-02-7

4-nitro-phenol

iodobenzene
591-50-4

iodobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 4h;97%
4-(phenylimino)cyclohexa-2,5-dienone
2406-04-4

4-(phenylimino)cyclohexa-2,5-dienone

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With triethylsilane; palladium diacetate In 2,2,2-trifluoroethanol at 20℃; for 0.333333h;95%
With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol; trichloroacetic acid In chlorobenzene at 25.05℃; Kinetics; Further Variations:; Reagents;
With N,N'-diphenyl-1,4-phenylenediamine In chlorobenzene at 68.45℃; Equilibrium constant; Thermodynamic data; Further Variations:; Temperatures;
iodobenzene
591-50-4

iodobenzene

4-amino-phenol
123-30-8

4-amino-phenol

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 2.6h;95%
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;64%
bromobenzene
108-86-1

bromobenzene

4-amino-phenol
123-30-8

4-amino-phenol

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 110℃; for 1h; Inert atmosphere;92%
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 3h;92%
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 90℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere;82.37%
With copper(l) iodide
4-(phenylamino)phenyl acetate
13515-47-4

4-(phenylamino)phenyl acetate

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 4h;92%
4-Iodophenol
540-38-5

4-Iodophenol

nitrobenzene
98-95-3

nitrobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 6.5h;92%
bromobenzene
108-86-1

bromobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 4.5h;92%
triphenyl phosphite
101-02-0

triphenyl phosphite

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With aniline; hydroquinone In water91%
4-Iodophenol
540-38-5

4-Iodophenol

aniline
62-53-3

aniline

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With copper(l) iodide; C12H13N3O; triethylamine In diethylene glycol dimethyl ether at 30℃; for 15h; Sealed tube;90%
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 5h;90%
With potassium phosphate; copper(l) iodide; N',N'-diphenyl-1H-pyrrole-2-carbohydrazide In diethylene glycol at 20℃; Sealed tube;84%
aniline
62-53-3

aniline

hydroquinone
123-31-9

hydroquinone

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With alumina at 270℃; under 15001.5 Torr; for 4h; Autoclave; Inert atmosphere;85%
With calcium chloride at 250 - 260℃;
With calcium chloride at 250 - 260℃; Man loest das Reaktionsprodukt in Salzsaeure, faellt die filtrierte Loesung mit Natriumacetat und destilliert das abgeschiedene 4-Oxy-diphenylamin im Wasserstoffstrom;
(p-hydroxyphenyl)boronic acid
71597-85-8

(p-hydroxyphenyl)boronic acid

Nitrosobenzene
586-96-9

Nitrosobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With triethyl phosphite In toluene at 20℃; for 0.75h;80%
4-bromo-phenol
106-41-2

4-bromo-phenol

aniline
62-53-3

aniline

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 6.5h;80%
With potassium phosphate; copper(l) iodide In diethylene glycol at 70℃; for 14h; Sealed tube;68%
With [(di-tert-butylneopentylphosphine)PdCl2]2; pentan-3-one; sodium t-butanolate In toluene at 22℃; for 15h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;30 %Chromat.
4-bromo-phenol
106-41-2

4-bromo-phenol

nitrobenzene
98-95-3

nitrobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 7.7h;80%
4-nitro-phenol
100-02-7

4-nitro-phenol

chlorobenzene
108-90-7

chlorobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 9h;80%
4-chloro-phenol
106-48-9

4-chloro-phenol

aniline
62-53-3

aniline

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 9h;80%
p-nitrosophenol
104-91-6

p-nitrosophenol

phenylboronic acid
98-80-6

phenylboronic acid

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With triethyl phosphite In toluene at 20℃; for 0.75h;78%
4-amino-phenol
123-30-8

4-amino-phenol

chlorobenzene
108-90-7

chlorobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 8h;76%
4-chloro-phenol
106-48-9

4-chloro-phenol

nitrobenzene
98-95-3

nitrobenzene

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 10.5h;76%
4-amino-phenol
123-30-8

4-amino-phenol

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

A

biphenyl
92-52-4

biphenyl

B

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: phenylmagnesium bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique; chemoselective reaction;
A n/a
B 75%
4-amino-phenol
123-30-8

4-amino-phenol

phenylboronic acid
98-80-6

phenylboronic acid

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With copper diacetate; caesium carbonate; benzoic acid In 1,4-dioxane at 90℃; for 12h; Reagent/catalyst; Solvent; Chan-Lam Coupling; chemoselective reaction;75%
With C13H11N2O3S(1-)*CF3O3S(1-)*Cu(2+); oxygen In methanol at 50℃; for 12h; Catalytic behavior; Time; Chan-Lam Coupling;
With C14H11CuF3N2O6S2; oxygen In methanol at 50℃; for 12h; Chan-Lam Coupling;100 %Chromat.
aniline
62-53-3

aniline

p-benzoquinone
106-51-4

p-benzoquinone

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
In toluene at 80℃;72%
iodobenzene
591-50-4

iodobenzene

4-amino-phenol
123-30-8

4-amino-phenol

A

4-anilinophenol
122-37-2

4-anilinophenol

B

4-phenoxyanilin
139-59-3

4-phenoxyanilin

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In propyl cyanide at 70℃; for 24h; Inert atmosphere;A 2%
B 67%
Diphenyliodonium triflate
66003-76-7

Diphenyliodonium triflate

4-amino-phenol
123-30-8

4-amino-phenol

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With potassium phosphate; copper diacetate In 1,4-dioxane at 40℃; for 24h; Inert atmosphere;62%

A

2-(phenylamino)phenol
644-71-3

2-(phenylamino)phenol

B

4-anilinophenol
122-37-2

4-anilinophenol

C

4-(2-hydroxyanilino)-1,2-benzenediol

4-(2-hydroxyanilino)-1,2-benzenediol

Conditions
ConditionsYield
With Streptomyces lividans expressing pIJ6021-bphA1(2072)A2A3A4 at 30℃; for 24h; Microbiological reaction;A 42%
B 6.7%
C 3.1%
aniline
62-53-3

aniline

1,4-Cyclohexanedione
637-88-7

1,4-Cyclohexanedione

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With triethylamine In ethanol at 50 - 60℃; for 8h;27.4%
N,N-diphenylhydroxylamine
1079-64-7

N,N-diphenylhydroxylamine

A

9H-carbazole
86-74-8

9H-carbazole

B

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sulfuric acid; acetic acid at -20℃;
N-phenyl-p-benzoquinone imine N-oxide
2206-58-8

N-phenyl-p-benzoquinone imine N-oxide

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With acetic acid; zinc
(4-anilino-phenyl)-amidosulfuric acid
100143-35-9

(4-anilino-phenyl)-amidosulfuric acid

4-anilinophenol
122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium hydroxide
4-anilinophenol
122-37-2

4-anilinophenol

4-(phenylimino)cyclohexa-2,5-dienone
2406-04-4

4-(phenylimino)cyclohexa-2,5-dienone

Conditions
ConditionsYield
With silver carbonate In toluene at 110℃; for 0.25h; Inert atmosphere;100%
With air; chloroform In cyclohexane Mechanism; Quantum yield; Irradiation; var. polychloromethanes, var. solvents; fluorescence quenching constants;
With mercury(II) oxide; benzene
1-(2-chloroethyl)pyrrolidine hydrochloride
7250-67-1

1-(2-chloroethyl)pyrrolidine hydrochloride

4-anilinophenol
122-37-2

4-anilinophenol

N-phenyl-4-(2-(pyrrolidin-1-yl)ethoxy)aniline
60709-31-1

N-phenyl-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Conditions
ConditionsYield
Stage #1: 4-anilinophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h;
Stage #2: 1-(2-chloroethyl)pyrrolidine hydrochloride In N,N-dimethyl-formamide; mineral oil at 20 - 70℃;
100%
Stage #1: 4-anilinophenol With sodium hydride In N,N-dimethyl-formamide for 0.5h;
Stage #2: 1-(2-chloroethyl)pyrrolidine hydrochloride In N,N-dimethyl-formamide at 20 - 70℃;
96%
4-anilinophenol
122-37-2

4-anilinophenol

aniline
62-53-3

aniline

(E)-2,5-bis(phenylamino)-4-(phenylimino)cyclohexa-2,5-dienone

(E)-2,5-bis(phenylamino)-4-(phenylimino)cyclohexa-2,5-dienone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ferrocene In toluene at 80℃; for 24h; Schlenk technique;98%
3-chloro-4-fluorobenzonitrile
117482-84-5

3-chloro-4-fluorobenzonitrile

4-anilinophenol
122-37-2

4-anilinophenol

4-(4-anilinophenoxy)-3-chlorobenznitrile
158769-75-6

4-(4-anilinophenoxy)-3-chlorobenznitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;90%
4,4'-thiobisaniline
139-65-1

4,4'-thiobisaniline

4-anilinophenol
122-37-2

4-anilinophenol

bis(4-diphenylamino)-4,4'-diaminodiphenylsulfide
1013336-07-6

bis(4-diphenylamino)-4,4'-diaminodiphenylsulfide

Conditions
ConditionsYield
Stage #1: With tetrabutoxytitanium; 1-acetoxy-4-methylbenzene at 60℃; for 1h;
Stage #2: 4,4'-thiobisaniline; 4-anilinophenol In toluene at 110℃; for 48h;
90%
4,4'-oxydiphenylene diamine
101-80-4

4,4'-oxydiphenylene diamine

4-anilinophenol
122-37-2

4-anilinophenol

bis(4-diphenylamino)-4,4'-diaminodiphenyl ether
1013336-05-4

bis(4-diphenylamino)-4,4'-diaminodiphenyl ether

Conditions
ConditionsYield
Stage #1: With tetrabutoxytitanium; 1-acetoxy-4-methylbenzene at 60℃; for 1h;
Stage #2: 4,4'-oxydiphenylene diamine; 4-anilinophenol In toluene at 110℃; for 48h;
89%
2,2'-dimethylbenzidine
84-67-3

2,2'-dimethylbenzidine

4-anilinophenol
122-37-2

4-anilinophenol

bis(4-diphenylamino)-2,2'-dimethyl-4,4'-diaminobiphenyl
1013336-06-5

bis(4-diphenylamino)-2,2'-dimethyl-4,4'-diaminobiphenyl

Conditions
ConditionsYield
Stage #1: With tetrabutoxytitanium; 1-acetoxy-4-methylbenzene at 60℃; for 1h;
Stage #2: 2,2'-dimethylbenzidine; 4-anilinophenol In toluene at 110℃; for 48h;
88%
2,2'-bis[4-(4-fluorobenzoyl)phenoxy]-1,1'-binaphthyl

2,2'-bis[4-(4-fluorobenzoyl)phenoxy]-1,1'-binaphthyl

4-anilinophenol
122-37-2

4-anilinophenol

C70H48N2O6

C70H48N2O6

Conditions
ConditionsYield
Stage #1: 2,2'-bis[4-(4-fluorobenzoyl)phenoxy]-1,1'-binaphthyl; 4-anilinophenol With potassium carbonate In N,N-dimethyl-formamide; toluene for 2h; Reflux; Inert atmosphere;
Stage #2: In N,N-dimethyl-formamide for 8h; Reflux; Inert atmosphere;
Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide Inert atmosphere;
88%
4-anilinophenol
122-37-2

4-anilinophenol

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N1,N1'-(1,4-phenylene)bis(N4-phenylbenzene-1,4-diamine)
19099-70-8

N1,N1'-(1,4-phenylene)bis(N4-phenylbenzene-1,4-diamine)

Conditions
ConditionsYield
85%
85%
Stage #1: 1,4-phenylenediamine With tetrabutoxytitanium In toluene at 70℃; for 0.5h;
Stage #2: 4-anilinophenol In toluene at 100℃; for 24h;
75%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-anilinophenol
122-37-2

4-anilinophenol

N-(4-(tert-butyldimethylsilyloxy)phenyl)benzenamine
207386-63-8

N-(4-(tert-butyldimethylsilyloxy)phenyl)benzenamine

Conditions
ConditionsYield
Stage #1: 4-anilinophenol With triethylamine In dichloromethane at 0℃; for 0.333333h;
Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃;
84.6%
With 1H-imidazole In acetonitrile at 70℃; for 4h;
With 1H-imidazole In acetonitrile at 70℃; for 4h;
4-anilinophenol
122-37-2

4-anilinophenol

isopropenylbenzene
98-83-9

isopropenylbenzene

C21H21NO

C21H21NO

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; sodium acetate at 80℃; for 12h; chemoselective reaction;84%
N-(4-(phenylazo)phenyl)-2,6-difluorobenzamide
476277-71-1

N-(4-(phenylazo)phenyl)-2,6-difluorobenzamide

4-anilinophenol
122-37-2

4-anilinophenol

C43H33N5O3

C43H33N5O3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 130 - 150℃; Inert atmosphere;83%
4-anilinophenol
122-37-2

4-anilinophenol

N-phenylphenylene-1,4-diamine
101-54-2

N-phenylphenylene-1,4-diamine

Conditions
ConditionsYield
With alumina; ammonia at 350℃; under 26252.6 Torr; for 2h; Autoclave; Inert atmosphere;82.1%
With 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;45%
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

4-anilinophenol
122-37-2

4-anilinophenol

(Z)-N-(2-((4-hydroxyphenyl)(phenyl)amino)-2-phenylvinyl)-4-methylbenzenesulfonamide

(Z)-N-(2-((4-hydroxyphenyl)(phenyl)amino)-2-phenylvinyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 90℃; for 2h; regioselective reaction;82%
3,4-dibromo-4-methyltetrahydropyran
79862-81-0

3,4-dibromo-4-methyltetrahydropyran

4-anilinophenol
122-37-2

4-anilinophenol

4-[(4-methyl-3,6-dihydro-2H-pyran-3-yl)-phenyl-amino]-phenol
196521-10-5

4-[(4-methyl-3,6-dihydro-2H-pyran-3-yl)-phenyl-amino]-phenol

Conditions
ConditionsYield
In triethylamine at 90℃; for 18h; Condensation;81%
4-anilinophenol
122-37-2

4-anilinophenol

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-(4-phenylaminophenoxymethyl)benzonitrile
512834-69-4

2-(4-phenylaminophenoxymethyl)benzonitrile

Conditions
ConditionsYield
With caesium carbonate; potassium iodide In acetone for 1h; Heating / reflux;80.8%
2,2'-(5'-chloro-[1,1':3',1''-terphenyl]-4,4''-diyl)bis(1,3-dioxolane)

2,2'-(5'-chloro-[1,1':3',1''-terphenyl]-4,4''-diyl)bis(1,3-dioxolane)

4-anilinophenol
122-37-2

4-anilinophenol

C36H31NO5

C36H31NO5

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene at 90℃; for 3h;80%

122-37-2Relevant articles and documents

The N-H and O-H bond dissociation energies in 4-hydroxydiphenylamine and its phenoxyl and aminyl radicals

Varlamov

, p. 306 - 312 (2004)

The N-H and O-H bond dissociation energies in 4-hydroxydiphenylamine Ph-NH-C6H4-OH (DNH= 353.4, DOH=339.3 kJ mol-1) and its semiquinone radicals DNH(Ph-NH-C 6H4-O.) = 273.6, DOH(Ph-N .-C6H4-OH) = 259.5 kJ mol-1 were first estimated using the parabolic model and experimental data (rate constants) on two elementary reactions with participation of N-phenyl-1,4- benzoquinonemonoimine (2). One of the reactions, namely, that of 2 with aromatic amines, was studied in this work using a specially developed method.

Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines

Feng, Yadong,Liu, Ying,Fu, Qi,Zou, Zhongai,Shen, Jinhai,Cui, Xiuling

, p. 733 - 735 (2020)

A ferrocene-initiated radical reaction of benzoquinone with amines has been successfully developed for the direct access to diaminobenzoquinone imines in high yields, in which the commercially available and cheap ferrocene was employed as a radical initiator and TBHP was used as an oxidant. Moreover, this reaction could be achieved with low loading of ferrocene (0.5 mol%). This protocol is highly efficient with good substrate tolerance and provides a new approach for the construction of benzoquinone imines with potential pharmaceutical interest.

Palladium-catalyzed carbonylation of iminoquinones and aryl iodides to access arylp-amino benzoates

Wang, Siqi,Wu, Xiao-Feng,Yao, Lingyun,Ying, Jun

, p. 8246 - 8249 (2021/10/12)

A palladium-catalyzed carbonylation of iminoquinones and aryl iodides has been developed for the construction of arylp-amino benzoates. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source, the reaction proceeded well to give various arylp-amino benzoates in good to excellent yields. Additionally, control experiments were conducted to gain more insights into the reaction mechanism.

Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof

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Paragraph 0071-0072, (2020/06/05)

The invention discloses a substituted anilino-benzothiazole-2-thioketone compound and a preparation method thereof. In addition, the invention also relates to an application of the compound in rubberproducts. The substituted anilino-benzothiazole-2-thioketone compound disclosed by the invention not only can promote rubber vulcanization, but also can prolong the service life of the rubber products.

Pd-Catalyzed Redox-Neutral C-N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones

Jillella, Raveendra,Raju, Selvam,Hsiao, Huan-Chang,Hsu, Day-Shin,Chuang, Shih-Ching

, p. 6252 - 6256 (2020/08/12)

A novel and efficient reductive N-alkenylation of iminoquinones with electron-deficient olefins has been successfully developed by Pd(II)-catalyzed redox-neutral reactions, which provides a synthesis of tertiary (E)-enamines. We further demonstrate that the tertiary enamines can be converted to multifarious N-heterocyclic compounds, indoles, and quinolones in good yields.

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