608-31-1

Basic information

• Product Name: 2,6-Dichloroaniline
• Synonyms: 1-aMino-2,6-dichlorobenzene;Clonidine IMpurity-C(BP);2,6- twochloro aniline;2.6-Dichloroan;Clonidine Impurity C (2,6-Dichloroaniline);6-Dichlorobenzenamine;2,6-dichloro;2,6-DICHLOROANILINE
• CAS NO: 608-31-1
• Molecular Formula: C₆H₅Cl₂N
• Molecular Weight: 162.02
• EINECS: 210-160-5
• Product Categories: Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;C2 to C6;Nitrogen Compounds;Alpha sort;Amines;AromaticsPesticides&Metabolites;Chemical Class;D;DAlphabetic;DIA - DIC;Aromatics;Miscellaneous Reagents
• Mol File: 608-31-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 36-38 °C(lit.)
• Boiling Point: 228 °C
• Flash Point: >230 °F
• Appearance: White to brown/Crystalline Solid
• Density: 1,275 g/cm3
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: 1.6g/l
• PKA: 0.71±0.10(Predicted)
• Water Solubility: 1.6 g/L (20 ºC)
• BRN: 775084
• CAS DataBase Reference: 2,6-Dichloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloroaniline(608-31-1)
• EPA Substance Registry System: 2,6-Dichloroaniline(608-31-1)

Safety Data

• Hazard Codes: T,N,Xi
• Statements: 23/24/25-33-50/53
• Safety Statements: 28-36/37-45-60-61-28A
• RIDADR: UN 3442 6.1/PG 2
• WGK Germany: 3
• RTECS: CX9862655
• F: 8
• TSCA: T
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 608-31-1(Hazardous Substances Data)

Usage

Uses

2,6-Dichloroaniline is used in the pharmaceutical industry for the synthesis of antibacterial agents of lomefloxacin, Lee uric acid and clonidine.

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

• 515-74-2 sodium sulfanilate 
• 10286-88-1 N-(2,6-dichlorophenyl)benzamide 
• 634-93-5 2,4,6-trichloroaniline 
• 697-88-1 4-bromo-2,6-dichloroaniline 
• 63-74-1 sulfanilamide 
• 94-09-7 p-aminoethylbenzoate 
• 87-65-0 2,6-Dichlorophenol 
• 95-51-2 o-chloroaniline 
• 601-88-7 2,6-dichloronitrobenzene 
• 98141-54-9 4-amino-3,5-dichloro-phenylsulphonic acid chloride 
• 62-53-3 aniline 
• 106-40-1 4-bromo-aniline 
• 57341-09-0 1-azido-2,6-dichlorobenzene 
• 2129-31-9 4-diphenylphosphanobenzoic acid 

Downstream Products

• 17700-54-8 2,6-dichloroacetanilide 
• 35452-50-7 N-benzyl-2,6-dichloroaniline 
• 65051-21-0 N-(2,6-dichlorophenyl)malonamic acid ethyl ester 
• 35370-41-3 N-(2,6-Dichloro-phenyl)-propionamidine 
• 136343-72-1 N-(2,6-dichlorophenyl)pyridin-2-amine 
• 134937-81-8 N-(2,6-Dichloro-phenyl)-2-(1H-indol-3-yl)-2-oxo-acetamide 
• 134890-42-9 9,9-diethyl-6,8-dioxo-3-(2,6-dichlorophenyl)-2,3,4,5,6,7,8,9-octahydropyrimido<3,4-a>-s-triazine 
• 134937-85-2 N-(2,6-Dichloro-phenyl)-2-(5-methoxy-1H-indol-3-yl)-2-oxo-acetamide 
• 117781-62-1 cyclohexanone 2,6-dichloroanil 
• 134937-82-9 2-(5-Bromo-1H-indol-3-yl)-N-(2,6-dichloro-phenyl)-2-oxo-acetamide 
• 120343-19-3 (2,6-Dichloro-phenyl)-carbamic acid 2-chloro-ethyl ester 
• 72340-25-1 -(2,6-dichlorophenyl)-benzamidine 
• 24096-56-8 N-(2,6-dichlorophenyl)succinimide 
• 73750-44-4 N-tert-Butyl-N'-(2,6-dichloro-phenyl)-acrylamidine 

Relevant articles and documents

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