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615-36-1 Usage

Chemical Description

2-bromoaniline is an organic compound that is used as a building block in the synthesis of other chemicals.

Description

O-bromoaniline, m-bromoaniline and p-bromoaniline corresponds to the three isomers of bromoaniline. All of them three are toxic with its toxicity being more severe than chloroanilines. It can be all via percutaneous absorption, being hemolytic and able to cause bladder cancer. It is mainly used for dye raw materials, such as azo dyes, quinazoline dyes and so on. Heating together with glycerol, concentrated sulfuric acid and o-bromonitrobenzene can generate 8-bromoquinoline. The preparation of the three isomers is as follows: Take the corresponding nitroaniline as raw material, have it reacted with sodium nitrite in sulfuric acid, leading to the formation of diazonium salt, followed by reaction with hydrobromic acid under the action of cuprous bromide, leading to the formation of nitrobromobenzene, further subjecting to iron powder reaction in the bromic acid to generate the above three isomers. Take benzene as raw material, under the action of iron powder, have it reacted with bromine to generate bromobenzene. It is then reacted with mixed acid (the mixture of sulfuric acid and nitric acid) to generate o-nitrobenzene and p-nitro bromobenzene (orthoaccounts of 35%; paraaccounts of 65%), so that the two are separated, followed by the same process as method one to generate o-bromoaniline and p-bromoaniline. Take bromoacetanilide as raw material, put it into sodium hydroxide solution; apply water vapor reflux to obtain the bromoaniline.

Chemical Properties

Different sources of media describe the Chemical Properties of 615-36-1 differently. You can refer to the following data:
1. It appears as white needle crystal with a melting point of 32 ° C, boiling point of 229 ° C, 138-141 ° C (6.38-6.92 kPa), 110.5 ° C (2.53 kPa), relative density of 1.578 (20/4 ° C) and a refractive index of 1.6133. It is soluble in alcohol and ether, but can’t be dissolved in water.
2. CLEAR YELLOW TO RED-BROWN LIQUID AFTER MELTING

Uses

Different sources of media describe the Uses of 615-36-1 differently. You can refer to the following data:
1. Organic synthesis intermediates
2. 2-Bromoaniline is used as a corrosion inhibitor, emulsifying and antiseptic agents. It is used in the rubber industry, e.g. diphenylguanidines, phenylenediamines mercaptobenzothiazoles, aniline ketones and etc.

Check Digit Verification of cas no

The CAS Registry Mumber 615-36-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 5 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 615-36:
(5*6)+(4*1)+(3*5)+(2*3)+(1*6)=61
61 % 10 = 1
So 615-36-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H6BrN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2

615-36-1 Well-known Company Product Price

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  • TCI America

  • (B0541)  2-Bromoaniline  >98.0%(GC)(T)

  • 615-36-1

  • 25g

  • 390.00CNY

  • Detail
  • TCI America

  • (B0541)  2-Bromoaniline  >98.0%(GC)(T)

  • 615-36-1

  • 250g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (A11788)  2-Bromoaniline, 98%   

  • 615-36-1

  • 25g

  • 585.0CNY

  • Detail
  • Alfa Aesar

  • (A11788)  2-Bromoaniline, 98%   

  • 615-36-1

  • 100g

  • 906.0CNY

  • Detail
  • Alfa Aesar

  • (A11788)  2-Bromoaniline, 98%   

  • 615-36-1

  • 500g

  • 2705.0CNY

  • Detail

615-36-1SDS

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 2-Bromoaniline

1.2 Other means of identification

Product number -
Other names 2-Bromobenzenamine

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:615-36-1 SDS

615-36-1Synthetic route

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 4h; Autoclave;99%
With hydrazine In ethanol at 80℃; for 0.333333h; Catalytic behavior; chemoselective reaction;99.6%
With hydrogen In water at 120℃; under 15001.5 Torr; for 5h; Green chemistry; chemoselective reaction;99%
1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;99%
With 2-(di-tert-butylphosphino)-1-mesityl-4,5-diphenyl-1H-imidazole; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;> 99 %Chromat.
2-bromo-N-hydroxybenzamide
2593-27-3

2-bromo-N-hydroxybenzamide

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
Stage #1: o-bromo-N-hydroxybenzamide With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 50℃; for 2h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃;
99%
With sodium hydroxide In dimethyl sulfoxide at 80℃; for 1.5h; Lossen rearrangement;
Stage #1: o-bromo-N-hydroxybenzamide With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.0833333h;
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

A

aniline
62-53-3

aniline

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With hydrazine hydrate In toluene at 20℃; for 3h; Inert atmosphere;A n/a
B 97%
With hydrogenchloride; zinc(II) chloride In benzene Ambient temperature; electrolysis; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With water; zinc at 250℃; for 0.3h; Reduction; Title compound not separated from byproducts;
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 80℃; for 0.0833333h; Overall yield = 95 %;
With hydrogen In toluene at 110℃; under 7500.75 Torr; for 0.75h; Autoclave;
N-(2-bromophenyl)formamide
10113-38-9

N-(2-bromophenyl)formamide

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 110℃; under 15001.5 Torr; for 3h; Catalytic behavior;97%
With sodium hydroxide In ethanol; water at 40℃; Kinetics;
1-azido-2-bromobenzene
3302-39-4

1-azido-2-bromobenzene

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 1.25h;96%
With D-glucose; potassium hydroxide In water at 85℃; for 0.166667h; Green chemistry; chemoselective reaction;85%
With tributylgermanium hydride; thiophenol In toluene for 0.5h; Heating;5%
bis-(2-bromo-phenyl)-diazene
15426-16-1

bis-(2-bromo-phenyl)-diazene

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With aminomethyl polystyrene resin formic acid salt; zinc In methanol at 20℃; for 0.25h;94%
With formic acid; zinc In methanol at 20℃; for 0.116667h;93%
With ammonium formate; nickel In methanol at 20℃; for 0.116667h;93%
(E)-1,2-bis(2-bromophenyl)diazene
15426-16-1

(E)-1,2-bis(2-bromophenyl)diazene

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With nickel; hydrazinium monoformate In methanol for 0.116667h; Heating;93%
aniline
62-53-3

aniline

A

4-bromo-aniline
106-40-1

4-bromo-aniline

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With dihydrogen peroxide; potassium bromide In water; acetonitrileA 87%
B 12%
With pyridinium hydrobromide perbromide In tetrahydrofuran for 0.25h; Product distribution; other aromatic amines;A 84%
B n/a
With N-Bromosuccinimide; silver hexafluoroantimonate; 1-methylthiotriptycene In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; Overall yield = 95 percentSpectr.;A 76%
B n/a
(2-bromophenyl)boronic acid
244205-40-1

(2-bromophenyl)boronic acid

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 16h;87%
With copper(I) oxide; ammonium hydroxide; oxygen; sodium hydroxide In water at 25℃; for 15h;78%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;70%
N-(2-bromophenyl)-O-benzyl carbamate
132431-13-1

N-(2-bromophenyl)-O-benzyl carbamate

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; ethanethiol for 36h; Ambient temperature;85%
C86H71BrN2O5Si4W

C86H71BrN2O5Si4W

A

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With water Inert atmosphere;A 51%
B 73%
N-acetyl-2-bromoaniline
614-76-6

N-acetyl-2-bromoaniline

A

2-bromo-N-ethylbenzeneamine
69083-47-2

2-bromo-N-ethylbenzeneamine

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); formic acid; bis(trifluoromethanesulfonyl)amide; triethylamine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In dibutyl ether at 130℃; for 24h;A n/a
B 73%
2-(2-bromophenyl)-1,3,2-dioxaborolane
1164112-16-6

2-(2-bromophenyl)-1,3,2-dioxaborolane

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 15h;71%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 45℃; for 48h; Inert atmosphere; Sealed tube; chemoselective reaction;71%
Stage #1: 1-Bromo-2-iodobenzene With TurboGrignard In tetrahydrofuran at -45℃; for 2h; Inert atmosphere;
Stage #2: With C10H17NO In tetrahydrofuran; toluene at -45℃; for 2h; Inert atmosphere;
29%
2-bromostyrene
2039-88-5

2-bromostyrene

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;70%
aniline
62-53-3

aniline

A

3-bromoaniline
591-19-5

3-bromoaniline

B

4-bromo-aniline
106-40-1

4-bromo-aniline

C

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With bromine; hydrogen fluoride; antomony(V) at -40℃; for 0.25h;A 29%
B 62%
C 3%
With bromine; hydrogen fluoride; antomony(V) at -40℃; for 0.25h; Mechanism; Product distribution; dependence of product distribution on ammount of catalyst;
1,8-diazabicyclo[5.4.0]undec-7-ene
6674-22-2

1,8-diazabicyclo[5.4.0]undec-7-ene

2-bromophenyl carbamic acid methyl ester
25216-70-0

2-bromophenyl carbamic acid methyl ester

air

air

A

2-bromoaniline
615-36-1

2-bromoaniline

B

bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene

bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene

Conditions
ConditionsYield
In 1,4-dioxane; water at 80℃; under 760.051 Torr; for 2h;A 61%
B 53%
N-Dibutylaniline
613-29-6

N-Dibutylaniline

A

3-(N,N-dibutylaminophenyl)-acrolein

3-(N,N-dibutylaminophenyl)-acrolein

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
A 60%
B n/a
2-(2-bromophenoxy)propanamide
915920-68-2

2-(2-bromophenoxy)propanamide

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 4h; Green chemistry;60%
ethanol
64-17-5

ethanol

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

A

2-bromo-N,N-diethylaniline
90944-48-2

2-bromo-N,N-diethylaniline

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With Au NCs/TiO2 for 4h; Kinetics; Reagent/catalyst; Inert atmosphere; UV-irradiation;A 24.2%
B 52.8%
aniline
62-53-3

aniline

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With dihydrogen peroxide; copper diacetate; potassium bromide In water at 20℃; for 2h; Concentration; Reagent/catalyst;50%
With D-glucose; Escherichia coli flavin reductase; Bacillus megaterium glucose dehydrogenase; Lechevalieria aerocolonigenes tryptophan-7-halogenase; flavin adenine dinucleotide; NADH In aq. phosphate buffer; isopropyl alcohol pH=7.4; Enzymatic reaction;
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 12h;
With N-Bromosuccinimide In dichloromethane
E-Ethyl ester of 4-methyl-4,5-epoxy-2-pentenoic acid
82127-40-0

E-Ethyl ester of 4-methyl-4,5-epoxy-2-pentenoic acid

(2-Bromo-phenyl)-[1-phenyl-meth-(E)-ylidene]-amine
104669-28-5

(2-Bromo-phenyl)-[1-phenyl-meth-(E)-ylidene]-amine

A

ethyl-(3Z)-2-[[(2-bromophenyl)amino](phenyl)methyl]-4-methyl-5-oxopent-3-enoate

ethyl-(3Z)-2-[[(2-bromophenyl)amino](phenyl)methyl]-4-methyl-5-oxopent-3-enoate

B

ethyl-(3E)-2-[[(2-bromophenyl)amino](phenyl)methyl]-4-methyl-5-oxopent-3-enoate

ethyl-(3E)-2-[[(2-bromophenyl)amino](phenyl)methyl]-4-methyl-5-oxopent-3-enoate

C

benzaldehyde
100-52-7

benzaldehyde

D

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) In tetrahydrofuran at 0℃; Title compound not separated from byproducts;A n/a
B 48%
C n/a
D n/a
bromobenzene
108-86-1

bromobenzene

A

4-bromo-aniline
106-40-1

4-bromo-aniline

B

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h;A 40.2%
B 26.8%
thiophene boronic acid
6165-68-0

thiophene boronic acid

1-azido-2-bromobenzene
3302-39-4

1-azido-2-bromobenzene

A

2-(2-azidephenyl)thiophene
545442-25-9

2-(2-azidephenyl)thiophene

B

2-(thiophen-2-yl)aniline
62532-99-4

2-(thiophen-2-yl)aniline

C

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 100℃; for 6h; Suzuki-Miyaura cross-coupling reaction;A 40%
B 3%
C 2%
bromobenzene
108-86-1

bromobenzene

A

3-bromoaniline
591-19-5

3-bromoaniline

B

4-bromo-aniline
106-40-1

4-bromo-aniline

C

2-bromoaniline
615-36-1

2-bromoaniline

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 60℃; for 3h;A 10%
B 25%
C 30%
With hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; acetic acid at 40℃; for 2h; Yield given. Yields of byproduct given;
With hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; acetic acid at 40℃; for 2h; Product distribution; Mechanism; k(C6H5Br)/k(C6H6);
benzoyl chloride
98-88-4

benzoyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

N-(2-bromophenyl)benzamide
70787-27-8

N-(2-bromophenyl)benzamide

Conditions
ConditionsYield
With 1,10-Phenanthroline In acetonitrile at 90℃; for 1h; Temperature; Inert atmosphere; Sealed tube;100%
In tetrahydrofuran at 20℃; for 24h;99%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;99%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

2-bromoaniline
615-36-1

2-bromoaniline

1-(2-bromophenyl)-3-phenylthiourea
25688-29-3

1-(2-bromophenyl)-3-phenylthiourea

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;100%
In N,N-dimethyl-formamide Heating;99%
With C64H52CaN6 In neat (no solvent) at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;85%
2-bromoaniline
615-36-1

2-bromoaniline

p-trifluoromethyl-phenylisocyanate
1548-13-6

p-trifluoromethyl-phenylisocyanate

1-(2-bromophenyl)-3-(4-(trifluoromethyl)phenyl)urea
23742-77-0

1-(2-bromophenyl)-3-(4-(trifluoromethyl)phenyl)urea

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h; Inert atmosphere;100%
In acetonitrile
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

N-(2-bromophenyl)-2,2-dimethylpropanamide
65854-92-4

N-(2-bromophenyl)-2,2-dimethylpropanamide

Conditions
ConditionsYield
In ethyl acetate at 85℃;100%
With triethylamine In dichloromethane at 0 - 20℃; for 16h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;98%
benzyl bromide
100-39-0

benzyl bromide

2-bromoaniline
615-36-1

2-bromoaniline

N-benzyl-2-bromoaniline
71687-81-5

N-benzyl-2-bromoaniline

Conditions
ConditionsYield
Stage #1: 2-bromoaniline With n-butyllithium In tetrahydrofuran; hexane at -40℃; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; hexane at -60 - 20℃; Inert atmosphere;
100%
Stage #1: 2-bromoaniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: benzyl bromide In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;
95%
Stage #1: 2-bromoaniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Schlenk technique;
Stage #2: benzyl bromide In tetrahydrofuran; hexane at 20℃; for 10h; Inert atmosphere; Schlenk technique;
90%
acetic anhydride
108-24-7

acetic anhydride

2-bromoaniline
615-36-1

2-bromoaniline

N-acetyl-2-bromoaniline
614-76-6

N-acetyl-2-bromoaniline

Conditions
ConditionsYield
for 0.5h; Heating;100%
at 70℃; for 20h;100%
With dmap In chloroform for 0.5h; Reflux;100%
maleic anhydride
108-31-6

maleic anhydride

2-bromoaniline
615-36-1

2-bromoaniline

(Z)-3-(2-Bromo-phenylcarbamoyl)-acrylic acid

(Z)-3-(2-Bromo-phenylcarbamoyl)-acrylic acid

Conditions
ConditionsYield
In diethyl ether Ring cleavage; Substitution;100%
In diethyl ether at 20℃;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

N-ethoxycarbonyl-4-piperidone
29976-53-2

N-ethoxycarbonyl-4-piperidone

2-bromoaniline
615-36-1

2-bromoaniline

ethyl 4-(2-bromophenylamino)-4-cyano-1-piperidinecarboxylate
240486-10-6

ethyl 4-(2-bromophenylamino)-4-cyano-1-piperidinecarboxylate

Conditions
ConditionsYield
Stage #1: trimethylsilyl cyanide; N-ethoxycarbonyl-4-piperidone; 2-bromoaniline With acetic acid for 40h;
Stage #2: With ammonia In water
100%
In acetic acid at 20℃; for 112h; Condensation; modified Strecker reaction;94%
2-(2-iodophenyl)acetonitrile
40400-15-5

2-(2-iodophenyl)acetonitrile

2-bromoaniline
615-36-1

2-bromoaniline

2-{2'-amino-[1,1'-biphenyl]-2-yl}acetonitrile
325141-76-2

2-{2'-amino-[1,1'-biphenyl]-2-yl}acetonitrile

Conditions
ConditionsYield
Stage #1: 2-bromoaniline With Pinacolborane; triethylamine; CyJohnPhos; palladium diacetate In 1,4-dioxane at 80℃;
Stage #2: 2-(2-iodophenyl)acetonitrile With barium dihydroxide In 1,4-dioxane at 100℃; Suzuki-Miyaura coupling; Further stages.;
100%
Stage #1: 2-bromoaniline With palladium diacetate; triethylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; CyJohnPhos In 1,4-dioxane at 25 - 80℃; Inert atmosphere;
Stage #2: 2-(2-iodophenyl)acetonitrile With barium hydroxide octahydrate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere;
99%
Stage #1: 2-bromoaniline With palladium diacetate; triethylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; CyJohnPhos In 1,4-dioxane at 25 - 80℃; for 1h; Inert atmosphere;
Stage #2: 2-(2-iodophenyl)acetonitrile With barium hydroxide octahydrate In 1,4-dioxane at 100℃; for 1h;
99%
Stage #1: 2-bromoaniline With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; CyJohnPhos In 1,4-dioxane at 80℃; for 1h;
Stage #2: 2-(2-iodophenyl)acetonitrile With barium dihydroxide In 1,4-dioxane; water at 100℃; for 1h; Suzuki coupling; Further stages.;
79%
Stage #1: 2-bromoaniline With palladium diacetate; triethylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; CyJohnPhos In 1,4-dioxane at 80℃;
Stage #2: 2-(2-iodophenyl)acetonitrile With barium hydroxide octahydrate In 1,4-dioxane; water at 100℃; Suzuki Coupling;
77%
2-bromoaniline
615-36-1

2-bromoaniline

Acetoxyacetyl chloride
13831-31-7

Acetoxyacetyl chloride

acetic acid (2-bromo-phenylcarbamoyl)-methyl ester
901335-15-7

acetic acid (2-bromo-phenylcarbamoyl)-methyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h;100%
With pyridine In dichloromethane at 20℃; for 2h;
iodobenzene
591-50-4

iodobenzene

2-bromoaniline
615-36-1

2-bromoaniline

2-bromodiphenylamine
61613-22-7

2-bromodiphenylamine

Conditions
ConditionsYield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate In 1,4-dioxane at 110℃; for 16h;100%
With potassium hydroxide In neat (no solvent) at 90℃; for 7.5h;60%
With tris(dibenzylideneacetone)dipalladium (0); sodium t-butanolate In 1,4-dioxane at 45℃;
1-acetyl-4-piperidinone
32161-06-1

1-acetyl-4-piperidinone

2-bromoaniline
615-36-1

2-bromoaniline

1-(4-(2-bromophenylamino)piperidin-1-yl)ethanone
919118-89-1

1-(4-(2-bromophenylamino)piperidin-1-yl)ethanone

Conditions
ConditionsYield
Stage #1: 1-acetyl-4-piperidinone; 2-bromoaniline With sodium tris(acetoxy)borohydride; acetic acid In toluene at 120℃; for 0.25h; Microwave irradiation;
Stage #2: With water; sodium hydrogencarbonate In toluene
100%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-bromoaniline
615-36-1

2-bromoaniline

4'-fluoro-biphenyl-2-ylamine
321-63-1

4'-fluoro-biphenyl-2-ylamine

Conditions
ConditionsYield
Stage #1: 4-fluoroboronic acid; 2-bromoaniline With potassium carbonate In 1,4-dioxane; water for 0.333333h; Inert atmosphere;
Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 100℃;
100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane at 100℃; for 3h; Suzuki Coupling;94%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane at 100℃; for 3h;94%
2-bromoaniline
615-36-1

2-bromoaniline

1-bromo-2-nitrosobenzene
19519-75-6

1-bromo-2-nitrosobenzene

Conditions
ConditionsYield
With potassium peroxomonosulphate In dichloromethane; water at 20℃; Inert atmosphere;100%
With Oxone In dichloromethane; water at 20℃; Inert atmosphere;99%
With Oxone In dichloromethane; water at 20℃; for 20h; Inert atmosphere;98%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

N-(2-bromophenyl)-3-phenylacrylamide
71910-51-5

N-(2-bromophenyl)-3-phenylacrylamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃;98%
With pyridine In dichloromethane at 0 - 20℃;98%
phenylvinylboronic acid
14900-39-1

phenylvinylboronic acid

2-bromoaniline
615-36-1

2-bromoaniline

2-(1-phenylvinyl)aniline
64097-92-3

2-(1-phenylvinyl)aniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 24h; Suzuki Coupling; Inert atmosphere;85%
thiophene boronic acid
6165-68-0

thiophene boronic acid

2-bromoaniline
615-36-1

2-bromoaniline

2-(thiophen-2-yl)aniline
62532-99-4

2-(thiophen-2-yl)aniline

Conditions
ConditionsYield
With C11H8Cl4N2O3Pd; tetrabutylammomium bromide; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki Coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In chloroform; water at 80 - 100℃; for 0.166667h; Suzuki Coupling;99%
With 2-[5-(4-methylphenyl)isoxazol-3-yl]-5-(5-phenylisoxazol-3-yl)-1,3,4-oxadiazole·2PdCl2; tetrabutylammomium bromide; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.0166667h; Suzuki Coupling;98%
benzyl bromide
100-39-0

benzyl bromide

2-bromoaniline
615-36-1

2-bromoaniline

N,N-dibenzyl-2-bromoaniline
1075193-04-2

N,N-dibenzyl-2-bromoaniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 48h;100%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 48h; Inert atmosphere;100%
Stage #1: 2-bromoaniline With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.25h;
Stage #2: benzyl bromide In tetrahydrofuran for 0.25h; Further stages;
83%
With N-ethyl-N,N-diisopropylamine In toluene for 24h; Reflux;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 120℃; for 24h;82 %Spectr.
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-bromoaniline
615-36-1

2-bromoaniline

2-bromophenyl isocyanate
1592-00-3

2-bromophenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
Stage #1: bis(trichloromethyl) carbonate; 2-bromoaniline In dichloromethane at 20℃; for 0.5h;
Stage #2: With triethylamine In dichloromethane at -35 - 20℃; for 2h;
81%
With triethylamine In toluene for 7h; Reflux; Cooling with ice;65.6%
3-bromobenzoyl chloride
1711-09-7

3-bromobenzoyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

2‐(3‐bromophenyl)benzo[d]oxazole
99586-31-9

2‐(3‐bromophenyl)benzo[d]oxazole

Conditions
ConditionsYield
With caesium carbonate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 120℃; for 24h; Product distribution / selectivity; Inert atmosphere;100%
With caesium carbonate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 120℃; for 8h;76%
O-methylresorcine
150-19-6

O-methylresorcine

2-bromoaniline
615-36-1

2-bromoaniline

C21H20N3O2Pol

C21H20N3O2Pol

Conditions
ConditionsYield
With pyridine; copper(I) bromide dimethylsulfide complex; sodium carbonate In acetonitrile at 75℃; for 48h; Inert atmosphere; solid phase reaction;100%
N-methylpyrrole aldehyde
1192-58-1

N-methylpyrrole aldehyde

2-bromoaniline
615-36-1

2-bromoaniline

2-bromo-N-[(1-methyl-1H-pyrrol-2-yl)methylene]aniline

2-bromo-N-[(1-methyl-1H-pyrrol-2-yl)methylene]aniline

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 36h; Dean-Stark; Reflux; Inert atmosphere;100%
1,4-diisocyanatobenzene
104-49-4

1,4-diisocyanatobenzene

2-bromoaniline
615-36-1

2-bromoaniline

C20H16Br2N4O2

C20H16Br2N4O2

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 19h;100%
styrene
292638-84-7

styrene

2-bromoaniline
615-36-1

2-bromoaniline

(E)-2-styrylaniline
27652-35-3

(E)-2-styrylaniline

Conditions
ConditionsYield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 125℃;99%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 125℃;88%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 125℃;88%
2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

thiophene-2-carboxylic acid (2-bromophenyl)amide
136340-96-0

thiophene-2-carboxylic acid (2-bromophenyl)amide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;99%
In tetrahydrofuran at 20℃; for 24h;96%
With triethylamine In dichloromethane at 0 - 20℃;84%
In toluene
With triethylamine In dichloromethane at 20℃; for 3h;
Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

E-N-(2-bromophenyl)-3-phenylpropenamide
71910-51-5

E-N-(2-bromophenyl)-3-phenylpropenamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;99%
With potassium carbonate In water; acetone at 0℃; for 2h;97%
With potassium carbonate In water; acetone at 0℃; for 2h;92%
2-bromoaniline
615-36-1

2-bromoaniline

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-(2-bromophenyl)-2,2,2-trifluoroacetamide
2727-71-1

N-(2-bromophenyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With sodium carbonate In diethyl ether for 24h; Ambient temperature;99%
With triethylamine In dichloromethane at 0 - 20℃;89%
With triethylamine In dichloromethane at 0 - 20℃;89%
3-pyridinecarbonyl chloride
10400-19-8

3-pyridinecarbonyl chloride

2-bromoaniline
615-36-1

2-bromoaniline

N-(2-bromophenyl)-3-pyridinecarboxamide
75075-29-5

N-(2-bromophenyl)-3-pyridinecarboxamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;99%
With pyridine at 0 - 20℃; Acylation;
With N,N-diethyl-N-isopropylamine In acetonitrile at 60℃; for 24h; Inert atmosphere; Schlenk technique;
1,3-cyclopentadione
3859-41-4

1,3-cyclopentadione

2-bromoaniline
615-36-1

2-bromoaniline

3-[(2-bromophenyl)amino]cyclopent-2-en-1-one

3-[(2-bromophenyl)amino]cyclopent-2-en-1-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;99%
at 120℃;70%

615-36-1Relevant articles and documents

Highly Efficient Photo-Reduction of p-Nitrophenol by Protonated Graphitic Carbon Nitride Nanosheets

Qian, Jiajia,Yuan, Aili,Yao, Chengkai,Liu, Jiyang,Li, Benxia,Xi, Fengna,Dong, Xiaoping

, p. 4747 - 4754 (2018)

Photocatalytic reduction of p-nitrophenol to p-aminophenol is important because of the high toxicity of p-nitrophenol and the wide application of p-aminophenol. Graphitic carbon nitride (g-CN) is an excellent photocatalyst for various photo-reduction reac

Composite of β-cyclodextrin and bentonite clay: a promising support for Pd immobilization and developing a catalyst for hydrogenation of nitroarenes under mild reaction condition

Koohestani, Fatemeh,Sadjadi, Samahe

, (2021)

In attempt to take advantages of naturally occurring compounds for the catalysis, a novel composite composed of β-cyclodextrin, dendrimer and bentonite clay is fabricated and utilized as a support for the stabilization of Pd nanoparticles. To prepare the support, bentonite is amino functionalized and then successively reacted with 2,4,6-trichloro-1,3,5-triazine and ethylenediamine to furnish a dendrimer of generation II on bentonite. Afterwards, the terminal functionalities of the dendrimer were adorned with cyclodextrin. Bentonite played role in the heterogenation of the catalyst and improvement of the stability of the composite while, cyclodextrins served as molecular shuttles and capping agent for the as-prepared Pd nanoparticles. Dendrimer with multi nitrogen atoms, on the other hand, improved Pd anchoring through electrostatic interactions. The catalyst was applied for the hydrogenation of nitroarenes under mild reaction condition in aqueous media in a selective manner. Notably, the catalyst could be recovered and reused repeatedly.

Pd stabilized on nanocomposite of halloysite and β-cyclodextrin derived carbon: An efficient catalyst for hydrogenation of nitroarene

Sadjadi, Samahe,Ghoreyshi Kahangi, Fatemeh,Heravi, Majid M.

, (2020)

Carbon nanospheres, CCDs, were fabricated using β-cyclodextrin as carbon precursor. The as prepared CCD was then hybridized with halloysite nanotubes (Hal) through hydrothermal treatment to furnish a nanocomposite, Hal-CCD that was subsequently applied as

Palladated composite of Cu-BDC MOF and perlite as an efficient catalyst for hydrogenation of nitroarenes

Koohestani, Fatemeh,Sadjadi, Samahe

, (2021/11/04)

A novel composite of metal-organic framework and perlite is prepared through hydrothermal treatment of terephthalic acid and Cu(NO3)2·3H2O in the presence of perlite. The resulting composite was then utilized as a support for the immobilization of Pd nanoparticles. The obtained compound was characterized via XRD, TGA, ICP, FTIR, TEM, FE-SEM/EDS and elemental mapping analysis and applied as a catalyst for the hydrogenation of nitroarenes under mild reaction condition. The results approved that the catalyst could efficiently promote hydrogenation of various nitroarenes with different electronic densities and steric properties. Moreover, the catalyst showed high selectivity towards hydrogenation of nitro groups. Hot filtration test affirmed heterogeneous nature of catalysis. Furthermore, the present catalytic composite was highly recyclable with low Pd leaching. A comparative study also approved superior activity of the composite compared to palladated perlite and metal-organic framework.

Selective hydrodeoxygenation of acetophenone derivatives using a Fe25Ru75@SILP catalyst: a practical approach to the synthesis of alkyl phenols and anilines

Bordet, Alexis,Goclik, Lisa,Leitner, Walter,Walschus, Henrik

supporting information, p. 2937 - 2945 (2022/04/07)

A versatile synthetic pathway for the production of valuable alkyl phenols and anilines has been developed based on the selective hydrodeoxygenation of a wide range of hydroxy-, amino-, and nitro-acetophenone derivatives as readily available substrates. Bimetallic iron ruthenium nanoparticles immobilized on an imidazolium-based supported ionic liquid phase (Fe25Ru75@SILP) act as highly active and selective catalysts for the deoxygenation of the side-chain without hydrogenation of the aromatic ring. The catalytic system allows operation under continuous flow conditions with high robustness and flexibility as demonstrated for the alternating conversion of 3′,5′-dimethoxy-4′-hydroxyacetophenone and 4′-hydroxynonanophenone as model substrates.

A suitable modified palladium immobilized on imidazolium supported ionic liquid catalysed transfer hydrogenation of nitroarenes

Atheeswari, Alagudurai,Kanimozhi, Nallusamy,Karthikeyan, Parasuraman,Shanmugapriya, Ramasamy

, (2021/06/28)

The first well-defined modified palladium immobilized on imidazolium supported ionic liquid catalyst has been developed for the transfer hydrogenation of nitroarenes to anilines in good to excellent yields with formic acid as reducing agent. This methodology applies eco-friendly a reducing agent which is non-toxic, water soluble, more stable and simpler to handle. Particularly, the process constitutes a rare model of base-free transfer hydrogenations. The catalyst was reused up to nine consecutive cycles without any significance loss in its activity.

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