3096-71-7

Basic information

• Product Name: 4-Amino-2,5-dimethylphenol
• Synonyms: 4-Amino-2,5-dimethylphenol technical grade;4-AMINO-2,5-XYLENOL;4-AMINO-2,5-DIMETHYLPHENOL;4-AMINO-2,5-DIMETHYLPHENOL, TECH.;2,5-Dimethyl-4-aminophenol;4-Amino-2,5-dimethylphenol,95%;2,5-dimethyl-4-hydroxy aniline;4-azanyl-2,5-dimethyl-phenol
• CAS NO: 3096-71-7
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 221-449-0
• Product Categories: Phenoles and thiophenoles;API intermediates
• Mol File: 3096-71-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 242-243 °C(lit.)
• Boiling Point: 288.4 °C at 760 mmHg
• Flash Point: 128.2 °C
• Appearance: White to beige/Powder
• Density: 1.118 g/cm³
• Vapor Pressure: 0.00135mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: pK1: 5.28(+1);pK2: 10.40(0) (25°C)
• Stability: Stable. Incompatible with acids, chloroformates, acid anhydrides, acid chlorides, strong oxidizing agents.
• CAS DataBase Reference: 4-Amino-2,5-dimethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2,5-dimethylphenol(3096-71-7)
• EPA Substance Registry System: 4-Amino-2,5-dimethylphenol(3096-71-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3096-71-7(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

4-Amino-2,5-dimethylphenol may be used in chemical synthesis studies.

InChI:InChI=1/C8H11NO/c1-5-4-8(10)6(2)3-7(5)9/h3-4,10H,9H2,1-2H3

Synthetic route

2,5-dimethyl-p-benzoquinone 4-oxime (2593-53-5) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In dichloromethane; water for 16h; Reagent/catalyst; Reflux;	81%
With hydrogenchloride; tin
With hydrogen sulfide in ammoniakalischer Loesung;
With hydrogenchloride; tin(ll) chloride In dichloromethane; water for 24h; Reflux;

2,5-Dimethylphenol (95-87-4) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With sodium hydroxide; 4-sulfo-benzenediazonium-(1)-salt anschliessend Erwaermen der Reaktionsloesung mit Natriumdithionit;
Multi-step reaction with 3 steps 1: KOH / ethanol 2: HNO3, AcOH 3: H2 / Pd-C / ethanol View Scheme
Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / ethanol; water / 1 h / 0 °C 2: hydrogenchloride; tin(ll) chloride / water; dichloromethane / 16 h / Reflux View Scheme

mononitro-p-xylene (89-58-7) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With sulfuric acid Electrolysis.Reduktion;
With sulfuric acid In ethanol at 90℃; (electrochemical reduction);

N-(2,5-dimethylphenyl)hydroxylamine (3096-64-8) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With sulfuric acid In water at 25℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);
With sulfuric acid in Kohlendioxyd-Atmosphaere;

2,4-Xylidine (95-68-1) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With sulfuric acid bei der elektrolytischen Oxydation an Platin-Anoden;

4-nitro-2,5-xylenol (3139-05-7) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

2,5-Dimethyl-4-nitro-phenyl-benzylether (19499-98-0) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

N-(2,5-dimethylphenyl)hydroxylamine (3096-64-8) → 4-chloro-2,5-dimethylaniline (20782-94-9) + 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With perchloric acid; sodium perchlorate; sodium chloride In water; acetonitrile at 25℃; Rate constant;

sulfuric acid (7664-93-9) + 2,4-Xylidine (95-68-1) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
bei der elektrolytischen Oxydation an Platin-Anoden.Electrolysis;

ethanol (64-17-5) + 2,5-dimethylphenyl azide (35774-21-1) + sulfuric acid (7664-93-9) → 2,5-dimethylhydroquinone (615-90-7) + 2,5-dimethyl-4-amino phenol (3096-71-7)

2.5-dimethyl-benzoquinone-(1.4)-mono- → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With titanium(III) chloride; water

2-azido-p-xylene → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With sulfuric acid
With sulfuric acid
With sulfuric acid

4-oxy-2.5-dimethyl-acetophenone oxime → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + 2,5-dimethyl-p-benzoquinone 4-oxime (2593-53-5) + tin → 2,5-dimethyl-4-amino phenol (3096-71-7)

sulfuric acid (7664-93-9) + N-(2,5-dimethylphenyl)hydroxylamine (3096-64-8) → 2,5-dimethylhydroquinone (615-90-7) + 2,5-dimethyl-4-amino phenol (3096-71-7)

hydrogenchloride (7647-01-0) + 1-(4-hydroxy-2,5-dimethyl-phenyl)-ethanone oxime → 2,5-dimethyl-4-amino phenol (3096-71-7)

N-(2,4-dimethylphenyl)hydroxylamine (70853-94-0) + hot diluted sulfuric acid → 2,5-dimethyl-4-amino phenol (3096-71-7)

2,5-Dimethyl-1,4-benzoquinone (137-18-8) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; hydroxylamine hydrochloride 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 1.5 h / Reflux 2: hydrogenchloride; tin(ll) chloride / water; dichloromethane / 16 h / Reflux View Scheme

2-(benzyloxy)-1,4-dimethylbenzene (835-84-7) → 2,5-dimethyl-4-amino phenol (3096-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, AcOH 2: H2 / Pd-C / ethanol View Scheme

2,5-dimethyl-4-amino phenol (3096-71-7) + acetic anhydride (108-24-7) → 1-Acetoxy-4-acetylamino-2,5-dimethylbenzene (3096-93-3)

Conditions	Yield
With pyridine In ethyl acetate for 1h; Heating / reflux;	95%
With potassium acetate In chloroform at 20℃; Heating / reflux;

pyridine-2-carbaldehyde (1121-60-4) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 2,5-Dimethyl-4-{[1-pyridin-2-yl-meth-(E)-ylidene]-amino}-phenol

Conditions	Yield
In toluene	91%

di-tert-butyl dicarbonate (24424-99-5) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-hydroxy-2,5-dimethylphenylcarbamic acid tert-butyl ester (185063-84-7)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	90%
With triethylamine In methanol at 20℃; for 13h;	80%
In tetrahydrofuran for 4h; Heating;
In tetrahydrofuran Reflux;

N-methyl-N-ethylformamide (28860-25-5) + 2,5-dimethyl-4-amino phenol (3096-71-7) → N-ethyl-N'-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide hydrochloride (1357382-69-4)

Conditions	Yield
With trichlorophosphate In acetonitrile at 60℃; for 1h;	85%

2,5-dimethyl-4-amino phenol (3096-71-7) + trimethyl orthoformate (149-73-5) → methyl N-(4-hydroxy-2,5-dimethylphenyl)formimidate (1357382-71-8)

Conditions	Yield
With toluene-4-sulfonic acid for 2h; Reflux;	83.8%
With toluene-4-sulfonic acid for 1h; Reflux;

5-chloro-3-(4-chlorobenzyl)-1,2,4-thiadiazole (90418-16-9) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline (1357382-68-3)

Conditions	Yield
Stage #1: 2,5-dimethyl-4-amino phenol With sodium hydroxide In N,N-dimethyl acetamide at 40℃; for 0.5h; Inert atmosphere; Stage #2: 5-chloro-3-(4-chlorobenzyl)-1,2,4-thiadiazole In N,N-dimethyl acetamide at 20℃; for 2h; Inert atmosphere;	83.8%

2,5-dimethyl-4-amino phenol (3096-71-7) + 5-chloro-3-phenyl-isothiazole (21905-46-4) → 2,5-dimethyl-4-[(3-phenylisothiazol-5-yl)oxy]aniline (1239257-83-0)

Conditions	Yield
Stage #1: 2,5-dimethyl-4-amino phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: 5-chloro-3-phenyl-isothiazole In N,N-dimethyl-formamide; mineral oil at 100℃; for 3h;	80%

2,5-dimethyl-4-amino phenol (3096-71-7) + Benzoyl isothiocyanate (532-55-8) → C16H16N2O2S

Conditions	Yield
In acetone at 40℃; for 1h;	80%

2,5-dimethyl-4-amino phenol (3096-71-7) + p-toluenesulfonyl chloride (98-59-9) → N-(4-hydroxy-2,5-dimethylphenyl)-4-methylbenzenesulfonamide

Conditions	Yield
With pyridine at 0 - 20℃; for 5h; Inert atmosphere;	80%
With pyridine at 0 - 20℃; for 24h; Inert atmosphere;
With pyridine at 0 - 25℃; for 12h; Inert atmosphere;

3-tert-butyl-5-chloroisothiazole-4-carbonitrile (1239257-77-2) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 5-(4-amino-2,5-dimethylphenoxy)-3-tert-butylisothiazole-4-carbonitrile (1239257-75-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 6h; Reflux;	79%

3-[1-(4-chloro-phenyl)cyclopropyl]-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole (1202783-66-1) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-({3-[1-(4-chlorophenyl)cyclopropyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylaniline (1202783-65-0)

Conditions	Yield
Stage #1: 2,5-dimethyl-4-amino phenol With potassium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: 3-[1-(4-chloro-phenyl)cyclopropyl]-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole In acetonitrile at 50℃; for 12h;	76.9%

4,5-dichloro-3-phenylisothiazole (1239257-86-3) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-[(4-chloro-3-phenylisothiazol-5-yl)oxy]-2,5-dimethylaniline (1239257-85-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 4h;	72%

2,5-dimethyl-4-amino phenol (3096-71-7) + 4-methylphenylacetyl chloride (35675-44-6) → N-(4-hydroxy-2,5-dimethylphenyl)-2-(4-methylphenyl)acetamide (1413925-56-0)

Conditions	Yield
With sodium acetate; acetic acid In N,N-dimethyl-formamide at 20℃;	72%

2,5-dimethyl-4-amino phenol (3096-71-7) + methanesulfonyl chloride (124-63-0) → N-(4-hydroxy-2,5-dimethylphenyl)methanesulfonamide (321947-91-5)

Conditions	Yield
With sodium hydrogencarbonate In water at 70℃; for 0.5h;	70%

4-formyl indole (1074-86-8) + 2-Butynoic acid (590-93-2) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 2,5-dimethyl-4-amino phenol (3096-71-7) → N-(2-(tert-butylamino)-1-(1H-indol-4-yl)-2-oxoethyl)-N-(4-hydroxy-2,5-dimethylphenyl)but-2-ynamide

Conditions	Yield
In methanol at 50℃; Ugi Condensation;	70%

2,5-dimethyl-4-amino phenol (3096-71-7) + N-phenylsulfonylbenzimidoyl chloride (4513-25-1) → N-(4-hydroxy-2,5-dimethylphenyl)-N'-(phenylsulfonyl)benzimidamide (461672-41-3)

Conditions	Yield
With sodium acetate In acetic acid; N,N-dimethyl-formamide	69%

2,5-dimethyl-4-amino phenol (3096-71-7) + Cinnamoyl chloride (102-92-1) → (2E)-N-(4-hydroxy-2,5-dimethylphenyl)-3-phenylprop-2-enamide (1413925-72-0)

Conditions	Yield
With sodium acetate; acetic acid In N,N-dimethyl-formamide at 20℃;	66%

2,5-dimethyl-4-amino phenol (3096-71-7) + 2,6-dichloro-4-(trifluoromethyl)pyridine (39890-98-7) → 4-(2-chlor-4-trifluormethylpyridyl-6-oxy)-2,5-xylidine

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 6h;	64%

2,5-dimethyl-4-amino phenol (3096-71-7) + phenyl isocyanate (103-71-9) → 1-(4-hydroxy-2,5-dimethylphenyl)-3-phenylurea (218134-92-0)

Conditions	Yield
In 1,4-dioxane at 100℃;	64%

N-(tolylsulfonyl)benzimidoyl chloride (4513-27-3) + 2,5-dimethyl-4-amino phenol (3096-71-7) → N-(4-hydroxy-2,5-dimethylphenyl)-N'-(4-methylphenylsulfonyl)benzimidamide (461672-30-0)

Conditions	Yield
With sodium acetate In acetic acid; N,N-dimethyl-formamide	62%

4-nitro-benzenesulfinyl chloride (13088-17-0) + 2,5-dimethyl-4-amino phenol (3096-71-7) → N-4-nitrophenylthio-2,5-dimethyl-1,4-benzoquinone imine (1057963-27-5)

Conditions	Yield
With triethylamine In diethyl ether	60%

2,5-dimethyl-4-amino phenol (3096-71-7) + 3,4-dichloro-2-ethylpyridine (186767-23-7) → 4-(2-ethyl-3-chloropyridyl-4-oxy)-2,5-xylidine

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 6h;	59%

N-Ethylmethylamine (624-78-2) + 2,5-dimethyl-4-amino phenol (3096-71-7) + trimethyl orthoformate (149-73-5) → N-ethyl-N'-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide

Conditions	Yield
Stage #1: 2,5-dimethyl-4-amino phenol; trimethyl orthoformate With toluene-4-sulfonic acid for 2h; Heating / reflux; Stage #2: N-Ethylmethylamine In toluene at 50℃; for 20h;	55%

2,5-dimethyl-4-amino phenol (3096-71-7) + N-p-chlorophenylsulfonylbenzimidoyl chloride (4513-26-2) → N'-(4-chlorophenylsulfonyl)-N-(4-hydroxy-2,5-dimethylphenyl)benzimidamide (1332847-25-2)

Conditions	Yield
With sodium acetate In acetic acid; N,N-dimethyl-formamide	54%

4-nitro-benzenesulfinyl chloride (13088-17-0) + 2,5-dimethyl-4-amino phenol (3096-71-7) → N-[(4-nitrophenyl)sulfinyl]-2,5-dimethyl-1,4-benzoquinone imine

Conditions	Yield
Stage #1: 4-nitro-benzenesulfinyl chloride; 2,5-dimethyl-4-amino phenol With triethylamine In diethyl ether for 0.166667h; Stage #2: With silver(l) oxide In acetone for 0.5h; Further stages.;	53%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylaniline (286371-50-4)

Conditions	Yield
With dimethyl sulfoxide In methanol; water	52%

4-chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine (438249-84-4) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine hydrochloride

Conditions	Yield
	47%

4-chloro-2-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine (438249-85-5) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-(2,5-Dimethyl-4-hydroxyanilino)-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine hydrochloride

Conditions	Yield
	47%

Upstream product

• 95-87-4 2,5-Dimethylphenol 
• 95-68-1 2,4-Xylidine 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 35774-21-1 2,5-dimethylphenyl azide 
• 835-84-7 2-(benzyloxy)-1,4-dimethylbenzene 
• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 70853-94-0 N-(2,4-dimethylphenyl)hydroxylamine 
• 7647-01-0 hydrogenchloride 
• 3096-64-8 N-(2,5-dimethylphenyl)hydroxylamine 
• 2593-53-5 2,5-dimethyl-p-benzoquinone 4-oxime 
• 19499-98-0 2,5-Dimethyl-4-nitro-phenyl-benzylether 
• 3139-05-7 4-nitro-2,5-xylenol 
• 89-58-7 mononitro-p-xylene 

Downstream Products

• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 929640-96-0 4-(2-chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine 
• 872675-95-1 C₁₄H₁₃NOS 
• 872675-99-5 C₁₄H₁₂ClNOS 
• 1057963-27-5 N-4-nitrophenylthio-2,5-dimethyl-1,4-benzoquinone imine 
• 218134-92-0 1-(4-hydroxy-2,5-dimethylphenyl)-3-phenylurea 
• 1174550-14-1 1-cyclohexyl-3-(4-hydroxy-2,5-dimethylphenyl)urea 
• 1202783-62-7 4-{[3-(3-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline 
• 1202783-65-0 4-({3-[1-(4-chlorophenyl)cyclopropyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylaniline 
• 1357382-71-8 methyl N-(4-hydroxy-2,5-dimethylphenyl)formimidate 
• 1357382-68-3 4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline 
• 1299975-03-3 N-(2,5-dimethyl-4-hydroxyphenyl)-4-(4-fluorophenyl)-1,3-thiazole-2-amine 
• 810664-79-0 C₂₁H₂₀N₄OS 
• 810662-79-4 C₂₃H₂₄N₄OS 

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