3096-71-7

Usage

Uses

Used in Chemical Synthesis Studies:
4-Amino-2,5-dimethylphenol is used as a chemical intermediate for the synthesis of various compounds. Its unique structure allows it to be a versatile building block in the creation of different organic molecules, contributing to the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
4-Amino-2,5-dimethylphenol is used as a key component in the development of pharmaceuticals, particularly those targeting specific medical conditions. Its chemical properties make it a valuable asset in the design and synthesis of novel drug molecules.
Used in Material Science:
In the field of material science, 4-Amino-2,5-dimethylphenol is used as a precursor for the development of advanced materials with specific properties. Its solid-state structure and reactivity contribute to the creation of materials with tailored characteristics for various applications.
Used in Analytical Chemistry:
4-Amino-2,5-dimethylphenol is utilized as a reference compound or standard in analytical chemistry for the calibration of instruments and the development of new analytical methods. Its distinct chemical properties make it suitable for these purposes, ensuring accurate and reliable results in chemical analysis.

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

Downstream Products

• 185063-84-7 4-hydroxy-2,5-dimethylphenylcarbamic acid tert-butyl ester 
• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 185063-85-8 tert-Butyl (4-methoxy-2,5-dimethylphenyl)carbamate 
• 185063-87-0 [4-Methoxy-5-methyl-2-(2-oxo-butyl)-phenyl]-carbamic acid tert-butyl ester 
• 75552-07-7 4-Amino-2-aminomethyl-3,6-dimethyl-phenol; hydrochloride 
• 861796-92-1 (4-amino-2,5-dimethyl-phenoxy)-acetic acid 
• 861296-03-9 (4-acetylamino-2,5-dimethyl-phenoxy)-acetic acid 
• 3096-93-3 1-Acetoxy-4-acetylamino-2,5-dimethylbenzene 
• 438249-37-7 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(3-pyridinyl)-6-trifluoromethylpyrimidine 
• 438248-85-2 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine 
• 35940-81-9 N-[(2',4' diamino-3'-aza) phenyl-] 2,5-dimethyl benzoquinone imine 
• 286371-46-8 4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline 
• 929640-96-0 4-(2-chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine 
• 1379347-34-8 C₈H₁₀NO^(1-)*Na⁽¹⁺⁾ 

Relevant academic research and scientific papers

TRANSITION METAL FREE METHODS OF SYNTHESIS OF BIARYL COMPOUNDS

The present disclosure provides methods of preparing biaryl compounds which do not require transition metal catalysts. In yet another aspect, the present disclosure provides pharmaceutical compositions comprising compounds as described herein and pharmaceutically acceptable carriers.

Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives

Herein we disclose a scalable organocatalytic direct arylation approach for the regio- and atroposelective synthesis of non-C2-symmetric 2,2′-dihydroxy-1,1′-binaphthalenes (BINOLs). In the presence of catalytic amounts of axially chiral phosphoric acids, phenols and naphthols are coupled with iminoquinones via a cascade process that involves sequential aminal formation, sigmatropic rearrangement, and rearomatization to afford enantiomerically enriched BINOL derivatives in good to excellent yields. Our studies suggest that the (local) symmetry of the initially formed aminal intermediate has a dramatic impact on the level of enantioinduction in the final product. Aminals with a plane of symmetry give rise to BINOL derivatives with significantly lower enantiomeric excess than unsymmetrical ones featuring a stereogenic center. Presumably asymmetric induction in the sigmatropic rearrangement step is significantly more challenging than during aminal formation. Sigmatropic rearrangement of the enantiomerically enriched aminal and subsequent rearomatization transfers the central chirality into axial chirality with high fidelity.

The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study

An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.

One step hair coloring compositions using salts

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Hair colouring and conditioning compositions

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