89-64-5

Basic information

• Product Name: 4-CHLORO-2-NITROPHENOL
• Synonyms: 4-chloro-2-nitro-pheno;O-NITRO-P-CHLOROPHENOL;AKOS BBS-00004667;4-CHLORO-2-NITROPHENOL;1-CHLORO-4-HYDROXY-3-NITROBENZENE;2-NITRO-4-CHLOROPHENOL;o-nitro-p-chorophenol;4-Chloro-2-nitrophenol,98%,containsuptoca10%water
• CAS NO: 89-64-5
• Molecular Formula: C₆H₄ClNO₃
• Molecular Weight: 173.55
• EINECS: 201-927-5
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Phenols;Phenoles and thiophenoles;Organic Building Blocks;Oxygen Compounds;Phenols;Dyestuff Intermediates
• Mol File: 89-64-5.mol
• Article Data: 138

Chemical Properties

• Melting Point: 85-87 °C(lit.)
• Boiling Point: 242.5 °C at 760 mmHg
• Flash Point: 100.4 °C
• Appearance: yellow powder
• Density: 1.4914 (rough estimate)
• Vapor Pressure: 0.0218mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Solubility: dioxane: soluble0.5g/5mL, clear, faintly yellow to yellow
• PKA: pK1: 6.48 (25°C)
• BRN: 2048031
• CAS DataBase Reference: 4-CHLORO-2-NITROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-NITROPHENOL(89-64-5)
• EPA Substance Registry System: 4-CHLORO-2-NITROPHENOL(89-64-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 89-64-5(Hazardous Substances Data)

Usage

Description

4-Chloro-2-nitrophenol, is a kind of chloronitrophenols (CNPs), being widely used in the synthesis of dyes, drugs and pesticides. Furthermore, it can be used to produce 2-Amino-4-chloro-phenol.It has become a major group of environmental pollutants. 4-Chloro-2-nitrophenol has been detected in various industrial effluents. Therefore, it has also been used as a model compound for evaluation of biodegradation strategy using microbes.

Chemical Properties

yellow powder

Sources

https://microbialcellfactories.biomedcentral.com/articles/10.1186/1475-2859-11-150 https://www.sciencedirect.com/science/article/pii/S0304389407009570 https://www.lookchem.com/4-Chloro-2-nitrophenol/

InChI:InChI=1/C6H4ClNO3/c7-4-1-2-6(9)5(3-4)8(10)11/h1-3,9H/p-1

Synthetic route

4-chloro-phenol (106-48-9) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With dinitrogen tetraoxide; ferric nitrate In acetone Ambient temperature;	99%
With trichloroisocyanuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.25h;	99%
With 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.25h;	99%

4-chloromethoxybenzene (623-12-1) → 4-chloro-2-nitroanisole (89-21-4) + p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With nitric acid In sulfuric acid at 25℃;	A 98.9% B 0.6%

4-bromo-1-methoxy-2-nitrobenzene (33696-00-3) → 4-bromo-2-nitrophenol (7693-52-9) + p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With lithium chloride In N,N-dimethyl-formamide for 4h; Heating;	A 95% B n/a

2-hydroxynitrobenzene (88-75-5) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h;	85%
Stage #1: 2-hydroxynitrobenzene In acetonitrile at 80℃; for 0.166667h; Stage #2: With N-chloro-succinimide In acetonitrile at 80℃; for 8h; regioselective reaction;	80%
beim Chlorieren;

4-chloromethoxybenzene (623-12-1) → 4-chloro-2-nitroanisole (89-21-4) + p-chloro-o-nitrophenol (89-64-5) + 4-chloro-phenol (106-48-9)

Conditions	Yield
With nitric acid In sulfuric acid at 25℃; Rate constant; Product distribution; various acid concentrations, molar ratios;	A 83.4% B 17.5% C 5.4%
With nitric acid In sulfuric acid at 25℃;	A 65.4% B 28% C 9.2%

4-chloro-phenol (106-48-9) → p-chloro-o-nitrophenol (89-64-5) + 4-chloro-4-nitrocyclohexa-2,5-dienone (123871-57-8)

Conditions	Yield
With nitric acid In chloroform at -60℃; for 0.25h; Title compound not separated from byproducts;	A 20% B 80%
With nitric acid; trifluoroacetic anhydride In diethyl ether at -78℃; for 1.5h;	A 66% B 9%

3-Chloronitrobenzene (121-73-3) → 2-chloro-4-nitrophenol (619-08-9) + p-chloro-o-nitrophenol (89-64-5) + 2-chloro-6-nitrophenol (603-86-1)

Conditions	Yield
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h;	A 79% B 1% C 3%
With potassium hydroxide; oxygen In ammonia at -35 - -33℃; for 5h; Product distribution; Mechanism;	A .66 g B n/a C n/a
With Cumene hydroperoxide; potassium tert-butylate In ammonia at -33℃; for 0.25h; Yield given. Yields of byproduct given;

tert.-butylnitrite (540-80-7) + 4-chloro-phenol (106-48-9) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With water In tetrahydrofuran at 25℃; for 2.5h; Schlenk technique;	62%

1-(benzyloxy)-4-chloro-2-nitrobenzene (92044-52-5) → 5-chloro-2-phenyl-1,3-benzoxazole (1019-90-5) + p-chloro-o-nitrophenol (89-64-5) + 4-chloro-2-nitrophenyl benzoate (37593-94-5) + N-(4-chloro-2-hydroxyphenyl)benzamide (3743-12-2)

Conditions	Yield
In isopropyl alcohol for 10h; Irradiation;	A 3% B 2% C 2% D 50%
In isopropyl alcohol for 10h; Product distribution; Mechanism; Irradiation;	A 3% B 3% C 2% D 50%

4-chloro-2-nitrophenyl 4-methylbenzylether (93099-44-6) → p-chloro-o-nitrophenol (89-64-5) + N-(4-methylbenzoyl)-2-amino-4-chloro-phenol + 2-(4-methylphenyl)-5-chlorobenzoxazole (16715-75-6)

Conditions	Yield
In isopropyl alcohol for 11h; Irradiation;	A 3% B 41% C 4%
In isopropyl alcohol for 11h; Product distribution; Mechanism; Irradiation;	A 3% B 41% C 4%

2-hydroxynitrobenzene (88-75-5) → p-chloro-o-nitrophenol (89-64-5) + 2,4-dichloro-6-nitrophenol (609-89-2) + 2-chloro-6-nitrophenol (603-86-1)

Conditions	Yield
With oxone; potassium chloride In acetonitrile at 20℃; for 48h;	A 39% B 18% C 6%

bis(4-chloro-1,2-benzoquinone 2-oximato)copper(II) (81191-50-6, 61721-88-8) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With polymer-supported thiourea In acetone at 20℃; for 24h; Molecular sieve; Inert atmosphere;	5%

methanol (67-56-1) + 4-chlorophenyldiazonium nitrate → p-chloro-o-nitrophenol (89-64-5)

ethanol (64-17-5) + 4-chlorophenyldiazonium nitrate → 1-chloro-4-ethoxybenzene (622-61-7) + p-chloro-o-nitrophenol (89-64-5) + chlorobenzene (108-90-7)

2-Nitroanisole (91-23-6) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With aluminium trichloride; sulfuryl dichloride

4-Fluoro-3-nitroaniline (364-76-1) → p-chloro-o-nitrophenol (89-64-5) + 2-fluoro-5-chloronitrobenzene (345-18-6)

Conditions	Yield
und Zersetzen mit Kupfer und wss.HCl.Diazotization;

2-fluoro-5-chloronitrobenzene (345-18-6) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With sodium hydroxide

3-nitro-4-propoxy-aniline (60569-15-5) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With hydrogenchloride Diazotization.Behandlung mit CuCl in wss. HCl, zuletzt bei 60grad, und Kochen des Reaktionsprodukts mit AlCl3 in Benzol;

4-chloro-2-nitro-benzenesulfonic acid + furan-2,3,5(4H)-trione pyridine (1:1) → p-chloro-o-nitrophenol (89-64-5)

4-amino-2,3-dinitro-phenol → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With Nitrite; acetic acid Diazotization.man kocht das Produkt mit CuCl;

4-chloro-aniline (106-47-8) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With sulfuric acid at 5℃; Diazotization.Erwaermen der Diazoniumsalz-Loesung mit wss. HNO3;

4-amino-2,3-dinitro-phenol + acetic acid (64-19-7) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
bei der Zers. der bei Abwesenheit von Mineralsaeure gewonnenen Diazoverbindung mit CuCl;

chlorobenzene (108-90-7) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; sodium nitrite

2-hydroxynitrobenzene (88-75-5) → p-chloro-o-nitrophenol (89-64-5) + 2-chloro-6-nitrophenol (603-86-1)

Conditions	Yield
With methanol; chlorine

2,5-dichloronitrobenzene (89-61-2) → p-chloro-o-nitrophenol (89-64-5)

Conditions	Yield
With sodium hydroxide
With potassium carbonate
With sodium hydroxide In water at 120 - 150℃; Autoclave;

2.6-dimethylphenol (576-26-1) + 4-chloro-4-nitrocyclohexa-2,5-dienone (123871-57-8) → 2,6-dimethyl-4-nitro phenol (2423-71-4) + p-chloro-o-nitrophenol (89-64-5) + 4-chloro-phenol (106-48-9)

Conditions	Yield
In chloroform-d1; chloroform -60 deg C to rt; Yield given. Yields of byproduct given;

tetranitromethane (509-14-8) + 4-chloromethoxybenzene (623-12-1) → 4-chloro-2-nitroanisole (89-21-4) + p-chloro-o-nitrophenol (89-64-5) + 4-chloro-2,6-dinitrophenol (88-87-9) + 4-chloro-2-(trinitromethyl)anisole (110175-20-7) + cis-4-chloro-5-hydroxy-2-trinitromethylanisole + cis-4-chloro-2-trinitromethyl-5-nitritoanisole

Conditions	Yield
In dichloromethane Product distribution; Irradiation; var. solvent, var.temperature;

3-Chloronitrobenzene (121-73-3) → 2-chloro-4-nitrophenol (619-08-9) + p-chloro-o-nitrophenol (89-64-5) + 2-chloro-6-nitrophenol (603-86-1) + 3,3'-dichloroazoxybenzene (139-24-2, 71297-98-8)

Conditions	Yield
With potassium hydroxide In ammonia at -35 - -33℃; for 5h; Product distribution; Mechanism;	A .34 g B n/a C n/a D .19 g

phenolate (3229-70-7) + 4-chloro-2-nitrophenyl 4-nitrobenzenesulfonate → p-chloro-o-nitrophenol (89-64-5) + Phenyl p-nitrobenzenesulphonate (32337-46-5)

Conditions	Yield
With potassium chloride In 1,4-dioxane; water at 50℃; Rate constant;

1-acetoxy-6-bromohexane (68797-94-4) + p-chloro-o-nitrophenol (89-64-5) → 6-(4-chloro-2-nitrophenoxy)-1-hexanol acetate ester (892413-80-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 60 - 90℃;	100%

p-chloro-o-nitrophenol (89-64-5) → 2-hydroxy-5-chloro-aniline (95-85-2)

Conditions	Yield
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;	99%
With hydrazine hydrate In ethanol at 70℃; for 0.133333h;	96%
With hydrazine hydrate In isopropyl alcohol at 110℃; for 0.2h; Catalytic behavior; Sealed tube; chemoselective reaction;	94%

p-chloro-o-nitrophenol (89-64-5) + 2-bromobutyric acid ethyl ester (533-68-6) → 2-(4-chloro-2-nitro-phenoxy)-butyric acid ethyl ester (57463-15-7)

Conditions	Yield
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%
With potassium carbonate In acetone for 48h; Heating;

p-chloro-o-nitrophenol (89-64-5) + ethyl bromoacetate (105-36-2) → ethyl 4-chloro-2-nitrophenoxyacetate (344443-67-0)

Conditions	Yield
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 24h; Further stages.;	99%
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%
With tetrabutylammomium bromide; potassium carbonate In acetone at 50℃; for 2h;	91%
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 2h;

2-bromo-pentanoic acid ethyl ester (615-83-8) + p-chloro-o-nitrophenol (89-64-5) → C13H16ClNO5 (1225014-17-4)

Conditions	Yield
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromo-pentanoic acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%

p-chloro-o-nitrophenol (89-64-5) + ethyl 2-phenyl-2-bromoacetate (2882-19-1) → C16H14ClNO5 (1225014-18-5)

Conditions	Yield
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl 2-phenyl-2-bromoacetate In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%

p-chloro-o-nitrophenol (89-64-5) + 4-methoxy-benzoyl chloride (100-07-2) → C14H10ClNO5 (1290636-90-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	98%
With triethylamine In diethyl ether
With triethylamine In diethyl ether

p-chloro-o-nitrophenol (89-64-5) → potassium salt of 4-chloro-2-nitrophenol

Conditions	Yield
With potassium hydroxide In dichloromethane; water	98%

formaldehyd (50-00-0) + p-chloro-o-nitrophenol (89-64-5) + 3-Methylpiperidine (626-56-2, 53152-98-0) → 4-chloro-6-(3'-methylpiperidin-1'-ylmethyl)-2-nitrophenol (157831-70-4)

Conditions	Yield
In ethanol at 97℃; Heating;	97%

p-chloro-o-nitrophenol (89-64-5) + allyl bromide (106-95-6) → 1-(allyloxy)-4-chloro-2-nitrobenzene (100246-31-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃; for 24h; Schlenk technique;	97%
With potassium carbonate In acetone for 6h; Heating;

p-chloro-o-nitrophenol (89-64-5) + isopropyl bromide (75-26-3) → 4-chloro-2-isopropoxynitrobenzene (692284-82-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 6h;	97%

p-chloro-o-nitrophenol (89-64-5) + benzoyl chloride (98-88-4) → 4-chloro-2-nitrophenyl benzoate (37593-94-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	97%
With triethylamine In diethyl ether
With triethylamine In diethyl ether
With triethylamine In diethyl ether

methyl 2-bromomethylbenzoate (2417-73-4) + p-chloro-o-nitrophenol (89-64-5) → methyl 2-((4-chloro-2-nitrophenoxy)methyl)benzoate (1451261-90-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	96%

p-chloro-o-nitrophenol (89-64-5) + 3-methoxycarbonylbenzyl bromide (1129-28-8) → methyl 3-((4-chloro-2-nitrophenoxy)methyl)benzoate (1451261-96-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	96%

p-chloro-o-nitrophenol (89-64-5) → 2-bromo-4-chloro-6-nitro-phenol (15969-10-5)

Conditions	Yield
With bromine In water at 20℃; for 0.166667h;	95%
With bromine; acetic acid at 5 - 20℃;	90.9%
With bromine; acetic acid at 5 - 20℃; for 3.5h;	84%
With bromine; acetic acid at 20℃; for 4h; Cooling with ice;	76%
With bromine; acetic acid

p-chloro-o-nitrophenol (89-64-5) + prenyl bromide (870-63-3) → 4-chloro-1-(3'-methylbut-2'-enyloxy)-2-nitrobenzene

Conditions	Yield
With potassium carbonate In acetone Heating;	95%

p-chloro-o-nitrophenol (89-64-5) + benzyl alcohol (100-51-6) → 5-chloro-2-phenyl-1,3-benzoxazole (1019-90-5)

Conditions	Yield
With Au NCs/TiO2 In toluene at 130℃; for 24h; Inert atmosphere;	95%
With 1,1'-bis-(diphenylphosphino)ferrocene In toluene at 150℃; for 24h; Inert atmosphere;	80%

formaldehyd (50-00-0) + p-chloro-o-nitrophenol (89-64-5) + dimethyl amine (124-40-3) → 4-chloro-6-(dimethylaminomethyl)-2-nitrophenol (157831-66-8)

Conditions	Yield
In ethanol at 97℃; Heating;	94%

p-chloro-o-nitrophenol (89-64-5) + benzyl bromide (100-39-0) → 1-(benzyloxy)-4-chloro-2-nitrobenzene (92044-52-5)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 22h;	94%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;

(2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoic acid methyl ester + p-chloro-o-nitrophenol (89-64-5) → (2R,5S)-2-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

Conditions	Yield
With potassium iodide; potassium carbonate In butanone	93%

p-chloro-o-nitrophenol (89-64-5) + glycerol (56-81-5) + 2-hydroxy-5-chloro-aniline (95-85-2) → 5-chloro-8-hydroxyquinoline hydrochloride (25395-13-5)

Conditions	Yield
Stage #1: p-chloro-o-nitrophenol; glycerol; 2-hydroxy-5-chloro-aniline With sulfuric acid; boric acid In water at 120℃; for 5h; Large scale; Stage #2: With hydrogenchloride In water Temperature; Large scale;	92%

p-chloro-o-nitrophenol (89-64-5) + benzaldehyde (100-52-7) → 5-chloro-2-phenyl-1,3-benzoxazole (1019-90-5)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; sulfur at 130℃; for 2h;	92%

N-chloroacetylmorpholine (1440-61-5) + p-chloro-o-nitrophenol (89-64-5) → 2-(4-Chloro-2-nitro-phenoxy)-1-morpholin-4-yl-ethanone (708995-00-0)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 70℃;	91%

p-chloro-o-nitrophenol (89-64-5) + 4-chloro-benzoyl chloride (122-01-0) → C13H7Cl2NO4 (1290636-91-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	91%

tert-butyl 2-(2-(2-hydroxyethoxy)ethoxy)acetate (149299-82-1) + p-chloro-o-nitrophenol (89-64-5) → {2-[2-(4-chloro-2-nitrophenoxy)ethoxy]ethoxy}acetic acid tert-butyl ester (1144518-54-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;	90%

4-tert-Butylbenzaldehyde (939-97-9) + p-chloro-o-nitrophenol (89-64-5) → 5-chloro-2-benzoxazole (5998-48-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; sulfur at 130℃; for 2h;	90%

p-chloro-o-nitrophenol (89-64-5) + 2,2,2-trifluoroethyl trifluoromethanesulphonate (6226-25-1) → 4-chloro-2-nitro-1-(2,2,2-trifluoroethoxy)benzene (99366-81-1)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 3h; Inert atmosphere;	90%
With potassium carbonate In acetone Inert atmosphere;	90%

Upstream product

• 896447-72-6 2-Chloro-4-(trifluoromethyl)nicotinonitrile 
• 896447-13-5 1-hexoxy-1-isopentyloxy-hexane 
• 89643-23-2 GM 53 
• 89642-54-6 AKOS BB-9146 
• 89642-53-5 2-Chloro-6-iodobenzonitrile 
• 89642-50-2 5-BROMO-2-NITROBENZONITRILE 
• 89642-49-9 4-BROMO-3-NITROBENZONITRILE 
• 89642-41-1 1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-one 
• 89642-32-0 2-BROMO-5,6-DICHLOROBENZOTHIAZOLE 
• 896423-15-7 3-Pyridinecarboxamide, 5-hydroxy-N-methyl- 
• 89642-24-0 2-aMino-5-broMo-4-nitrobenzoic acid 
• 89642-23-9 5-bromo-2-nitrobenzamide 
• 89642-21-7 1-(bromomethyl)-2-iodo-4-nitrobenzene 
• 89642-17-1 Benzene, 2-bromo-1-chloro-3-methyl-5-nitro- 

Downstream Products

• 95-85-2 2-Amino-4-chlorophenol 
• 95-25-0 Chlorzoxazone 

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