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128-37-0

Basic Information
CAS No.: 128-37-0
Name: Butylated hydroxytoluene
Article Data: 122
Cas Database
Molecular Structure:
Molecular Structure of 128-37-0 (Butylated hydroxytoluene)
Formula: C15H24O
Molecular Weight: 220.355
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;
EINECS: 204-881-4
Density: 0.927 g/cm3
Melting Point: 69-73 °C(lit.)
Boiling Point: 263.6 °C at 760 mmHg
Flash Point: 118.4 °C
Solubility: methanol: 0.1 g/mL, clear, colorless
Appearance: white crystals or crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-36/38
Safety: 26-36-37/39
Transport Information: N/A
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
ConditionsYield
In triethylamineA 3.9%
B 99%
C 54%
D 17%
67-56-1

methanol

128-39-2

2,6-di-tert-butylphenol

128-37-0

2,6-di-tert-butyl-4-methyl-phenol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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.
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
ConditionsYield
In triethylamine Further byproducts given;A 14%
B 87%
C 4.6%
D 43%
2511-22-0

methyl 3,5-di-tert-butyl-4-hydroxybenzoate

128-37-0

2,6-di-tert-butyl-4-methyl-phenol

Conditions
ConditionsYield
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
ConditionsYield
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

128-37-0

2,6-di-tert-butyl-4-methyl-phenol

Conditions
ConditionsYield
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
ConditionsYield
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%
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  • 2,6-Di-tert-butyl-4-methylphenol   CAS: 128-37-0

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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