608-31-1

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichloroaniline is used as a key intermediate in the synthesis of various antibacterial agents, such as lomefloxacin, which is a fluoroquinolone antibiotic used to treat a wide range of bacterial infections. Its presence in the compound contributes to its antimicrobial properties, making it an essential component in the development of effective treatments for bacterial infections.
Additionally, 2,6-dichloroaniline is used in the synthesis of uric acid-lowering agents, such as febuxostat, which is a xanthine oxidase inhibitor. This medication is used to treat hyperuricemia, a condition characterized by elevated levels of uric acid in the blood, often associated with gout and kidney stones.
Furthermore, 2,6-dichloroaniline is also utilized in the production of clonidine, an imidazoline receptor agonist with central and peripheral effects. Clonidine is primarily used to treat high blood pressure and attention deficit hyperactivity disorder (ADHD), as well as to manage symptoms of opioid withdrawal.

InChI:InChI=1/C6H5Cl2N/c7-4-2-1-3-5(8)6(4)9/h1-3H,9H2

Synthetic route

4-amino-3,5-dichloro-benzenesulfonamide (22134-75-4) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With sulfuric acid at 180℃;	96.2%

2,6-dichloronitrobenzene (601-88-7) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With ammonium formate at 20℃; for 0.75h; Reduction;	91%
With hydrogenchloride; tin
With hydrogen; silver; silica gel In ethanol at 140℃; under 15001.2 Torr; for 3h;	100 % Chromat.

4-bromo-2,6-dichloroaniline (697-88-1) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 72h;	91%
With hydrogen bromide; acetic acid; aniline for 24h; Heating;	86%
With hydrogen bromide; acetic acid; aniline Reflux;	80%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With copper(I) oxide In quinoline at 220℃; for 6h; Autoclave;	85%
In water	80%

N-(2,6-dichlorophenyl)benzamide (10286-88-1) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With sulfuric acid for 3h; Heating;	68%

2,6-Dichlorophenol (87-65-0) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With potassium carbonate; potassium iodide; Chloroacetamide In N,N-dimethyl-formamide at 90 - 150℃; for 4h; Reagent/catalyst; Smiles Aromatic Rearrangement;	65%

2-Chloroaniline (95-51-2) → 2,4-Dichloroaniline (554-00-7) + 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With chlorine In chlorobenzene at 15℃; for 6h; Solvent; Reagent/catalyst; Temperature;	A 60% B 35%

aniline (62-53-3) → 2,4-Dichloroaniline (554-00-7) + 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With hydrogenchloride; potassium permanganate In acetonitrile at 60℃;	A 19% B 29%

sodium sulfanilate (515-74-2) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With carbon dioxide; water; chlorine Behandeln des Reaktionsprodukts mit 98 prozentiger Schwefelsaeure und Dampf bei 180grad;

tert-butyl (2,6-dichlorophenyl)carbamate (56700-68-6) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With hydrogenchloride In ethanol

N,N-diacetyl-2,6-dichloroaniline (91573-20-5) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With hydrogenchloride In acetic acid for 1h; Heating;

5-(2,6-dichlorophenyl)-1-phenyl-1H-1,2,5-triazapentadiene (90454-74-3) → 5-chloro-quinoxaline (62163-09-1) + 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
at 600℃; under 0.01 Torr; for 0.416667h; Title compound not separated from byproducts;	A 13 % Chromat. B 37 % Chromat.

aniline (62-53-3) → 2,4-Dichloroaniline (554-00-7) + 4-chloro-aniline (106-47-8) + 2-Chloroaniline (95-51-2) + 2,6-Dichloroaniline (608-31-1) + 2,4,6-trichloroaniline (634-93-5)

Conditions	Yield
With hydrogenchloride; calcium hypochlorite; ammonia In water pH=1.3; other concentration of chlorinating agent; other pH;

2,4,6-trichloroaniline (634-93-5) → 2,4-Dichloroaniline (554-00-7) + 4-chloro-aniline (106-47-8) + aniline (62-53-3) + 2-Chloroaniline (95-51-2) + 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In acetonitrile at 80℃; for 2h; Product distribution; other haloanilines; other H-donors; var. solvents, temperatures, reaction times;

2-chloro-N-hydroxybenzenamine (10468-16-3) → 4-amino-3-chlorophenol (17609-80-2) + 2,4-Dichloroaniline (554-00-7) + 2,6-Dichloroaniline (608-31-1)

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

2,2,6,6-tetrachlorohexaneimine → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 5h; Dehydrochlorination;	2.32 g

2.6-dichloro-aniline-sulfonic acid-(4)-amide → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With sulfuric acid Darstellung; Destillation mit Dampf;

2,6-dichlorobenzamide (2008-58-4) + bromine (7726-95-6) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Behandeln mit Kalilauge;

hydrogenchloride (7647-01-0) + 2,6-dichloronitrobenzene (601-88-7) + tin → 2,6-Dichloroaniline (608-31-1)

4-bromo-aniline (106-40-1) + 9-methyl-tridecanoyl chloride → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaClO3; HCl 2: 86 percent / HBr; AcOH; aniline / 24 h / Heating View Scheme

2,2,6,6-tetrachlorocyclohexanone (3776-30-5) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5.74 g / NH3; TiCl4 / toluene / 2 h / -1 - 10 °C 2: 2.32 g / (CH3CH2)3N / dimethylformamide / 5 h / 100 °C View Scheme

sulfanilamide (63-74-1) → 2,6-Dichloroaniline (608-31-1)

2,4,6-trichloro-diacetanilide (62715-81-5) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / sodium formate / 5percent Pd/C / acetonitrile / 24 h / Heating 2: conc. HCl / acetic acid / 1 h / Heating View Scheme

aniline (62-53-3) + ethane-α.β-bis-sulfonic acid chloride → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: HCl(gas), Cl2 / CCl4; ethanol / ice-bath 2: 96 percent / CH3SO3H / Heating 3: 65 percent / sodium formate / 5percent Pd/C / acetonitrile / 24 h / Heating 4: conc. HCl / acetic acid / 1 h / Heating View Scheme

2,4,6-trichloroaniline (634-93-5) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / CH3SO3H / Heating 2: 65 percent / sodium formate / 5percent Pd/C / acetonitrile / 24 h / Heating 3: conc. HCl / acetic acid / 1 h / Heating View Scheme

sulfanilamide (63-74-1) + copper → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / conc.HCl, perhydrol / H2O 2: 96.2 percent / 70 percent H2SO4 / 180 °C View Scheme

2-chloro-N-hydroxybenzenamine (10468-16-3) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaHCO3 / diethyl ether; H2O / 1 h / T < 5 deg C; or in benzene 2: 77 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 3: 68 percent / 70percent H2SO4 / 3 h / Heating View Scheme

N-(o-chlorophenyl)benzohydroxamic acid (82344-31-8) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 2: 68 percent / 70percent H2SO4 / 3 h / Heating View Scheme

2,4-dichloro-3-nitroaniline (129825-24-7) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: tin; hydrochloric acid View Scheme

trimethylacetic formic anhydride (10535-67-8) + 2,6-Dichloroaniline (608-31-1) → N-(2,6-dichlorophenyl)-formamide (10113-35-6)

Conditions	Yield
In chloroform at 25℃;	100%

acetic acid (64-19-7) + acetyl chloride (75-36-5) + 2,6-Dichloroaniline (608-31-1) → 2,6-dichloroacetanilide (17700-54-8)

Conditions	Yield
at 90℃; for 0.333333h;	100%

C17H17ClN4O3 + 2,6-Dichloroaniline (608-31-1) → 2-[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenoxymethyl]-oxazole-4-carboxylic acid (2,6-dichloro-phenyl)-amide

Conditions	Yield
In dichlorometane at 45℃;	99.9%

Benzoyl isothiocyanate (532-55-8) + 2,6-Dichloroaniline (608-31-1) → N-(2,6-dichlorophenyl)-N'-benzoyl thiourea (41542-10-3)

Conditions	Yield
In acetone for 0.5h; Heating;	99%
In tetrahydrofuran at 60 - 65℃; for 0.166667h; Microwave irradiation;	89%
In benzene	82%
In ethyl acetate for 2h; Reflux;
In acetone at 60℃; for 0.5h;

potassium isopropylxanthate (140-92-1) + 2,6-Dichloroaniline (608-31-1) → 4-chloro-2-mercaptobenzothiazole (1849-65-6)

Conditions	Yield
In N,N-dimethyl acetamide at 150℃; for 0.0833333h; Solvent; Temperature; Microwave irradiation;	99%

acetic anhydride (108-24-7) + 2,6-Dichloroaniline (608-31-1) → 1-(4-amino-3,5-dichlorophenyl)-1-ethanone (37148-48-4)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃;	98.9%

phenylacetyl chloride (103-80-0) + 2,6-Dichloroaniline (608-31-1) → N-(2,6-dichlorophenyl)phenylacetamide

Conditions	Yield
With pyridine; calcium chloride for 4h; Reagent/catalyst; Reflux; Cooling with ice;	98.3%
With pyridine for 4h; Reagent/catalyst; Cooling with ice; Reflux;	98.3%

2-Iodo-N,N-dimethylbenzamide (54616-46-5) + 2,6-Dichloroaniline (608-31-1) → 2-(2,6-dichloro-phenylamino)-N,N-dimethyl-benzamide (51225-04-8)

Conditions	Yield
With copper(l) iodide; copper; potassium carbonate In xylene Condensation; Heating;	98%

2,6-Dichloroaniline (608-31-1) + 4-methyl-3-nitrobenzoyl chloride (10397-30-5) → N-(2,6-dichlorophenyl)-4-methyl-3-nitrobenzamide

Conditions	Yield
at 130℃; for 0.25h; Inert atmosphere; Microwave irradiation;	98%

Ethoxycarbonyl isothiocyanate (16182-04-0) + 2,6-Dichloroaniline (608-31-1) → ethyl 3-(2,6-dichlorophenyl)thioureidocarboxylate (23822-56-2)

Conditions	Yield
In acetone at 20 - 40℃; for 12.33h;	98%

acetic anhydride (108-24-7) + 2,6-Dichloroaniline (608-31-1) → 2,6-dichloroacetanilide (17700-54-8)

Conditions	Yield
With supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate on Silica Gel at 20℃; for 1.2h; Green chemistry;	97%
With acetic acid; zinc for 0.5h; Ambient temperature;	50%
With dmap In dichloromethane at 0 - 40℃;	47.64%
With pyridine for 2h; Heating;
With sulfuric acid

2,6-Dichloroaniline (608-31-1) → 1-azido-2,6-dichlorobenzene (57341-09-0)

Conditions	Yield
Stage #1: 2,6-Dichloroaniline With trifluoroacetic acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 2.16667h;	97%
Stage #1: 2,6-Dichloroaniline With trifluoroacetic acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 2.16667h;	97%
With sodium azide; trifluoroacetic acid; sodium nitrite In water at 0 - 20℃; for 2.16667h;	97%

2,6-Dichloroaniline (608-31-1) → (2,6-Dichlorophenylimino)phosphorus(V) trichloride

Conditions	Yield
With phosphorus pentachloride In chloroform for 22h; Heating;	97%
With phosphorus pentachloride In tetrachloromethane Substitution; Heating;

2,6-Dichloroaniline (608-31-1) → 2,6-dichloro-N-trimethylsilylaniline (115910-92-4)

Conditions	Yield
With trimethylsilyl bromide; triethylamine In benzene	97%

methyl (2-iodophenyl)acetate (66370-75-0) + 2,6-Dichloroaniline (608-31-1) → 2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester (15307-78-5)

Conditions	Yield
With copper(l) iodide; (+)-D-glucosamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 110℃; for 8h; Temperature;	96.1%

acetyl chloride (75-36-5) + 2,6-Dichloroaniline (608-31-1) → 2,6-dichloroacetanilide (17700-54-8)

Conditions	Yield
In acetic acid	96%
In acetic acid at 70℃; for 0.5h;	78%
With acetic acid
With acetic acid at 100℃;

chloro-trimethyl-silane (75-77-4) + tetrakis(dimethylamido)vanadium(IV) + 2,6-Dichloroaniline (608-31-1) → [VNC6H3Cl2Cl2(NH(CH3)2)2] (455254-24-7)

Conditions	Yield
In toluene ligand was added to toluene soln. of V(NMe2)4 at room temp., Me3SiCl wasadded at room temp. under Ar, heated at 100°C for 20 h; volatiles were pumped off, washed with pentane, dried under vac.; elem. anal.;	96%

2,6-Dichloroaniline (608-31-1) + methyl iodide (74-88-4) → 2,6-Dichloro-N-methylaniline (56462-00-1)

Conditions	Yield
Stage #1: 2,6-Dichloroaniline With n-butyllithium In tetrahydrofuran; hexane at -78 - -40℃; Stage #2: methyl iodide In tetrahydrofuran; hexane Cooling;	96%
Stage #1: 2,6-Dichloroaniline With n-butyllithium In tetrahydrofuran; hexane at -78 - -40℃; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at 20℃;	96%

dicyclohexyl-carbodiimide (538-75-0) + 2,6-Dichloroaniline (608-31-1) → N-2,6-dichlorophenyl-N',N''-dicyclohexylguanidine

Conditions	Yield
With C24H50N5Si2Y In toluene at 20℃; for 2h; Inert atmosphere; Schlenk technique;	96%

2,6-Dichloroaniline (608-31-1) → 4-bromo-2,6-dichloroaniline (697-88-1)

Conditions	Yield
With dihydrogen peroxide; potassium bromide; HZSM-5 In acetic acid at 20℃; for 4h; Bromination;	95%
With tetrabutylammomium bromide; copper(ll) bromide In ethanol at 25℃; regioselective reaction;	93%
With sodium tungstate; sodium perborate; sulfuric acid; acetic anhydride; potassium bromide In acetic acid for 1h; Ambient temperature;	70%

o-benzenedisulfonimide (4482-01-3) + 2,6-Dichloroaniline (608-31-1) → 2,6-dichlorobenzenediazonium o-benzenedisulfonimide

Conditions	Yield
With isopentyl nitrite In acetic acid for 0.0833333h;	95%

orthoformic acid triethyl ester (122-51-0) + 2,6-Dichloroaniline (608-31-1) → 1-(2,6-dichlorophenyl)-1H-tetrazole

Conditions	Yield
With sodium azide In neat (no solvent) at 100℃; for 0.75h;	95%

benzoyl chloride (98-88-4) + 2,6-Dichloroaniline (608-31-1) → N-(2,6-dichlorophenyl)benzamide (10286-88-1)

Conditions	Yield
at 130℃; for 0.25h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Microwave irradiation;	95%

4-chlorobenzoyl chloride (586-75-4) + 2,6-Dichloroaniline (608-31-1) → 4-bromo-N-(2,6-dichlorophenyl)benzamide

Conditions	Yield
at 130℃; for 0.25h; Inert atmosphere; Microwave irradiation;	95%

Tosyl isocyanate (4083-64-1) + 2,6-Dichloroaniline (608-31-1) → N-(2,6-dichlorophenylcarbamoyl)-4-methylbenzenesulfonamide

Conditions	Yield
In acetonitrile at 20℃;	95%

chlorobenzene (108-90-7) + 2,6-Dichloroaniline (608-31-1) → N-phenyl-2,6-dichloroaniline (15307-93-4)

Conditions	Yield
With copper(II) oxide In 1,4-dioxane at 130℃; for 20h; Reagent/catalyst; Solvent;	95%

4-bromoohenyl methyl sulfone (3466-32-8) + 2,6-Dichloroaniline (608-31-1) → 2,6-dichloro-N-(4-(methylsulfonyl)phenyl)aniline

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 80℃; for 8h; Reagent/catalyst; Inert atmosphere;	95%

methanesulfonyl isocyanate (3611-92-5) + 2,6-Dichloroaniline (608-31-1) → 1-(2,6-dichlorophenyl)-3-methanesulfonylurea (78182-07-7)

Conditions	Yield
In benzene	94.6%

bromobenzene (108-86-1) + 2,6-Dichloroaniline (608-31-1) → N-phenyl-2,6-dichloroaniline (15307-93-4)

Conditions	Yield
With johnphos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene for 1h; Heating;	94%

Upstream product

• 601-88-7 2,6-dichloronitrobenzene 
• 515-74-2 sodium sulfanilate 
• 56700-68-6 tert-butyl (2,6-dichlorophenyl)carbamate 
• 22134-75-4 4-amino-3,5-dichloro-benzenesulfonamide 
• 10286-88-1 N-(2,6-dichlorophenyl)benzamide 
• 91573-20-5 N,N-diacetyl-2,6-dichloroaniline 
• 90454-74-3 5-(2,6-dichlorophenyl)-1-phenyl-1H-1,2,5-triazapentadiene 
• 62-53-3 aniline 
• 634-93-5 2,4,6-trichloroaniline 
• 10468-16-3 2-chloro-N-hydroxybenzenamine 
• 2008-58-4 2,6-dichlorobenzamide 
• 7726-95-6 bromine 
• 7647-01-0 hydrogenchloride 
• 697-88-1 4-bromo-2,6-dichloroaniline 

Downstream Products

• 97028-51-8 1,3-bis(2,6-dichlorophenyl)urea 
• 17700-54-8 2,6-dichloroacetanilide 
• 3644-56-2 2-chloro-N-(2,6-dichlorophenyl)acetamide 
• 33560-50-8 dichloro-acetic acid-(2,6-dichloro-anilide) 
• 103261-07-0 trans-crotonic acid-(2,6-dichloro-anilide) 
• 33715-65-0 N-(2,6-dichlorophenyl)-2,2,2,-trichloroacetamide 
• 2268-05-5 1,3-dichloro-2-fluorobenzene 
• 19230-28-5 1,3-dichloro-2-iodobenzene 
• 20595-49-7 (2E)-3-(2,6-dichlorophenyl)prop-2-enoic acid 
• 98141-54-9 4-amino-3,5-dichloro-phenylsulphonic acid chloride 
• 87-61-6 1,2,3-trichlorobenzene 
• 26179-26-0 5-(2,6-dichloro-phenylazo)-4-phenyl-thiazol-2-ylamine 
• 50470-13-8 (2,6-dichloro-phenyl)-thiazolo[5,4-b]pyridin-2-yl-amine 
• 35452-50-7 N-benzyl-2,6-dichloroaniline 

Relevant academic research and scientific papers

Ag/SiO2: A novel catalyst with high activity and selectivity for hydrogenation of chloronitrobenzenes

Ag/SiO2 prepared by an in situ reduction method are found, for the first time, to be highly effective and recyclable catalysts for the selective hydrogenation of a range of chloronitrobenzes to their corresponding chloroanilines, which are of great potential as industrially viable and cheap novel catalysts for the production of chloroanilines. The Royal Society of Chemistry 2005.

NEW INSIGTHS on the KINETICS and MECHANISM of the ELECTROCHEMICAL OXIDATION of DICLOFENAC in NEUTRAL AQUEOUS MEDIUM

The diclofenac (DCF) electrochemical oxidation mechanism was studied through: linear voltammetry (LV), chronoamperometry (CA) sampled-current voltammetry (SCV), potentiostatic coulometry (PC) cyclic voltammetry (CV) under stagnant conditions and linear voltammetry under forced convection conditions (FCLV) over a carbon paste electrode (CPE) from an aqueous medium containing 0.1 M phosphate buffer at pH 7. It was found that the DCF electrochemical oxidation involves an EC mechanism, where the electrochemical reaction is carried out through a one electron-exchange while the chemical reaction involves breaking up the DCF through the nitrogen atom, thereby generating the fragments 2,6 dichloroaniline and 2-(2hydroxyprop-2-enyl)phenol. Reverting the potential scan in the cathodic direction at different scan rates and regardless of its rate, after the oxidation peak, it was found that it was possible to reduce only 38% of the DCF oxidized. The spectrophotometric study carried out during different macro-electrolysis periods allowed observing that the current decrease of the oxidation peak coupled to the DCF absorption (at 270 nm), together with the development of a new spectrophotometric absorption maximum (450 nm), all confirm the EC mechanism proposed. With the use of several experimental techniques (CA, LV and FCLV) and theoretical ones using the Stokes-Einstein approach, the DCF diffusion coefficient was determined, this being in average 8.1 × 10-6 cm2 s-1.

Method for preparing dichloroaniline through chlorination

The invention relates to a method for preparing dichloroaniline by chlorination. The method comprises the following steps: adding o-chloroaniline into a solvent, and carrying out chlorination reactionat 0-80 DEG C for 2-12 hours; neutralizing the reaction solution with alkali until the pH value is 9-10, and separating the organic phase from the water phase to obtain an organic phase; and carryingout rectification separation on the organic phase to respectively obtain pure products 2,4-dichloroaniline and 2,6-dichloroaniline. According to the invention, the main raw material o-chloroaniline is easy to obtain and low in price, so that the method has relatively high economical efficiency; the method has the advantages of no need of special reagents or solvents, one-step chlorination reaction, mild reaction conditions, simple operation, less wastewater, simple treatment and environmental friendliness, and only generates a small amount of salt-containing wastewater in the neutralization step; and the total yield is greater than 90%, and the purity can reach 99.5% or above, which is higher than the purity of 99% of the product in the prior art.

Method for synthesizing 2,6-dichloroaniline at low cost

The invention discloses a method for synthesizing 2,6-dichloroaniline at low cost, which comprises the following steps: preparing N,N-diphenyl urea from aniline, urea, a solvent and a catalyst; then preparing a 1,3-diphenyl urea sulfonyl chloride mixed solution by using a chlorosulfonic acid non-sulfonating agent and using N,N-diphenyl urea as a reaction raw material; feeding chlorine into the reaction system, and carrying out a chlorination reaction to prepare 3,5-dichloro-4-aminobenzenesulfonyl chloride; and finally, carrying out evaporative hydrolysis reaction to obtain the target product 2,6-dichloroaniline. The method is low in raw material cost and high in target yield, and sulfuric acid can be recycled.

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Hydrodebromination of Aromatic Bromides Catalyzed by Unsupported Nanoporous Gold: Heterolytic Cleavage of Hydrogen Molecule

Unsupported nanoporous gold (AuNPore) is a highly efficient, practically applicable, and recyclable catalyst for hydrodebromination of aromatic bromides. The AuNPore-catalyzed hydrodebromination of aromatic bromides proceeded smoothly at relatively low hydrogen pressure and temperature to achieve good to excellent yields of the corresponding non-bromine variants. The selective hydrodebromination reaction occurred exclusively in the coexistence of chlorine atom. For the first time, a mechanistic study revealed that the H?H bond splits in a heterolysis manner on the surface of AuNPore to generate Au?H hydride species.

Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells

Efficient formation of water- and air-stable aza-ylides has been achieved using the Staudinger reaction between electron-deficient aromatic azides such as 2,6-dichlorophenyl azide and triarylphosphines. The reaction proceeds rapidly and has been successfully applied to chemical modification of proteins in living cells.

Electron transfer-induced reduction of organic halides with amines

Reduction of a variety of organo halides was examined by using amines as a sacrificial hydrogen source. UV light-induced reduction of vinyl and aryl halides with triethylamine proceeded smoothly to give the corresponding reduced products. High temperature heating also caused the reduction and DABCO (1,4-diazabicyclo[2.2.2]octane) also served as a good reducing reagent.

Preparation of aniline derivatives

In the present invention, provided is a novel manufacturing method of aniline derivative, which is more simple and eco-friendly and takes less cost compared with an existing synthesizing aniline method, comprising a step of manufacturing chemical formula 1 by making chemical formula 2 react with chemical formula 3 under catalyst, bases and solvents wherein the manufacturing method aniline derivative is manufactured through one pot in a simple manner and accordingly easily removes the solvent with use of distillation under reduced pressure after reaction.

Simultaneous identification of Fenton degradation by-products of diclofenac, ibuprofen and ketoprofen in aquatic media by comprehensive two-dimensional gas chromatography coupled with mass spectrometry

Diclofenac, ibuprofen and ketoprofen are anti-inflammatory drugs intensively used both in human and animal treatment. Due to their high stability these compounds are partially removed by wastewater treatment plants and from this reason the development of some alternative treatments such as advanced oxidative processes are necessary. The main problems in the optimization of an advanced oxidative process rise from the difficulties which appear in the identification of degradation by-products necessary for the establishment of degradation pathway. In this paper a developed method for the simultaneous identification of Fenton degradation by-products of the three above mentioned pharmaceuticals is presented. The obtained results show the comprehensive two-dimensional gas chromatography coupled with mass spectrometry as a proper method for the analysis of the complex mixture of compounds resulted from the Fenton degradation process. Moreover, some compounds never mentioned in the scientific literature were identified. (Chemical Equation Presented).