5930-28-9

Basic information

• Product Name: 4-Amino-2,6-dichlorophenol
• Synonyms: 3,5-Dichloro-4-hydroxyaniline;4-amino-2,6-dichloro-pheno;4-Amino-2,6-Dichlorophenol 2,6-Dichloro-4-Aminophenol;2,6-dichloro-4-chloro phenol;2,6-dichloro-4-amine phenol;4-Amino-2,6-dichlorophenol, 97+%;4-AMINO-2,6-DICHLOROPHENOL / 3,5-DICHLORO-4-HYDROXYANILINE;4-Amino-2,6-dichlorophenol,98%
• CAS NO: 5930-28-9
• Molecular Formula: C₆H₅Cl₂NO
• Molecular Weight: 178.02
• EINECS: 227-671-4
• Product Categories: Aromatic Phenols;Phenoles and thiophenoles;Organic Building Blocks;Oxygen Compounds;Phenols;Dyestuff Intermediates
• Mol File: 5930-28-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 167-170 °C(lit.)
• Boiling Point: 303.629 °C at 760 mmHg
• Flash Point: 137.431 °C
• Appearance: Beige or slightly brown to pale reddish/Powder
• Density: 1.2549 (rough estimate)
• Refractive Index: 1.5680 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 7.29±0.23(Predicted)
• Stability: Stable. Incompatible with acids, acid chlorides, acid anhydrides, chloroformates, strong oxidizing agents.
• BRN: 2361665
• CAS DataBase Reference: 4-Amino-2,6-dichlorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2,6-dichlorophenol(5930-28-9)
• EPA Substance Registry System: 4-Amino-2,6-dichlorophenol(5930-28-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: SJ5774500
• TSCA: Yes
• Hazardous Substances Data: 5930-28-9(Hazardous Substances Data)

Usage

Chemical Properties

solid

InChI:InChI=1/C6H5Cl2NO/c7-4-1-3(9)2-5(8)6(4)10/h1-2,10H,9H2

Synthetic route

2,6-dichloro-4-nitrophenol (618-80-4) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;	98%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 3h;	98%
With palladium 10% on activated carbon; hydrogen In methanol at 50℃; under 7500.75 Torr; for 2h; Reagent/catalyst; Pressure; Solvent; Autoclave;	96.21%

2,6-dichloroquinone-4-chloroimide (101-38-2) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
With ascorbic acid In water; acetone for 0.05h; Ambient temperature;	68%

3,3',5,5'-tetrachloroazobenzene-4,4'-diol (92050-15-2) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

hydrogenchloride (7647-01-0) + 3,3',5,5'-tetrachloroazobenzene-4,4'-diol (92050-15-2) + tin (II)-chloride → 4-amino-2,6-dichlorophenol (5930-28-9)

2-chloro-4,4'-azo-di-phenol (855836-85-0) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrochloric acid; glacial acetic acid 2: diluted hydrochloric acid; glacial acetic acid 3: diluted hydrochloric acid; glacial acetic acid 4: tin (II)-chloride; hydrochloric acid View Scheme

2,2'-dichloro-4,4'-azo-di-phenol (200710-27-6) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: diluted hydrochloric acid; glacial acetic acid 2: diluted hydrochloric acid; glacial acetic acid 3: tin (II)-chloride; hydrochloric acid View Scheme

2,6,2'-trichloro-4,4'-azo-di-phenol (858853-84-6) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: diluted hydrochloric acid; glacial acetic acid 2: tin (II)-chloride; hydrochloric acid View Scheme

4,4'-dihydroxyazobenzene (2050-16-0) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: diluted hydrochloric acid; glacial acetic acid 2: hydrochloric acid; glacial acetic acid 3: diluted hydrochloric acid; glacial acetic acid 4: diluted hydrochloric acid; glacial acetic acid 5: tin (II)-chloride; hydrochloric acid View Scheme

4-nitro-phenol (100-02-7) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; chlorine 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: chlorine / 4 h / Reflux 2: hydrogen / 1 h View Scheme

2,6-dichloro-4-nitrophenol (618-80-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
With iron; acetic acid; platinum

2-chloro 4-aminophenol (3964-52-1) → 4-amino-2,6-dichlorophenol (5930-28-9)

4-amino-2,6-dichlorophenyl phosphate (124219-30-3) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
With bovine serum albumine; Tris buffer; magnesium chloride at 20℃; pH=9.0; Enzyme kinetics; Further Variations:; pH-values; Solvents;

2,6-Dichlorophenol (87-65-0) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / water; 1,2-dichloro-ethane / 4 h / 30 - 35 °C 2: iron doped carbon; hydrogen / N,N-dimethyl-formamide / 60 - 80 °C / 7500.75 Torr View Scheme

N-(3,5-dichloro-4-hydroxyphenyl)but-2-ynamide → 4-amino-2,6-dichlorophenol (5930-28-9) + 7,9-dichloro-4-methyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 50℃; for 24h; Sealed tube;

4-nitro-aniline (100-01-6) → 4-amino-2,6-dichlorophenol (5930-28-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: chlorine / methanol / 55 - 60 °C 2.1: sulfuric acid; nitrosylsulfuric acid / toluene / 1 h / 5 - 15 °C 2.2: 7 h / Reflux 3.1: 1% platinum on charcoal; hydrogen / toluene / 6 h / 90 - 100 °C / 7500.75 Torr / Sealed tube View Scheme

quinoline-4-carboxaldehyde (4363-93-3) + 4-amino-2,6-dichlorophenol (5930-28-9) → 4-(N-quinolin-4-ylmethylideneamino)-2,6-dichlorophenol

Conditions	Yield
In ethanol for 3h; Heating;	95%

4-amino-2,6-dichlorophenol (5930-28-9) + 1-isocyanato-3-trifluoromethyl-benzene (329-01-1) → N-(3,5-dichloro-4-hydroxy-phenyl)-N'-(3-trifluoromethyl-phenyl)urea

Conditions	Yield
In pyridine Inert atmosphere;	94%

pyridine-4-carbaldehyde (872-85-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → N-(4-pyridylmethylidene)-4-amino-2,6-dichlorophenol (190844-71-4)

Conditions	Yield
In ethanol Heating;	93%

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → (3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid tert-butyl ester (155891-93-3)

Conditions	Yield
In tetrahydrofuran for 2.5h; Heating / reflux;	93%
In tetrahydrofuran for 2.5h; Heating / reflux;	93%
In tetrahydrofuran at 80℃; for 2h;	75%

di-tert-butyl oxalate (691-64-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → (3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid tert-butyl ester (155891-93-3)

Conditions	Yield
In tetrahydrofuran for 2.5h; Reflux; Inert atmosphere;	93%

ethyl 2-phenyldiazoacetate (22065-57-2) + 4-amino-2,6-dichlorophenol (5930-28-9) → ethyl 2-((3,5-dichloro-4-hydroxyphenyl)amino)-2-phenylacetate

Conditions	Yield
With C43H37Br2CuN3P2(1+)*ClO4(1-) In methanol at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique; chemoselective reaction;	93%

4-amino-2,6-dichlorophenol (5930-28-9) + 4,5-Dibromo-2-(2-oxo-propyl)-2H-pyridazin-3-one (186792-10-9) → 5-(4-Amino-2,6-dichloro-phenoxy)-4-bromo-2-(2-oxo-propyl)-2H-pyridazin-3-one

Conditions	Yield
With potassium carbonate In acetonitrile for 10h; Heating;	91%

6-chloro-4-methyl-3-nitropyridine (22280-60-0) + 4-amino-2,6-dichlorophenol (5930-28-9) → 3,5-dichloro-4-[(6-methyl-5-nitropyridin-2-yl)oxy]aniline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	91%

4-amino-2,6-dichlorophenol (5930-28-9) → C6H3(2)H2Cl2NO

Conditions	Yield
With water-d2; hydrogen chloride for 72h; Reflux; Inert atmosphere;	91%

4-amino-2,6-dichlorophenol (5930-28-9) + 4,5-dichloro-2-propyl-pyridazin-3-one (51659-95-1) → 4-(4-amino-2,6-dichlorophenoxy)-5-chloro-1-propylpyridazin-6-one

Conditions	Yield
With potassium fluoride; potassium carbonate In acetonitrile for 8h; Heating;	90%

4-amino-2,6-dichlorophenol (5930-28-9) + N-phenylsulfonylbenzimidoyl chloride (4513-25-1) → N-[1-(3,5-Dichloro-4-hydroxy-phenylamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide (314751-12-7, 408346-36-1)

Conditions	Yield
With sodium acetate In acetic acid; N,N-dimethyl-formamide for 0.5h;	90%

4-amino-2,6-dichlorophenol (5930-28-9) + 3,6-dichloro-4-methyl-5-(propan-2-yl)pyridazine → C14H14Cl3N3O

Conditions	Yield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 90℃; Inert atmosphere;	90%

4-amino-2,6-dichlorophenol (5930-28-9) + 4-chloro-6,7-dimethoxyquinoline-3-carbonitrile (214470-55-0) → 4-(3,5-dichloro-4-hydroxy-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

Conditions	Yield
In 2-ethoxy-ethanol for 3h; Substitution; Heating;	89%
With pyridine hydrochloride In 2-ethoxy-ethanol for 1h; Heating / reflux;	88.8%
With pyridine hydrochloride In 2-ethoxy-ethanol; ethyl acetate	346.7 mg (88.8%)
With pyridine hydrochloride In 2-ethoxy-ethanol	346.7 mg (88.8%)
With pyridine hydrochloride In 2-ethoxy-ethanol; ethyl acetate	346.7 mg (88.8 %)

3,5-dichlorobenzensulfonyl chloride (705-21-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → C12H7Cl4NO3S (1044266-20-7)

Conditions	Yield
With pyridine at 20℃;	89%

4-amino-2,6-dichlorophenol (5930-28-9) + 4,5-dibromo-2-ethylpyridazin-3-(2H)-one (103977-71-5) → 4-(4-amino-2,6-dichlorophenoxy)-5-bromo-1-ethylpyridazin-6-one

Conditions	Yield
With potassium fluoride; potassium carbonate In acetonitrile for 8h; Heating;	86%

4-amino-2,6-dichlorophenol (5930-28-9) + (4,5-dibromo-6-oxo-6H-pyridazin-1-yl)-acetic acid methyl ester → 4-(4-amino-2,6-dichlorophenoxy)-5-bromo-1-(methoxycarbonylmethyl)pyridazin-6-one

Conditions	Yield
With potassium fluoride; potassium carbonate In acetonitrile for 3h; Heating;	86%

diaetyl-β-resorcyloyl chloride + diacetyl-β-resorcyloyl chloride + diacetyl-β-resorcylic acid + 4-amino-2,6-dichlorophenol (5930-28-9) → 3',5'-dichloro-2,4,4'-trihydroxybenzanilide (55411-38-6)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; thionyl chloride In N,N-dimethyl-aniline; acetone	84.8%

5-nitrofurane-2-carboxaldehyde (698-63-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → (E)-2,6-dichloro-4-(((5-nitrofuran-2-yl)methylene)amino) phenol

Conditions	Yield
With acetic acid In ethanol at 85℃; for 1.5h; Molecular sieve;	84%

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → 4-((2-amino-6-methylpyrimidin-4-yl)amino)-2,6-dichlorophenol

Conditions	Yield
With hydrogenchloride In ethanol; water at 140℃; for 1.5h; Microwave irradiation; Sealed tube;	82%

4-amino-2,6-dichlorophenol (5930-28-9) → 3,3',5,5'-tetrachloroazobenzene-4,4'-diol (92050-15-2)

Conditions	Yield
With KO2 In pyridine at 80℃; for 8h;	80%

4-amino-2,6-dichlorophenol (5930-28-9) → 4-azido-2,6-dichlorophenol (33354-61-9)

Conditions	Yield
With hydrogenchloride; sodium azide; acetic acid	80%
Stage #1: 4-amino-2,6-dichlorophenol With hydrogenchloride; sodium nitrite In water; acetic acid for 0.25h; Diazotization; ice cooling; Stage #2: With sodium azide In water; acetic acid Substitution;	80%
(i) aq. HCl, NaNO2, (ii) AcOH, (iii) NaN3; Multistep reaction;

4-amino-2,6-dichlorophenol (5930-28-9) + orthoformic acid triethyl ester (122-51-0) + phosphonic acid diethyl ester (762-04-9) → tetraethyl (3,5-dichloro-4-hydroxyphenylamino)methylenebisphosphonate (1370709-85-5)

Conditions	Yield
With amberlyst-15 at 20℃; for 1.5h;	80%

4-amino-2,6-dichlorophenol (5930-28-9) + C12H7F3N4O2S → 1-(3,5-dichloro-4-hydroxyphenyl)-3-(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)urea

Conditions	Yield
In acetonitrile for 20h; Reflux;	80%

4-chloro-6-isopropylpyrimidine (954222-10-7) + 4-amino-2,6-dichlorophenol (5930-28-9) → C13H13Cl2N3O

Conditions	Yield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere;	79%

4-amino-2,6-dichlorophenol (5930-28-9) + 1-Butyl-4,5-dichlor-pyridazon (51659-49-5) → 4-(4-amino-2,6-dichlorophenoxy)-5-chloro-1-butylpyridazin-6-one

Conditions	Yield
With potassium fluoride; potassium carbonate In acetonitrile for 3h; Heating;	78%

4-amino-2,6-dichlorophenol (5930-28-9) + aspirin (50-78-2) → 2N-sodium hydroxide + 3',5'-dichloro-2,4'-dihydroxybenzanilide (55411-56-8)

Conditions	Yield
With pyridine In ethyl acetate; acetone	A n/a B 78%

3,6-dichloro-4-cyclopentylpyridazine + 4-amino-2,6-dichlorophenol (5930-28-9) → 3,5-dichloro-4-((6-chloro-5-cyclopentylpyridazin-3-yl)oxy)aniline

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 110℃; for 3h; Microwave irradiation;	78%

4-amino-2,6-dichlorophenol (5930-28-9) + C18H25ClN4O → (R)-8-cyclopentyl-7-(cyclopentylmethyl)-2-((3,5-dichloro-4-hydroxyphenyl)amino)-5-methyl-7,8-dihydropteridin-6(5H)-one

Conditions	Yield
With hydrogenchloride In ethanol; water Reflux;	77.1%

4-methyl-1,2,3-thiadiazole-5-yl-formyl isocyanate (1254781-51-5) + 4-amino-2,6-dichlorophenol (5930-28-9) → 1-(3,5-dichloro-4-hydroxyphenyl)-3-[(4-methyl-1,2,3-thiadiazol-5-yl)carbonyl]urea (1417340-72-7)

Conditions	Yield
In 1,2-dichloro-ethane at 20℃; for 8h;	77%
In 1,2-dichloro-ethane at 20℃; for 8.25h;	77%

Upstream product

• 618-80-4 2,6-dichloro-4-nitrophenol 
• 855836-85-0 2-chloro-4,4'-azo-di-phenol 
• 200710-27-6 2,2'-dichloro-4,4'-azo-di-phenol 
• 858853-84-6 2,6,2'-trichloro-4,4'-azo-di-phenol 
• 68-12-2 N,N-dimethyl-formamide 
• 3964-52-1 2-chloro 4-aminophenol 
• 100-01-6 4-nitro-aniline 
• 124219-30-3 4-amino-2,6-dichlorophenyl phosphate 
• 100-02-7 4-nitro-phenol 
• 2050-16-0 4,4'-dihydroxyazobenzene 
• 101-38-2 2,6-dichloroquinone-4-chloroimide 
• 92050-15-2 3,3',5,5'-tetrachloroazobenzene-4,4'-diol 
• 87-65-0 2,6-Dichlorophenol 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 146901-66-8 2,6-dichloro-4-phenylazo-phenol 
• 2852-70-2 2,6-Dichlor-p-benzochinonmonoimin 
• 93886-04-5 6-Methyl-4-oxo-9-[1-phenyl-meth-(E)-ylidene]-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (3,5-dichloro-4-hydroxy-phenyl)-amide 
• 42468-33-7 2,6-dichloro-4-mercapto-phenol 
• 92050-15-2 3,3',5,5'-tetrachloroazobenzene-4,4'-diol 
• 141890-86-0 N-(3,5-dichloro-4-hydroxyphenyl)succinic acid monoamide 
• 697-91-6 2,6-dichloro-1,4-benzoquinone 
• 101-38-2 2,6-dichloroquinone-4-chloroimide 
• 6245-87-0 [1,4]benzoquinone-mono-(4-amino-phenylimine) 
• 108997-68-8 3,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropyloxy)aniline 
• 1104591-47-0 N-(phenylsulfinyl)-2,6-dichloro-1,4-benzoquinone imine 
• 5147-73-9 N-[(4-nitrophenyl)thio]-2,6-dichloro-1,4-benzoquinone imine 
• 1104591-49-2 N-[(4-chlorophenyl)sulfinyl]-2,6-dichloro-1,4-benzoquinone imine 
• 1104591-51-6 N-[(4-nitrophenyl)sulfinyl]-2,6-dichloro-1,4-benzoquinone imine 

Relevant articles and documents

Synthesis method of 2, 6-dichloro-4-aminophenol

The invention discloses a synthesis method of 2, 6-dichloro-4-aminophenol, and belongs to the field of preparation of pesticide, medicine and dye intermediates, 2, 6-dichloro-4-aminophenol is obtained by adopting paranitroaniline as a raw material through the steps of chlorination, diazonium hydrolysis, hydrogenation and the like, methanol is adopted as a solvent for chlorination, filtrate can be repeatedly used, and the use of a large amount of acid water is reduced; toluene is selected as a solvent in diazotization, diazonium liquid is directly layered after being hydrolyzed, an organic layer is separated out, water vapor distillation is not needed, and the distillation risk and energy consumption are reduced; toluene is selected as a hydrogenation solvent, and an organic layer separated after the diazonium liquid is hydrolyzed is directly hydrogenated, so that the process flow is simplified.

Synthesis method of aminophenol

The invention provides a synthesis method of aminophenol. According to the method, by reacting nitrophenol with hydrogen under the conditions of an auxiliary agent and a solvent, an aminophenol product with high selectivity and yield can be prepared, the auxiliary agent can well control the reaction depth of nitrophenol and hydrogen, thereby inhibiting the side reaction, enhancing the purity of the final product, overcoming the problems of poor selectivity and high three-waste amount in the common hydrazine hydrate, sodium hydrosulfite and other reducing agents in the prior art, and having higher industrial application value.

Gold-Catalyzed Dearomative Spirocyclization of N-Aryl Alkynamides for the Synthesis of Spirolactams

A catalytic redox-neutral method for the synthesis of spirolactams proceeding through the dearomative spirocyclization of N-aryl alkynamides is reported. In contrast to stoichiometric activating agents employed for related transformations, we show that the use of 5 mol % of Au(PPh3)Cl and AgOTf in dichloroethane at 50-80 °C leads to selective spirocyclization, furnishing the products in yields of 35-87%. The substrate scope of the reaction is good, with both electron-donating and electron-withdrawing groups being tolerated around the arene ring, as well as substitution at the amide nitrogen. The identity of the para-alkoxy group on the arene ring is key to achieving selectivity for spirocyclization over alternative mechanistic pathways. While the presence of a para-methoxy group leads to trace amounts of the desired spirolactams, the para-tert-butoxy or para-hydroxy substrate analogues furnish the spirolactams in good yield with high selectivity.