5428-54-6

Basic information

• Product Name: 2-Methyl-5-nitrophenol
• Synonyms: Phenol, 2-methyl-5-nitro-;5-NITRO-2-CRESOL;5-NITRO-2-METHYL PHENOL;5-NITRO-O-CRESOL;4-NITRO-2-HYDROXYTOLUENE;2-HYDROXY-4-NITROTOLUENE;2-METHYL-4-NITROPHENOL;2-METHYL-5-NITROPHENOL
• CAS NO: 5428-54-6
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• EINECS: 226-580-7
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;hair dye intermediate
• Mol File: 5428-54-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 111-115 °C(lit.)
• Boiling Point: 180 °C / 15mmHg
• Flash Point: 134.2 °C
• Appearance: /
• Density: 1.32 g/cm³
• Vapor Pressure: 8.52E-10mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.68±0.19(Predicted)
• CAS DataBase Reference: 2-Methyl-5-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-nitrophenol(5428-54-6)
• EPA Substance Registry System: 2-Methyl-5-nitrophenol(5428-54-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• RIDADR: UN 2446 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5428-54-6(Hazardous Substances Data)

Usage

Uses

2-Methyl-5-nitrophenol is used as a reactant in the preparation of pyranocarbazole alkaloids.

Chemical Properties

Brown solid

InChI:InChI=1/C18H19Cl2NO4/c1-2-24-18(23)11-3-5-21(6-4-11)9-12-10-25-17-14(16(12)22)7-13(19)8-15(17)20/h7-8,10-11H,2-6,9H2,1H3

Synthetic route

2-methyl-5-nitroaniline (99-55-8) → 2-methyl-5-nitrophenol (5428-54-6)

Conditions	Yield
With sulfuric acid; sodium nitrite In water for 0.333333h; Heating;	93%
With sulfuric acid; sodium nitrite In water Heating;	87%
Diazotization.Reaktion ueber mehrere Stufen;

5-Nitroso-o-kresol (21565-00-4) → 2-methyl-5-nitrophenol (5428-54-6)

Conditions	Yield
With sodium hydroxide; water; dihydrogen peroxide; sodium tungstate for 3h;	61%

2-methyl-5-nitroaniline (99-55-8) → 2-methyl-5-nitrophenol (5428-54-6) + 6-nitroindazole (7597-18-4)

Conditions	Yield
With sulfuric acid; water; sodium nitrite Diazotization;

sulfuric acid (7664-93-9) + 2-methyl-5-nitroaniline (99-55-8) + sodium nitrite → 2-methyl-5-nitrophenol (5428-54-6) + 6-nitroindazole (7597-18-4)

Conditions	Yield
Diazotization;

sulfuric acid (7664-93-9) + di-o-tolyl carbonate (617-09-4) + nitric acid (7697-37-2) → 2-methyl-4-nitrophenol (99-53-6) + 2-methyl-5-nitrophenol (5428-54-6) + 2-methyl-6-nitrophenol (13073-29-5)

Conditions	Yield
at -15 - 0℃; Kochen des Reaktionsprodukts mit wss. K2CO3-Loesung;

N-(2-methyl-5-nitro-phenyl)-N'-p-tolyl-triazene + acid → 2-methyl-5-nitrophenol (5428-54-6) + p-toluidine (106-49-0) + nitrogen

hydrogenchloride (7647-01-0) + N-(2-methyl-5-nitro-phenyl)-N'-o-tolyl-triazene (861519-76-8) → 2-methyl-5-nitrophenol (5428-54-6) + o-toluidine (95-53-4) + nitrogen

sulfuric acid (7664-93-9) + N-(2-methyl-5-nitro-phenyl)-N'-o-tolyl-triazene (861519-76-8) → 2-methyl-5-nitrophenol (5428-54-6) + o-toluidine (95-53-4) + nitrogen

N-(2-methyl-5-nitro-phenyl)-N'-o-tolyl-triazene (861519-76-8) + acetic acid (64-19-7) → 2-methyl-5-nitrophenol (5428-54-6) + o-toluidine (95-53-4) + nitrogen

hydrogenchloride (7647-01-0) + N-(2-methyl-5-nitro-phenyl)-N'-o-tolyl-triazene (861519-76-8) + β-naphthol (135-19-3) → 2-methyl-5-nitrophenol (5428-54-6) + o-toluidine (95-53-4) + pigment orange 3 (6410-15-7) + nitrogen

o-toluidine (95-53-4) + ester of glycine → 2-methyl-5-nitrophenol (5428-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / conc. HNO3, conc. H2SO4 / 2 - 5 °C 2: 1.) H2SO4, NaNO2 / 1.) 2-5 deg C, 2.) heating View Scheme

N-(2-methylphenyl)acetamide (120-66-1) → 2-methyl-5-nitrophenol (5428-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; HNO3+H2SO4 / Verseifung der Acetylverbindung 2: concentrated sulfuric acid; water; NaNO2 / Diazotization View Scheme

o-toluidine (95-53-4) → 2-methyl-5-nitrophenol (5428-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: concentrated sulfuric acid; water; NaNO2 / Diazotization View Scheme

2,4-dinitrotoluene (121-14-2) → 2-methyl-5-nitrophenol (5428-54-6) + 4-Methyl-3-nitroanilin (119-32-4) + 2-methyl-5-nitroaniline (99-55-8)

Conditions	Yield
With hydrogen In methanol at 36℃; under 760.051 Torr; for 0.25h;

2-methyl-5-nitrophenol (5428-54-6) + acetic anhydride (108-24-7) → 2-acetoxy-4-nitrotoluene (54362-24-2)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.666667h;	100%
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	99%
With pyridine at 20℃; for 6h;	91%
With pyridine at 0 - 20℃; for 6h;	91%
With pyridine at 20℃; for 24h;	86%

1-iodohexadecane (544-77-4) + 2-methyl-5-nitrophenol (5428-54-6) → 2-hexadecyloxy-4-nitrotoluene (915711-10-3)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran Reflux;	100%
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran at 80℃;	95%

2-methyl-5-nitrophenol (5428-54-6) → 2-acetoxy-4-nitrotoluene (54362-24-2)

Conditions	Yield
With acetic anhydride; sodium hydroxide In water at 20℃; for 0.666667h;	100%

2-methyl-5-nitrophenol (5428-54-6) → 3-acetoxy-4-methylaniline (61995-11-7) + 2-acetoxy-4-nitrotoluene (54362-24-2)

Conditions	Yield
With sodium hydroxide; acetic anhydride; palladium In ethyl acetate	A 94% B 100%
With sodium hydroxide; acetic anhydride	A 94% B 100%

2-methyl-5-nitrophenol (5428-54-6) + tert-butylchlorodiphenylsilane (58479-61-1) → 3-tert-butyldiphenylsilyloxy-4-methylnitrobenzene

Conditions	Yield
Stage #1: 2-methyl-5-nitrophenol With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: tert-butylchlorodiphenylsilane In N,N-dimethyl-formamide at 20℃; for 4h;	100%
With 1H-imidazole In dichloromethane at 20℃; for 5h;	88%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; under 3750.38 Torr; for 4h;
With 1H-imidazole In dichloromethane

2-methyl-5-nitrophenol (5428-54-6) + ethyl iodide (75-03-6) → 2-ethoxy-1-methyl-4-nitrobenzene (2486-63-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; Inert atmosphere;	100%
With potassium carbonate In acetone for 48h; Reflux;

2-methyl-5-nitrophenol (5428-54-6) + benzyl bromide (100-39-0) → 2-(benzyloxy)-1-methyl-4-nitrobenzene (219492-11-2)

Conditions	Yield
With potassium carbonate In acetone for 2h; Inert atmosphere; Reflux;	99%
With potassium carbonate In acetonitrile at 80℃; for 2h;	97%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	90%
With sodium carbonate In acetone	1.06 g (33%)

2-methyl-5-nitrophenol (5428-54-6) + 5-fluoro-2-nitrobenzoic acid (320-98-9) → 5-(2-methyl-5-nitrophenoxy)-2-nitrobenzoic acid (878743-92-1)

Conditions	Yield
Stage #1: 2-methyl-5-nitrophenol; 5-fluoro-2-nitrobenzoic acid With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 48h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide	99%

2-methyl-5-nitrophenol (5428-54-6) + chloroacetone (78-95-5) → 4-Methyl-1-nitro-3-(2'-oxopropyloxy)benzene (107188-56-7)

Conditions	Yield
With potassium carbonate In acetone Heating;	98%

2-methyl-5-nitrophenol (5428-54-6) + 3-chloro-2-butanone (4091-39-8) → 1-methyl-2-(1-methyl-2-oxoprop-1-yloxy)-4-nitrobenzene (203940-76-5)

Conditions	Yield
With potassium carbonate In acetone for 10h; Heating;	98%

2-methyl-5-nitrophenol (5428-54-6) → 2-chloro-6-methyl-3-nitro-phenol (39183-20-5)

Conditions	Yield
With chlorine In chloroform for 0.5h; Heating;	96%
With chloroform; chlorine

2-methyl-5-nitrophenol (5428-54-6) + methyl iodide (74-88-4) → 2-methyl-5-nitroanisole (13120-77-9)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In water; toluene at 20℃;	96%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; Inert atmosphere;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 9h;	74%
With potassium carbonate In acetone for 5h; Heating / reflux;	72%

2-methyl-5-nitrophenol (5428-54-6) + 1-iodo-propane (107-08-4) → 1-methyl-4-nitro-2-n-propoxybenzene (854256-33-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; Inert atmosphere;	96%

2-methyl-5-nitrophenol (5428-54-6) + phenoxyethyl bromide (589-10-6) → 1-methyl-4-nitro-2-(2-phenoxyethoxy)benzene

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃;	96%

2-methyl-5-nitrophenol (5428-54-6) + 2-propynyl chloride (624-65-7) → 4-methyl-1-nitro-3-propargyloxybenzene (136187-53-6)

Conditions	Yield
With potassium carbonate In acetone Heating;	95%

2-methyl-5-nitrophenol (5428-54-6) + 1,1-dimethyl-2-propynyl trifluoroacetate (61570-79-4) → 1-methyl-2-[(2-methylbut-3-yn-2-yl)oxy]-4-nitrobenzene (184896-34-2)

Conditions	Yield
With copper(II) choride dihydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -10 - 20℃; Inert atmosphere;	95%
With copper(II) chloride dihydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; for 7h;

1-iodo-butane (542-69-8) + 2-methyl-5-nitrophenol (5428-54-6) → 2-butoxy-1-methyl-4-nitrobenzene (57264-52-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; Inert atmosphere;	93%

2-methyl-5-nitrophenol (5428-54-6) + isopropyl bromide (75-26-3) → 2-isopropyloxy-1-methyl-4-nitrobenzene (136187-51-4)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 90℃; for 2.5h;	92%

2-methyl-5-nitrophenol (5428-54-6) + 2-methyl-but-3-yn-2-ol (115-19-5) → 1-methyl-2-[(2-methylbut-3-yn-2-yl)oxy]-4-nitrobenzene (184896-34-2)

Conditions	Yield
Stage #1: 2-methyl-but-3-yn-2-ol With 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride In acetonitrile at -10℃; Inert atmosphere; Stage #2: 2-methyl-5-nitrophenol With copper(II) choride dihydrate at -10 - 20℃; Inert atmosphere;	92%

2-methyl-5-nitrophenol (5428-54-6) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethyl(2-methyl-5-nitrophenoxy)silane (1226973-96-1)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;	91%

triisopropylsilyl chloride (13154-24-0) + 2-methyl-5-nitrophenol (5428-54-6) → 4-methyl-3-(triisopropylsilyloxy)aniline (582322-76-7)

Conditions	Yield
Stage #1: triisopropylsilyl chloride; 2-methyl-5-nitrophenol With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 21h; Inert atmosphere; Stage #2: With iron; acetic acid at 40℃; for 4h;	90%

2-methyl-5-nitrophenol (5428-54-6) + 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate (141699-59-4) → 4-(2-methyl-5-nitrophenoxy)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 85℃;	89%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	89%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	89%
With potassium carbonate In N,N-dimethyl-formamide at 90℃;

2-methyl-5-nitrophenol (5428-54-6) + benzyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate (14000-67-0) → benzyl 4-[2-(2-methyl-5-nitrophenoxy)ethyl]piperazine-1-carboxylate (1257423-70-3)

Conditions	Yield
Stage #1: 2-methyl-5-nitrophenol; benzyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate With triphenylphosphine In tetrahydrofuran at 0℃; for 0.166667h; Mitsunobu reaction; Inert atmosphere; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Mitsunobu reaction; Inert atmosphere;	86%

2-methyl-5-nitrophenol (5428-54-6) + dimethyl sulfate (77-78-1) → 2-methyl-5-nitroanisole (13120-77-9)

Conditions	Yield
With sodium hydroxide In water at 70 - 75℃; for 2h;	86%

1-bromo-butane (109-65-9) + 2-methyl-5-nitrophenol (5428-54-6) → 2-butoxy-1-methyl-4-nitrobenzene (57264-52-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 4h; Heating;	81%
With sodium ethanolate

3-chloro-3-methylbut-1-yne (1111-97-3) + 2-methyl-5-nitrophenol (5428-54-6) → 1-methyl-2-[(2-methylbut-3-yn-2-yl)oxy]-4-nitrobenzene (184896-34-2)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 82℃; for 48h;	81%
With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 70℃;	80%

2-methyl-5-nitrophenol (5428-54-6) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 3-(2,2-Diethoxyethoxy)-4-methylnitrobenzene (185684-93-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 153℃; for 3.5h;	81%
With potassium carbonate In N,N-dimethyl-formamide at 153℃;	81%
With potassium carbonate In N,N-dimethyl-formamide for 3.5h; Reflux;	81%

2-methyl-5-nitrophenol (5428-54-6) + sodium chlorodifluoroacetate (1895-39-2) → 2-(difluoromethoxy)-1-methyl-4-nitrobenzene

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	81%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2-methyl-5-nitrophenol (5428-54-6) → 2-(2,2-dimethoxyethoxy)-1-methyl-4-nitrobenzene (603305-53-9)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 2.5h; Heating / reflux;	77%
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 2.5h; Heating / reflux;	77%

Upstream product

• 99-55-8 2-methyl-5-nitroaniline 
• 21565-00-4 5-Nitroso-o-kresol 
• 121-14-2 2,4-dinitrotoluene 
• 95-53-4 o-toluidine 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 7647-01-0 hydrogenchloride 
• 861519-76-8 N-(2-methyl-5-nitro-phenyl)-N'-o-tolyl-triazene 
• 135-19-3 β-naphthol 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 617-09-4 di-o-tolyl carbonate 
• 7697-37-2 nitric acid 

Downstream Products

• 57264-52-5 2-butoxy-1-methyl-4-nitrobenzene 
• 100496-39-7 sulfuric acid mono-(2-methyl-5-nitro-phenyl ester) 
• 128988-95-4 (2-chloro-ethyl)-(2-methyl-5-nitro-phenyl)-ether 
• 54362-24-2 2-acetoxy-4-nitrotoluene 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 2835-95-2 amino-4 hydroxy-2 toluene 
• 39183-20-5 2-chloro-6-methyl-3-nitro-phenol 
• 219492-11-2 2-(benzyloxy)-1-methyl-4-nitrobenzene 
• 854256-33-0 1-methyl-4-nitro-2-n-propoxybenzene 
• 136187-53-6 4-methyl-1-nitro-3-propargyloxybenzene 
• 61995-03-7 2-Methyl-5-p-tolylazo-phenol 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 19240-94-9 3-chloro-2-methoxy-4-nitrotoluene 
• 678969-95-4 3-chloro-2-methoxy-4-nitrobenzaldehyde 

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