87-63-8

Basic information

• Product Name: 2-Chloro-6-methylaniline
• Synonyms: 6COT;6-CHLORO-2-METHYLANILINE;6-CHLORO-2-TOLUIDINE;6-CHLORO-O-TOLUIDINE;3-CHLORO-2-AMINOTOLUENE;1-AMINO-2-CHLORO-6-METHYLBENZENE;2-METHYL-6-CHLORO ANILINE;2-AMINO-3-CHLOROTOLUENE
• CAS NO: 87-63-8
• Molecular Formula: C₇H₈ClN
• Molecular Weight: 141.6
• EINECS: 201-759-2
• Product Categories: benzene derivative;Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 87-63-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 10-12 °C(lit.)
• Boiling Point: 215 °C(lit.)
• Flash Point: 210 °F
• Appearance: clear yellow to red-brown liquid
• Density: 1.152 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.151mmHg at 25°C
• Refractive Index: n20/D 1.576(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 2.51±0.10(Predicted)
• Water Solubility: Immiscible
• BRN: 774624
• CAS DataBase Reference: 2-Chloro-6-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-6-methylaniline(87-63-8)
• EPA Substance Registry System: 2-Chloro-6-methylaniline(87-63-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: UN 3429 6.1/PG 3
• WGK Germany: 3
• RTECS: XU5100000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 87-63-8(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 87-63-8 differently. You can refer to the following data:
1. clear yellow to red-brown liquid
2. The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.

Uses

2-Chloro-6-methylaniline is a substituted aniline used in the preparation of various pharmaceutical compounds. 2-Chloro-6-methylaniline showed inhibition of the polymerization of vinyl acetate.

Potential Exposure

Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill birds. It is marketed as pelleted bait for control of bird populations.

Shipping

UN2239 Chlorotoluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3429 Chlorotoluidines, liquid, Hazard Class: 6.1; Labels: 6.1- Poisonous materials

Incompatibilities

Incompatible with oxidizers, strong acids; chloroformates, and acid anhydrides, isocyanates, aldehydes forming fire and explosive hazards.

InChI:InChI=1/C7H8ClN/c1-5-3-2-4-6(8)7(5)9/h2-4H,9H2,1H3

Synthetic route

3-chloro-5-methyl-4-nitroaniline → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
Stage #1: 3-chloro-5-methyl-4-nitroaniline With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hypophosphorous acid In water at 0℃; for 3h; Stage #3: With iron In water at 90℃; for 4h; Reagent/catalyst;	82.5%

2-bromo-1-chloro-3-methylbenzene (69190-56-3) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h;	82%

o-toluidine (95-53-4) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With N-chloro-succinimide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2S)-2-(mesitylselanyl)-2,3-dihydro-1H-inden-1-yl)thiourea In chloroform-d1 at 0℃; for 12h; regioselective reaction;	65%

N-(2-chloro-6-methylphenyl)acetamide (21352-09-0) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With hydrogenchloride In water at 50 - 55℃; for 7h; Time;	61.7%

C9H10ClNO4S → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With hydrogenchloride In sulfolane; water at 120℃; for 26h;	60%

1-azido-2-methyl-benzene (31656-92-5) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With hydrogenchloride

6-amino-5-chloro-toluene-3-sulfonic acid (6387-14-0) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With sulfuric acid at 165℃;
With sulfuric acid at 150 - 160℃;

N-(o-tolyl)hydroxylamine (611-22-3) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With hydrogenchloride

N-(2-chloro-6-methylphenyl)pivalamide (150545-04-3) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With hydrogen bromide for 4.5h; Heating; Yield given;

N-(o-tolyl)hydroxylamine (611-22-3) → 4-amino-3-methylphenol (2835-99-6) + o-toluidine (95-53-4) + 2-chloro-6-methylaniline (87-63-8) + 4-chloro-2-methylbenzeneamine (95-69-2)

Conditions	Yield
With perchloric acid; sodium perchlorate; sodium chloride In water; acetonitrile at 25℃; Rate constant;

hydrogenchloride (7647-01-0) + N-(o-tolyl)hydroxylamine (611-22-3) → N,N'-Di-o-tolyl-diazene N-oxide (956-31-0, 51284-68-5, 116723-89-8) + 2-chloro-6-methylaniline (87-63-8) + 5-chloro-2-methyl-benzenamine (95-79-4) + 4-chloro-2-methylbenzeneamine (95-69-2)

hydrogenchloride (7647-01-0) + 1-azido-2-methyl-benzene (31656-92-5) → 2-chloro-6-methylaniline (87-63-8) + 4-chloro-2-methylbenzeneamine (95-69-2)

Conditions	Yield
Aufbewahren an einem kuehlen dunklen Ort;

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + 1-methyl-2-nitrobenzene (88-72-2) + tin dichloride → o-toluidine (95-53-4) + 2-chloro-6-methylaniline (87-63-8) + 4-chloro-2-methylbenzeneamine (95-69-2)

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + 1-methyl-2-nitrobenzene (88-72-2) + tin → o-toluidine (95-53-4) + 2-chloro-6-methylaniline (87-63-8) + 4-chloro-2-methylbenzeneamine (95-69-2)

sulfuric acid (7664-93-9) + 6-amino-5-chloro-toluene-3-sulfonic acid (6387-14-0) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
at 150 - 160℃;

N-(2-chlorophenyl)-2,2,2-trimethylacetamide (62662-74-2) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72.1 percent / TMEDA, n-BuLi / various solvent(s); hexane / 1.) -12 to -20 deg C, 50min, 2.) -20 deg C, 2 h 2: conc. aq. HBr / 4.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: TMEDA, BuLi / various solvent(s); hexane / 1.) 65min, 2.) 1 h 2: conc. aq. HBr / 4.5 h / Heating View Scheme

2-Chloroaniline (95-51-2) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 25 percent aq. NaOH / various solvent(s) 2: 72.1 percent / TMEDA, n-BuLi / various solvent(s); hexane / 1.) -12 to -20 deg C, 50min, 2.) -20 deg C, 2 h 3: conc. aq. HBr / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 25 percent aq. NaOH / various solvent(s) 2: TMEDA, BuLi / various solvent(s); hexane / 1.) 65min, 2.) 1 h 3: conc. aq. HBr / 4.5 h / Heating View Scheme

2-aminotoluene-5-sulfonic acid (98-33-9) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 2 h / 50 °C 2: acetic acid; hydrogenchloride; dihydrogen peroxide / water / 40 - 50 °C 3: hydrogenchloride / water; sulfolane / 26 h / 120 °C View Scheme

3-chloro-2-nitrotoluene (5367-26-0) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
With hydrogen In ethanol at 80℃; under 15001.5 Torr; for 2.5h; Catalytic behavior; chemoselective reaction;

o-toluidine (95-53-4) → 2-chloro-6-methylaniline (87-63-8) + 4-chloro-2-methylbenzeneamine (95-69-2)

Conditions	Yield
With N-chloro-succinimide In chloroform-d1 at 0℃; for 12h;

2-Methyl-6-nitroaniline (570-24-1) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: chloroform / 12 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 40 °C / 1800.18 - 3000.3 Torr / Inert atmosphere; Autoclave 3.1: sodium nitrite; hydrogenchloride / water / 0.5 h / -3 - 3 °C 3.2: 5.5 h / -3 - 3 °C 4.1: hydrogenchloride / water / 7 h / 50 - 55 °C View Scheme

N-(2-methyl-6-nitrophenyl)acetamide (59907-22-1) → 2-chloro-6-methylaniline (87-63-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 40 °C / 1800.18 - 3000.3 Torr / Inert atmosphere; Autoclave 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / -3 - 3 °C 2.2: 5.5 h / -3 - 3 °C 3.1: hydrogenchloride / water / 7 h / 50 - 55 °C View Scheme

2-chloro-6-methylaniline (87-63-8) → 4-bromo-2-chloro-6-methylphenylamine hydrobromide salt (877149-11-6)

Conditions	Yield
With bromine; acetic acid In methanol at 0℃;	99%

C21H22O4 (1300605-91-7) + 2-chloro-6-methylaniline (87-63-8) → C28H28ClNO3 (1309360-29-9)

Conditions	Yield
With hafnium tetrakis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.5h; Friedel Crafts alkylation;	99%
In dichloromethane for 72h; Inert atmosphere; Reflux;	51%

(E)-1,3-diphenyl-2-propen-1-ol (62668-02-4) + 2-chloro-6-methylaniline (87-63-8) → (E)-2-chloro-4-(1,3-diphenylallyl)-6-methylaniline

Conditions	Yield
With 1,3-bis(carboxymethyl)imidazolium iodide In neat (no solvent) at 80℃; for 6h; regioselective reaction;	99%

chloroacetyl chloride (79-04-9) + 2-chloro-6-methylaniline (87-63-8) → 2-chloro-N-(2-chloro-6-methylphenyl)acetamide (6307-67-1)

Conditions	Yield
Stage #1: 2-chloro-6-methylaniline With pyridine In dichloromethane at -10℃; for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at -10 - 20℃; for 2h;	98%
at 0 - 25℃; for 2.5h;	87.6%
With sodium acetate In water; acetone at 20 - 50℃; for 16h;	71%

2-chloro-6-methylaniline (87-63-8) + 2,6-dichloroimidazo[1,5-a]pyrido[3,2-e]pyrazine (240815-53-6) → 2-Chloro-N-(2-chloro-6-methylphenyl)imidazo[1,5-a]pyrido[3,2-e]pyrazin-6-amine (240813-70-1)

Conditions	Yield
Stage #1: 2-chloro-6-methylaniline With sodium hexamethyldisilazane In tetrahydrofuran for 0.5h; Heating; Stage #2: 2,6-dichloroimidazo[1,5-a]pyrido[3,2-e]pyrazine In tetrahydrofuran for 0.5h; Heating;	98%

3-oxo-propionic acid ethyl ester (34780-29-5) + 2-chloro-6-methylaniline (87-63-8) → C10H10ClNO2 (1044209-25-7)

Conditions	Yield
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 10h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 1h; Solvent; Reflux;	97.3%

acetylacetone (123-54-6) + 2-chloro-6-methylaniline (87-63-8) → (Z)-4-(2-chloro-6-methylphenylamino)pent-3-en-2-one (1590398-72-3)

Conditions	Yield
With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.1h; Green chemistry;	97%
With zinc trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.2h; stereoselective reaction;	96%

2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxylic acid (1245157-80-5) + 2-chloro-6-methylaniline (87-63-8) → N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide (1245157-85-0)

Conditions	Yield
Stage #1: 2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxylic acid With thionyl chloride; sodium hydroxide In water; 1,2-dichloro-ethane at 55 - 60℃; for 4h; Stage #2: 2-chloro-6-methylaniline With triethylamine In 1,2-dichloro-ethane at 40 - 45℃; for 1h; Solvent; Reagent/catalyst; Temperature;	95.6%
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	71.7%
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	71.7%

aqueous trimethylamine + 2-methyl-4,6-dichloroaniline (30273-00-8) + o-toluidine (95-53-4) + 2-chloro-6-methylaniline (87-63-8) + 4-chloro-2-methylbenzeneamine (95-69-2) → trimethylammonium 4-chloro-2-methylphenyl dithiocarbamate

Conditions	Yield
With carbon disulfide In acetone	95.5%

2-chloro-6-methylaniline (87-63-8) + 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid (302964-02-9) → [5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester (302964-06-3)

Conditions	Yield
With Dichlorophenylphosphine; N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 20℃; for 14h;	95%
Stage #1: 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Stage #2: 2-chloro-6-methylaniline With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 24h;	48%

ethyl acetoacetate (141-97-9) + 2-chloro-6-methylaniline (87-63-8) → (Z)-ethyl 3-(2-chloro-6-methylphenylamino)but-2-enoate (1590398-71-2)

Conditions	Yield
With zinc trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.25h; stereoselective reaction;	94%
With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.133333h; Green chemistry;	93%

2-chloro-6-methylaniline (87-63-8) → 2-chloro-6-methylbenzenediazonium tetrafluoroborate (85070-46-8)

Conditions	Yield
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃;	94%

3-oxo-propionic acid ethyl ester (34780-29-5) + thiourea (17356-08-0) + 2-chloro-6-methylaniline (87-63-8) → 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (302964-24-5)

Conditions	Yield
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 0.75h; Reflux; Stage #3: thiourea Solvent; Further stages;	92.31%
Stage #1: 3-oxo-propionic acid ethyl ester; 2-chloro-6-methylaniline With sodium methylate In tetrahydrofuran for 0.75h; Reflux; Stage #2: With copper(ll) bromide In tetrahydrofuran for 1h; Reflux; Stage #3: thiourea In tetrahydrofuran at 20 - 25℃; for 0.25h; Reagent/catalyst;	90.94%

3-oxo-propionic acid ethyl ester (34780-29-5) + 2-chloro-6-methylaniline (87-63-8) → C10H9BrClNO2

Conditions	Yield
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 1h; Reflux; Stage #3: With copper(ll) bromide In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Reflux;	91.6%
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 1h; Reflux; Stage #3: With copper(I) bromide In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Reflux;	91.6%
Stage #1: 3-oxo-propionic acid ethyl ester; 2-chloro-6-methylaniline With sodium methylate In tetrahydrofuran for 1h; Reflux; Stage #2: With copper(I) bromide In tetrahydrofuran for 2h; Solvent; Reflux;	91.6%

2-methylphenyl bromide (95-46-5) + 2-chloro-6-methylaniline (87-63-8) → 1,8-dimethyl-9H-carbazole (6558-83-4)

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 160℃; for 3h; microwave irradiation;	91.5%

4-oxo-5-{[(trifluoromethyl)sulfonyl]oxy}-4H-pyran-2-carboxylic acid (1191276-41-1) + 2-chloro-6-methylaniline (87-63-8) → 6-(2-chloro-6-methylphenylcarbamoyl)-4oxo-4H-pyran-3-yl trifluoromethanesulfonate (1191276-46-6)

Conditions	Yield
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0℃; Inert atmosphere;	90%

(Z)-but-2-ene-1,4-diyl dimethanesulfonate (1953-56-6, 70886-56-5, 2303-47-1) + 2-chloro-6-methylaniline (87-63-8) → 1-(2-Chloro-6-methyl-phenyl)-2,5-dihydro-1H-pyrrole (127839-96-7)

Conditions	Yield
In dichloromethane Ambient temperature;	89%

para-bromotoluene (106-38-7) + 2-chloro-6-methylaniline (87-63-8) → N-(2'-chloro-6'-methylphenyl)-4-methylaniline (332903-62-5)

Conditions	Yield
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 60 - 90℃; Buchwald-Hartwig coupling;	89%

carbon disulfide (75-15-0) + allyl bromide (106-95-6) + 2-chloro-6-methylaniline (87-63-8) → S-allyl-N-(2-chloro-6-methylphenyl)dithiocarbamate (1273422-92-6)

Conditions	Yield
With tin(II) chloride dihdyrate at 20℃; neat (no solvent);	89%

2-bromoanisole (578-57-4) + 2-chloro-6-methylaniline (87-63-8) → 1-Methoxy-8-methyl-9H-carbazole (73910-81-3)

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 160℃; for 3h; microwave irradiation;	88%

2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carboxylic acid (956388-76-4) + 2-chloro-6-methylaniline (87-63-8) → 2-chloro-N-(2-chloro-6-methylphenyl)-4-morpholinothieno[3,2-d]pyrimidine-6-carboxamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 80℃; for 0.5h;	86.8%

2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (885618-31-5) + 2-chloro-6-methylaniline (87-63-8) → 1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-(2-chloro-6-methylphenyl)methanimine

Conditions	Yield
With acetic acid In ethanol at 80℃; for 3h;	86.5%

benzoyl chloride (98-88-4) + 2-chloro-6-methylaniline (87-63-8) → N-(2-chloro-6-methylphenyl)benzamide (10286-86-9)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;	86%
With triethylamine In toluene Heating;	70%
With triethylamine In dichloromethane at 20℃;	52%
Schotten-Baumann reaction;
With triethylamine

Benzoyl isothiocyanate (532-55-8) + 2-chloro-6-methylaniline (87-63-8) → 1-Benzoyl-3-(2-chloro-6-methyl-phenyl)-thiourea (82635-64-1)

Conditions	Yield
In benzene	86%
In acetone at 20℃; for 2h;

Upstream product

• 31656-92-5 1-azido-2-methyl-benzene 
• 6387-14-0 6-amino-5-chloro-toluene-3-sulfonic acid 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 150545-04-3 N-(2-chloro-6-methylphenyl)pivalamide 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 88-72-2 1-methyl-2-nitrobenzene 
• 7664-93-9 sulfuric acid 
• 62662-74-2 N-(2-chlorophenyl)-2,2,2-trimethylacetamide 
• 95-51-2 o-chloroaniline 
• 98-33-9 2-aminotoluene-5-sulfonic acid 
• 5367-26-0 3-chloro-2-nitrotoluene 
• 21352-09-0 N-(6-chloro-2-methylphenyl)acetamide 
• 59907-22-1 N-(2-methyl-6-nitrophenyl)acetamide 

Downstream Products

• 102433-33-0 N-(2-chloro-ethyl)-N'-(2-chloro-6-methyl-phenyl)-urea 
• 19241-34-0 2-chloro-6-methylphenyl isothiocyanate 
• 118923-96-9 2-chloro-6-methylphenyl isocyanide 
• 3785-21-5 2-(butylamino)-N-(2-chloro-6-methylphenyl)acetamide 
• 99859-66-2 methacrylic acid-(2-chloro-6-methyl-anilide) 
• 21352-09-0 N-(6-chloro-2-methylphenyl)acetamide 
• 5367-26-0 3-chloro-2-nitrotoluene 
• 72992-34-8 N-(β-hydroxypropyl)-2-chloro-6-methyl-aniline 
• 19348-45-9 N-(2-chloro-6-methyl-phenyl)-phthalimide 
• 49872-70-0 1-(2-methyl-6-chlorophenyl)biguanide 
• 6307-67-1 2-chloro-N-(2-chloro-6-methylphenyl)acetamide 
• 67624-96-8 N,N-diethyl-DL-alanine-(2-chloro-6-methyl-anilide) 
• 100248-72-4 N,N-dimethyl-β-alanine-(2-chloro-6-methyl-anilide) 
• 124678-41-7 N-(2-chloro-6-methylphenyl)-2,5-dimethylpyrrole 

Relevant articles and documents

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The hydrogenation of nitrobenzene to aniline is an important process in the industry of fine chemicals, but developing inexpensive catalysts with expected activity and selectivity still remains a challenge. By using density functional theory calculations, we demonstrated that the isolated Fe atom not only can weaken the adsorption of reactants and reaction intermediates as compared to Fe nanoparticles, but also remarkably decrease the reaction barrier for the hydrogenation of nitrobenzene to aniline. Thus, the Fe single-atom (Fe SA) catalyst is considered as an ideal catalyst for this reaction. This theoretical prediction has been subsequently confirmed by experimental results obtained for the Fe SAs loaded on N-doped hollow carbon spheres (Fe SAs/NHCSs) which achieved a conversion of 99% with a selectivity of 99% for the hydrogenation of nitrobenzene. The results significantly outperformed the Fe nanoparticles for this reaction. This work provides theoretical insight for the rational design of new catalytic systems with excellent catalytic properties.

Highly selective hydrogenation of halogenated nitroarenes over Ru/CN nanocomposites by: In situ pyrolysis

A highly chemoselective and recyclable ruthenium catalyst for the hydrogenation of halogenated nitroarenes has been prepared via the simple in situ calcination of a mixture of melamine, glucose and ruthenium trichloride. Superfine Ru particles (2.3 ± 0.3 nm) were obtained and highly dispersed in the nitrogen-doped carbon matrix. The Ru/CN catalyst smoothly transforms a variety of halogenated nitroarenes to the corresponding haloanilines with high intrinsic activity (e.g. TOF = 1333 h-1 for p-chloronitrobenzene) and selectivity of more than 99.6percent. Furthermore, through an analysis of the products in the reaction process, it was concluded that there are two parallel reaction pathways (a direct pathway and an indirect pathway) for the hydrogenation of aromatic nitro compounds over the Ru/CN catalyst, and the direct pathway was proved to be dominant in catalyzing the intermediates. This journal is