2835-95-2

Basic information

• Product Name: 5-Amino-o-cresol
• Synonyms: JAROCOL 2M5AP;3-HYDROXY-4-METHYLANILINE;4-AMINO-2-HYDROXYTOLUENE;5-AMINO-2-METHYLPHENOL;5-AMINO-O-CRESOL;2-Hydroxy-4-aminotoluene;2-hydroxy-p-toluidine;2-methyl-5-aminophenol
• CAS NO: 2835-95-2
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• EINECS: 220-618-6
• Product Categories: Intermediates of Dyes and Pigments;Amines;blocks;Aromatic Hydrocarbons (substituted) & Derivatives;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Organic Chemicals;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;Pyridines
• Mol File: 2835-95-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 160-162 °C(lit.)
• Boiling Point: 229.26°C (rough estimate)
• Flash Point: 116.3 °C
• Appearance: Pale brown/Powder
• Density: 1.0877 (rough estimate)
• Vapor Pressure: 0.0232mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.36±0.10(Predicted)
• Water Solubility: 4.11g/L at 20℃
• BRN: 2802317
• CAS DataBase Reference: 5-Amino-o-cresol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-o-cresol(2835-95-2)
• EPA Substance Registry System: 5-Amino-o-cresol(2835-95-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: SJ6090000
• TSCA: Yes
• Hazardous Substances Data: 2835-95-2(Hazardous Substances Data)

Usage

Chemical Properties

Beige crystals

General Description

Brown powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

5-Amino-o-cresol reacts with strong oxidizing agents.

Fire Hazard

Flash point data are not available for 5-Amino-o-cresol, but 5-Amino-o-cresol is probably combustible.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H9NO/c1-5-2-3-6(8)7(9)4-5/h2-4,9H,8H2,1H3

Synthetic route

3-chloro-p-toluidine (95-74-9) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
With copper; copper(l) chloride; sodium hydroxide In ethanol at 175℃; for 4h; Reagent/catalyst; Autoclave; Inert atmosphere; Industrial scale;	85.36%

p-toluidine (106-49-0) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
With dihydrogen peroxide; antimony pentafluoride In hydrogen fluoride at -20℃; for 0.25h; Mechanism; Product distribution;	71%
With dihydrogen peroxide; antimony pentafluoride In hydrogen fluoride at -20℃; for 0.25h;	71%

N-(4-dimethylaminomethyl-3-hydroxyphenyl)acetamide (133914-73-5) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
palladium on activated carbon In potassium hydroxide	68%

2-methyl-5-nitrophenol (5428-54-6) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
With hydrogenchloride; tin
With palladium on activated charcoal; ethyl acetate Hydrogenation;
With sodium hydroxide; sodium dithionite

3-hydroxy-4-methylacetanilide (5307-07-3) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
With hydrogenchloride

2-amino-4-acetylaminotoluene (6375-16-2) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite; hydrochloric acid / anschliessend Verkochen 2: hydrochloric acid View Scheme

N-(2-methylphenyl)acetamide (120-66-1) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; HNO3+H2SO4 / Verseifung der Acetylverbindung 2: concentrated sulfuric acid; water; NaNO2 / Diazotization 3: tin; hydrochloric acid View Scheme

o-toluidine (95-53-4) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid 2: concentrated sulfuric acid; water; NaNO2 / Diazotization 3: tin; hydrochloric acid View Scheme

2-methyl-5-nitroaniline (99-55-8) → amino-4 hydroxy-2 toluene (2835-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; water; NaNO2 / Diazotization 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: (i) aq. NaNO2, H2SO4, (ii) aq. H2SO4 2: N2H4*H2O / Raney-Ni View Scheme

amino-4 hydroxy-2 toluene (2835-95-2) + 4-chloro-benzoyl chloride (122-01-0) → 4-chloro-benzoic acid 5-(4-chloro-benzoylamino)-2-methyl-phenyl ester (929290-81-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 16h;	100%

amino-4 hydroxy-2 toluene (2835-95-2) + m-Chlorobenzoyl chloride (618-46-2) → 3-chloro-benzoic acid 5-(3-chloro-benzoylamino)-2-methyl-phenyl ester (929291-99-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 16h;	100%
With triethylamine In tetrahydrofuran at 20℃; for 16h;

amino-4 hydroxy-2 toluene (2835-95-2) + 3-chloro-4-fluorobenzoyl chloride (65055-17-6) → 3-Chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester (929291-96-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 16h;	100%
With triethylamine In tetrahydrofuran at 20℃; for 16h;
With triethylamine In tetrahydrofuran at 20℃; for 16h;

potassium cyanate (590-28-3) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-hydroxy-4-methyl-phenyl urea (16704-78-2)

Conditions	Yield
With acetic acid In water at 35℃; for 24h;	99%

amino-4 hydroxy-2 toluene (2835-95-2) + 4-chloro-7-methoxy-quinoline-3-carbonitrile (73387-74-3) → 4-(3-hydroxy-4-methyl-phenylamino)-7-methoxy-quinoline-3-carbonitrile

Conditions	Yield
With pyridine hydrochloride In 2-ethoxy-ethanol for 1h; Heating / reflux;	99%
With pyridine hydrochloride In 2-ethoxy-ethanol; water	277 mg (99%)
With pyridine hydrochloride In 2-ethoxy-ethanol; water	277 mg (99 %)

amino-4 hydroxy-2 toluene (2835-95-2) + 2-(7-hydroxy-5,8-dimethyl-1,2,3,4-tetrahydronapthalen-2-yl)propanoic acid (13744-00-8) → N-(3-hydroxy-4-methylphenyl)-2-(7-hydroxy-5,8-dimethyl-1,2,3,4-tetrahydronapthalen-2-yl)propanamide

Conditions	Yield
Stage #1: 2-(7-hydroxy-5,8-dimethyl-1,2,3,4-tetrahydronapthalen-2-yl)propanoic acid With thionyl chloride In benzene Reflux; Stage #2: amino-4 hydroxy-2 toluene With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	98%

amino-4 hydroxy-2 toluene (2835-95-2) + 4-amino-phenol (123-30-8) → N-<-(4'-Hydroxy)-phenyl>-3-amino-6-methyl-benzochinon (30749-78-1)

Conditions	Yield
With CotA-laccase from Bacillus subtilis; oxygen In aq. phosphate buffer; ethanol at 37℃; for 24h; pH=7; Green chemistry; Enzymatic reaction;	98%

amino-4 hydroxy-2 toluene (2835-95-2) → 5-amino-4-iodo-2-methylphenol (388616-53-3)

Conditions	Yield
With hydrogenchloride; potassium iodate; potassium iodide In water at 0 - 25℃; for 1h;	97%
With [K(18-crown-6)]ICl2; calcium carbonate In acetonitrile at 50℃; for 4h; regioselective reaction;	62%

amino-4 hydroxy-2 toluene (2835-95-2) + pivaloyl chloride (3282-30-2) → N-(3-hydroxy-4-methylphenyl)-2,2-dimethylpropionamide (1312305-91-1)

Conditions	Yield
With sodium carbonate In water; ethyl acetate at 20℃; for 1h;	97%
With sodium hydrogencarbonate In water at 0 - 20℃;	96%
Inert atmosphere; Schlenk technique; Alkaline conditions;

2,4-dimethylaniline-5-sulfonic acid (6370-23-6) + amino-4 hydroxy-2 toluene (2835-95-2) → (E)-5-((2-amino-4-hydroxy-5-methylphenyl)diazenyl)-2,4-dimethylbenzenesulfonic acid (1357059-00-7)

Conditions	Yield
Stage #1: 2,4-dimethylaniline-5-sulfonic acid With hydrogenchloride; sodium nitrite at 0℃; for 2h; Stage #2: amino-4 hydroxy-2 toluene With sodium hydroxide In water at 0℃; for 1h; pH=8 - 10; Inert atmosphere;	95%
Stage #1: 2,4-dimethylaniline-5-sulfonic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 2h; Stage #2: amino-4 hydroxy-2 toluene With sodium hydroxide In water at 0℃; pH=8;	76.9%

carbon monoxide (201230-82-2) + amino-4 hydroxy-2 toluene (2835-95-2) + phenylacetylene (536-74-3) → C16H15NO2

Conditions	Yield
With 5-chloro-2-hydroxybenzoic acid; boric acid; palladium diacetate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In acetonitrile at 110℃; under 18100.7 Torr; for 48h;	95%

oxirane (75-21-8) + amino-4 hydroxy-2 toluene (2835-95-2) → 5-(2-hydroxyethylamino)-2-methylphenol (55302-96-0)

Conditions	Yield
With NaY In diethylene glycol dimethyl ether at 150℃; for 3.5h; Reagent/catalyst; Solvent; Green chemistry;	94.1%

2-amino-4-chloropyrimidine (3993-78-0) + amino-4 hydroxy-2 toluene (2835-95-2) → 5-(2-aminopyrimidin-4-ylamino)-2-methylphenol (933045-98-8)

Conditions	Yield
Stage #1: 2-amino-4-chloropyrimidine; amino-4 hydroxy-2 toluene With hydrogenchloride In ethanol; water at 90℃; for 18h; Stage #2: With potassium carbonate In ethanol; water; ethyl acetate Product distribution / selectivity;	94%
With hydrogenchloride In ethanol; water at 80 - 90℃; Product distribution / selectivity;

3-(1-cyanocyclopropyl)benzoyl chloride (1092395-14-6) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide (1092395-08-8)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 5h;	94%

5-bromo-1,3-xylene (556-96-7) + amino-4 hydroxy-2 toluene (2835-95-2) → 5-(3,5-dimethylphenylamino)-2-methylphenol (1198117-30-4)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1h; Inert atmosphere;	94%

3-(1-cyano-1-methylethyl)benzoyl chloride (1092395-13-5) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide (1092395-08-8)

Conditions	Yield
Stage #1: amino-4 hydroxy-2 toluene With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; Stage #2: 3-(1-cyano-1-methylethyl)benzoyl chloride In tetrahydrofuran; water at 20℃; Cooling with ice;	94%

1-chloro-3-methoxy-benzene (2845-89-8) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-[(3-methoxyphenyl)amino]-6-methylphenol (1198117-41-7)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1.16667h; Inert atmosphere;	92%

carbon monoxide (201230-82-2) + amino-4 hydroxy-2 toluene (2835-95-2) + phenylacetylene (536-74-3) → C16H15NO2

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; toluene-4-sulfonic acid In tetrahydrofuran; acetonitrile at 120℃; under 23272.3 Torr; for 72h; regioselective reaction;	92%

4-(pyrrolidin-1-ylsulfonyl)aniline (88327-91-7) + amino-4 hydroxy-2 toluene (2835-95-2) → (E)-5-amino-2-methyl-4-((4-(pyrrolidin-1-ylsulfonyl)phenyl)diazenyl)phenol

Conditions	Yield
Stage #1: 4-(pyrrolidin-1-ylsulfonyl)aniline With hydrogenchloride; isopentyl nitrite In methanol; water; acetonitrile at 0℃; for 1h; Inert atmosphere; Stage #2: amino-4 hydroxy-2 toluene With potassium carbonate In methanol; water; acetonitrile at 0℃; for 1h;	92%

amino-4 hydroxy-2 toluene (2835-95-2) + 4-chloro-6-methoxy-quinoline-3-carbonitrile (13669-62-0) → 4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

Conditions	Yield
With pyridine hydrochloride In 2-ethoxy-ethanol for 1h; Heating / reflux;	91%
With pyridine hydrochloride In 2-ethoxy-ethanol; water	278.3 mg (91%)
With pyridine hydrochloride In 2-ethoxy-ethanol; water	278.3 mg (91 %)

3-methoxyphenyl bromide (2398-37-0) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-[(3-methoxyphenyl)amino]-6-methylphenol (1198117-41-7)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1h; Inert atmosphere;	91%

amino-4 hydroxy-2 toluene (2835-95-2) + benzoyl chloride (98-88-4) → N-(3-hydroxy-4-methylphenyl)benzamide (92199-49-0)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 0℃; for 2h; Inert atmosphere; Schlenk technique;	91%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.5h;	81%

ethyl 2-phenyldiazoacetate (22065-57-2) + amino-4 hydroxy-2 toluene (2835-95-2) → ethyl 2-((3-hydroxy-4-methylphenyl)amino)-2-phenylacetate

Conditions	Yield
With C43H37Br2CuN3P2(1+)*ClO4(1-) In methanol at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique; chemoselective reaction;	91%

4-Nitrophthalonitrile (31643-49-9) + amino-4 hydroxy-2 toluene (2835-95-2) → 4-(5-amino-2-methylphenoxy)phthalonitrile

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 65℃; for 6h; Inert atmosphere;	90.8%

amino-4 hydroxy-2 toluene (2835-95-2) + 4-chloro-6-fluoro-[1,7]naphthyridine-3-carbonitrile (305371-18-0) → 6-fluoro-4-(3-hydroxy-4-methyl-phenylamino)-[1.7]naphthyridine-3-carbonitrile

Conditions	Yield
In ethanol for 16h;	90%
In ethanol for 16h;	90%

amino-4 hydroxy-2 toluene (2835-95-2) + 4-chloro-6-(4-nitrophenyl)furo[2,3-d]pyrimidine (475585-11-6) → 2-methyl-5-{[6-(4-nitrophenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenol (475585-19-4)

Conditions	Yield
In butan-1-ol for 3h; Heating;	89%

3,5-dimethylphenyl iodide (22445-41-6) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-(3,5-dimethylphenoxy)-4-methylaniline (1198117-28-0)

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;	87%

4-(4-aminophenyl)thiomorpholine 1,1-dioxide (105297-10-7) + amino-4 hydroxy-2 toluene (2835-95-2) → (E)-4-(4-((2-amino-4-hydroxy-5-methylphenyl)diazenyl)phenyl)thiomorpholine 1,1-dioxide

Conditions	Yield
Stage #1: 4-(4-aminophenyl)thiomorpholine 1,1-dioxide With hydrogenchloride; isopentyl nitrite In methanol; water; acetonitrile at 0℃; for 1h; Inert atmosphere; Stage #2: amino-4 hydroxy-2 toluene With potassium carbonate In methanol; water; acetonitrile at 0℃; for 1h;	87%

2-chloropyrimidin-4-amine (7461-50-9) + amino-4 hydroxy-2 toluene (2835-95-2) → 5-(4-aminopyrimidin-2-ylamino)-2-methylphenol (933045-96-6)

Conditions	Yield
Stage #1: 2-chloropyrimidin-4-amine; amino-4 hydroxy-2 toluene With hydrogenchloride In ethanol; water at 90℃; for 18h; Stage #2: With potassium carbonate In ethanol; water; ethyl acetate Product distribution / selectivity;	86%
With hydrogenchloride In ethanol; water at 80 - 90℃; Product distribution / selectivity;

1-Chloro-4-fluorobenzene (352-33-0) + amino-4 hydroxy-2 toluene (2835-95-2) → 3-[(4-fluorophenyl)amino]-6-methylphenol (1198117-37-1)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1.16667h; Inert atmosphere;	86%

Upstream product

• 5307-07-3 3-hydroxy-4-methylacetanilide 
• 99-55-8 2-methyl-5-nitroaniline 
• 133914-73-5 N-(4-dimethylaminomethyl-3-hydroxyphenyl)acetamide 
• 95-74-9 3-chloro-p-toluidine 
• 95-53-4 o-toluidine 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 6375-16-2 2-amino-4-acetylaminotoluene 
• 106-49-0 p-toluidine 
• 5428-54-6 2-methyl-5-nitrophenol 

Downstream Products

• 77994-62-8 N-(3-hydroxy-4-methyl-phenyl)-α-D-ribopyranosylamine 
• 16704-78-2 3-hydroxy-4-methyl-phenyl urea 
• 55303-61-2 C₁₉H₂₆N₄O₃S 
• 55303-66-7 C₁₈H₂₂N₄O₂ 
• 55302-72-2 C₁₇H₂₁N₃O₃ 
• 55303-58-7 C₁₈H₂₃N₃O₄ 
• 56330-85-9 5-Amino-2-methyl-4-[(E)-3-methyl-4-methylamino-phenylimino]-cyclohexa-2,5-dienone 
• 56330-38-2 5-Amino-4-[(Z)-4-(2-hydroxy-ethylamino)-3-methoxy-phenylimino]-2-methyl-cyclohexa-2,5-dienone 
• 723290-46-8 4-tert-butyl-N-(3-hydroxy-4-methyl-phenyl)-benzenesulfonamide 
• 723256-66-4 N-(3-hydroxy-4-methyl-phenyl)-4-methoxy-benzenesulfonamide 
• 783324-13-0 4-bromo-N-(3-hydroxy-4-methyl-phenyl)-benzenesulfonamide 
• 847833-00-5 3-[1-(2-chloro-ethyl)-2-methyl-propoxy]-4-methyl-phenylamine 
• 183803-06-7 3-hydroxy-4-methyliodobenzene 

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