950-58-3

Basic information

• Product Name: 4-amino-2,6-di-tert-butylphenol
• Synonyms: 4-amino-2,6-di-tert-butylphenol;Phenol, 4-aMino-2,6-bis(1,1-diMethylethyl)-
• CAS NO: 950-58-3
• Molecular Formula: C₁₄H₂₃NO
• Molecular Weight: 221.33852
• Product Categories: Industrial/Fine Chemicals
• Mol File: 950-58-3.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 309.3 °C at 760 mmHg
• Flash Point: 140.8 °C
• Appearance: /
• Density: 0.99 g/cm³
• Vapor Pressure: 0.000355mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 4-amino-2,6-di-tert-butylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-2,6-di-tert-butylphenol(950-58-3)
• EPA Substance Registry System: 4-amino-2,6-di-tert-butylphenol(950-58-3)

Safety Data

• Hazardous Substances Data: 950-58-3(Hazardous Substances Data)

Usage

General Description

4-amino-2,6-di-tert-butylphenol is a chemical compound with the formula C14H23N. It is a white solid that is slightly soluble in water and is commonly used as an antioxidant and stabilizer in various products such as polymers, plastics, and rubber. The compound is also used in the production of lubricants and as an additive in gasoline and motor oil. It has been shown to have low toxicity and is generally considered to be safe for use in these applications. However, proper handling and storage of this chemical are still necessary to prevent potential hazards.

InChI:InChI=1/C14H23NO/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8,16H,15H2,1-6H3

Synthetic route

2,6-di-tert-butyl-1,4-benzoquinone monooxime (15052-28-5) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr;	80%
With hydrogen; platinum In 1,4-dioxane
Multi-step reaction with 2 steps 1: 2 h / 180 - 185 °C 2: acid hydrolysis View Scheme
With palladium 10% on activated carbon; hydrogen; trifluoroacetic acid In methanol under 760.051 Torr; for 2h; Inert atmosphere;

4-nitro-2,6-di-tert-butylphenol (728-40-5) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
With hydrogen; palladium on activated carbon In ethanol; dichloromethane at 30℃; under 1034.32 Torr; for 2h;	50%
With hydrogen; palladium 10% on activated carbon In ethanol; dichloromethane at 20℃; under 1034.32 Torr; for 2h;	50%
With hydrogen; palladium 10% on activated carbon In ethanol; dichloromethane at 20℃; under 1034.32 Torr; for 2h;	50%

4-nitroso-2,6-di-tert-butylphenol (955-03-3) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
With hydrogen; nickel
With sodium hydroxide; sodium dithionite at 45 - 60℃;
With potassium hydroxide; sodium hydrogensulfide
With sodium dithionite; sodium hydroxide In water at 30 - 65℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;

3,5-di-tert-butyl-4-hydroxyformanilide (69230-90-6) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
acid hydrolysis; Yield given;

2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / 2 h / 180 - 185 °C 2: acid hydrolysis View Scheme
Multi-step reaction with 2 steps 1: hydroxylamine 2: 5percent sodium hydroxide, sodium dithionite / 45 - 60 °C View Scheme

2,6-di-tert-butyl-4-(phenylimino)cyclohexa-2,5-dienone (14329-20-5) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / 180 - 185 °C 2: acid hydrolysis View Scheme

2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenylimino)-2,5-cyclohexadien-1-one (4610-03-1) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / 180 - 185 °C 2: acid hydrolysis View Scheme

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 16.2 percent / chromic anhydride 2: hydroxylamine 3: 5percent sodium hydroxide, sodium dithionite / 45 - 60 °C View Scheme

2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-aminophenol (950-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: H2 / Raney-Ni View Scheme
Multi-step reaction with 2 steps 1: N2O4 / benzene; petroleum ether 2: Zn, aq. HCl View Scheme
Stage #1: 2,6-di-tert-butylphenol With hydrogenchloride; sodium hydroxide; sodium carbonate; sodium nitrite; 4-aminobenzene sulfonic acid In water at 0℃; for 1h; Stage #2: With sodium dithionite In water at 80℃;

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 4-methoxy-benzoyl chloride (100-07-2) → N-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-4-methoxy-benzamide (178487-48-4)

Conditions	Yield
With triethylamine In benzene at 35 - 40℃; for 1h;	96%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 4-nitro-benzoyl chloride (122-04-3) → 2,6-di-tert-butyl-4-(4-nitrobenzoylamino)phenol (178487-45-1)

Conditions	Yield
With triethylamine In benzene at 35 - 40℃; for 1h;	94%
With triethylamine In diethyl ether

2,4 dichlorobenzoic acid (50-84-0) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → 2,4-dichloro-N-(3,5-di-tert-butyl-4-hydroxyphenyl)benzamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	92%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 4-methyl-benzoyl chloride (874-60-2) → N-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methylbenzamide (178487-47-3)

Conditions	Yield
With triethylamine In benzene at 35 - 40℃; for 1h;	90%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + benzoyl chloride (98-88-4) → 4-(N-benzoylamino)-2,6-di-t-butylphenol (29644-34-6)

Conditions	Yield
With triethylamine In benzene at 35 - 40℃; for 1h;	87%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 4-chloro-benzoyl chloride (122-01-0) → N-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-chlorobenzamide (178487-46-2)

Conditions	Yield
With triethylamine In benzene at 35 - 40℃; for 1h;	86%

bis(trichloromethyl) carbonate (32315-10-9) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) + N-amino-(4-nitrophenyl)carboxamide (636-97-5) → N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-[(4-nitrophenyl)-carbonylamino]-urea

Conditions	Yield
With sodium chloride; N-ethyl-N,N-diisopropylamine In n-heptane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide	86%
Stage #1: bis(trichloromethyl) carbonate; 2,6-di-tert-butyl-4-aminophenol With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: N-amino-(4-nitrophenyl)carboxamide With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 4h;	86%

bis(trichloromethyl) carbonate (32315-10-9) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) + N-amino-(4-nitrophenyl)carboxamide (636-97-5) → N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-[(4-nitrophenyl)-carbonylamino]-urea

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 2,6-di-tert-butyl-4-aminophenol With N-ethyl-N,N-diisopropylamine In dichloromethane Stage #2: N-amino-(4-nitrophenyl)carboxamide With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 4h;	86%

2-chloroethyl isothiocyanate (1943-83-5) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-(2-chloroethyl)urea

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 23℃; for 2h;	83%

tetrachlorophthalonitrile (1953-99-7) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → 3,5-di-tert-butyl-4-hydroxy-2',5',6'-trichloro-3',4'-dicyanodiphenylamine

Conditions	Yield
With triethylamine In various solvent(s) at 40 - 45℃; for 2h;	81%

bis(trichloromethyl) carbonate (32315-10-9) + 2-(p-nitrophenyl)ethylamine (24954-67-4) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-[2-(4-nitrophenyl)ethyl]-urea

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 2,6-di-tert-butyl-4-aminophenol Stage #2: 2-(p-nitrophenyl)ethylamine	80%
Stage #1: bis(trichloromethyl) carbonate; 2,6-di-tert-butyl-4-aminophenol With N-ethyl-N,N-diisopropylamine Stage #2: 2-(p-nitrophenyl)ethylamine With N-ethyl-N,N-diisopropylamine	80%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + (4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-dodecyl-phenyl)-amine (90850-59-2) → C49H74N6O2 (95335-62-9)

Conditions	Yield
With sodium hydroxide In acetone for 6h; Heating;	74%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 4-nitrobenzyl isocyanate (63289-53-2) → N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-[(4-nitrophenyl)methyl]-urea (214124-65-9)

Conditions	Yield
In chloroform at 20℃; for 2h;	72%
In chloroform at 20℃; for 2h;

2,6-di-tert-butyl-4-aminophenol (950-58-3) → N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-[(4-nitrophenyl)methyl]-urea (214124-65-9)

Conditions	Yield
In chloroform	72%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 6-chloro-N2,N4-diisobutyl-1,3,5-triazine-2,4-diamine (39605-41-9) → 4-(4,6-Bis-isobutylamino-[1,3,5]triazin-2-ylamino)-2,6-di-tert-butyl-phenol (95335-63-0)

Conditions	Yield
With sodium hydroxide In acetone Heating;	67%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 6-(4-hydroxy-3,5-di-tert-butylphenylamino)-2,4-dichloro-1,3,5-triazine (976-09-0) → 2,4,6-tris-(4-hydroxy-3,5-di-tert-butylanilino)-sym-triazine (51937-53-2)

Conditions	Yield
With sodium hydroxide In acetone for 6h; Heating;	67%

indan-1,2,3-trione hydrate (485-47-2) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → 2-(3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienylideneamino)-indan-1,3-dione

Conditions	Yield
Condensation;	67%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 2,4-di-(N-methyloctadecylamino)-6-chloro-sym-triazine (16666-02-7) → 4-[4,6-Bis-(methyl-octadecyl-amino)-[1,3,5]triazin-2-ylamino]-2,6-di-tert-butyl-phenol (95335-64-1)

Conditions	Yield
With sodium hydroxide In acetone Heating;	66%
With potassium hydroxide 1.) dioxane, reflux, 3 h, 2.) dioxane, reflux, 1 h; Yield given; Multistep reaction;

3-{4-[(1,1-dimethylethoxy)carbonyl]aminophenoxy}azetidine (218944-77-5) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → 1-{{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]amino}carbonyl}-3-{4-[(1,1-dimethylethoxy)carbonyl]aminophenoxy}azetidine

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-4-aminophenol With bis(trichloromethyl) carbonate In dichloromethane at 23℃; for 1.08333h; Stage #2: 3-{4-[(1,1-dimethylethoxy)carbonyl]aminophenoxy}azetidine With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 2h;	61%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + (+)-usnic acid (17669-01-1, 56190-51-3, 15853-98-2) → (R,E)-6-acetyl-2-(1-((3,5-di-tert-butyl-4-hydroxyphenyl)amino)ethylidene)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione

Conditions	Yield
In ethanol at 80℃; for 4h; Inert atmosphere;	61%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 2-(N-methyloctadecylamino)-4,6-dichloro-sym-triazine (32998-19-9) → C50H84N6O2 (95335-61-8)

Conditions	Yield
With sodium hydroxide In acetone for 6h; Heating;	59%
With potassium hydroxide 1.) dioxane, reflux, 3 h, 2.) dioxane, reflux, 1 h; Yield given; Multistep reaction;

benzenesulphinyl chloride (4972-29-6) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → N-(phenylsulfinyl)-2,6-di-tert-butyl-1,4-benzoquinone imine (1104591-41-4)

Conditions	Yield
Stage #1: benzenesulphinyl chloride; 2,6-di-tert-butyl-4-aminophenol With triethylamine In diethyl ether for 0.166667h; Stage #2: With silver(l) oxide In acetone for 0.5h; Further stages.;	58%

4-methylbenzenesulfinyl chloride (10439-23-3) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → N-[(4-methylphenyl)sulfinyl]-2,6-di-tert-butyl-1,4-benzoquinone imine (1104591-39-0)

Conditions	Yield
Stage #1: 4-methylbenzenesulfinyl chloride; 2,6-di-tert-butyl-4-aminophenol With triethylamine In diethyl ether for 0.166667h; Stage #2: With silver(l) oxide In acetone for 0.5h; Further stages.;	58%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 3,4,5-Trimethoxybenzoyl chloride (4521-61-3) → N-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-3,4,5-trimethoxy-benzamide (178487-49-5)

Conditions	Yield
With triethylamine In benzene at 35 - 40℃; for 1h;	57%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 5-(4-nitrophenyl)-furan-2-carboxylic acid (28123-73-1) → N-(3,5-di-t-butyl-4-hydroxyphenyl)-5-(4-nitrophenyl)-2-furan carboxamide

Conditions	Yield
Stage #1: 5-(4-nitrophenyl)-furan-2-carboxylic acid Stage #2: 2,6-di-tert-butyl-4-aminophenol	56%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → 6-(4-hydroxy-3,5-di-tert-butylphenylamino)-2,4-dichloro-1,3,5-triazine (976-09-0)

Conditions	Yield
With sodium hydroxide In water; acetone 1. 0 deg C, 1 h; 2. 20 deg C, 1 h;	54%
With sodium carbonate at 0 - 5℃; for 0.166667h; Inert atmosphere;

p-chlorophenylsulfinyl chloride (2901-92-0) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → N-[(4-chlorophenyl)sulfinyl]-2,6-di-tert-butyl-1,4-benzoquinone imine (1104591-43-6)

Conditions	Yield
Stage #1: p-chlorophenylsulfinyl chloride; 2,6-di-tert-butyl-4-aminophenol With triethylamine In diethyl ether for 0.166667h; Stage #2: With silver(l) oxide In acetone for 0.5h; Further stages.;	54%

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 2-azido-5-nitrobenzaldehyde (89642-02-4) → 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-nitroindazole

Conditions	Yield
In N,N-dimethyl-formamide for 0.333333h; Heating;	53%

pyridine-4-carbaldehyde (872-85-5) + 2,6-di-tert-butyl-4-aminophenol (950-58-3) → 2,6-Di-tert-butyl-4-{[1-pyridin-4-yl-meth-(E)-ylidene]-amino}-phenol

Conditions	Yield
In ethanol Heating;	52%

Upstream product

• 955-03-3 4-nitroso-2,6-di-tert-butylphenol 
• 69230-90-6 3,5-di-tert-butyl-4-hydroxyformanilide 
• 15052-28-5 2,6-di-tert-butyl-1,4-benzoquinone monooxime 
• 128-39-2 2,6-di-tert-butylphenol 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 4610-03-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenylimino)-2,5-cyclohexadien-1-one 
• 14329-20-5 2,6-di-tert-butyl-4-(phenylimino)cyclohexa-2,5-dienone 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 728-40-5 4-nitro-2,6-di-tert-butylphenol 

Downstream Products

• 95335-61-8 C₅₀H₈₄N₆O₂ 
• 95335-64-1 4-[4,6-Bis-(methyl-octadecyl-amino)-[1,3,5]triazin-2-ylamino]-2,6-di-tert-butyl-phenol 
• 29644-34-6 4-(N-benzoylamino)-2,6-di-t-butylphenol 
• 178487-48-4 N-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-4-methoxy-benzamide 
• 190844-69-0 4-{[1-(2-Bromo-phenyl)-meth-(E)-ylidene]-amino}-2,6-di-tert-butyl-phenol 
• 61551-39-1 N-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methylbenzenesulfonamide 

Relevant articles and documents

A novel synthesis method of antioxidant 565

The present invention proposes a novel synthesis method of antioxidant 565, the steps comprising: S1, the 2,6-di-tert-butylphenol dissolved in an organic solvent, add nitric acid dropwise, after the end of the reaction, the reaction liquid is steamed, petroleum ether washed, washed, vacuum dried to obtain 4-nitro-2,6-di-tert-butylphenol crystallization; S2, the dried 4-nitro-2,6-di-tert-butylphenol crystal dissolved in an organic solvent,N2 protection, and then added to the precious metal catalyst supported by a molecular sieve, filled with H 2,the reduction reaction was carried out to give 4-amino-2,6-di-tert-butylphenol; S3, the 4-amino-2,6-di-tert-butylphenol, melamine chloride, n-octylthiol and NaOH were added to the condensation tank, and the condensation reaction was carried out under the conditions ofN2 protection and 40-70 °C, and after the reaction, the reaction liquid was filtered and steamed to obtain the finished product. The present invention has the advantages of reaction safety, catalyst is not affected by halogens, product quality and high yield, is conducive to factory production.

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Discovery and SAR study of 3-(tert-butyl)-4-hydroxyphenyl benzoate and benzamide derivatives as novel farnesoid X receptor (FXR) antagonists

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