122455-84-9

Basic information

• Product Name: 4-FLUORO-6-METHYL-3-NITROPHENOL
• Synonyms: 4-FLUORO-6-METHYL-3-NITROPHENOL;4-Fluoro-5-nitro-o-cresol (OH=1);4-Fluoro-2-methyl-5-nitrophenol;5-Fluoro-2-hydroxy-4-nitrotoluene, 4-Fluoro-5-nitro-o-cresol
• CAS NO: 122455-84-9
• Molecular Formula: C₇H₆FNO₃
• Molecular Weight: 171.13
• Mol File: 122455-84-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 138-142 °C
• Boiling Point: 325.1°Cat760mmHg
• Flash Point: 150.4°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.571
• PKA: 8.55±0.24(Predicted)
• CAS DataBase Reference: 4-FLUORO-6-METHYL-3-NITROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUORO-6-METHYL-3-NITROPHENOL(122455-84-9)
• EPA Substance Registry System: 4-FLUORO-6-METHYL-3-NITROPHENOL(122455-84-9)

Safety Data

• Hazardous Substances Data: 122455-84-9(Hazardous Substances Data)

Usage

General Description

4-FLUORO-6-METHYL-3-NITROPHENOL is a chemical compound that contains a phenol group with a fluoride and methyl substituent as well as a nitro group attached to the aromatic ring. 4-FLUORO-6-METHYL-3-NITROPHENOL is used in various industrial applications such as in the synthesis of pharmaceuticals, agrochemicals, and dyes. It is known for its aromatic and slightly yellow crystalline appearance. The chemical properties of 4-FLUORO-6-METHYL-3-NITROPHENOL make it a useful building block in the production of other organic compounds, and it is also used in research and development in the chemical industry. It is important to handle this compound with care as it may have hazardous effects if not used properly.

InChI:InChI=1/C7H6FNO3/c1-4-2-5(8)6(9(11)12)3-7(4)10/h2-3,10H,1H3

Synthetic route

carbonic acid 4-fluoro-2-methyl-5-nitro-phenyl ester methyl ester (123401-18-3) → 2-methyl-4-fluoro-5-nitrophenol (122455-84-9)

Conditions	Yield
With ammonia In water at 20℃; for 1h;	100%
With water; sodium hydroxide for 2h; Reflux;	93%
With boron tribromide In dichloromethane at 0 - 20℃; for 18h;	85%

(4-fluoro-2-methylphenyl)methylcarbonate (122455-86-1) → 2-methyl-4-fluoro-5-nitrophenol (122455-84-9)

Conditions	Yield
With sulfuric acid; nitric acid at 50℃; for 2h; Nitration; Deacetylation;	22%
With nitric acid In sulfuric acid; water	22%
With nitric acid In sulfuric acid; water	22%

→ 2-methyl-4-fluoro-5-nitrophenol (122455-84-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / pyridine / dioxane / 0 - 20 °C 2: 90 percent / HNO3; H2SO4 / 0.5 h / 0 °C 3: 85 percent / BBr3 / CH2Cl2 / 18 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: 78 percent / aq. NaOH / 2 h / 0 °C 2: 22 percent / HNO3; H2SO4 / 2 h / 50 °C View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) + methyl iodide (74-88-4) → 1-fluoro-4-methoxy-5-methyl-2-nitro-benzene (134882-63-6)

Conditions	Yield
With sodium carbonate In acetone at 20℃;	100%
With sodium carbonate In acetone at 20℃;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	93%

benzyl bromide (100-39-0) + 2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 5-benzyloxy-2-fluoro-4-methyl-1-nitrobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	89%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 4h;	89%

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → 4-fluoro-2-methyl-5-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Conditions	Yield
With boron trifluoride diethyl etherate; triethylamine In dichloromethane at 40℃; for 48.5h; Inert atmosphere;	88%

isopropyl alcohol (67-63-0) + 2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 4-fluoro-2-methyl-5-nitrophenyl 1-methylethyl ether (932374-99-7)

Conditions	Yield
Stage #1: isopropyl alcohol; 2-methyl-4-fluoro-5-nitrophenol With 2-(diphenylphosphino)pyridine; di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 20℃; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether for 1h;	63%

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 2-fluoro-5-hydroxy-4-methylaniline (122455-85-0)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol under 1551.49 Torr; for 2h;	62%
With iron; iron(II) sulfate In water for 4h; Reduction; Heating;	47%
With iron; iron(II) sulfate In water for 4h; Heating / reflux;	47%

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 6-cyano-4-(2-fluoro-5-hydroxy-4-methylanilino)-7-(2-methoxyethoxy)quinoline hydrochloride (205447-27-4)

Conditions	Yield
With iron; iron(II) sulfate In water for 4h; Heating / reflux;	47%

iron (7439-89-6) + iron(II) sulfate + 2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 2-fluoro-5-hydroxy-4-methylaniline (122455-85-0)

Conditions	Yield
In water	47%
In water	47%
In water	47%

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 5-fluoro-2-methoxy-4-nitrobenzaldehyde (678969-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / K2CO3 / acetone / 1 h / Heating 2: CrO3; H2SO4; AcOH / 0 - 10 °C 3: aq. HCl / dioxane / Heating View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 2-fluoro-5-methoxy-4-oxazol-5-yl-phenylamine

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / K2CO3 / acetone / 1 h / Heating 2: CrO3; H2SO4; AcOH / 0 - 10 °C 3: aq. HCl / dioxane / Heating 4: K2CO3 / methanol / Heating 5: H2 / Pd/C / ethanol / 2068.59 Torr View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 5-(5-fluoro-2-methoxy-4-nitrophenyl)oxazole (678969-89-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / K2CO3 / acetone / 1 h / Heating 2: CrO3; H2SO4; AcOH / 0 - 10 °C 3: aq. HCl / dioxane / Heating 4: K2CO3 / methanol / Heating View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → acetic acid acetoxy-(5-fluoro-2-methoxy-4-nitro-phenyl)-methyl ester (678969-87-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K2CO3 / acetone / 1 h / Heating 2: CrO3; H2SO4; AcOH / 0 - 10 °C View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 4-(2-fluoro-5-hydroxy-4-methylanilino)-6,7-dimethoxyquinazoline hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: 47 percent / Fe; FeSO4 / H2O / 4 h / Heating 2: HCl / propan-2-ol / 4 h / 80 °C View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 4-(3,3-dimethylbutyrylamino)-5-fluoro-2-methoxy-N-thiazol-2-ylbenzamide (1262897-90-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 1.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / ethanol; acetic acid 3: pyridine / 1,2-dichloro-ethane / 3 h / 20 °C 4: pyridine; potassium permanganate; water / 18 h / 90 °C 5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 48 h / 20 °C View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → N-(2-fluoro-5-methoxy-4-methylphenyl)-3,3-dimethylbutyramide (1262897-93-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 1.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / ethanol; acetic acid 3: pyridine / 1,2-dichloro-ethane / 3 h / 20 °C View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 4-(3,3-dimethylbutyrylamino)-5-fluoro-2-methoxybenzoic acid (1262898-01-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 1.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / ethanol; acetic acid 3: pyridine / 1,2-dichloro-ethane / 3 h / 20 °C 4: pyridine; potassium permanganate; water / 18 h / 90 °C View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 3-(5-methyl-2-nitro-4-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenoxy)benzonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 48.5 h / 40 °C / Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 24 h / 40 °C / Inert atmosphere 2.2: pH 9 - 10 View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → N-(2-[4-(α-D-mannopyranosyloxy)-5-methyl-2-nitrophenoxy]phenyl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 48.5 h / 40 °C / Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 24 h / 25 °C / Inert atmosphere 2.2: pH 9 - 10 View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 4-[4-(α-D-mannopyranosyloxy)-5-methyl-2-nitrophenoxy]benzonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 48.5 h / 40 °C / Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 48 h / 25 - 40 °C / Inert atmosphere 2.2: pH 9 - 10 View Scheme

2-methyl-4-fluoro-5-nitrophenol (122455-84-9) → 2-[4-(α-D-mannopyranosyloxy)-5-methyl-2-nitrophenoxy]benzonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 48.5 h / 40 °C / Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 96 h / 25 - 40 °C / Inert atmosphere 2.2: pH 9 - 10 View Scheme

Upstream product

• 122455-86-1 (4-fluoro-2-methylphenyl)methylcarbonate 
• 452-72-2 4-fluoro-2-methylphenol 
• 123401-18-3 carbonic acid 4-fluoro-2-methyl-5-nitro-phenyl ester methyl ester 

Downstream Products

• 122455-85-0 2-fluoro-5-hydroxy-4-methylaniline 
• 1262898-01-0 4-(3,3-dimethylbutyrylamino)-5-fluoro-2-methoxybenzoic acid 
• 1262897-93-7 N-(2-fluoro-5-methoxy-4-methylphenyl)-3,3-dimethylbutyramide 
• 1262897-90-4 4-(3,3-dimethylbutyrylamino)-5-fluoro-2-methoxy-N-thiazol-2-ylbenzamide 
• 932374-99-7 4-fluoro-2-methyl-5-nitrophenyl 1-methylethyl ether 
• 205447-27-4 6-cyano-4-(2-fluoro-5-hydroxy-4-methylanilino)-7-(2-methoxyethoxy)quinoline hydrochloride 
• 678969-87-4 acetic acid acetoxy-(5-fluoro-2-methoxy-4-nitro-phenyl)-methyl ester 
• 678969-89-6 5-(5-fluoro-2-methoxy-4-nitrophenyl)oxazole 
• 678969-88-5 5-fluoro-2-methoxy-4-nitrobenzaldehyde 
• 134882-63-6 1-fluoro-4-methoxy-5-methyl-2-nitro-benzene 

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