527-62-8

Basic information

• Product Name: 2-AMINO-4,6-DICHLOROPHENOL
• Synonyms: 4,6-Dichloro-2-aminophenol;2-Amino-4,6-chlorophenol;4,6-Dichloro-α-aminophenol;3-Amino-2-hydroxy-1,5-dichlorbenzene;2,4-DICHLORO-6-AMINOPHENOL 99%;4,6-Dichloro-o-aminophenol;Phenol, 2-amino-4,6-dichloro-;2,4-Dichloro-6-amino
• CAS NO: 527-62-8
• Molecular Formula: C₆H₅Cl₂NO
• Molecular Weight: 178.02
• EINECS: 208-421-3
• Product Categories: Aromatic Phenols
• Mol File: 527-62-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 286.5 °C at 760 mmHg
• Flash Point: 127.1 °C
• Appearance: Yellow to brown/Solid
• Density: 1.2549 (rough estimate)
• Vapor Pressure: 0.00153mmHg at 25°C
• Refractive Index: 1.5680 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.85±0.23(Predicted)
• Merck: 14,437
• CAS DataBase Reference: 2-AMINO-4,6-DICHLOROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4,6-DICHLOROPHENOL(527-62-8)
• EPA Substance Registry System: 2-AMINO-4,6-DICHLOROPHENOL(527-62-8)

Safety Data

• RTECS: SJ5774000
• HazardClass: 6.1
• Hazardous Substances Data: 527-62-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-white or light brown crystals

Uses

2-Amino-4,6-dichlorophenol is used in preparation of novel heteroaryl-substituted Aminoalkyl Azole compounds as pesticides.

General Description

Long needles (from carbon disulfide). Sublimes (at 0.06 mm Hg) at 158-176°F.

Air & Water Reactions

May be sensitive to prolonged exposure to air/or light.

Reactivity Profile

2-AMINO-4,6-DICHLOROPHENOL may react with strong oxidizers and mineral acids or bases .

Fire Hazard

Flash point data for 2-AMINO-4,6-DICHLOROPHENOL are not available. 2-AMINO-4,6-DICHLOROPHENOL is probably combustible.

Purification Methods

Crystallise the phenol from CS2 or *benzene. It sublimes at 0.06mm. The hydrochloride has m 280-285o from EtOH. [Meyer Helv Chim Acta 41 1890 1958, Beilstein 13 II 185, 13 III 856, 13 IV 889.]

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

Synthetic route

2,4-dichloro-6-nitrophenol (609-89-2) → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol at 20℃; under 750.06 Torr; for 96h;	99%
With tin(ll) chloride In ethanol	97%
With sodium dithionite In ethanol; water at 65℃; for 4h;	60%

2,4-dichloro-6-nitrophenol (609-89-2) + stannous chloride (7772-99-8) → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
In ethanol	80%
In ethanol	80%
In ethanol	80%

trans-2,4-dichloro-6-phenylazo-phenol (139137-46-5) → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
With sodium dithionite

hydrogenchloride (7647-01-0) + 4,6,4',6'-tetrachloro-2,2'-azo-di-phenol (858013-68-0) + tin (II)-chloride → 2,4-dichloro-6-aminophenol (527-62-8)

2,4-dichloro-6-isopropylideneamino-phenol → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
With hydrogenchloride In benzene

propan-2-one O-(2,4-dichloro-phenyl)-oxime → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ZrCl4 / benzene / 0.2 h / reflux 2: 10 percent HCl / benzene View Scheme

2,4-dichlorophenol (120-83-2) → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming nitric acid 2: tin; hydrochloric acid View Scheme

phenol (108-95-2) → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorine 2: fuming nitric acid 3: tin; hydrochloric acid View Scheme

sodium dithionate + 2,4-dichloro-6-nitrophenol (609-89-2) → 2,4-dichloro-6-aminophenol (527-62-8)

Conditions	Yield
In water; sodium hydrogencarbonate

2,4-dichloro-6-aminophenol (527-62-8) + 4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride (219963-60-7) → N-(3,5-dichloro-2-hydroxyphenyl)-4-methoxy-3-[4-(2,2,2-trichloroethanoyl)-piperazin-1-yl]-benzenesulfonamide (1331830-34-2)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	96%

carbon disulfide (75-15-0) + 2,4-dichloro-6-aminophenol (527-62-8) → 5,7-dichloro-2-mercaptobenzoxazole (98279-11-9)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 6h; Reflux;	95%
Stage #1: carbon disulfide; 2,4-dichloro-6-aminophenol With potassium hydroxide In methanol for 8h; Cooling with ice; Reflux; Stage #2: With acetic acid In methanol pH=6; Cooling with ice;	84.25%
With potassium hydroxide In ethanol for 8h; Heating;
With potassium hydroxide In ethanol Heating;

2,4-dichloro-6-aminophenol (527-62-8) + acetic anhydride (108-24-7) → 2-acetamido-4,6-dichlorophenol (55202-45-4)

Conditions	Yield
for 0.25h; Ambient temperature;	92%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 2,4-dichloro-6-aminophenol (527-62-8) → 6,8,10-trichloro-5H-benzophenoxazin-5-one (73397-13-4)

Conditions	Yield
With potassium acetate In ethanol at 90 - 100℃; for 20h;	87%

2,4-dichloro-6-aminophenol (527-62-8) + bromocyane (506-68-3) → 5,7-dichloro-benzoxazol-2-ylamine (98555-67-0)

Conditions	Yield
In ethanol at 60℃; for 12h;	86%

2,4-dichloro-6-aminophenol (527-62-8) + tert-butylisonitrile (119072-55-8, 7188-38-7) → N-(tert-butyl)-5,7-dichlorobenzo[d]oxazol-2-amine (1427468-73-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 50℃; for 8h;	85%

2,4-dichloro-6-aminophenol (527-62-8) + 2-(2'-anthraquinonylamino-3'-hydroxy)-4-anilino-6-chloro-s-triazine (1395499-28-1) → C29H18Cl2N6O4 (1395499-23-6)

Conditions	Yield
In nitrobenzene at 60 - 65℃; for 5h;	83%

2,4-dichloro-6-aminophenol (527-62-8) + tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3) → C17H20Cl2N2O3

Conditions	Yield
With zinc dibromide In toluene Heating;	83%

2,4-dichloro-6-aminophenol (527-62-8) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4) → C16H20Cl2N2O4

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane	82%

2,4-dichloro-6-aminophenol (527-62-8) + tert-butylisonitrile (119072-55-8, 7188-38-7) → N-(tert-butyl)-2-(tert-butylimino)-6,8-dichloro-2H-benzo[b][1,4]oxazin-3-amine (1427468-91-4)

Conditions	Yield
With palladium dichloride In 1,4-dioxane at 50℃; for 4h;	82%

2,4-dichloro-6-aminophenol (527-62-8) → 2,4-dichloro-6-diazocyclohexa-2,4-dien-1-one (63969-35-7)

Conditions	Yield
Stage #1: 2,4-dichloro-6-aminophenol With hydrogenchloride In ethanol; water at 0℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: With sodium nitrite In ethanol; water at 0℃; for 2.16667h; Inert atmosphere; Schlenk technique;	81%
Stage #1: 2,4-dichloro-6-aminophenol With hydrogenchloride In ethanol Stage #2: With 1-nitro-3-methylbutane In methanol	80%
Stage #1: 2,4-dichloro-6-aminophenol With hydrogenchloride In ethanol; water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In ethanol; water at 0℃; for 2.16667h; Stage #3: With potassium carbonate In dichloromethane; water Cooling with ice;

2,4-dichloro-6-aminophenol (527-62-8) + C19H20O5 → tert-butyl 2-(benzyloxy)-4-(3,5-dichloro-2-hydroxybenzoyl)benzoate

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 16h;	81%

2,4-dichloro-6-aminophenol (527-62-8) + (1R,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hexane-2-yl-4-formyl-2-hydroxybenzoate → (1R,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hexane-2-yl 4-((3,5-dichloro-2-hydroxyanilino)methyl)-2-hydroxybenzoic acid

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In 1,2-dichloro-ethane for 1h; Reflux;	80%

2,4-dichloro-6-aminophenol (527-62-8) + 5-(4-trifluoromethylphenyl)-6-oxa-4-azaspiro[2.4]hept-4-ene-7-carboxylic acid (1060757-29-0) → 5-(4-trifluoromethylphenyl)-6-oxa-4-azaspiro[2.4]hept-4-ene-7-carboxylic acid (3,5-dichloro-2-hydroxyphenyl)amide

Conditions	Yield
Stage #1: 5-(4-trifluoromethylphenyl)-6-oxa-4-azaspiro[2.4]hept-4-ene-7-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: 2,4-dichloro-6-aminophenol With 2,4,6-trimethyl-pyridine In dichloromethane at 20℃; for 12h; Inert atmosphere;	79%

2,4-dichloro-6-aminophenol (527-62-8) + 2-amino-6-methyl-4-chloropyrimidine (5600-21-5) → 2-((2-amino-6-methylpyrimidin-4-yl)amino)-4,6-dichlorophenol

Conditions	Yield
With hydrogenchloride In ethanol; water at 140℃; for 1.5h; Microwave irradiation; Sealed tube;	71%

3-pyridinecarboxaldehyde (500-22-1) + 2,4-dichloro-6-aminophenol (527-62-8) → 2,4-dichloro-6-(pyridine-3-methylamino)phenol

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In 1,2-dichloro-ethane at 50℃; for 8h;	68%

2,4-dichloro-6-aminophenol (527-62-8) + formaldehyd (50-00-0) → 2-dimethylamino-4,6-dichlorophenol (1022250-47-0)

Conditions	Yield
Stage #1: 2,4-dichloro-6-aminophenol; formaldehyd With sodium cyanoborohydride; acetic acid In water; acetonitrile at 0℃; for 2h; Stage #2: With sodium hydrogencarbonate In water; acetonitrile	64%
With sodium cyanoborohydride; acetic acid In water; acetonitrile at 20℃; for 12h; Cooling with ice;	55.16%

2,4-dichloro-6-aminophenol (527-62-8) + 4-hydroxyquinazolin-7-benzaldehyde → 4-hydroxy-7-(((3,5-dichloro-2-hydroxyphenyl)amino)methyl)quinazoline

Conditions	Yield
Stage #1: 2,4-dichloro-6-aminophenol; 4-hydroxyquinazolin-7-benzaldehyde With titanium(IV) isopropylate In 1,2-dichloro-ethane for 5h; Reflux; Stage #2: With sodium cyanoborohydride In 1,2-dichloro-ethane Reflux;	63%

2,4-dichloro-6-aminophenol (527-62-8) + 2-bromo-3,3,3-trifluoropropene (1514-82-5) → 5,7-dichloro-2-(2,2,2-trifluoroethyl)benzoxazole

Conditions	Yield
With sulfur; 2,2'-azobis-(2,4-dimethylvaleronitrile); sodium hydrogencarbonate; bis(pinacol)diborane In N,N-dimethyl-formamide at 100℃; for 15h; Reagent/catalyst; Solvent; Inert atmosphere;	62%

2,4-dichloro-6-aminophenol (527-62-8) + 5-(bromomethyl)pyridine-2-carbonitrile (308846-06-2) → 5-((2-amino-4,6-dichlorophenyl)methyl)-2-cyanopyridine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile for 2h;	60%

2,4-dichloro-6-aminophenol (527-62-8) + pyrrole (109-97-7) → 2-(3,5-Dichlor-2-hydroxyphenyl)-1H-pyrrol (121789-62-6)

Conditions	Yield
Stage #1: 2,4-dichloro-6-aminophenol With tert.-butylnitrite In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: pyrrole With chlorpromazine hydrochloride In dimethyl sulfoxide at 0℃; Inert atmosphere;	55%

2,4-dichloro-6-aminophenol (527-62-8) + N-(2-formylquinolin-8-yl)-4-(trifluoromethyl)benzenesulfonamide → N-(2-(((3,5-dichloro-2-hydroxyphenyl)amino)methyl)quinolin-8-yl)-4-(trifluoromethyl)benzenesulfonamide

Conditions	Yield
With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 18h;	55%
With sodium tris(acetoxy)borohydride In ethanol; 1,2-dichloro-ethane at 20℃; for 18h;	38%

2,4-dichloro-6-aminophenol (527-62-8) + 2-cyanopyridine-5-carboxyaldehyde (131747-68-7) → 5-((3,5-dichloro-2-hydroxyphenyl)amino)methyl-2-cyanopyridine

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 60℃;	53%

2,4-dichloro-6-aminophenol (527-62-8) + sodium chlorodifluoroacetate (1895-39-2) → 5,7-dichloro-3-(difluoromethyl)benzo[d]oxazole-2(3H)-thione

Conditions	Yield
With sulfur; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium t-butanolate In N,N-dimethyl-formamide at 70℃; for 3h; Molecular sieve; Inert atmosphere;	52%
With sulfur; sodium t-butanolate In N,N-dimethyl-formamide at 70℃; for 3h; Molecular sieve;	52%

2,4-dichloro-6-aminophenol (527-62-8) → 5,7-dichloro-2-(2,2,2-trifluoroethyl)benzoxazole

Conditions	Yield
With 2,2'-azobis-(2,4-dimethylvaleronitrile); sodium hydrogencarbonate; sulfur; bis(pinacol)diborane In N,N-dimethyl-formamide at 100℃; for 15h; Inert atmosphere;	52%

2,4-dichloro-6-aminophenol (527-62-8) + (1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hexane-2-yl-4-formyl-2-hydroxybenzoate → (1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hexane-2-yl 4-((3,5-dichloro-2-hydroxyaniline)methyl)-2-hydroxybenzoic acid

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In 1,2-dichloro-ethane for 1h; Reflux;	50%

2,4-dichloro-6-aminophenol (527-62-8) + Acetylsalicylic acid chloride + aspirin (50-78-2) → salicylic acid-(3,5-dichloro-2-hydroxy-anilide) (81665-46-5)

Conditions	Yield
With sodium hydroxide; thionyl chloride In N,N-dimethyl-aniline; acetone	49%

2,4-dichloro-6-aminophenol (527-62-8) + N,N-diethyl-N'-chlorosulfonyl chloroformamidine (28621-54-7) → 7,9-dichloro-4-(diethylamino)-2,2-dioxo-2λ6-5H-[1,2,3,5]benzoxathiadiazepine (1155876-12-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In various solvent(s) at 20℃;	48%

Upstream product

• 609-89-2 2,4-dichloro-6-nitrophenol 
• 7772-99-8 stannous chloride 
• 108-95-2 phenol 
• 120-83-2 2,4-dichlorophenol 
• 7647-01-0 hydrogenchloride 
• 858013-68-0 4,6,4',6'-tetrachloro-2,2'-azo-di-phenol 
• 139137-46-5 trans-2,4-dichloro-6-phenylazo-phenol 

Downstream Products

• 98279-11-9 5,7-dichloro-2-mercaptobenzoxazole 
• 330791-16-7 cis-N₂-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-4-methyl-1,3-benzoxazol-2-amine 
• 330791-69-0 Cis-N₂-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dichloro-1,3-benzoxazol-2-amine 
• 134610-56-3 6,8-dichloro-3(3,4-dihydroxy-5-nitrophenyl)-2H-1,4-benzoxazin-2-one 
• 466679-94-7 (3,5-Dichloro-2-hydroxy-phenyl)-carbamic acid phenyl ester 
• 105679-37-6 C₈H₇Cl₂NO 
• 69640-38-6 2,4-dichloro-6-(3,4,5-trichloro-1H-pyrrol-2-yl)phenol 
• 121789-62-6 2-(3,5-Dichlor-2-hydroxyphenyl)-1H-pyrrol 

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