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95-51-2

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95-51-2 Usage

Chemical Properties

clear pale yellow to brown liquid with ammonia odor. darkens on exposure to air. almost insoluble in water, soluble in acids and most common organic solvents.

Uses

Different sources of media describe the Uses of 95-51-2 differently. You can refer to the following data:
1. 2-Chloroaniline is the raw material of herbicide green sulfuron, and also an important dye intermediate. It is the color base of ice dyeing dyestuff and can also be used as the diazo component of azo dyestuff to produce acid black, acid blue and organic color precipitation water solid yellow R, permanent red FR, Hansa yellow HR, etc.
2. 2-Chloroaniline used as petroleum solvents. It is used in biological studies to evaluate the mutagenicity and carcinogenicity of Salmonella typhimurium. Used as a Intermediates for dyestuff, pigment and specialty chemicals. 2-Chloroaniline is widely used in polymer, rubber, pharmaceutical and dye industries.

Preparation

The synthesis method of 2-chloroaniline is to reflux 2-nitrochlorobenzene with iron filings, dilute hydrochloric acid and water for 6~8h, distill to get crude product, and then distill to get finished product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2718, 1974 DOI: 10.1021/jo00932a011Tetrahedron Letters, 26, p. 3277, 1985 DOI: 10.1016/S0040-4039(00)98171-1

General Description

Clear amber liquid with an amine odor. Occurs in both alpha and beta forms.

Air & Water Reactions

Sensitive to prolonged exposure to air and darkens on exposure to light. Insoluble in water.

Reactivity Profile

2-Chloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

Hazard

Toxic by ingestion.

Fire Hazard

2-Chloroaniline is combustible.

Safety Profile

Poison by skin contact, ingestion, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also ANILINE DYES.

Purification Methods

Free it from small amounts of the p-isomer by dissolving in one equivalent of H2SO4 and steam distilling. The p-isomer remains behind as the sulfate. [Sidgwick & Rubie J Chem Soc 1013 1921.] An alternative method is to dissolve it in warm 10% HCl (11mL/g of amine) and on cooling, o-chloroaniline hydrochloride separates out. The latter can be recrystallised until the acetyl derivative has a constant melting point (m 90o). (In this way, yields are better than via the recrystallisation of the picrate from EtOH or of the acetyl derivative from pet ether.) [King & Orton J Chem Soc 1377 1911]. [Beilstein 12 III 1281, 12 IV 1115.]

Check Digit Verification of cas no

The CAS Registry Mumber 95-51-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 95-51:
(4*9)+(3*5)+(2*5)+(1*1)=62
62 % 10 = 2
So 95-51-2 is a valid CAS Registry Number.

95-51-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A15758)  2-Chloroaniline, 98+%   

  • 95-51-2

  • 500g

  • 386.0CNY

  • Detail
  • Alfa Aesar

  • (A15758)  2-Chloroaniline, 98+%   

  • 95-51-2

  • 2500g

  • 1667.0CNY

  • Detail
  • Alfa Aesar

  • (A15758)  2-Chloroaniline, 98+%   

  • 95-51-2

  • 10000g

  • 5345.0CNY

  • Detail
  • Sigma-Aldrich

  • (31215)  2-Chloroaniline  PESTANAL®, analytical standard

  • 95-51-2

  • 31215-1G

  • 200.07CNY

  • Detail

95-51-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloroaniline

1.2 Other means of identification

Product number -
Other names Benzenamine, 2-chloro-

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:95-51-2 SDS

95-51-2Synthetic route

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;100%
With [1-butyl-2,3-dimethylimidazolium][tppm] stabilized rhodium nanoarticles at 50℃; under 22502.3 Torr; for 5h; Ionic liquid; Autoclave; chemoselective reaction;100%
With hydrogen at 50℃; under 22502.3 Torr; for 5h; Autoclave; Sealed tube; Ionic liquid; chemoselective reaction;100%
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

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; chemoselective reaction;96%
With tris(dibenzylideneacetone)dipalladium (0); lithium hexamethyldisilazane; CyJohnPhos; 1,1,1-triphenylsilylamine In toluene at 100℃; for 19h;92%
With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 24h;81%
With ammonium hydroxide; copper(ll) sulfate pentahydrate; potassium carbonate; sodium L-ascorbate In dimethyl sulfoxide; glycerol at 100℃; for 8h;50%
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;68 %Chromat.
2-iodochlorobenzene
615-41-8

2-iodochlorobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere;87%
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry;74%
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 45℃; for 48h; Inert atmosphere; Sealed tube; chemoselective reaction;73%
With ammonium hydroxide; copper(ll) sulfate pentahydrate; potassium carbonate; sodium L-ascorbate In dimethyl sulfoxide; glycerol at 80℃; for 2h;54%
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; Sealed tube;38%
2-Chlorobenzeneboronic acid
3900-89-8

2-Chlorobenzeneboronic acid

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With potassium carbonate; ammonium hydroxide In methanol at 60℃; for 16h;91%
With copper(I) oxide; ammonium hydroxide In water for 0.0833333h; Microwave irradiation;
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

aniline
62-53-3

aniline

B

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With platinum on activated charcoal; hydrogen In neat (no solvent) at 90℃; for 1.5h; Temperature; Supercritical conditions; Autoclave; chemoselective reaction;A 5.8%
B 93.4%
With bis(acetylacetonato)palladium(II); phosphorus; hydrogen In N,N-dimethyl-formamide; benzene at 30℃; under 1520.1 Torr; for 5.41667h; Catalytic behavior; Time; Reagent/catalyst; chemoselective reaction;A 9%
B 90.6%
With isopropyl alcohol; sodium hydroxide for 12h; Inert atmosphere; Reflux; chemoselective reaction;A n/a
B 83%
2-chlorophenylhydroxamic acid
17512-69-5

2-chlorophenylhydroxamic acid

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
Stage #1: 2-chlorophenylhydroxamic acid 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;
1-azido-2-chlorobenzene
3296-07-9

1-azido-2-chlorobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With butyltriphenylphosphonium tetrahydroborate In dichloromethane at 20℃; for 0.0833333h;99%
With aluminum oxide; sodium formate; potassium hydroxide In neat (no solvent) for 1.5h; Milling;95%
With iron In water at 20℃; Inert atmosphere;91%
3-(2-chlorophenylamino)-N,N-dimethylpropionamide
1950-43-2

3-(2-chlorophenylamino)-N,N-dimethylpropionamide

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With Imidazole hydrochloride In neat (no solvent) at 150℃; for 12h; Schlenk technique;40%
2-chlorostyrene
2039-87-4

2-chlorostyrene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;65%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

o-Chloronitrosobenzene
932-33-2

o-Chloronitrosobenzene

B

2-Chloroaniline
95-51-2

2-Chloroaniline

C

2,2'-dichloroazobenzene
7334-33-0, 49795-06-4, 63213-02-5

2,2'-dichloroazobenzene

D

1,2-bis(2-chlorophenyl)hydrazine
782-74-1

1,2-bis(2-chlorophenyl)hydrazine

E

2,2'-azoxychlorobenzene
13556-84-8

2,2'-azoxychlorobenzene

Conditions
ConditionsYield
With hydrogen In ethanol at 35℃; under 30003 Torr; for 0.833333h;
With platinum on carbon; hydrogen In ethanol at 35℃; under 30003 Torr; for 0.0833333h; Reagent/catalyst; Time; Pressure; Solvent; Autoclave;
2-(2-Chlorophenoxy)propionamide
34373-88-1

2-(2-Chlorophenoxy)propionamide

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 4h; Green chemistry;52%
1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

2-Chloroaniline
95-51-2

2-Chloroaniline

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;75%
With ethanol; ammonia; copper; copper(l) chloride at 150 - 250℃; Darst.;
With ethanol; copper-compound; ammonia; copper at 150 - 250℃; Darst.;
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;89 %Chromat.
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

o-Chloronitrosobenzene
932-33-2

o-Chloronitrosobenzene

B

nitrobenzene
98-95-3

nitrobenzene

C

aniline
62-53-3

aniline

D

2-Chloroaniline
95-51-2

2-Chloroaniline

E

2,2'-dichloroazobenzene
7334-33-0, 49795-06-4, 63213-02-5

2,2'-dichloroazobenzene

F

1,2-bis(2-chlorophenyl)hydrazine
782-74-1

1,2-bis(2-chlorophenyl)hydrazine

G

2,2'-azoxychlorobenzene
13556-84-8

2,2'-azoxychlorobenzene

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethanol; water at 35℃; under 30003 Torr; for 0.416667h; Reagent/catalyst; Time; Solvent; Autoclave;
aniline
62-53-3

aniline

A

4-chloro-aniline
106-47-8

4-chloro-aniline

B

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With chlorine; natural kaolinitic clay In tetrachloromethane for 2h; Heating;A 20%
B 77%
With iron(III) chloride; N-chloro-succinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In tetrahydrofuran at 40℃; for 24h; Inert atmosphere; regioselective reaction;A 53%
B 30%
With 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate; N-chloro-succinimide; camphor-10-sulfonic acid In 1,4-dioxane at 25℃; for 24h;A 40%
B 20%
N-(2-chlorophenyl)acetamide
533-17-5

N-(2-chlorophenyl)acetamide

A

ethanol
64-17-5

ethanol

B

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 18h; Autoclave;A 98 %Chromat.
B 97 %Chromat.
With C16H25MnN3O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In cyclohexane at 100℃; under 22502.3 Torr; for 16h; Inert atmosphere; Autoclave;A 80 %Chromat.
B 84 %Chromat.
N-(2-chlorophenyl)acetamide
533-17-5

N-(2-chlorophenyl)acetamide

A

2-chloro-N-ethylaniline
13519-74-9

2-chloro-N-ethylaniline

B

2-Chloroaniline
95-51-2

2-Chloroaniline

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%
With C18H32ClIrO2P2; tris(pentafluorophenyl)borate; hydrogen; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In toluene at 120℃; under 38002.6 Torr; for 24h; Overall yield = 82 %; Overall yield = 85 %Chromat.; chemoselective reaction;
(2-chlorophenyl)-carbamic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-1,1-dimethylundecyl ester
956484-64-3

(2-chlorophenyl)-carbamic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-1,1-dimethylundecyl ester

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;92%
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-chlorobenzene
870195-94-1

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-chlorobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With O-Methylhydroxylamin; n-butyllithium In tetrahydrofuran; hexane at -78 - 60℃; for 24h; Inert atmosphere; Cooling with acetone-dry ice; stereospecific reaction;29%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

2-chloro-N-hydroxybenzenamine
10468-16-3

2-chloro-N-hydroxybenzenamine

B

aniline
62-53-3

aniline

C

2-Chloroaniline
95-51-2

2-Chloroaniline

D

2,2'-dichloroazobenzene
7334-33-0, 49795-06-4, 63213-02-5

2,2'-dichloroazobenzene

E

2,2'-azoxychlorobenzene
13556-84-8

2,2'-azoxychlorobenzene

Conditions
ConditionsYield
With bis(acetylacetonato)palladium(II); phosphorus; hydrogen In N,N-dimethyl-formamide; benzene at 30℃; under 1520.1 Torr; for 4.1h; Catalytic behavior; Time; Reagent/catalyst; chemoselective reaction;A n/a
B 14.6%
C 73.1%
D n/a
E n/a
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

2-chloro-N-hydroxybenzenamine
10468-16-3

2-chloro-N-hydroxybenzenamine

B

2-Chloroaniline
95-51-2

2-Chloroaniline

C

2,2'-dichloroazobenzene
7334-33-0, 49795-06-4, 63213-02-5

2,2'-dichloroazobenzene

D

2,2'-azoxychlorobenzene
13556-84-8

2,2'-azoxychlorobenzene

Conditions
ConditionsYield
With bis(acetylacetonato)palladium(II); phosphorus; hydrogen In N,N-dimethyl-formamide; benzene at 30℃; under 1520.1 Torr; for 1.6h; Catalytic behavior; Time; Reagent/catalyst; chemoselective reaction;A n/a
B 64.3%
C n/a
D n/a
ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolium azide; sulfuric acid; acetic acid at 54℃; for 4h; Schmidt Reaction;97%
Stage #1: ortho-chlorobenzoic acid With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; for 0.0633333h; Schmidt Reaction; Flow reactor;
Stage #2: With water In methanol; chloroform at 20℃; Schmidt Reaction; Flow reactor;
79%
With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 1h, reflux; Yield given. Multistep reaction;
2-bromoaniline
615-36-1

2-bromoaniline

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 36h; Inert atmosphere;97%
Multi-step reaction with 5 steps
1: d(4)-methanol
2: zinc; deuteriated sodium hydroxide / water-d2 / 72 h / Reflux
3: pyridine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4: N-chloro-succinimide; oxygen; copper dichloride / acetonitrile / 1 h / 100 °C / 760.05 Torr
5: magnesium / methanol / 20 °C / Sonication
View Scheme
aniline
62-53-3

aniline

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With calcium hypochlorite In water; acetic acid; acetone at 0℃; for 0.0833333h;30%
Multi-step reaction with 3 steps
1: pyridine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: N-chloro-succinimide; oxygen; copper dichloride / acetonitrile / 0.75 h / 100 °C / 760.05 Torr / Inert atmosphere
3: magnesium / methanol / 20 °C / Sonication
View Scheme
Multi-step reaction with 3 steps
1: pyridine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: N-chloro-succinimide; oxygen; copper dichloride / acetonitrile / 24 h / 130 °C / 760.05 Torr
3: magnesium / methanol / 20 °C / Sonication
View Scheme
Multi-step reaction with 3 steps
1: pyridine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: N-chloro-succinimide; oxygen; copper dichloride / acetonitrile / 4 h / 100 °C / 760.05 Torr
3: magnesium / methanol / 20 °C / Sonication
View Scheme
With D-glucose; Escherichia coli flavin reductase; Bacillus megaterium glucose dehydrogenase; Lechevalieria aerocolonigenes tryptophan-7-halogenase; flavin adenine dinucleotide; NADH; sodium chloride In aq. phosphate buffer; isopropyl alcohol pH=7.4; Enzymatic reaction;
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

2-Chloroaniline
95-51-2

2-Chloroaniline

B

2,2'-azoxychlorobenzene
13556-84-8

2,2'-azoxychlorobenzene

Conditions
ConditionsYield
With sodium ethanolate
With water; sodium hydroxide for 5.5h; Electrochemical reaction;
2-[(2-chlorophenylamino)-methylene]-malonic acid diethyl ester
19056-78-1

2-[(2-chlorophenylamino)-methylene]-malonic acid diethyl ester

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 2.15h;90%
2-chloro-4-iodoaniline
42016-93-3

2-chloro-4-iodoaniline

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With formic acid; tributyl-amine; fac-tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 25 - 30℃; for 32h; Inert atmosphere; Irradiation;94%
N-(2-chlorophenyl)pyridine-2-sulfonamide

N-(2-chlorophenyl)pyridine-2-sulfonamide

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With magnesium In methanol at 20℃; Sonication;85%
2,2'-dichloroazobenzene
7334-33-0, 49795-06-4, 63213-02-5

2,2'-dichloroazobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol Heating;92%
With hydrazine hydrate; aluminium In ethanol Heating;92%
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.733333h; pH=2; Inert atmosphere; Irradiation;84%
controlled potential electrolysis; pH=6.5-9.2; -0.25 V;
N-benzyl-2-chloroaniline
98018-66-7

N-benzyl-2-chloroaniline

A

2-Chloroaniline
95-51-2

2-Chloroaniline

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 50℃; under 750.075 Torr; Catalytic behavior;
formic acid
64-18-6

formic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

2-chloro-N-phenylformamide
2596-93-2

2-chloro-N-phenylformamide

B

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With cobalt nanoparticles anchoring on nitrogen doped carbon, pyrolysis at 700 °C In acetonitrile at 110℃; under 750.075 Torr; for 5h; Inert atmosphere; chemoselective reaction;A 20.4%
B n/a
maleic anhydride
108-31-6

maleic anhydride

2-Chloroaniline
95-51-2

2-Chloroaniline

(2-chlorophenyl)maleamic acid
53616-16-3

(2-chlorophenyl)maleamic acid

Conditions
ConditionsYield
In diethyl ether Ring cleavage; Substitution;100%
In benzene at 25℃; for 1h;92%
In diethyl ether at 20℃;88%
acetic anhydride
108-24-7

acetic anhydride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)acetamide
533-17-5

N-(2-chlorophenyl)acetamide

Conditions
ConditionsYield
for 0.5h; Heating;100%
In dichloromethane at 20℃; Inert atmosphere;100%
With cadmium(II) oxide at 80℃; for 0.166667h; Neat (no solvent); Microwave irradiation;98%
N-methylacetonitrilium trifluoromethanesulphonate
76893-86-2

N-methylacetonitrilium trifluoromethanesulphonate

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-Chloro-phenyl)-N'-methyl-acetamidine; compound with trifluoro-methanesulfonic acid

N-(2-Chloro-phenyl)-N'-methyl-acetamidine; compound with trifluoro-methanesulfonic acid

Conditions
ConditionsYield
In benzene at 20℃; for 0.5h;100%
2-Chloroaniline
95-51-2

2-Chloroaniline

3-benzoyloxy-4-methoxybenzoyl chloride
144036-22-6

3-benzoyloxy-4-methoxybenzoyl chloride

3-(benzoyloxy)-N-(2-chlorophenyl)-4-methoxybenzamide
155997-12-9

3-(benzoyloxy)-N-(2-chlorophenyl)-4-methoxybenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 5h; Ambient temperature;100%
2-Chloroaniline
95-51-2

2-Chloroaniline

trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride

trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride

N-(2-chloro)phenyl-5,6-dihydro-2-trifluoromethyl-1,4-dioxin-3-carboxamide

N-(2-chloro)phenyl-5,6-dihydro-2-trifluoromethyl-1,4-dioxin-3-carboxamide

Conditions
ConditionsYield
Stage #1: trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride With pyridine; polystyrene-bound 4-hydroxy-3-nitrobenzophenone In dichloromethane at 20℃; for 24h; Acylation;
Stage #2: o-chloroaniline With triethylamine In acetonitrile for 24h; Acylation; Heating;
100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-Chloroaniline
95-51-2

2-Chloroaniline

2-chloro-N-(4-methoxyphenyl)aniline
53595-99-6

2-chloro-N-(4-methoxyphenyl)aniline

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene for 22h; Heating;100%
With sodium t-butanolate; palladium diacetate; (2,2-dimethylpropane-1,3-diyl)bis(diphenylphosphane) In 1,4-dioxane at 80℃; for 72h; Heating / reflux;73%
With C22H26Cl2NPPd; sodium t-butanolate In toluene at 110℃; for 22h; Inert atmosphere;
tert-Butyl 2,2,2-trichloroacetimidate
98946-18-0

tert-Butyl 2,2,2-trichloroacetimidate

2-Chloroaniline
95-51-2

2-Chloroaniline

tert-butyl-(2-chloro-phenyl)-amine
939-36-6

tert-butyl-(2-chloro-phenyl)-amine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In cyclohexane at 20℃;100%
diethyl (morpholinoethynyl)phosphonate

diethyl (morpholinoethynyl)phosphonate

2-Chloroaniline
95-51-2

2-Chloroaniline

N'-(2-chlorophenyl)-2,2-(diethoxyphosphinoyl)-N,N-oxydiethyleneacetamidine

N'-(2-chlorophenyl)-2,2-(diethoxyphosphinoyl)-N,N-oxydiethyleneacetamidine

Conditions
ConditionsYield
In tetrachloromethane for 1h; Heating;100%
diethyl (piperidin-1-yl)ethynephosphonate

diethyl (piperidin-1-yl)ethynephosphonate

2-Chloroaniline
95-51-2

2-Chloroaniline

N'-(2-chlorophenyl)-2,2-(diethoxyphosphinoyl)-N,N-pentamethyleneacetamidine

N'-(2-chlorophenyl)-2,2-(diethoxyphosphinoyl)-N,N-pentamethyleneacetamidine

Conditions
ConditionsYield
In tetrachloromethane for 1h; Heating;100%
diethyl [(diethylamino)ethynyl]phosphonate
5074-75-9

diethyl [(diethylamino)ethynyl]phosphonate

2-Chloroaniline
95-51-2

2-Chloroaniline

N'-(2-chlorophenyl)-2,2-(diethoxyphosphinoyl)-N,N-diethylacetamidine

N'-(2-chlorophenyl)-2,2-(diethoxyphosphinoyl)-N,N-diethylacetamidine

Conditions
ConditionsYield
In tetrachloromethane for 1h; Heating;100%
p-toluidine
106-49-0

p-toluidine

2-Chloroaniline
95-51-2

2-Chloroaniline

C13H12ClN3
1256450-74-4

C13H12ClN3

Conditions
ConditionsYield
Stage #1: o-chloroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.333333h;
Stage #2: p-toluidine With sodium acetate In water at 0 - 5℃;
100%
ammonium thiocyanate

ammonium thiocyanate

2-Chloroaniline
95-51-2

2-Chloroaniline

o-chlorophenylthiourea
5344-82-1

o-chlorophenylthiourea

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 12h;100%
Stage #1: o-chloroaniline With hydrogenchloride In water Reflux;
Stage #2: ammonium thiocyanate In water Reflux;
propionyl chloride
79-03-8

propionyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)-2-methylacetamide
2760-32-9

N-(2-chlorophenyl)-2-methylacetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)-3-phenylacrylamide
73108-79-9

N-(2-chlorophenyl)-3-phenylacrylamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
2-Chloroaniline
95-51-2

2-Chloroaniline

3-(1-methyl-1H-indol-3-yl)-3-oxopropanenitrile
343778-74-5

3-(1-methyl-1H-indol-3-yl)-3-oxopropanenitrile

(E)-N-(2-chlorophenyl)-2-(1-methyl-1H-indol-3-yl)-2-oxoacetohydrazonoyl cyanide

(E)-N-(2-chlorophenyl)-2-(1-methyl-1H-indol-3-yl)-2-oxoacetohydrazonoyl cyanide

Conditions
ConditionsYield
Stage #1: o-chloroaniline With hydrogenchloride In water; acetonitrile at 0 - 20℃; for 0.5h;
Stage #2: With sodium nitrite In water; acetonitrile at 0℃; for 0.0833333h;
Stage #3: 3-(1-methyl-1H-indol-3-yl)-3-oxopropanenitrile With sodium acetate In ethanol; water; N,N-dimethyl-formamide; acetonitrile
100%
2-Chloroaniline
95-51-2

2-Chloroaniline

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

N-o-chlorophenyl-N', N
96405-47-9

N-o-chlorophenyl-N', N"-dicyclohexylguanidine

Conditions
ConditionsYield
With Sm[N(TMS)2]2(THF)3 at 20℃; for 0.25h; Inert atmosphere;99.3%
Stage #1: o-chloroaniline With C76H124N6Nd2O6Si4 In neat (no solvent) for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #2: dicyclohexyl-carbodiimide In neat (no solvent) at 60℃; for 0.25h; Schlenk technique; Inert atmosphere;
98%
With C114H132N6O6Yb3*2C7H8 at 60℃; for 0.25h; Schlenk technique; Inert atmosphere;98%
benzoyl chloride
98-88-4

benzoyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyI)benzamide
1020-39-9

N-(2-chlorophenyI)benzamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;99%
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h;99%
With N,N-dimethyl-aniline at 100℃; for 0.75h;96%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

2-Chloroaniline
95-51-2

2-Chloroaniline

1-(2-chloro-phenyl)-3-phenyl-thiourea
1932-36-1

1-(2-chloro-phenyl)-3-phenyl-thiourea

Conditions
ConditionsYield
In N,N-dimethyl-formamide Heating;99%
for 0.00833333h; Microwave irradiation; Neat (no solvent);98%
With [κ2-{(Ph2P-(=Se))}2NCH2(C5H4N)ZnCl2] In toluene at 25℃; Schlenk technique; Inert atmosphere;84%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N‐(2‐chlorophenyl)methanesulfonamide
7022-20-0

N‐(2‐chlorophenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane99%
In water at 20℃; for 0.583333h;85%
With pyridine In dichloromethane Ambient temperature;82%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)chloroacetamide
3289-76-7

N-(2-chlorophenyl)chloroacetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;99%
With dmap In dichloromethane for 2h; Inert atmosphere;99%
With acetic acid at 20℃; for 1.5h; Cooling with ice;98%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)-N-(2-nitrophenyl)amine
74002-26-9

N-(2-chlorophenyl)-N-(2-nitrophenyl)amine

Conditions
ConditionsYield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃;99%
With sodium acetate; nitrobenzene
With copper; potassium carbonate at 160℃;
2-Chloroaniline
95-51-2

2-Chloroaniline

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

2-[(2-chlorophenylamino)-methylene]-malonic acid diethyl ester
19056-78-1

2-[(2-chlorophenylamino)-methylene]-malonic acid diethyl ester

Conditions
ConditionsYield
In ethanol at 28℃; for 5h;99%
In neat (no solvent) at 120℃; for 0.75h;98%
In toluene for 1h; Heating;85%
2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)thiophene-2-carboxamide
136340-94-8

N-(2-chlorophenyl)thiophene-2-carboxamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;99%
In toluene
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-Chloroaniline
95-51-2

2-Chloroaniline

N-(2-chlorophenyl)-2,2,2-trimethylacetamide
62662-74-2

N-(2-chlorophenyl)-2,2,2-trimethylacetamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;99%
With sodium hydroxide In tert-butyl methyl ether; water at 0 - 20℃; for 6h;98.2%
With sodium hydroxide In tert-butyl methyl ether; water at 20℃;97%
2-Chloroaniline
95-51-2

2-Chloroaniline

acryloyl chloride
814-68-6

acryloyl chloride

N-(2-chlorophenyl)acrylamide
17090-09-4

N-(2-chlorophenyl)acrylamide

Conditions
ConditionsYield
With potassium carbonate In water; acetone at 20℃;99%
Stage #1: o-chloroaniline With potassium carbonate In water; acetone at 0℃; for 0.0833333h;
Stage #2: acryloyl chloride In water; acetone at 0 - 20℃;
87%
With pyridine Yield given;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;
2-Chloroaniline
95-51-2

2-Chloroaniline

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

N-o-chlorophenyl-N', N

N-o-chlorophenyl-N', N"-diisopropylguanidine

Conditions
ConditionsYield
With Sm[N(TMS)2]2(THF)3 at 20℃; for 0.0333333h; Inert atmosphere;99%
With (1,4-bis(4-imino-2-pentanone)(-1H))[Yb(2,6-tBu2-4-MeC6H2O)2(THF)]2 In neat (no solvent) at 60℃; for 0.5h; Schlenk technique; Inert atmosphere;99%
Stage #1: o-chloroaniline With C76H124N6Nd2O6Si4 In neat (no solvent) for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #2: diisopropyl-carbodiimide In neat (no solvent) at 60℃; for 0.25h; Schlenk technique; Inert atmosphere;
98%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-Chloroaniline
95-51-2

2-Chloroaniline

o-chlorobenzenecarbamic acid tert-butyl ester
35426-69-8

o-chlorobenzenecarbamic acid tert-butyl ester

Conditions
ConditionsYield
In neat (no solvent) at 80℃; for 0.166667h; Green chemistry; chemoselective reaction;99%
aminosulfonic acid In water at 25 - 28℃; for 0.25h; ultrasound;90%
With iron(III) chloride In dichloromethane at 20℃; for 24h;20%

95-51-2Relevant articles and documents

Coupling of ortho-chloronitrobenzene hydrogenation with 1,4-butanediol dehydrogenation over Cu[sbnd]MgO catalysts: A hydrogen free process

Reddy, Kannapu Hari Prasad,Suh, Young-Woong,Anand, Narani,Raju, Burri David,Rao, Kamaraju Seetha Rama

, p. 21 - 25 (2017)

Aiming at an efficient method for the hydrogenation of o-chloronitrobenzene to o-chloroaniline under hydrogen free environment, the reaction was coupled with 1,4-butanediol dehydrogenation over Cu[sbnd]MgO catalysts containing various amounts of copper lo

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter

supporting information, p. 133 - 146 (2021/11/04)

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water

Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao

, p. 299 - 306 (2021/05/10)

An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]

In situcreation of multi-metallic species inside porous silicate materials with tunable catalytic properties

Liu, Yang-Yang,Wu, Chuan-De,Zhan, Guo-Peng

supporting information, p. 6185 - 6188 (2021/06/30)

Porous metal silicate (PMS) material PMS-11, consisting of uniformly distributed multi-metallic species inside the pores, is synthesized by using a discrete multi-metal coordination complex as the template, demonstrating high catalytic activity and selectivity in hydrogenation of halogenated nitrobenzenes by synergistically activating different reactant moleculesviaNi and Co transition metal centers, while GdIIILewis acid sites play a role in tuning the catalytic properties.

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