Butylated hydroxytoluene supplier

Name
2,6-Di-tert-butyl-4-methylphenol
EINECS 204-881-4
CAS No. 128-37-0
Article Data122
CAS DataBase
Density 0.927 g/cm³
Solubility methanol: 0.1 g/mL, clear, colorless
Melting Point 69-73 °C(lit.)
Formula C₁₅H₂₄O
Boiling Point 263.6 °C at 760 mmHg
Molecular Weight 220.355
Flash Point 118.4 °C
Transport Information
Appearance white crystals or crystalline powder
Safety 26-36-37/39
Risk Codes 22-36/37/38-36/38
Molecular Structure
Hazard Symbols Xn
Synonyms Butylated hydroxytoluene;2,6-Di-tart-buty-p-cresol;2,6-Bis(1,1-dimethylethyl)-4-methylphenol;2,6-Di(tert-butyl)hydroxytoluene;2,6-Di-tert-butyl-4-hydroxytoluene;2,6-Di-tert-butyl-4-methylhydroxybenzene;Swanox BHT;2,6-Di-tert-butyl-p-cresol;2,6-Di-tert-butyl-p-methylphenol;DBPC;Deenax;Di-tert-butyl-p-cresol;Dibunol;Dibutylatedhydroxytoluene;Dibutylcresol;Dibutylhydroxytoluene;E 321;Impruvol;Ionol 1;Ionol BHT;Ionole;Lubrizol 817;2,6-Di-tert-butylcresol;2,6-tert-Butyl-4-methylphenol;3,5-Di-tert-butyl-p-hydroxytoluene;Agidol;Alkofen BP;Antage BHT;Antioxidant 264;Antioxidant 30;Antioxidant 4K;AntioxidantKB;Antioxidant MPJ;
PSA 20.23000
LogP 4.29560

Synthetic route

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

: 105-67-9
2,4-Xylenol

A: 1516-94-5
1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 131544-07-5
2,6-di-tert-butyl-4-(3,5-dimethyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one

D: 131544-12-2
3,5-di-tert-butyl-4-hydroxybenzyl 2,4-dimethylphenyl ether

Conditions

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

...Expand

: 67-56-1
methanol

: 128-39-2
2,6-di-tert-butylphenol

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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%

: 106-44-5
p-cresol

: 115-11-7
isobutene

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

: 106-44-5
p-cresol

: 75-65-0
tert-butyl alcohol

A: 2409-55-4
2-tert-Butyl-4-methylphenol

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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.

...Expand

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

: 108-95-2
phenol

A: 1516-94-5
1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 13693-18-0
2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxybenzyl)-4-methylcyclohexa-2,5-dienone

D: 131544-03-1
3,5-di-tert-butyl-4-hydroxybenzyl phenyl ether

Conditions

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

...Expand

: 2511-22-0
methyl 3,5-di-tert-butyl-4-hydroxybenzoate

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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%

: 106-44-5
p-cresol

: 1634-04-4
tert-butyl methyl ether

: 555-16-8
4-nitrobenzaldehdye

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 6,6-((4-nitrophenyl)methylene)bis(2-(tert-butyl)4-methylphenol)

Conditions

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%

...Expand

: Carbonic acid tert-butyl ester 2,6-di-tert-butyl-4-methyl-phenyl ester

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

: 88-26-6
3,5-di-tert-butyl-4-hydroxybenzyl alcohol

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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%

: 106-44-5
p-cresol

: 555-16-8
4-nitrobenzaldehdye

: 75-65-0
tert-butyl alcohol

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 6,6-((4-nitrophenyl)methylene)bis(2-(tert-butyl)4-methylphenol)

Conditions

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

...Expand

: 1206795-79-0
2,6-di-tert-butyl-4-methylbromobenzene

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

: 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

A: 87-97-8
2,6-di-tert-butyl-4-methoxymethylene-phenol

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

...Expand

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 87-97-8
2,6-di-tert-butyl-4-methoxymethylene-phenol

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

: 106-44-5
p-cresol

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 1516-94-5
1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 131544-02-0
3,5-di-tert-butyl-4-hydroxybenzyl 4-methylphenyl ether

D: 131544-08-6
2,6-di-tert-butyl-4-(5-methyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one

Conditions

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

...Expand

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 1516-94-5
1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 809-73-4
3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone

Conditions

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

...Expand

: 1516-98-9
2-(allyloxy)-1,3-di-tert-butyl-5-methylbenzene

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 2253-69-2
2-allyl-6-(tert-butyl)-4-methylphenol

Conditions

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%

: 106-44-5
p-cresol

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 87-97-8
2,6-di-tert-butyl-4-methoxymethylene-phenol

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 131544-02-0
3,5-di-tert-butyl-4-hydroxybenzyl 4-methylphenyl ether

D: 131544-08-6
2,6-di-tert-butyl-4-(5-methyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one

Conditions

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

...Expand

: 67-56-1
methanol

: 128-39-2
2,6-di-tert-butylphenol

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 2455-14-3
3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone

C: 118-82-1
4,4'-Methylenebis(2,6-di-tert-butylphenol)

Conditions

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

...Expand

: 128-39-2
2,6-di-tert-butylphenol

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

: 118-82-1
4,4'-Methylenebis(2,6-di-tert-butylphenol)

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

Conditions	Yield
With sodium methylate at 200℃;

: 106-44-5
p-cresol

: 115-11-7
isobutene

A: 2409-55-4
2-tert-Butyl-4-methylphenol

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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

...Expand

: 128-39-2
2,6-di-tert-butylphenol

: 74-88-4
methyl iodide

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 1516-95-6
2,6-di-tert-butyl-anisole

C: 94065-08-4
2,6-Di-tert.-butyl-6-methyl-cyclohexadien-(2,4)-on-(1)

Conditions

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

...Expand

: 128-39-2
2,6-di-tert-butylphenol

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 1516-94-5
1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 128-38-1
4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl

D: 14387-13-4
2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one

Conditions

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

...Expand

: 128-39-2
2,6-di-tert-butylphenol

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 14387-13-4
2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one

Conditions

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

...Expand

: 128-39-2
2,6-di-tert-butylphenol

: 6858-01-1, 24473-56-1
2,6-di-tert-butyl-4-methylphenoxy radical

A: 1516-94-5
1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

C: 2455-14-3
3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone

D: 128-38-1
4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl

E: 14387-13-4
2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one

Conditions

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

...Expand

: 62926-71-0
Ethaneperoxoic acid 3,5-di-tert-butyl-1-methyl-4-oxo-cyclohexa-2,5-dienyl ester

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 10396-80-2
2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone

C: 62926-78-7
(3,5-Di-tert-butyl-1-methyl-4-oxo-cyclohexa-2,5-dienyloxy)-acetic acid

Conditions

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.

...Expand

: 2179-51-3
4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one

A: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

B: 2607-52-5
2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one

Conditions

Conditions	Yield
In chloroform

: 489-01-0
2,6-Di-t-butyl-4-methoxyphenol

: 6858-01-1, 24473-56-1
2,6-di-tert-butyl-4-methylphenoxy radical

A: 20137-67-1, 3425-36-3
2,6-di-tert-butyl-4-methoxyphenoxyl radical

B: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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;

...Expand

: 6858-01-1, 24473-56-1
2,6-di-tert-butyl-4-methylphenoxy radical

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

Conditions

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;

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 108-24-7
acetic anhydride

: 29311-34-0
2,6-ditertbutyl-4-methylphenyl acetate

Conditions

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%

: 24424-99-5
di-tert-butyl dicarbonate

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: Carbonic acid tert-butyl ester 2,6-di-tert-butyl-4-methyl-phenyl ester

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 96-32-2
bromoacetic acid methyl ester

: 1572184-69-0
methyl 2-(2,6-di-tert-butyl-4-methylphenoxy)acetate

Conditions

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

: 75-91-2
tert.-butylhydroperoxide

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 13154-57-9
2,6-di-tert-butyl-4-(tert-butylperoxy)-4-methylcyclohexa-2,5-dien-1-one

Conditions

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;

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 10396-80-2
2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 79-03-8
propionyl chloride

: 72959-50-3
2,6-di-tert-butyl-4-methylphenyl propionate

Conditions

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;

: 423-39-2
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 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

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 30038-94-9
1-bromocyclopentane-carboxylic acid ethyl ester

: benzyl 1-(3,5-di-tert-butyl-1-methyl-4-oxocyclohexa-2,5-dien-1-yl)cyclopentane-1-carboxylate

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 163119-16-2
2,6-di-tert-butyl-4-methylcyclohexanol

Conditions

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;

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 809-73-4
3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 25534-61-6
4-bromo-4-bromomethyl-2,6-di-t-butyl-2,5-cyclohexadienone

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 100-99-2
triisobutylaluminum

: 56252-57-4
isobutylbis(3,5-di-tert-butyl-4-hydroxytoluene)aluminum

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 75-24-1
trimethylaluminum

: 56252-55-2
bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 555-31-7
aluminum isopropoxide

: {Al(CH3CHOCH3)2((CH3CH3CCH3)2CH3C6H2O)}

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: C15H24O(18)O

Conditions

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

: 109-99-9
tetrahydrofuran

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 1191-47-5
dibutylmagnesium

: 2,6-di-tertbutyl-4-methylphenoxide

Conditions

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%

...Expand

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 2-(2,6-di-tert-butyl-4-methylphenoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: C40H99N13P4

: C15H24O*C40H99N13P4

Conditions

Conditions	Yield
In diethyl ether at 20℃;	98%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 88-26-6
3,5-di-tert-butyl-4-hydroxybenzyl alcohol

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 42031-71-0
lithium 2,6-di-tert-butyl-4-methylphenoxide

Conditions

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;

: 1000401-33-1
[Zn(μ-1,1,3,3-tetramethylguanidinato)(Et)]3

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 1000401-36-4
[Zn(1,1,3,3-tetramethylguanidine)(Et)(OC6H2(CMe3)2-2,6-Me-4)]

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 638-29-9
n-valeryl chloride

: 1420117-15-2
2,6-di-tert-butyl-4-methylphenyl pentanoate

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

A: 106-44-5
p-cresol

B: 98-51-1
4-tert-butyltoluene

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 108-88-3
toluene

A: 106-44-5
p-cresol

B: 98-51-1
4-tert-butyltoluene

Conditions

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

...Expand

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 6485-57-0
2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone

Conditions

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

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 1620-98-0
3,5-di-t-butyl-4-hydroxybenzaldehyde

Conditions

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%

: 128-37-0
2,6-di-tert-butyl-4-methyl-phenol

: 75-36-5
acetyl chloride

: 29311-34-0
2,6-ditertbutyl-4-methylphenyl acetate

Conditions

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;

Butylated hydroxytoluene Specification

Butylated hydroxytoluene, its cas register number is 128-37-0. It also can be called 2,6-Di-tert-butyl-4-methylphenol ; 2,6-Bis(1,1-dimethylethyl)-4-methylphenol ; 2,6-Di-tert-butyl-p-cresol ; 2,6-Di-tert-butyl-4-methylphenol ; 2,6-Di-tert-butyl-4-methylphenol ; DBPC .It is a white crystalline solid and insoluble in water.

Physical properties about Butylated hydroxytoluene are: (1)ACD/LogP: 5.319; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.32; (4)ACD/LogD (pH 7.4): 5.32; (5)ACD/BCF (pH 5.5): 6489.35; (6)ACD/BCF (pH 7.4): 6489.32; (7)ACD/KOC (pH 5.5): 18636.54; (8)ACD/KOC (pH 7.4): 18636.46; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.498; (13)Molar Refractivity: 69.734 cm³; (14)Molar Volume: 237.514 cm³; (15)Polarizability: 27.645 10-24cm³; (16)Surface Tension: 30.0310001373291 dyne/cm; (17)Density: 0.928 g/cm³; (18)Flash Point: 118.431 °C ; (19)Enthalpy of Vaporization: 52.167 kJ/mol; (20)Boiling Point: 263.604 °C at 760 mmHg; (21)Vapour Pressure: 0.00600000005215406 mmHg at 25°C

Preparation of Butylated hydroxytoluene: Butylated hydroxytoluene is prepared by the reaction of p-cresol (4-methylphenol) with isobutylene (2-methylpropene) catalysed by sulfuric acid:
CH₃(C₆H₄)OH + 2 CH₂=C(CH₃)₂→ ((CH₃)₃C)₂CH₃C₆H₂OH
It is prepared from 2,6-di-tert-butylphenol by hydroxymethylation or aminomethylation followed by hydrogenolysis.

Uses of Butylated hydroxytoluene is primarily used as an antioxidant food additive (E number E321) as well as an antioxidant additive in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, electrical transformer oil, and embalming fluid.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3;
(2)InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N;
(3)Smilesc1(c(O)c(C(C)(C)C)cc(c1)C)C(C)(C)C;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	oral	940mg/kg (940mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	AMA Archives of Industrial Health. Vol. 11, Pg. 93, 1955.
guinea pig	LD50	oral	10700mg/kg (10700mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: TREMOR GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	AMA Archives of Industrial Health. Vol. 11, Pg. 93, 1955.
mouse	LD50	intraperitoneal	138mg/kg (138mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BLOOD: HEMORRHAGE LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA	Toxicology and Applied Pharmacology. Vol. 61, Pg. 475, 1981.
mouse	LD50	intravenous	180mg/kg (180mg/kg)	BEHAVIORAL: SLEEP	Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980.
mouse	LD50	oral	650mg/kg (650mg/kg)	BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA	Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
rabbit	LDLo	oral	2100mg/kg (2100mg/kg)	BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	AMA Archives of Industrial Health. Vol. 11, Pg. 93, 1955.
rat	LD50	oral	890mg/kg (890mg/kg)		Neoplasma. Vol. 24, Pg. 253, 1977.
women	TDLo	oral	80mg/kg (80mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: COMA GASTROINTESTINAL: GASTRITIS	New England Journal of Medicine. Vol. 314, Pg. 648, 1986

Product Name

2,6-Di-tert-butyl-4-methylphenol

Synthetic route

Butylated hydroxytoluene Specification

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