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Aniline, also known as phenylamine or aminobenzene, is a versatile aromatic amine widely used as a precursor in organic synthesis, including the production of dyes, pharmaceuticals, and polymers. It participates in reductive amination reactions, serves as a substrate in multicomponent syntheses (e.g., for quinolines and piperidines), and can be functionalized via C-H borylation. Its derivatives, such as electron-deficient anilines or carboxyl-substituted trimers, exhibit unique redox properties, corrosion inhibition potential, and utility in drug development (e.g., anti-HIV agents or kinase inhibitors). Aniline's reactivity and adaptability make it a cornerstone in both industrial and research applications.

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  • 62-53-3 Structure
  • Basic information

    1. Product Name: Aniline
    2. Synonyms: ai3-03053;amino-benzen;Aminophen;Anilin;anilin(czech);Anilina;anilina(italian,polish);Aniline reagent
    3. CAS NO:62-53-3
    4. Molecular Formula: C6H7N
    5. Molecular Weight: 93.13
    6. EINECS: 200-539-3
    7. Product Categories: Industrial/Fine Chemicals;Aniline;ACS GradeNitrogen Compounds;C2 to C6;Essential Chemicals;Routine Reagents;A;A-BAlphabetic;Alpha Sort;AM to AQAnalytical Standards;Amines;Aromatics;AromaticsChemical Class;Chemical Class;Volatiles/ Semivolatiles;Alphabetic;AM to AQ;Pesticides&Metabolites;Reagent Plus;AM to AQChemical Class;A-B, Puriss p.a.Nitrogen Compounds;Analytical Reagents for General Use;Puriss p.a.
    8. Mol File: 62-53-3.mol
  • Chemical Properties

    1. Melting Point: -6.2 °C
    2. Boiling Point: 184 °C(lit.)
    3. Flash Point: 76 °C
    4. Appearance: APHA: ≤250/Liquid
    5. Density: 1.022 g/mL at 25 °C(lit.)
    6. Vapor Density: 3.22 (185 °C, vs air)
    7. Vapor Pressure: 0.7 mm Hg ( 25 °C)
    8. Refractive Index: n20/D 1.586(lit.)
    9. Storage Temp.: 2-8°C
    10. Solubility: water: soluble
    11. PKA: 4.63(at 25℃)
    12. Relative Polarity: 0.42
    13. Explosive Limit: 1.2-11%(V)
    14. Water Solubility: 36 g/L (20 ºC)
    15. Stability: Stable. Incompatible with oxidizing agents, bases, acids, iron and iron salts, zinc, aluminium. Light sensitive. Combustible.
    16. Merck: 14,659
    17. BRN: 605631
    18. CAS DataBase Reference: Aniline(CAS DataBase Reference)
    19. NIST Chemistry Reference: Aniline(62-53-3)
    20. EPA Substance Registry System: Aniline(62-53-3)
  • Safety Data

    1. Hazard Codes: T,N,F
    2. Statements: 23/24/25-40-41-43-48/23/24/25-50-68-48/20/21/22-39/23/24/25-11
    3. Safety Statements: 26-27-36/37/39-45-46-61-63-36/37-16
    4. RIDADR: UN 1547 6.1/PG 2
    5. WGK Germany: 2
    6. RTECS: BW6650000
    7. F: 8-9
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: II
    11. Hazardous Substances Data: 62-53-3(Hazardous Substances Data)

62-53-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 62-53-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 2 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 62-53:
(4*6)+(3*2)+(2*5)+(1*3)=43
43 % 10 = 3
So 62-53-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

62-53-3 Well-known Company Product Price

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  • TCI America

  • (A0463)  Aniline  >98.0%(GC)(T)

  • 62-53-3

  • 500g

  • 255.00CNY

  • Detail
  • Alfa Aesar

  • (A14443)  Aniline, 99+%   

  • 62-53-3

  • 100g

  • 232.0CNY

  • Detail
  • Alfa Aesar

  • (A14443)  Aniline, 99+%   

  • 62-53-3

  • 500g

  • 327.0CNY

  • Detail
  • Alfa Aesar

  • (A14443)  Aniline, 99+%   

  • 62-53-3

  • 1000g

  • 442.0CNY

  • Detail
  • Alfa Aesar

  • (A14443)  Aniline, 99+%   

  • 62-53-3

  • 5000g

  • 1697.0CNY

  • Detail
  • Alfa Aesar

  • (36238)  Aniline, ACS, 99+%   

  • 62-53-3

  • 100ml

  • 229.0CNY

  • Detail
  • Alfa Aesar

  • (36238)  Aniline, ACS, 99+%   

  • 62-53-3

  • 500ml

  • 611.0CNY

  • Detail
  • Alfa Aesar

  • (36238)  Aniline, ACS, 99+%   

  • 62-53-3

  • 1L

  • 1045.0CNY

  • Detail

62-53-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name aniline

1.2 Other means of identification

Product number -
Other names Aniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Aniline is predominantly used as a chemical intermediate for the dye, agricultural, polymer, and rubber industries. It is also used as a solvent, and has been used as an antiknock compound for gasolines.
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:62-53-3 SDS

62-53-3Synthetic route

bromobenzene
108-86-1

bromobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;100%
With ammonia; copper In water at 100℃; for 24h; Ullmann reaction;99.1%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;98%
nitrobenzene
98-95-3

nitrobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; platinum In water at 20℃; Product distribution; other temp.;100%
With ethanol; water; tetrabutylammonium hypophosphite; benzene; palladium on activated charcoal for 5h; Product distribution; Heating; hydrogenation in a biphasic solvent system;100%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;100%
nitrobenzene
98-95-3

nitrobenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With ammonia borane; gold on titanium oxide In ethanol at 20℃; for 0.5h; Inert atmosphere;A 92%
B 100%
With samarium; iodine; ammonium chloride In tetrahydrofuran; water at 20℃; for 4h; Reduction;A 56%
B 20%
Electrolysis;
Nitrosobenzene
586-96-9

Nitrosobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; chemoselective reaction;100%
With ammonium hydroxide; nickel boride at 40℃; for 0.5h; Product distribution; further medium: 3N HCl;94.4%
With copper(I) chloride; potassium borohydride In methanol for 0.416667h; Product distribution; Ambient temperature; reduction of aromatic nitro compounds, nitrozobenzene, azobenzene and azoxybenzene with potassium borohydride-copper(I) chloride to primary amines;94%
Phenyl azide
622-37-7

Phenyl azide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sodium hydrogen telluride In diethyl ether; ethanol for 0.25h; Ambient temperature;100%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.05h; Microwave irradiation; chemoselective reaction;99%
With dibutyltin In benzene at 15℃; for 5h; other reagents;98%
benzene
71-43-2

benzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 40℃; for 12h; Product distribution; Mechanism; various acids, various substrates;100%
With trifluorormethanesulfonic acid; trimethylsilylazide at 55℃; for 0.833333h; Product distribution; Mechanism; other arenes or substituted arenes; var. temperatures and time;95%
With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; under 5250.53 Torr; for 0.0466667h; Flow reactor;86%
carbamic acid, phenyl-, 1-methylethyl ester
122-42-9

carbamic acid, phenyl-, 1-methylethyl ester

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 100℃; for 0.666667h; Product distribution;100%
3-(4-nitro-phenoxy)-benz[d]isothiazole-1,1-dioxide
132636-65-8

3-(4-nitro-phenoxy)-benz[d]isothiazole-1,1-dioxide

A

aniline
62-53-3

aniline

B

saccharin
81-07-2

saccharin

Conditions
ConditionsYield
With sodium hypophosphite; palladium on activated charcoal In water; benzene for 0.25h; Heating;A 100%
B n/a
benzamide
55-21-0

benzamide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide In 1,4-dioxane; water at 80℃; for 0.25h; Hofmann degradation;100%
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water for 2h; Ambient temperature;72%
With water; bromine; sodium hydroxide Hofmann Rearrangement; Cooling with ice;
N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; chemoselective reaction;100%
With sodium tetrahydroborate; meso-tetraphenylporphyrin iron(III) chloride In methanol; diethylene glycol dimethyl ether at 25℃; for 3h; Product distribution; Further Variations:; Reagents;98%
With hydrogen In ethanol at 30℃; under 1875.19 Torr; for 1h; Irradiation; Autoclave;95%
isobutyric acid-(N'-phenyl-hydrazide)
5461-50-7

isobutyric acid-(N'-phenyl-hydrazide)

A

ISOPROPYLAMIDE
563-83-7

ISOPROPYLAMIDE

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; palladium In ethanol; acetic acid under 2585.7 Torr;A 100%
B n/a
As,As-bis(p-bromophenyl)-N,N'-diphenylarsinimidic amide

As,As-bis(p-bromophenyl)-N,N'-diphenylarsinimidic amide

A

bis(p-bromophenyl)arsinic acid
113827-90-0

bis(p-bromophenyl)arsinic acid

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With water In diethyl etherA 100%
B n/a
t-butyl N-phenyl sulfinamoyl acetate
82185-52-2

t-butyl N-phenyl sulfinamoyl acetate

benzylamine
100-46-9

benzylamine

A

Benzylamino-thioxo-acetic acid tert-butyl ester
130293-09-3

Benzylamino-thioxo-acetic acid tert-butyl ester

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
In diethyl ether for 72h; Ambient temperature;A 63%
B 100%
In diethyl ether for 72h; Mechanism; Ambient temperature; reaction of other substituted t-butyl sulfinamoyl acetates;A 63%
B 100%
azoxybenzene
495-48-7

azoxybenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With copper(I) chloride; potassium borohydride In methanol for 0.25h; Product distribution; Ambient temperature; reduction of aromatic nitro compounds , nitrosobenzene, azobenzene and azoxybenzene with potassium borohydride-copper(I) chloride to primary amines;100%
With N-doped TiO2 In methanol at 20℃; for 3h; UV-irradiation; Inert atmosphere;92%
With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran at 20℃; for 10h; Reduction; deoxygenation;66%
(HRu3(CO)9((C6H5)N))(1-)

(HRu3(CO)9((C6H5)N))(1-)

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With H2 In not given Ru compound heated at 80°C under CO-H2 (1:1);100%
(((C6H5)3P)2N)(1+)*(HRu3(CO)9((C6H5)NCO))(1-)=(((C6H5)3P)2N)(HRu3(CO)9((C6H5)NCO))

(((C6H5)3P)2N)(1+)*(HRu3(CO)9((C6H5)NCO))(1-)=(((C6H5)3P)2N)(HRu3(CO)9((C6H5)NCO))

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With H2 In not given Ru compound heated at 80°C under CO-H2 (1:1);100%
iodobenzene
591-50-4

iodobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With iron(III) oxide; sodium hydroxide; copper(l) iodide; ammonia In ethanol; water at 90℃; for 16h;100%
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;99%
With ammonia; triethylamine In water at 20℃; for 2.5h; Reagent/catalyst; Solvent; Time;98%
anilino(tert-butyldimethyl)silane
53742-62-4

anilino(tert-butyldimethyl)silane

aniline
62-53-3

aniline

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
2-methyl-1,2,3,4-tetrahydroquinolin-4-yl-(phenyl)amine
1026-05-7

2-methyl-1,2,3,4-tetrahydroquinolin-4-yl-(phenyl)amine

A

2-methylquinoline
91-63-4

2-methylquinoline

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With palladium dichloride In acetonitrileA 100%
B 100%
4-chloro-aniline
106-47-8

4-chloro-aniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With hydrogen; triethylamine In water at 120 - 140℃; under 22502.3 - 37503.8 Torr;99%
With hydrogen; NiCl2-Li-[poly(2-vinyl-naphthalene)-co-(divinylbenzene)] In tetrahydrofuran at 20℃; under 760.051 Torr; for 2h;98%
3-chloro-aniline
108-42-9

3-chloro-aniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; triethylamine In water at 120 - 140℃; under 22502.3 - 37503.8 Torr;99%
With lithium at 230℃; Zersetzen der Reaktionsprodukte mit Wasser;
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.75h;94 % Spectr.
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water at 20℃; for 3h;99%
With ammonium formate; PdMCM-41 In methanol at 69.84℃; for 0.666667h;95%
With palladium on activated charcoal; formic acid; N,N-dimethyl-formamide for 3h; Heating;90%
4-bromo-aniline
106-40-1

4-bromo-aniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; triethylamine In water at 120 - 140℃; under 22502.3 - 37503.8 Torr; Temperature;99%
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 155h;80%
Stage #1: 4-bromo-aniline With palladium dichloride In water at 20℃; for 0.0333333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 0.383333h;
79%
tert-butyl phenylcarbamate
3422-01-3

tert-butyl phenylcarbamate

aniline
62-53-3

aniline

Conditions
ConditionsYield
With water at 100℃; for 10h; Inert atmosphere;99%
HY-Zeolite In dichloromethane for 1.5h; Heating;92%
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 70 - 72℃; for 1h;92%
styrene
292638-84-7

styrene

nitrobenzene
98-95-3

nitrobenzene

A

ethylbenzene
100-41-4

ethylbenzene

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; 5% rhodium-on-charcoal; tris(acetylacetonato)cobalt In tetrahydrofuran at 20℃; for 16h;A 99%
B 89%
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 16h;A 98%
B 80%
With hydrogen; 5% rhodium-on-charcoal In tetrahydrofuran at 20℃; for 16h; Product distribution / selectivity;A 93%
B 31%
With hydrogen at 110℃; under 4560.31 Torr; for 24h; Autoclave; chemoselective reaction;
4-nitrobenzanilide
3460-11-5

4-nitrobenzanilide

A

aniline
62-53-3

aniline

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With 40% potassium fluoride/alumina for 0.0666667h; Microwave irradiation; Neat (no solvent);A 90%
B 99%
3,5-Dichloroaniline
626-43-7

3,5-Dichloroaniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With Raney aluminium-nickel alloy; water; sodium hydroxide In dimethoxymethane at 25℃; for 17h;
2,4-Dichloroaniline
554-00-7

2,4-Dichloroaniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With methylene blue; sodium hydroxide Kinetics; Concentration; pH-value; Temperature; Irradiation;
nitrobenzene
98-95-3

nitrobenzene

12percent nickel/Al-SBA-15 fiber

12percent nickel/Al-SBA-15 fiber

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

aniline
62-53-3

aniline

trans-2-(phenylamino)cyclopentanol
77924-49-3, 101593-89-9

trans-2-(phenylamino)cyclopentanol

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;100%
With lithium bromide at 20℃; for 5h;100%
With sulfated zirconia In neat (no solvent) at 20℃; for 0.5h; regioselective reaction;98%
furfural
98-01-1

furfural

aniline
62-53-3

aniline

N-(2-furylmethylene)aniline
3237-23-8

N-(2-furylmethylene)aniline

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0166667h;100%
With aluminum oxide for 5h; Milling;100%
sodium hydrogen sulfate; silica gel at 56 - 58℃; for 0.0244444h; microwave irradiation;98%
maleic anhydride
108-31-6

maleic anhydride

aniline
62-53-3

aniline

N-phenylmaleamic acid
555-59-9, 4437-08-5, 37902-58-2

N-phenylmaleamic acid

Conditions
ConditionsYield
In diethyl ether Ring cleavage; Substitution;100%
In dichloromethane at 20℃; for 1h;100%
at 20℃; for 2h;99%
phthalic anhydride
85-44-9

phthalic anhydride

aniline
62-53-3

aniline

N-phenylphthalimide
520-03-6

N-phenylphthalimide

Conditions
ConditionsYield
Stage #1: phthalic anhydride; aniline In N,N-dimethyl acetamide at 20℃; for 24h;
Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;
100%
In 1,2-dichloro-benzene at 180 - 190℃; for 5h; Dean-Stark;100%
In 1,2-dichloro-benzene at 180 - 190℃; for 5h; Dean-Stark;100%
Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

aniline
62-53-3

aniline

N-(2-hydroxy-3-phenoxypropyl)aniline
16112-55-3, 113279-34-8

N-(2-hydroxy-3-phenoxypropyl)aniline

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;100%
With lithium bromide at 20℃; for 5h;100%
silica gel at 20℃; for 3h;100%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
In water at 60℃; for 18h;100%
With acetic acid at 20 - 25℃; for 1h; Temperature; Reagent/catalyst;100%
With PhCNAl(OC(CF3)2PhCH3)3 at 25℃; for 4h; Inert atmosphere; Neat (no solvent);99%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium at 20℃; for 20h; without solvent;100%
With zirconium(IV) chloride at 20℃; for 0.25h;100%
Montmorillonite K 10 at 20℃; for 3h; Product distribution; Further Variations:; Catalysts; reaction times;100%
acetic anhydride
108-24-7

acetic anhydride

aniline
62-53-3

aniline

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
With pyridine; aluminum oxide at 93 - 95℃; for 1h; microwave irradiation;100%
In dichloromethane at 20℃; Inert atmosphere;100%
In dichloromethane at 21℃; Inert atmosphere;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

aniline
62-53-3

aniline

N-(4-chlorobenzylidene)aniline
2362-79-0

N-(4-chlorobenzylidene)aniline

Conditions
ConditionsYield
With acetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;100%
With formic acid In ethanol; water at 20℃; for 0.0166667h; Green chemistry;99%
at 20℃; for 14h; Molecular sieve;98%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

aniline
62-53-3

aniline

Conditions
ConditionsYield
With pyridine In toluene for 12h;100%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With triethylamine In ethyl acetate at 0 - 20℃;94%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

aniline
62-53-3

aniline

[1]naphthylmethylen-aniline
890-50-6

[1]naphthylmethylen-aniline

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
In benzene Heating;74%
In water at 20℃; for 2h;69%
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

aniline
62-53-3

aniline

2-(N-phenylcarbamoyl)cyclopentanone
4874-65-1

2-(N-phenylcarbamoyl)cyclopentanone

Conditions
ConditionsYield
In neat (no solvent) at 180℃; for 0.75h; Microwave irradiation; Green chemistry;100%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; Inert atmosphere;90%
With dmap In toluene for 9.5h; Reflux; Inert atmosphere;39%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

aniline
62-53-3

aniline

N-(3,4,5-trimethoxybenzylidene)aniline
114468-30-3, 32349-41-0

N-(3,4,5-trimethoxybenzylidene)aniline

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
sodium hydrogen sulfate; silica gel at 60 - 62℃; for 0.025h; microwave irradiation;94%
In ethanol at 20℃;87%
trityl chloride
76-83-5

trityl chloride

aniline
62-53-3

aniline

Phenyl-trityl-amine
4471-22-1

Phenyl-trityl-amine

Conditions
ConditionsYield
Stage #1: trityl chloride; aniline at 190℃; for 0.5h;
Stage #2: With hydrogenchloride In methanol for 0.5h; Reflux;
100%
at 50℃; for 1.5h;63%
With pyridine at 20℃; for 24h; Substitution;44%
benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

N-Benzylaniline
758640-21-0

N-Benzylaniline

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; silica gel at 20℃; for 1h;100%
With sodium tetrahydroborate; triethylamine In methanol100%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 1h; Solvent; Reagent/catalyst; Green chemistry;100%
benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

benzylidene phenylamine
538-51-2

benzylidene phenylamine

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
In toluene at 120℃; for 24h;100%
With alumina-entrapped Ag at 120℃; under 750.075 Torr; for 1h; Inert atmosphere; Autoclave;100%
benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

Conditions
ConditionsYield
In ethanol for 6h; Reflux;100%
In toluene Inert atmosphere; Schlenk technique; Molecular sieve;100%
With silica gel In ethanol at 20℃; Ultrasound irradiation;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

aniline
62-53-3

aniline

p-methoxybenzylidene-phenylamine
836-41-9

p-methoxybenzylidene-phenylamine

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
In toluene for 1h; Ambient temperature;100%
In benzene for 4h; Reflux; Dean-Stark;100%
salicylaldehyde
90-02-8

salicylaldehyde

aniline
62-53-3

aniline

N-phenylsalicylaldimine
779-84-0

N-phenylsalicylaldimine

Conditions
ConditionsYield
at 50℃; for 4h;100%
With sodium sulfate In dichloromethane for 4h; Reflux;100%
In methanol at 20℃; for 1h;98%
benzoyl chloride
98-88-4

benzoyl chloride

aniline
62-53-3

aniline

N-phenyl benzoyl amide
93-98-1

N-phenyl benzoyl amide

Conditions
ConditionsYield
With pyridine; aluminum oxide at 92 - 94℃; for 0.0166667h; microwave irradiation;100%
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique; Glovebox;99.5%
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%
vanillin
121-33-5

vanillin

aniline
62-53-3

aniline

N-(4-hydroxy-3-methoxybenzylidene)aniline
17696-53-6

N-(4-hydroxy-3-methoxybenzylidene)aniline

Conditions
ConditionsYield
With aluminum oxide for 5h; Milling;100%
sodium hydrogen sulfate; silica gel at 58 - 60℃; for 0.0208333h; microwave irradiation;96%
With aqueous extract of pericarp of Sapindus trifoliatus fruits at 20℃; for 0.333333h;93%
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

aniline
62-53-3

aniline

4-nitrobenzanilide
3460-11-5

4-nitrobenzanilide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2.5h;100%
With pyridine Reflux;95%
With pyridine at 20℃; Inert atmosphere; Reflux;91%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

aniline
62-53-3

aniline

N-(3,4-dimethoxybenzylidene)aniline
27895-67-6

N-(3,4-dimethoxybenzylidene)aniline

Conditions
ConditionsYield
In toluene Heating;100%
sodium hydrogen sulfate; silica gel at 56 - 58℃; for 0.0222222h; microwave irradiation;95%
magnesium(II) perchlorate In 1,2-dichloro-ethane at 20℃; for 4h;94%
Conditions
ConditionsYield
With iron(III) chloride hexahydrate In toluene for 6.5h; Solvent; Reagent/catalyst; Reflux;100%
at 20 - 120℃; for 15h;99%
at 120℃; for 15h;99%
acetic acid
64-19-7

acetic acid

aniline
62-53-3

aniline

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With zinc(II) oxide for 2.33h; Reflux; chemoselective reaction;99%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

aniline
62-53-3

aniline

4-phenylamino-butan-2-one
6220-79-7

4-phenylamino-butan-2-one

Conditions
ConditionsYield
In water at 20℃; for 24h; Michael condensation;100%
With Nafion(R) SAC-13 In acetonitrile at 20℃; for 12h;98%
With bis(trifluoromethanesulfonyl)amide In acetonitrile for 4h; Michael addition;98%
chloroacetonitrile
107-14-2

chloroacetonitrile

aniline
62-53-3

aniline

N-phenylglycinonitrile
3009-97-0

N-phenylglycinonitrile

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetonitrile for 3h; Reflux;100%
With potassium carbonate; sodium iodide In acetonitrile for 3h; Reflux;100%
With triethylamine In ethanol for 4h; Heating;22%
butyraldehyde
123-72-8

butyraldehyde

aniline
62-53-3

aniline

N-(n-butyl)aniline
1126-78-9

N-(n-butyl)aniline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 0.5h;100%
With 1.1 wt% Pd/NiO; hydrogen In ethanol at 25℃; under 760.051 Torr; for 10h;98%
With sodium tetrahydroborate In tetrahydrofuran at 20℃;96%

62-53-3Relevant articles and documents

Magnetic Field Effects on and Mechanism of Photoredox Reaction of Aromatic Nitro Group

Mutai, Kiyoshi,Nakagaki, Ryoichi,Tukada, Hideyuki

, p. 920 - 926 (1993)

Photoredox reaction mechanism of a homologous series p-O2NC6H4O(CH2)nNHPh (1) in acetonitrile and benzene is studied.The major products are p-ONC6H4O(CH2)n-1CHO (3) and aniline derived from intramolecular reaction, but the presence of minor amounts of intermolecular reaction products, p-O2NC6H4O(CH2)n-1CHO (4) and p-ONC6H4O(CH2)nNHPh (5) is confirmed in the reaction mixture.In the presence of an external magnetic field, the yield of 3 is suppressed and those of 4 and 5 are correspondingly increased, while the rates of the disappearance of 1 and of the formation of aniline remain unchanged, suggesting the presence of biradical recombination process accompanied by intersystem crossing in a rate-determining step.On the basis of these observations, two reaction schemes are proposed.The magnetic field effects provide strong evidence for the presence of a transient species with (nitro)N(OH)-O-CHN group generally supposed for nitro oxygen transfer process in this type photoreaction.

Structure and Catalytic Activity of Cr-Doped BaTiO3 Nanocatalysts Synthesized by Conventional Oxalate and Microwave Assisted Hydrothermal Methods

Srilakshmi, Chilukoti,Saraf, Rohit,Prashanth,Rao, G. Mohan,Shivakumara

, p. 4795 - 4805 (2016)

In the present study synthesis of BaTi1-xCrxO3 nanocatalysts (x = 0.0 ≤ x ≤ 0.05) by conventional oxalate and microwave assisted hydrothermal synthesis methods was carried out to investigate the effect of synthesis methods on the physicochemical and catalytic properties of nanocatalysts. These catalysts were thoroughly characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), N2 physisortion, and total acidity by pyridine adsorption method. Their catalytic performance was evaluated for the reduction of nitrobenzene using hydrazine hydrate as the hydrogen source. Structural parameters refined by Rietveld analysis using XRD powder data indicate that BaTi1-xCrxO3 conventional catalysts were crystallized in the tetragonal BaTiO3 structure with space group P4mm, and microwave catalysts crystallized in pure cubic BaTiO3 structure with space group Pm3μm. TEM analysis of the catalysts reveal spherical morphology of the particles, and these are uniformly dispersed in microwave catalysts whereas agglomeration of the particles was observed in conventional catalysts. Particle size of the microwave catalysts is found to be 20-35 nm compared to conventional catalysts (30-48 nm). XPS studies reveal that Cr is present in the 3+ and 6+ mixed valence state in all the catalysts. Microwave synthesized catalysts showed a 4-10-fold increase in surface area and pore volume compared to conventional catalysts. Acidity of the BaTiO3 catalysts improved with Cr dopant in the catalysts, and this could be due to an increase in the number of Lewis acid sites with an increase in Cr content of all the catalysts. Catalytic reduction of nitrobenzene to aniline studies reveals that BaTiO3 synthesized by microwave is very active and showed 99.3% nitrobenzene conversion with 98.2% aniline yield. The presence of Cr in the catalysts facilitates a faster reduction reaction in all the catalysts, and its effect is particularly notable in conventional synthesized catalysts.

Pd nanoparticles immobilized on halloysite decorated with a cyclodextrin modified melamine-based polymer: a promising heterogeneous catalyst for hydrogenation of nitroarenes

Sadjadi, Samahe,Akbari, Maryam,Monflier, Eric,Heravi, Majid M.,Leger, Bastien

, p. 15733 - 15742 (2018)

For the first time, a hybrid system composed of halloysite (Hal) and a cyclodextrin modified melamine-based polymer is developed and employed for immobilization of Pd(0) nanoparticles. The resulting catalytic hybrid system, Pd@HTMC, was then applied as a

Mesoporous silica supported cobalt catalysts for gas phase hydrogenation of nitrobenzene: role of pore structure on stable catalytic performance

Kondeboina, Murali,Enumula, Siva Sankar,Gurram, Venkata Ramesh Babu,Yadagiri, Jyothi,Burri, David Raju,Kamaraju, Seetha Rama Rao

, p. 15714 - 15725 (2018)

Highly dispersed cobalt nanoparticles were prepared over mesoporous silica with different pore structures (2D-hexagonal COK-12 and 3D-cubic SBA-16). These catalysts were evaluated for gas phase hydrogenation of nitrobenzene to aniline at atmospheric H2 pressure. A combination of catalytic activity and characterization results were assessed to establish the role of the support pore structure on hydrogenation activity. XRD, N2-physisorption, SEM and TEM analysis confirmed the presence of mesoporous structures in the supported cobalt catalysts. H2-TPR, H2-pulse chemisorption and TEM studies demonstrated higher dispersion of cobalt nanoparticles in Co/SBA-16 than in the Co/COK-12 catalyst. During the time-on-stream study the Co/SBA-16 catalyst experienced a gradual deactivation whereas the Co/COK-12 catalyst exhibited constant catalytic performance with respect to the hydrogenation of nitrobenzene. The interconnected cage type pores in Co/SBA-16 catalyst allowed the product molecules to participate in further reactions. This resulted in the formation of condensed products and coke deposition. The Co/SBA-16 catalyst was rapidly deactivated due to pore blocking through coke deposition. N2-Physisorption, TGA, H2-TPR and CHNS elemental analysis of spent catalysts confirmed the severe coke deposition in the Co/SBA-16 catalyst compared to the Co/COK-12 catalyst.

Well-dispersed bimetallic nanoparticles confined in mesoporous metal oxides and their optimized catalytic activity for nitrobenzene hydrogenation

Liu, Juanjuan,Zou, Shihui,Xiao, Liping,Fan, Jie

, p. 441 - 446 (2014)

Well-dispersed bimetallic nanoparticles (BMNPs = PtPd/AuPd/AuPt) confined in mesoporous metal oxides (MMOs = TiO2/Al2O 3/SiO2/ZrO2) are synthesized by a general and mild one-step sol-gel strategy. Thi

Palladium nanoparticles supported on silicate-based nanohybrid material: highly active and eco-friendly catalyst for reduction of nitrobenzene at ambient conditions

Ebadati, Esmat,Aghabarari, Behzad,Bagheri, Mozhgan,Khanlarkhani, Ali,Martinez Huerta, Maria Victoria

, p. 569 - 578 (2021)

In this study, spent bleaching earth (SBE), a hazardous industrial waste was used as raw material to synthesis carbon/silicate nanohybrid material (CSNH) as support for mono and bimetallic palladium and nickel nanoparticles. The synthesized catalysts were

Efficient reduction catalysis of viologen-bound iron porphyrin and its application to six-electron reduction of nitrobenzene to aniline

Sakaki, Shigcyoshi,Koga, Hiroaki,Tao, Kou-Ichiro,Yamashita, Takafumi,Iwashita, Tetsuro,Hamada, Taisuke

, p. 1015 - 1017 (2000)

A newly synthesized methylviologen-bound iron porphyrin chloro(5-{4-[3-(1′-methyl-4,4′-bipyridinium)ethylcarboxyamidyl] phenyl}-10,15,20-triphenylporphyrin)iron dichloride, efficiently catalyzes six-electron reduction of nitrobenzene to aniline, a model reaction of NO2- conversion to NH4+ by nitrite reductase. The Royal Society of Chemistry 2000.

A Modification of the Sheverdina-Kocheshkov Amination: The Use of Methoxyamine-Methyllithium as a Convenient Synthetic Equivalent for NH2+

Beak, Peter,Kokko, Bruce J.

, p. 2822 - 2823 (1982)

Direct stoichiometric amination of organolithiums can be achieved in high yields by methoxyamine and methyllithium in hexane-ether.The synthetic advantages of this approach are noted.

Transition Metal Catalyzed Reduction of Azidoarenes to Aminoarenes with Carbon Monoxide-Water System

Shim, Sang Chul,Choi, Kui Nam,Yeo, Young Kuk

, p. 1149 - 1150 (1986)

Azidoarenes were readily transformed to aminoarenes in good yields under mild conditions with carbon monoxide and water in the presence of a catalytic amount of rhodium(III) complex, which is more catalytically active than rhodium(I) or palladium(II) complexes.

Pd immobilized on polymeric network containing imidazolium salt, cyclodextrin and carbon nanotubes: Efficient and recyclable catalyst for the hydrogenation of nitroarenes in aqueous media

Sadjadi, Samahe,Koohestani, Fatemeh

, (2020)

A novel polymeric network benefiting from the chemistry of imidazolium salt (IL), cyclodextrin (CD) and carbon nanotube (CNT) is fabricated through a multi-step process, in which silica coated CNTs were vinyl functionalized and polymerized with poly (ethy

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