128-37-0

Basic information

• Product Name: 2,6-Di-tert-butyl-4-methylphenol
• Synonyms: BHT (BAGS);BHT FCC/NF;BHT,GRANULAR,FCC;BHT,GRANULAR,TECHNICAL;BUTYLATEDHYDROXYTOLUENE,GRANULAR,NF;di-tert-butylhydroxytoluene;2,6-DITERTIARY-BUTYL-4-METHYL-PHENOL(BHT);Butylated hydroxytoluene (BHT&2,6-DBPC)
• CAS NO: 128-37-0
• Molecular Formula: C15H24O
• Molecular Weight: 220.35
• EINECS: 204-881-4
• Product Categories: Industrial/Fine Chemicals;Aromatic Hydrocarbons (substituted) & Derivatives;Antioxidant;Biochemistry;Aromatics;BHT;antioxidants;Food additive
• Mol File: 128-37-0.mol
• Article Data: 84

Chemical Properties

• Melting Point: 69-73 °C(lit.)
• Boiling Point: 265 °C(lit.)
• Flash Point: 127 °C
• Appearance: white/Crystals
• Density: 1.048
• Vapor Density: 7.6 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: 1.4859
• Storage Temp.: 0-6°C
• Solubility: methanol: 0.1 g/mL, clear, colorless
• PKA: pKa 14(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
• Water Solubility: insoluble
• Stability: Stable, but light-sensitive. Incompatible with acid chlorides, acid anhydrides, brass, copper, copper alloys, steel, bases, oxid
• Merck: 14,1548
• BRN: 1911640
• CAS DataBase Reference: 2,6-Di-tert-butyl-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Di-tert-butyl-4-methylphenol(128-37-0)
• EPA Substance Registry System: 2,6-Di-tert-butyl-4-methylphenol(128-37-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-36/38-50/53
• Safety Statements: 26-36-37/39-61-60
• RIDADR: 3077
• WGK Germany: 1
• RTECS: GO7875000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 128-37-0(Hazardous Substances Data)

Usage

description

Butylated hydroxytoluene is a synthetic phenolic compound mainly used as an antioxidant and preservative in the food industry. It is used to prevent the lipid oxidation in oils and fat-containing foods.Butylated Hydroxytoluene?toxicity is generally considered as being low.Since Butylated Hydroxytoluene?is used in many near consumer products population wide exposure is expected.

Chemical Properties

Different sources of media describe the Chemical Properties of 128-37-0 differently. You can refer to the following data:
1. Butylated hydroxytoluene is white or light yellow crystal. Butylated Hydroxytoluene?has a melting point of 71°C, a boiling point of 265°C, a relative density of 1.048 (20/4°C), and a refractive index of 1.4859 (75°C). Solubility of Butylated Hydroxytoluene?at normal temperature: methanol 25, ethanol 25-26, isopropanol 30, mineral oil 30, acetone 40, petroleum ether 50, benzene 40, lard (40-50°C ) 40-50, corn oil and soybean oil 40-50. Butylated Hydroxytoluene?is insoluble in water, 10NaOH solution, glycerol, and propylene glycol. Butylated Hydroxytoluene?is odorless, odorless with good thermal stability.
2. BHA and BHT (butylated hydroxytoluene) are monohydric phenolic antioxidants that, prior to their introduction and acceptance in the food industry, were used to protect petroleum against oxidative degumming. Butylated Hydroxytoluene has a very faint, musty, occasional cresylictype odor. BHA and Butylated Hydroxytoluene are extensively used in foods as antioxidants. Most fats, oils and fat-containing foods are naturally susceptible to rapid rancification and other oxidative reactions that produce compounds having objectionable taste and odor, making foods containing them unpalatable. Lipid oxidation is autocatalytic and proceeds as a complex of chain reactions, the nature and speed of which vary with the substrate, temperature, light, availability of oxygen and presence or absence of oxidation catalysts. Antioxidants like BHT act as “chain breaks” in the autooxidation processes under the usual conditions of processing, storage and use of fat-containing foods (Burdock, 1997).
3. white crystalline solid
4. Butylated Hydroxytoluene is a white to pale yellow crystalline solid or powder.
5. Butylated hydroxytoluene occurs as a white or pale yellow crystalline solid or powder with a faint characteristic phenolic odor.

Application from Literature

The applications of butylated hydroxytoluene (BHT) have been reported as following [1-9]: ? Butylated hydroxytoluene metabolites causing DNA strand breaks in cultured cells and DNA breaks between nucleosomes (a typical feature of apoptosis), which result in relieving inflammation. ? Inhibiting secretion, aggregation, and protein phosphorylation caused by protein kinase C activators at the process of the pre-incubation of aspirin-treated platelets. ? Inhibiting liver cancer formation induced by aflatoxin B1. ? As Michael receptor, butylated hydroxytoluene can react with uninucleophiles and proteins. ? Reaction of 2, 6-di-tert-butyl-4-methylphenol with fluorine (II) - benzophenone dianion complex. ? Food additive 2, 6-di-tert-butyl-4-methylphenol can promote acute lung toxicity and tumor growth in mice. ? Butylated hydroxytoluene can be used to prepare organoaluminum compound methylaluminum bis (2, 6-di-tert-butyl-4-alkylphenol oxide).

Uses

Different sources of media describe the Uses of 128-37-0 differently. You can refer to the following data:
1. Butylated hydroxytoluene has wide application, such as flavors, fragrances, biochemical reagents-other chemical reagents, chemical raw materials, organic chemical raw materials, biochemical, inorganic salts, antioxidants, food additives, feed additives, feed storage additives, aromatic hydrocarbons, bulk drugs and so on. As a phenolic antioxidant, butylated hydroxytoluene can inhibit lipid peroxidation and exhibit electrophilic quinone methyl ether toxicity mediated by oxidative metabolism. The BHT metabolites, 6-tert-butyl-2- [2 ′-(2′-hydroxymethyl) -propyl] -4-methylphenol, may cause lung damage in mice and promote tumor growth.
2. Because they prevent rancidity, antioxidants are of great interest to the food industry. For example, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and EDTA are frequently used to preserve various foods, such as cheese or fried products. Butylated hydroxytoluene is a powerful inhibitor of lipid peroxidation, yet large doses of it can induce oxidative DNA damage and cancer development in the rat forestomach.
3. Butylated Hydroxytoluene is also known as butylated hydroxy toluene. It is an anti-oxidant that also has preservative and masking capabilities.
4. Butylated Hydroxytoluene (BHT) is an antioxidant that functions similarly to butylated hydroxyanisole (BHA) but is less stable at high temperatures. It is also termed 2,6-di-tert-butyl-para-cresol. See Butylated Hydroxyanisole.
5. Antioxidant 264 as general antioxidants is used widely in polymer materials, petroleum products and food processing industries. Antioxidant 264 is commonly used rubber antioxidant, heat, oxygen aging have some protective effect, but also can inhibit copper harm. This product does not change color, not pollution. Antioxidants 264 high solubility in oil, no precipitation, less volatile, non-toxic and non-corrosive.
6. Antioxidant for food, animal feed, petroleum products, synthetic rubbers, plastics, animal and vegetable oils, soaps. Antiskinning agent in paints and inks.

Mammalian physiology

Butylated Hydroxytoluene is a phenolic antioxidant. Butylated Hydroxytoluene can inhibit lipid peroxidation and cause lung injury in mice and promote tumor growth, which may be due to the metabolites of Butylated Hydroxytoluene, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-Methylphenol. Butylated Hydroxytoluene metabolites have also been reported to cause DNA strand breaks in cultured cells and DNA breaks between nucleosomes (a typical feature of apoptosis). A single intraperitoneal injection of Butylated Hydroxytoluene (60mg/kg body weight) into rats caused a significant increase in nuclear DNA methyltransferase activity in the liver, kidney, heart, spleen, brain, and lung.

Description

Different sources of media describe the Description of 128-37-0 differently. You can refer to the following data:
1. The antioxidant butylated hydroxytoluene is contained in food, adhesive glues, industrial oils and greases, including cutting fluids. Sensitization seems very rare.
2. Butylated Hydroxytoluene is a synthetic antioxidant. It scavenges peroxide, 2,2-diphenyl-1-picrylhydrazyl (DPPH; ), superoxide, and ABTS radicals in cell-free assays, as well as inhibits lipid peroxidation of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) in vitro when used at a concentration of 45 μg/ml. Butylated Hydroxytoluene (0.025-3.2 mM) reduces freeze-thaw-induced malondialdehyde (MDA) production and increases sperm viability in boar spermatozoa preparations. Formulations containing BHT have been used as antioxidant cosmetic and food additives.

Occurrence

Not reported found naturally.

Definition

ChEBI: A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.

Preparation

Butylated Hydroxytoluene is produced commercially by the alkylation of para-cresol with isobutylene. Butylated Hydroxytoluene is also produced by several western European manufacturers, production/processing plants in Germany, France, the Netherlands, United Kingdom and Spain.

Production Methods

Prepared by the reaction of p-cresol with isobutene.

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, such as 2,6-Di-tert-butyl-4-methylphenol, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. May react with oxidizing materials.

Health Hazard

2,6-Di-tert-butyl-p-cresol or Butylated Hydroxytoluene is of relatively low acute toxicity in animals, and there is no evidence of either acute or chronic effects among exposed workers.

Fire Hazard

2,6-Di-tert-butyl-4-methylphenol is combustible.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Butylated hydroxytoluene is used as an antioxidant in cosmetics, foods, and pharmaceuticals. It is mainly used to delay or prevent the oxidative rancidity of fats and oils and to prevent loss of activity of oil-soluble vitamins. Butylated hydroxytoluene is also used at 0.5–1.0% w/w concentration in natural or synthetic rubber to provide enhanced color stability. Butylated hydroxytoluene has some antiviral activity and has been used therapeutically to treat herpes simplex labialis.

Biochem/physiol Actions

Butylated hydroxytoluene is a phenolic antioxidant. It has been shown to inhibit lipid peroxidation. It causes lung injury and promotes tumors in mice, but this may be due to a metabolite of Butylated Hydroxytoluene, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-methylphenol. Metabolites of Butylated Hydroxytoluene have also been reported to induce DNA strand breaks and internucleosomal DNA fragmentation (a characteristic of apoptosis) in cultured cells. In rats, a single intraperitoneal injection of Butylated Hydroxytoluene (60 mg/kg body mass) results in a significant increase in nuclear DNA methyl transferase activity in the liver, kidneys, heart, spleen, brain and lungs. Incubation of alveolar macrophages with Butylated Hydroxytoluene?significantly reduced the level of TNF-α which may explain the mechanism by which this antioxidant reduces inflammation. Preincubation of aspirin-treated platelets with Butylated Hydroxytoluene inhibits the secretion, aggregation, and protein phosphorylation induced by protein kinase C activators. Butylated Hydroxytoluene was also found to inhibit the initiation of hepatocarcinogenesis by aflatoxin B1.

Contact allergens

This antioxidant is contained in food, adhesive glues, industrial oils, and greases, including cutting fluids. Sensitization seems very rare.

Carcinogenicity

The IARC has determined that there is limited evidence for the carcinogenicity of Butylated Hydroxytoluene?in experimental animals.Butylated Hydroxytoluene?has given primarily negative results in a large number of in vivo and in vitro genotoxic assays.No significant reproductive effects were observed in three-generation toxicity studies in mice administered up to 0.4% in the diet.6 The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for 2,6-ditert- butyl-p-cresol is 2mg/m3.

Environmental Fate

The metabolites of Butylated Hydroxytoluene can bind to cellular macromolecules, such as proteins and DNA, and cause toxicity.

Potential Exposure

DBPC is used as a food and feed additive, flavor, and packaging material; as an antioxidant in human foods and animal feeds. It is also used as an antioxidant to sta- bilize petroleum fuels, rubber and vinyl plastics.

Safety Profile

Poison by intraperitoneal andintravenous routes. Moderately toxic by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. A human skin irritant. A skin and eye irritant.Questionable carcinogen with experimental carcinogenicand.

Safety

Butylated hydroxytoluene is readily absorbed from the gastrointestinal tract and is metabolized and excreted in the urine mainly as glucuronide conjugates of oxidation products. Although there have been some isolated reports of adverse skin reactions, butylated hydroxytoluene is generally regarded as nonirritant and nonsensitizing at the levels employed as an antioxidant. The WHO has set a temporary estimated acceptable daily intake for butylated hydroxytoluene at up to 125 μg/kg body-weight. Ingestion of 4 g of butylated hydroxytoluene, although causing severe nausea and vomiting, has been reported to be nonfatal. LD50 (guinea pig, oral): 10.7 g/kg LD50 (mouse, IP): 0.14 g/kg LD50 (mouse, IV): 0.18 g/kg LD50 (mouse, oral): 0.65 g/kg LD50 (rat, oral): 0.89 g/kg

storage

Exposure to light, moisture, and heat causes discoloration and a loss of activity. Butylated hydroxytoluene should be stored in a wellclosed container, protected from light, in a cool, dry place.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Dissolve Butylated Hydroxytoluene in n-hexane at room temperature, then cool with rapid stirring, to -60o. The precipitate is separated, redissolved in hexane, and the process is repeated until the mother liquor is no longer coloured. The final product is stored under N2 at 0o [Blanchard J Am Chem Soc 82 2014 1960]. It has also been recrystallised from EtOH, MeOH, *benzene, n-hexane, methylcyclohexane or pet ether (b 60-80o), and is dried in a vacuum. [Beilstein 6 IV 3511.]

Toxicity evaluation

Butylated Hydroxytoluene is a white crystalline solid. It is insoluble in water and alkalies; but soluble in most common organic solvents such as alcohol and ether. Its melting point is 70°C, boiling point is 265°C, flash point is 127°C, and specific gravity is 1.048 at 20°C.

Incompatibilities

Different sources of media describe the Incompatibilities of 128-37-0 differently. You can refer to the following data:
1. Butylated hydroxytoluene is phenolic and undergoes reactions characteristic of phenols. It is incompatible with strong oxidizing agents such as peroxides and permanganates. Contact with oxidizing agents may cause spontaneous combustion. Iron salts cause discoloration with loss of activity. Heating with catalytic amounts of acids causes rapid decomposition with the release of the flammable gas isobutene.
2. Contact with oxidizers may cause fire and explosion hazard.

Regulatory Status

GRAS listed. Accepted as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM and IV injections, nasal sprays, oral capsules and tablets, rectal, topical, and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

Synthetic route

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) + 2,4-Xylenol (105-67-9) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-(3,5-dimethyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one (131544-07-5) + 3,5-di-tert-butyl-4-hydroxybenzyl 2,4-dimethylphenyl ether (131544-12-2)

Conditions	Yield
In triethylamine	A 3.9% B 99% C 54% D 17%

methanol (67-56-1) + 2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With sodium hydroxide; zinc(II) oxide at 200℃; for 8h; Methylation;	96%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide at 65℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	82%

p-cresol (106-44-5) + isobutene (115-11-7) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
Stage #1: p-cresol With zinc Autoclave; Heating; Large scale; Stage #2: isobutene at 70 - 105℃; Large scale;	95.1%
Stage #1: p-cresol With toluene-4-sulfonic acid In water at 56℃; for 9h; Autoclave; Inert atmosphere; Large scale; Stage #2: isobutene With thiourea In water for 9h; Temperature; Reagent/catalyst; Inert atmosphere; Autoclave; Large scale;	80.9%
With tetraphosphoric acid at 40℃;
With phosphotungstic acid at 90 - 110℃; for 8h; Reagent/catalyst;

C15H25BO2 → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 0.0833333h; Microwave irradiation; Green chemistry;	94%

p-cresol (106-44-5) + tert-butyl alcohol (75-65-0) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
at 70℃; for 8h; Kinetics; Concentration; Reagent/catalyst; Temperature; Time; Friedel-Crafts alkylation; Ionic liquid; Autoclave; regioselective reaction;	A 90% B 9.5%
With carbon tetrabromide at 175℃; for 6h; Sealed tube;	A 68% B 29%
With carbon tetrabromide at 175℃; for 6h; Sealed tube;	A 62% B 38%
1-butyl-3-methylimidazolium heptachlorodiindate (III) at 110℃; for 4h; Product distribution / selectivity; In ionic liquid;
With multi-walled carbon nanotubes supported on SO3H In neat (no solvent) for 10h; Reagent/catalyst; Reflux;	A 85.6 %Chromat. B 6.7 %Chromat.

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) + phenol (108-95-2) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxybenzyl)-4-methylcyclohexa-2,5-dienone (13693-18-0) + 3,5-di-tert-butyl-4-hydroxybenzyl phenyl ether (131544-03-1)

Conditions	Yield
In triethylamine Further byproducts given;	A 14% B 87% C 4.6% D 43%

methyl 3,5-di-tert-butyl-4-hydroxybenzoate (2511-22-0) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); 1,1,3,3-Tetramethyldisiloxane; potassium tert-butylate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 90℃; for 6h; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	81%

p-cresol (106-44-5) + tert-butyl methyl ether (1634-04-4) + 4-nitrobenzaldehdye (555-16-8) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 6,6-((4-nitrophenyl)methylene)bis(2-(tert-butyl)4-methylphenol)

Conditions	Yield
With sulfonated multi-walled carbon nanotubes In neat (no solvent) at 100℃; for 4h; Temperature; Concentration; regiospecific reaction;	A 8 %Chromat. B 80%
With sulfonated multi-walled carbon nanotubes In neat (no solvent) for 4h; Reflux; regiospecific reaction;	A 33 %Chromat. B 25%

Carbonic acid tert-butyl ester 2,6-di-tert-butyl-4-methyl-phenyl ester → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 21h; Product distribution; deprotection;	79%

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene at 120℃; for 4h;	77%
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene at 120℃; for 4h; Product distribution; Mechanism; var.reag. NaBH4, CaH2, KH; var. time and solv.;	77%

p-cresol (106-44-5) + 4-nitrobenzaldehdye (555-16-8) + tert-butyl alcohol (75-65-0) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 6,6-((4-nitrophenyl)methylene)bis(2-(tert-butyl)4-methylphenol)

Conditions	Yield
With sulfonated multi-walled carbon nanotubes In neat (no solvent) at 100℃; for 5h; Concentration; regiospecific reaction;	A 18 %Chromat. B 75%

2,6-di-tert-butyl-4-methylbromobenzene (1206795-79-0) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With iron(III) chloride; potassium phosphate; tetrabutylammomium bromide; N,N`-dimethylethylenediamine In water at 180℃; under 5250.53 Torr; for 20h;	47%

methanol (67-56-1) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With potassium hydroxide; iodine for 2h;	A 44% B 41%

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
In methanol for 2h;	A 44% B 41%

p-cresol (106-44-5) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,5-di-tert-butyl-4-hydroxybenzyl 4-methylphenyl ether (131544-02-0) + 2,6-di-tert-butyl-4-(5-methyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one (131544-08-6)

Conditions	Yield
In triethylamine Further byproducts given. Yields of byproduct given;	A 11% B n/a C 43% D 8.7%

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone (809-73-4)

Conditions	Yield
In diethyl ether for 0.666667h;	A 42% B 27% C 19%

2-(allyloxy)-1,3-di-tert-butyl-5-methylbenzene (1516-98-9) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2-allyl-6-(tert-butyl)-4-methylphenol (2253-69-2)

Conditions	Yield
With phosphomolybdic acid In 1-methyl-pyrrolidin-2-one at 300℃; for 0.0333333h; Claisen Rearrangement; Microwave irradiation; Inert atmosphere;	A 15% B 39%

p-cresol (106-44-5) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,5-di-tert-butyl-4-hydroxybenzyl 4-methylphenyl ether (131544-02-0) + 2,6-di-tert-butyl-4-(5-methyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one (131544-08-6)

Conditions	Yield
triethylamine In methanol	A 34% B n/a C 11% D 33%

methanol (67-56-1) + 2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium hydroxide at 65℃; Catalytic behavior; Inert atmosphere;	A 6% B n/a C n/a

2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With methanol; sodium hydroxide; formaldehyd at 225℃;
Multi-step reaction with 2 steps 1: water; ethanol / 3 h / 80 °C 2: platinum; hydrogen / 4 h / 160 °C View Scheme

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With sodium methylate at 200℃;

p-cresol (106-44-5) + isobutene (115-11-7) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With sulfuric acid; glycerol at 20 - 100℃;
With sulfuric acid; glycerol at 70℃;
With acidic ion exchanger

2,6-di-tert-butylphenol (128-39-2) + methyl iodide (74-88-4) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-anisole (1516-95-6) + 2,6-Di-tert.-butyl-6-methyl-cyclohexadien-(2,4)-on-(1) (94065-08-4)

Conditions	Yield
(i) KOtBu, tBuOH, (ii) /BRN= 969135/; Multistep reaction;

2,6-di-tert-butylphenol (128-39-2) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one (14387-13-4)

Conditions	Yield
In hexane at 30℃; for 1h; Further byproducts given;	A 0.01 mol B 1.89 mol C 0.85 mol D 0.02 mol

2,6-di-tert-butylphenol (128-39-2) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one (14387-13-4)

Conditions	Yield
In triethylamine at 30℃; for 1h;	A 1.02 mol B 0.87 mol

2,6-di-tert-butylphenol (128-39-2) + 2,6-di-tert-butyl-4-methylphenoxy radical (6858-01-1, 24473-56-1) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one (14387-13-4)

Conditions	Yield
In hexane at 30℃; for 1h; Product distribution; Mechanism; other solvents or solvent mixtures; reaction with other phenols;

Ethaneperoxoic acid 3,5-di-tert-butyl-1-methyl-4-oxo-cyclohexa-2,5-dienyl ester (62926-71-0) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone (10396-80-2) + (3,5-Di-tert-butyl-1-methyl-4-oxo-cyclohexa-2,5-dienyloxy)-acetic acid (62926-78-7)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide; Petroleum ether at -60℃; for 2h;	A 4 % Spectr. B 3 % Spectr. C 81 % Spectr.

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one (2607-52-5)

Conditions	Yield
In chloroform

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 2,6-di-tert-butyl-4-methylphenoxy radical (6858-01-1, 24473-56-1) → 2,6-di-tert-butyl-4-methoxyphenoxyl radical (20137-67-1, 3425-36-3) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
In toluene; benzene at -22.1 - 30.9℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS;
In benzene Equilibrium constant; Thermodynamic data; Ambient temperature; ΔG; also in tert-butanol;
In benzene Thermodynamic data; Η, Σ;

2,6-di-tert-butyl-4-methylphenoxy radical (6858-01-1, 24473-56-1) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone In benzene at 24.9℃; Equilibrium constant;
With Methyl oleate at 20℃; Kinetics; Further Variations:; Reagents;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + acetic anhydride (108-24-7) → 2,6-ditertbutyl-4-methylphenyl acetate (29311-34-0)

Conditions	Yield
With perchloric acid at 20℃; for 0.25h;	100%
cerium triflate In acetonitrile at 50℃; for 24h;	98%
With silica gel-supported phosphotungstic acid In chloroform at 62℃; for 0.0833333h;	98%

di-tert-butyl dicarbonate (24424-99-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → Carbonic acid tert-butyl ester 2,6-di-tert-butyl-4-methyl-phenyl ester

Conditions	Yield
With dmap In hexane for 28h;	100%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(2,6-di-tert-butyl-4-methylphenoxy)acetate (1572184-69-0)

Conditions	Yield
With caesium carbonate In acetonitrile for 16h; Reflux;	100%

tert.-butylhydroperoxide (75-91-2) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-di-tert-butyl-4-(tert-butylperoxy)-4-methylcyclohexa-2,5-dien-1-one (13154-57-9)

Conditions	Yield
With dirhodium(II) tetrakis(caprolactam) In water; 1,2-dichloro-ethane at 40℃; for 0.75h; chemoselective reaction;	99%
With tetra-(n-butyl)ammonium iodide In nonane; 1,2-dichloro-ethane at 20℃; for 24h;	99%
With cobalt naphthenate
(electrochemical oxidation);
With sodium chloride; sodium hydroxide; benzyl alcohol In water at 70℃; for 12h; Sealed tube; Green chemistry;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone (10396-80-2)

Conditions	Yield
With cesium hydroxide; oxygen; triethyl phosphite In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h;	99%
With oxygen; Cu4Cl4O2 (CH3CN)3 In acetonitrile under 760 Torr; Ambient temperature;	95%
With perchloric acid; water; lead dioxide In acetone for 0.133333h;	89%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + propionyl chloride (79-03-8) → 2,6-di-tert-butyl-4-methylphenyl propionate (72959-50-3)

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-4-methyl-phenol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	99%
With n-butyllithium In tetrahydrofuran; hexane at 0℃;	96%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In 1,4-dioxane Ambient temperature;
With n-butyllithium 1)THF, hexane 0 deg C; Yield given. Multistep reaction;

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-ditert-butyl-4-methyl-4-(1,1,2,2,3,3,4,4,4-nonafluorobuta-1-yl)cyclohexa-2,5-dien-1-one

Conditions	Yield
With water; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Irradiation;	99%
With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; Irradiation;	95%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 1-bromocyclopentane-carboxylic acid ethyl ester (30038-94-9) → benzyl 1-(3,5-di-tert-butyl-1-methyl-4-oxocyclohexa-2,5-dien-1-yl)cyclopentane-1-carboxylate

Conditions	Yield
With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 1h; Inert atmosphere;	99%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-di-tert-butyl-4-methylcyclohexanol (163119-16-2)

Conditions	Yield
With hydrogen In water at 60℃; under 7500.75 Torr; for 12h; Autoclave;	98.1%
With palladium on activated charcoal; potassium tert-butylate; hydrogen In ethyl acetate at 90℃; under 3000.3 Torr; for 0.25h; Temperature; Pressure; Autoclave;	95.3%
With nickel(II) oxide; hydrogen; palladium In hexane at 130℃; under 37503.8 Torr; for 12h;	84%
With 5% rhodium on activated aluminium oxide; 10.3% Ni/Al2O3 In isopropyl alcohol at 160℃; under 75007.5 Torr; for 12h; Temperature; Reagent/catalyst; Pressure; Autoclave;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone (809-73-4)

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-4-methyl-phenol With potassium iodide In isopropyl alcohol at 70℃; for 0.5h; Stage #2: With dihydrogen peroxide In isopropyl alcohol at 70 - 75℃; for 9h;	98%
Stage #1: 2,6-di-tert-butyl-4-methyl-phenol With potassium iodide In isopropyl alcohol at 70℃; for 0.5h; Stage #2: With dihydrogen peroxide In water; isopropyl alcohol at 70 - 75℃; for 9h;	98%
Stage #1: 2,6-di-tert-butyl-4-methyl-phenol With potassium iodide In isopropyl alcohol at 70℃; for 0.5h; Stage #2: With dihydrogen peroxide In water; isopropyl alcohol at 70 - 75℃; for 9h;	98%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 4-bromo-4-bromomethyl-2,6-di-t-butyl-2,5-cyclohexadienone (25534-61-6)

Conditions	Yield
With benzyltrimethylammonium tribromide In dichloromethane; water for 3h; Ambient temperature;	98%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + triisobutylaluminum (100-99-2) → isobutylbis(3,5-di-tert-butyl-4-hydroxytoluene)aluminum (56252-57-4)

Conditions	Yield
In pentane byproducts: isobutane; under Ar; soln. of 2,6-di-tert-butyl-4-methylphenol added to soln. of triisobutylaluminum (30 min); refluxed with stirring (70 min); cooled to room temp.; pentane removed (vac.);	98%
In n-heptane Addn. of H-BHT soln. to Al(i-Bu)3 soln. under reflux (70 min), stirring and refluxing (70 min), cooling to room temp.; Evapn., recrystn. (heptane), cooling (to -35°C), filtn., elem. anal.;	78.1%
In pentane

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + trimethylaluminum (75-24-1) → bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum (56252-55-2)

Conditions	Yield
In hexane (Ar); std. Schlenk technique; soln. of Me3Al in hexane was slowly added over 5 min to stirred soln. of phenol in hexane; soln. was stirred at 25°C for 1 h; evapd. in vac. overnight;	98%
In hexane; benzene To a benzene soln. of phenol is added a hexane soln. of AlMe3 at room temp. under N2. The soln. is refluxed for 3 h and cooled.; evapn., recrystn. from boiling pentane; IR, NMR;	91%
In toluene N2-atmosphere; addn. of 2 equiv. of phenol derivative to AlMe3 at -78°C, stirring (room temp., 1 h); solvent removal, dissoln. in hexane/hot PhMe, crystn. (room temp., 12 h); elem. anal.;	89%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + aluminum isopropoxide (555-31-7) → {Al(CH3CHOCH3)2((CH3CH3CCH3)2CH3C6H2O)}

Conditions	Yield
In benzene Stoichiometric quantity of a soln. of Al(OCH3CHCH3)3 in C6H6 is refluxed with phenol derivate for 6 h, benzene-isopropanol azeotrope is colected, exess solvent is removed under reduced pressure.; Elem. anal.;	98%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → C15H24O(18)O

Conditions	Yield
With cesium hydroxide; oxygen-18; triethyl phosphite In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h; Mechanism;	98%

tetrahydrofuran (109-99-9) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + dibutylmagnesium (1191-47-5) → 2,6-di-tertbutyl-4-methylphenoxide

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-4-methyl-phenol; dibutylmagnesium In n-heptane; toluene at 20 - 60℃; for 2h; Stage #2: tetrahydrofuran for 2h;	98%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2,6-di-tert-butyl-4-methylphenoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
With triethylamine In [D3]acetonitrile at 120℃; Inert atmosphere;	98%
With styrene; silver hexafluoroantimonate at 60℃; for 24h; Inert atmosphere; Glovebox;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + C40H99N13P4 → C15H24O*C40H99N13P4

Conditions	Yield
In diethyl ether at 20℃;	98%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6)

Conditions	Yield
With benzyltrimethylammonium tribromide In dichloromethane; water for 0.5h; Ambient temperature;	97%
Multi-step reaction with 2 steps 1: bromine; aqueous acetic acid 2: LiAlH4; diethyl ether View Scheme

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → lithium 2,6-di-tert-butyl-4-methylphenoxide (42031-71-0)

Conditions	Yield
With n-butyllithium In diethyl ether; hexane at 0℃; for 0.5h;	97%
With n-butyllithium In thiophene; hexane at 0 - 20℃; Title compound not separated from byproducts;

[Zn(μ-1,1,3,3-tetramethylguanidinato)(Et)]3 (1000401-33-1) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → [Zn(1,1,3,3-tetramethylguanidine)(Et)(OC6H2(CMe3)2-2,6-Me-4)] (1000401-36-4)

Conditions	Yield
In hexane (Ar); addn. dropwise of soln. of HOC6H2(Me)(CMe3)2 (3 equiv.) to stirredsoln. of (Zn(μ-1,1,3,3-tetramethylguanidine)Et)3 (1 equiv.) in hexan e; stirring for 15 min; evapn., recrystn. from concd. hexanes soln. at -37°C; elem. anal..;	97%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + n-valeryl chloride (638-29-9) → 2,6-di-tert-butyl-4-methylphenyl pentanoate (1420117-15-2)

Conditions	Yield
With potassium iodide In acetonitrile at 82℃; for 24h; Friedel-Crafts Acylation; Inert atmosphere; Sealed tube;	97%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → p-cresol (106-44-5) + 4-tert-butyltoluene (98-51-1)

Conditions	Yield
With Nafion-H; toluene for 2h; Heating;	A 96% B 94 % Chromat.

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + toluene (108-88-3) → p-cresol (106-44-5) + 4-tert-butyltoluene (98-51-1)

Conditions	Yield
With Nafion-H for 2h; Heating;	A 96% B 94 % Chromat.

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone (6485-57-0)

Conditions	Yield
With 2,8-dibromo-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinin-4-ium-5-uide; oxygen In 1,4-dioxane for 6h; Irradiation;	95%
With potassium hydroxide; oxygen
With cobalt naphthenate; dihydrogen peroxide; tert-butyl alcohol

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With bromine In tert-butyl alcohol at 25℃; for 1h;	95%
With N-Bromosuccinimide; dimethyl sulfoxide	93%
With iodine; potassium carbonate In methanol for 0.416667h;	85%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + acetyl chloride (75-36-5) → 2,6-ditertbutyl-4-methylphenyl acetate (29311-34-0)

Conditions	Yield
With potassium iodide In acetonitrile at 82℃; for 24h; Friedel-Crafts Acylation; Inert atmosphere; Sealed tube;	95%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In 1,4-dioxane Ambient temperature;
With n-butyllithium Yield given. Multistep reaction;

Upstream product

• 128-39-2 2,6-di-tert-butylphenol 
• 67-56-1 methanol 
• 2179-51-3 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one 
• 6858-01-1 2,6-di-tert-butyl-4-methylphenoxy radical 
• 489-01-0 2,6-Di-t-butyl-4-methoxyphenol 
• 62926-71-0 Ethaneperoxoic acid 3,5-di-tert-butyl-1-methyl-4-oxo-cyclohexa-2,5-dienyl ester 
• 106-44-5 p-cresol 
• 74-88-4 methyl iodide 
• 115-11-7 isobutene 
• 118-82-1 4,4'-Methylenebis(2,6-di-tert-butylphenol) 
• 2511-22-0 methyl 3,5-di-tert-butyl-4-hydroxybenzoate 
• 1516-98-9 2-(allyloxy)-1,3-di-tert-butyl-5-methylbenzene 
• 88-27-7 N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine 
• 56252-56-3 diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum 

Downstream Products

• 1518-53-2 1,3-di-tert-butyl-2-methoxy-5-methylbenzene 
• 87-97-8 2,6-di-tert-butyl-4-methoxymethylene-phenol 
• 2411-18-9 4-methoxy-4-methyl-2,6-ditert-butylcyclohexa-2,5-dienone 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 13154-57-9 2,6-di-tert-butyl-4-(tert-butylperoxy)-4-methylcyclohexa-2,5-dien-1-one 
• 2607-52-5 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one 
• 1516-94-5 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane 
• 2455-14-3 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone 
• 14387-13-4 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one 
• 137649-09-3 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl>-2,6-di-tert-butylcyclohexa-2,5-dien-1-one 
• 106-44-5 p-cresol 
• 98-54-4 para-tert-butylphenol 
• 2409-55-4 2-tert-Butyl-4-methylphenol 
• 128-39-2 2,6-di-tert-butylphenol 

Related news

In vitro and in vivo effect of 2,6-Di-tert-butyl-4-methylphenol (cas 128-37-0) as an antibiofilm agent against quorum sensing mediated biofilm formation of Vibrio spp.09/28/2019

This study unveils the in vitro and in vivo antibiofilm potential of 2,6-Di-tert-butyl-4-methylphenol (DTBMP) from Chroococcus turgidus against Vibrio spp. In the preliminary study, cell free culture supernatant (CFCS) of C. turgidus inhibited the violacein production in biomarker strain Chromob...detailed

Radiolysis of 2,6-Di-tert-butyl-4-methylphenol (cas 128-37-0) (ionol) in a lipid membrane in the presence of oxygen09/27/2019

Radiation-induced destruction of the ionol molecules in liposomes built of L-α-lecithin depends on the ionol concentration in the lipids and on the concentration of the lipid in the dispersion.detailed

Relevant articles and documents

Antioxidant Synergism Between Butylated Hydroxyanisole and Butylated Hydroxytoluene

Decay of the 2,6-di-tert-butyl-4-methylphenoxy radical in the presence of butylated hydroxyanisole (BHA) was investigated in 1,2-dimethoxyethane with or without triethylamine.BHT-radical was conveniently generated by dissociation of its unstable dimer in solution.The products were BHT, 3,3'-di-tert-butyl-5,5'-dimethoxy-2,2'-dihydroxybiphenyl (BHA-dimer), 2,6-di-tert-butyl-p-quinone methide (QM), 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane, and 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone.The reaction without added triethylamine gave larger quantities of the last two products and BHA (recovery), whereas the reaction with it provided larger quantities of the first two products.The marked difference in the product distribution can be accounted for by a series of reactions including reversible dehydrogenation of BHA with BHT-radical, which generates 2-tert-butyl-4-methoxyphenoxy radical (BHA-radical) and BHT, reversible dimerization of BHA-radical, which affords an intermediary bis(cyclohexadienone), and spontaneous and base-catalysed prototropic rearrangement of the intermediate into BHA-dimer.Products of coupling between BHT-radical and BHA-radical were not obtained.BHA was found to undergo facile acid-catalyzed addition to QM, providing two isomeric bis(hydroxyphenyl)methanes.The results help to elucidate the mechanism of antioxidant synergism between BHA and BHT and may suggest that the synergism can be affected by base or acid. - Key words: Antioxidant synergism; butylated hydroxyanisole; butylated hydroxytoluene; effect of acid; effect of base; fate of phenoxy radicals involved.

Bond Dissociation Enthalpy of α-Tocopherol and Other Phenolic Antioxidants

The equilibrium constants, K1, for the reaction between galvinoxyl and a series of phenolic antioxidants have been determined by means of EPR spectroscopy.With aroxyl radicals decaying at appreciable rates, K1 was obtained by performing kinetic analyses of the time dependence of the concentrations of the equilibrating radicals after mixing the reactants.In two cases the temperature dependence of K1 was also studied and the entropy change for the equilibration reaction was determined.Bond dissociation enthalpies, DH, of the ArO-H bond of the examined phenols were calculated by comparison with the known value of 2,4,6-tri-tert-butylphenol (81.24 kcal mol-1).A larger than expected DH value was found for probucol (81.03 kcal mol-1) and an explanation of this behavior was given in terms of the preferred conformation adopted by the para alkylthio group.The DH value of α-tocopherol (78.93 kcal mol-1) was found to be very close to that of the phenolic precursor of galvinoxyl (78.80 kcal mol-1) and somewhat larger than that of 2,6-di-tert-butyl-4-methoxyphenyl (77.61 kcal mol-1).

Identification of Degradation Products of Terbutol in Environmental Water from Golf Courses

Degradation products of terbutol (2,6-di-tert-butyl-4-methylphenyl N-methylcarbamate) in drainage and ground water from golf courses, on which terbutol had been applied as a herbicide, were identified by capillary GC/MS and reversed-phase HPLC. terbutol and 4-carboxy-, N-demethyl-, and 4-carboxy-N-demethylterbutol were detected in all water samples at concentrations of parts per billion levels.In addition, 4-(hydroxymethyl)- and 4-formylterbutol, 2,6-di-tert-butyl-4-methylphenol (BHT), and 4-(hydroxymethyl)-, 4-formyl-, and 4-carboxy-BHT were observed in some water samples at concentrations of parts per thousand levels.These results demonstrated that terbutol applied on golf courses was mainly degraded by N-demethylation, oxidation of the 4-methyl group, and hydrolysis of the carbamate ester linkage. Keywords:Terbutol; 2,6-di-tert-butyl-4-methylphenyl N-methylcarbamate; identification; degradation

Synthesis, characterization and investigation of catalytic activity of Cu1-xCoxFe2O4 nanocatalysts in t-butylation of p-cresol

In this work, tertiary butylation of p-cresol was carried out in the presence of Cu1-xCoxFe2O4 (x = 0 to 1) nanocatalysts by employing methyl-tert-butyl ether (MTBE) and tert-butyl alcohol (TBA) as alkylation agents. Effects of temperature, mole ratio, type and catalyst composition, time and solvent in reaction conditions were investigated. These nanocatalysts were synthesized using hydrothermal method. The characterization of these catalysts was investigated by means of X-ray diffraction (XRD), Scanning Electron Microscopy (SEM) and Fourier Transform Infrared (FT-IR). These nanocatalysts can be recovered and recycled. A good correlation was found between the activity, in terms of p-cresol conversion and various product selectivities for this reaction, and also the acid-base properties of the catalysts. Nano-sized Cu0.5Co0.5Fe 2O4, in comparison to the other nanocatalysts discussed in this report is the most active nanocatalyst. The only product of this reaction is 2-t-butyl p-cresol with selectivity of 100% and p-cresol conversion is 70%. The possible mechanism for this reaction system was discussed based on the reaction results. The reaction mechanism proposed involves the interaction of phenoxide from phenol and the tert-butyl cation from isobutene on Cu 1-xCoxFe2O4. Indian Academy of Sciences.

Multi SO3H supported on carbon nanotubes: A practical, reusable, and regioselective catalysts for the tert-butylation of p-cresol under solvent-free conditions

The present study describes the synthesis, characterization, and catalytic activity of sulfonated multi-walled carbon nanotubes and sulfonated single-walled carbon nanotubes in the tert-butylation of p-cresol. The catalysts were prepared using a chemical and simple process and it characterized by scanning electron microscopy, Fourier transform infrared, and Raman spectroscopy, thermogravimetric analysis, and acid-base titration. The sulfonated multi-walled carbon nanotubes and sulfonated single-walled carbon nanotubes have been used as practical heterogeneous catalytic systems in the tert-butylation of p-cresol under solvent-free conditions. Sulfonated multi-walled carbon nanotubes with the highest total density of SO3H groups possessed high activity for p-cresol conversion and high selectivity than the sulfonated single-walled carbon nanotubes. This methodology offers some advantages of high selectivity, and high yields, easy work-up, solvent-free conditions, and reusable catalyst. Moreover, the catalytic system was used in scale-up under similar optimized reaction conditions.

Phenol-Phenoxyl Radical Equilibria by Electron Spin Resonance: are Radicals derived from Tocopherol and Analogues Exceptionally Stabilized?

The extra 'stabilization' of the 2,2,4,6,7,-pentamethyl-2,3-dihydrobenzofuran-5-oxyl radical compared with the 2,6-di-tert-butyl-4-methoxyphenoxyl radical is attributed to entropy differences between the parent phenols.

KINETICS OF THE REACTION OF 2,6-DI-t-BUTYLPHENOL WITH METHYL ACRYLATE IN THE PRESENCE OF POTASSIUM 2,6-DI-t-BUTYLPHENOLATE AND THE EFFECT OF PROTON-DONOR COMPONENTS ON THE MECHANISM OF THIS REACTION

A kinetic scheme is proposed for the reaction of 2,6-di-t-butylphenol with methyl acrylate in the presence of potassium 2,6-di-t-butylphenolate.Rate constants have been calculated for the elementary stages which describe the mechanism of catalysis and the effect on the kinetic laws of the proton-donor components 2,6-di-t-butylphenol, water, and methanol.The kinetic scheme contains 30 components and includes 62 rate constants for the elementary stages, which were calculated by mathematical modeling of the kinetics of the process.The calculated results are compared with experimental data for the dependence of the rate of consumption of 2,6-di-t-butylphenol on the concentration of potassium 2,6-di-t-butylphenolate and on the concentrations of the proton-donor components.

Zur Chemie des Dimesityleisens. VII. Die Reaktionen von Dimesityleisen mit Isocyanaten und Isothiocyanaten; Struktur des Produkts mit Phenylisocyanat

The reaction of 2> with the compounds Ph-NCO, Cy-NCO, 2-Naphth-NCO and Ph-NCS proceeds with insertion into all Fe-C-bonds.The structure of the compound 2>3>(THF) is determined.After hydrolysis the corresponding amides

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

New process for preparing food-grade 2,6-di-tert-butyl-p-methylphenol

The invention belongs to the technical field of organic synthesis technologies, and particularly relates to a new process for preparing food-grade 2,6-di-tert-butyl-p-methylphenol. The process comprises the steps: using p-cresol and isobutylene as reaction raw materials, selecting a solid acid catalyst, and performing an alkylation reaction under the heating condition so as to obtain the product,wherein the solid acid catalyst is cerium sulfate, ammonium ferric sulfate or phosphotungstic acid. According to the preparation process, the reaction yield of 2,6-di-tert-butyl-p-methylphenol which is prepared from cresol and isobutylene can be improved by using the solid acid catalyst, the reaction time is shortened, purification in the later stage is convenient, and the product can reach the food-grade requirement.