527-62-8

Usage

Uses

Used in Pesticide Industry:
2-AMINO-4,6-DICHLOROPHENOL is used as a key intermediate in the synthesis of novel heteroaryl-substituted Aminoalkyl Azole compounds. These compounds possess potent pesticidal properties, making them valuable for the development of new and effective pesticides. The unique structure of 2-AMINO-4,6-DICHLOROPHENOL allows for the creation of a diverse range of heteroaryl-substituted Aminoalkyl Azole compounds, which can be tailored to target specific pests and provide enhanced control in agricultural settings.

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

Downstream Products

• 5815-20-3 3,5-dichloro-2-hydroxy-benzoic acid-(3,5-dichloro-2-hydroxy-anilide) 
• 81665-46-5 salicylic acid-(3,5-dichloro-2-hydroxy-anilide) 
• 50710-33-3 5,7-dichloro-2-chloromethyl-benzooxazole 
• 75197-76-1 2-(3,5-dichloro-2-hydroxyanilino)-1,4-naphthoquinone-3-pyridinium chloride 
• 55202-45-4 2-acetamido-4,6-dichlorophenol 
• 156661-94-8 2--4,6-dichloro-O-(methylsulfonyl)phenol 
• 98279-11-9 5,7-dichloro-2-mercaptobenzoxazole 
• 79510-11-5 N-(3,5-Dichloro-2-hydroxy-phenyl)-oxalamic Acid Ethyl Ester 
• 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 
• 1022250-47-0 2-dimethylamino-4,6-dichlorophenol 
• 1253107-76-4 C₁₃H₇BrCl₂N₂O 

Relevant academic research and scientific papers

BENZIMIDAZOLE COMPOUNDS

There is provided a compound of the formula (1) wherein R1 is an optionally substituted C1-10 alkyl; R2 is H, or a C1-6 alkyl which may be substituted with 1 to 3 substituents; R3 is a 5- or 6-membered aromatic group which may be substituted with 1 to 5 substituents, wherein the 5- or 6-membered aromatic group may be fused with a 5- or 6- membered ring which may be substituted with 1 to 3 C1-6 alkyls; R4 is a hydrogen, a halogen, a hydroxy, a cyano, a C1-6 alkyl or a C1-6 alkoxy; Z is -O-, -S-, -SO-, -SO2-, or - NR5- wherein R5 is a hydrogen or a C1-6 alkyl; or a salt thereof or a prodrug thereof, which have CRF receptor antagonist activity and use thereof.

Regulatory molecules for the 5-HT3 receptor ion channel gating system

Substituted benzoxazole derivatives which possess a nitrogen-containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor.

Pyrazolopyrimidines as therapeutic agents

The present invention is directed to pyrazolopyrimidine derivatives of formula (I) wherein the substituents are defined herein, which are useful as kinase inhibitors and as such are useful for affecting angiogenesis and diseases and conditions associated with angiogenesis.

Oxamide inhibitors of plasminogen activator inhibitor-1

Methods of treating disorders associated with elevated levels of PAI-1 are disclosed comprising administering to a patient in need thereof a therapeutically effective amount of at least one compound of formula at least one compound of formula (I), or a pharmaceutically-acceptable salt, prodrug, stereoismer or solvate thereof, wherein: A is aryl or heteroaryl, X is O or S, and R1-R9 and R18 are defined herein. The invention also pertains to pharmaceutical compositions and compounds within the scope of formula (I) as well as medicaments and articles of manufacture comprising compounds of formula (I).

Pyrazolopyrimidines as therapeutic agents

The present invention provides compounds of Formula I, including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R2, and R3 are defined as described herein.

IL-8 RECEPTOR ANTAGONISTS

The present invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease states mediated by the chemokine Interleukin-8 (IL-8).

A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition

ZrCl4-mediated decomposition of O-arylketoximes in benzene leads to regioselective intramolecular migration of the imino group from the oxygen to the ortho position of the aryl group via electron-deficient nitrogen intermediates.

IL-8 RECEPTOR ANTAGONISTS

This invention relates to the novel use of phenyl ureas in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

IL-8 RECEPTOR ANTAGONISTS

This invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease scates mediated by the chemokine, Interleukin-8 (IL-8). In particular, this invention relates to the novel compounds of Formula (Ia) and their use in treating chemokine mediated diseases wherein the chemokine binds to an IL-8 a or b receptor. Compounds of Formula (Ia) are represented by the structure: STR1 wherein interalia, X is oxygen or sulfur;Rb is NR 6 R. sub.7, alkcyl, aryl, arylC 1-4 alkyl, aryl C 2-4 alkenyl, heteroaryl, heteroarylC 1-4 alkyl, heteroarylC 2-4 alkenyl, heterocyclic or heterocyclic C 1-4 alkyl, or a heterocyclic C 2-4 alkenyl moiety, camphor, all of which may be optionally substituted; R 1 is independently selected from hydrogen; halogen; nitro; cyano; C 1-10 alkyl; halosubstituted C 1-10 alkyl; C 2-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR. sub.8 R 8)q S(O) t R 4 ; hydroxy; hydroxy substituted C 1-4 alkyl; aryl; aryl C 1-4 alkyl; aryl C 2-10 alkenyl; aryloxy; aryl C 1-4 alkyloxy; heteroaryl; heteroarylalkyl; heteroaryl C 2-10 alkenyl; heteroaryl C 1-4 alkyloxy; heterocyclic; heterocyclic C 1-4 alkyl; heterocyclicC 1-4 alkyloxy; heterocyclic C 2-10 alkenyl; q is 0 or an integer having a value of 1 to 10; n is an integer having a value of 1 to 3;m is an integer having a value of 1 to 3; Y is hydrogen; halogen; nitro; cyano; halosubstituted C 1-10 alkyl; C 1-10 alkyl; C 2-10 alkenyl C. sub.1-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR 8 R. sub.8)qS(O) t R 4, (CR 8 R 8)qOR 4 ; hydorxy; hydroxy substituted C. sub.1-4 alkyl; aryl; aryl C 1-4 alkyl; aryloxy; arylC. sub.1-4 alkyloxy; aryl C 2-10 alkenyl; heteroaryl; heteroarylalkyl; heteroaryl C 1-4 alkyloxy; heteroaryl C 2-10 alkenyl; heterocyclic, heterocyclic C 1-4 alkyl; heterocyclicC 2-10 alkenyl;or a pharmaceutically acceptable salt thereof.

Novel inhibitors of bacterial two-component systems with gram positive antibacterial activity: Pharmacophore identification based on the screening hit closantel

This SAR study has shown that the salicylanilide is the pharmacophore for inhibition of the bacterial two-component system. Hydrophobic substituents improve the potency of inhibitors in this series; however, hydrophobicity is not the sole determinant for inhibition; structural and electronic requirements also exist. Closantel (1) was found to inhibit a two- component system and to have antibacterial activity against drug resistant S. aureus and E. faecium.