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tert-Butylhydroquinone
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Name

tert-Butylhydroquinone

 EINECS 217-752-2
CAS No. 1948-33-0 Density 1.086 g/cm3
PSA 40.46000 LogP 2.39530
Solubility Insoluble in water Melting Point 127-129 °C(lit.)
Formula C10H14O2 Boiling Point 291.3 °C at 760 mmHg
Molecular Weight 166.22 Flash Point 138.7 °C
Transport Information UN 3077 Appearance tan powder
Safety 26-36-28 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 1948-33-0 (tert-Butylhydroquinone) Hazard Symbols HarmfulXn
Synonyms

Hydroquinone,tert-butyl- (6CI,7CI,8CI);2-(1,1-Dimethylethyl)hydroquinone;2-(tert-Butyl)-p-hydroquinone;2-t-Butylhydroquinone;2-tert-Butyl-1,4-benzenediol;2-tert-Butyl-1,4-dihydroxybenzene;2-tert-Butyl-1,4-hydroquinone;2-tert-Butylhydroquinone;Banox 20BA;Grindox450;Keniox 20;MC-TB 20;MTBHQ;Mono-tert-butylhydroquinone;Mono-tertiarybutylhydroquinone;NSC 4972;TBHQ;Tenox 20;Tenox TBHQ;

Article Data 43

tert-Butylhydroquinone Synthetic route

123-31-9

hydroquinone

75-65-0

tert-butyl alcohol

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With phosphoric acid In water at 59 - 81℃; for 2h; Temperature;99.9%
With aminosulfonic acid In 1,4-dioxane; toluene at 135℃; for 8h; Temperature;50%
With phosphoric acid In water at 80℃; for 4h; Concentration; Temperature; Time; Large scale;44.8%
540-88-5

acetic acid tert-butyl ester

123-31-9

hydroquinone

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With sulfuric acid at 85℃; for 8h; Temperature; Large scale;99.9%
3602-55-9

2-tert-butyl-1,4-benzoquinone

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With (iPr4PCP)IrH4; hydrogen In toluene at 60℃; under 760.051 Torr; for 2h;99%
With palladium on activated charcoal; hydrogen In dichloromethane at 60℃; under 22502.3 Torr; for 2h; Temperature; Solvent; Pressure; Reagent/catalyst;97.3%
With 2,5-dihydrotoluene; trifluoroacetic acid In toluene at 30℃; for 2h;70%
88-18-6

2-tert-Butylphenol

A

3602-55-9

2-tert-butyl-1,4-benzoquinone

B

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With dihydrogen peroxide; Ti-superoxide In water; acetic acid at 50 - 60℃; for 1.25h; Product distribution / selectivity;A 97%
B 0.7%

2-tert-butyl-4-hydroxybenzaldehyde

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 35℃; for 12h; Dakin Phenol Oxidation;70%
3602-55-9

2-tert-butyl-1,4-benzoquinone

100-46-9

benzylamine

A

1948-33-0

tert-butylhydroquinone

B

2-(Benzylamino)-5-(tert-butyl)1,4-benzoquinone

C

2-(Benzylamino)-6-(tert-butyl)-1,4-benzoquinone

Conditions
ConditionsYield
With oxygen In acetonitrile for 1h; Ambient temperature;A 15.6%
B 18.8%
C 65.6%
123-31-9

hydroquinone

75-65-0

tert-butyl alcohol

A

5875-45-6

2,5-di-tert-butylphenol

B

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With aminosulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4h; Temperature; Solvent;A 17.2%
B 57.8%
3602-55-9

2-tert-butyl-1,4-benzoquinone

A

1948-33-0

tert-butylhydroquinone

B

2-(Benzylamino)-5-(tert-butyl)1,4-benzoquinone

C

2-(Benzylamino)-6-(tert-butyl)-1,4-benzoquinone

Conditions
ConditionsYield
With benzylamine In acetonitrile for 1h; Ambient temperature;A 52.8%
B 6.6%
C 40.6%
123-31-9

hydroquinone

75-65-0

tert-butyl alcohol

A

6669-13-2

t-butyl phenyl ether

B

2460-77-7

2,5-di-tert-butyl-p-benzoquinone

C

88-58-4

2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

D

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With porous pillared-zirconium phosphate functionalized with methyl group In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4h; Reagent/catalyst; Autoclave;A n/a
B n/a
C n/a
D 48.8%
With perfluorosulfonicacid-functionalized carbon nanotubes (PFSA-CNT-0.5) In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Catalytic behavior; Reagent/catalyst; Autoclave;
...Expand
123-31-9

hydroquinone

115-11-7

isobutene

1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With phosphoric acid; xylene at 105℃;
With aluminum oxide; silica gel; xylene at 200℃;
With aluminium tris-<4-hydroxy-phenolate>; xylene at 240℃;

tert-Butylhydroquinone Chemical Properties

IUPAC Name: 2-tert-Butylbenzene-1,4-diol    
Synonyms of tert-Butylhydroquinone (CAS NO.1948-33-0): 1,4-Benzenediol (1,1-dimethylethyl)- ; 2-(1,1-Dimethylethyl)-1,4-benzenediol ; 2-t-Butylhydroquinone ; 2-tert-Butyl(1,4)hydroquinone ; Mono-tert-butylhydroquinone ; tertiary-Butylhydroquinone
CAS NO: 1948-33-0
Molecular Formula: C10H14O2
Molecular Weight: 228.29
Molecular Structure:
EINECS: 217-752-2
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 18.46 Å2
Index of Refraction: 1.545
Molar Refractivity: 48.4 cm3
Molar Volume: 152.9 cm3
Surface Tension: 40.2 dyne/cm
Density: 1.086 g/cm3
Flash Point: 138.7 °C
Enthalpy of Vaporization: 55.2 kJ/mol
Boiling Point: 291.3 °C at 760 mmHg
Vapour Pressure: 0.00112 mmHg at 25°C 
Melting Point: 127-129 °C(lit.)
Appearance: tan powder
Solubility: Insoluble in water
Stability: Stable. Incompatible with strong bases, strong oxidizing agents. 
Product Categories of tert-Butylhydroquinone (CAS NO.1948-33-0): Industrial/Fine Chemicals;Anthraquinones, Hydroquinones and Quinones;Alcohols;Monomers;Polymer Science;Organic Building Blocks;Oxygen Compounds;Polyols

tert-Butylhydroquinone Uses

 tert-Butylhydroquinone (CAS NO.1948-33-0) is a highly effective preservative for many edible animal fats and unsaturated vegetable oils. It is added to a wide range of foods, with highest limit (1000 mg/kg) permitted for frozen fish and fish products.
Besides it is also used industrially as a stabilizer to inhibit autopolymerization of organic peroxides. In perfumery, it is used as a fixative to lower the evaporation rate and improve stability. It is also added to lacquers, resins,varnishes and oil field additives.

tert-Butylhydroquinone Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 790mg/kg (790mg/kg)   WHO Food Additives Series. Vol. 8, Pg. 26, 1975.
mouse LD50 intraperitoneal 144mg/kg (144mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS		 Drug and Chemical Toxicology. Vol. 7, Pg. 335, 1984.
mouse LD50 oral 1gm/kg (1000mg/kg)   Kodak Company Reports. Vol. 21MAY1971,
rat LCLo inhalation 2900mg/m3/4H (2900mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 753, 1992.
rat LD50 intraperitoneal 300mg/kg (300mg/kg)   Journal of the American Oil Chemists' Society. Vol. 52, Pg. 53, 1975.
rat LD50 oral 700mg/kg (700mg/kg)   Journal of the American Oil Chemists' Society. Vol. 52, Pg. 53, 1975.

tert-Butylhydroquinone Consensus Reports

Reported in EPA TSCA Inventory.

tert-Butylhydroquinone Safety Profile

Safety Information about tert-Butylhydroquinone (CAS NO.1948-33-0):
Hazard Codes: HarmfulXn
Risk Statements: 22-36/37/38
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-28
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S28: After contact with skin, wash immediately with plenty of soap-suds. 
S36: Wear suitable protective clothing.
RIDADR: UN3077
WGK Germany: 3
RTECS: MX4375000
HazardClass: 9
PackingGroup: III
HS Code: 29072900
Poison by intraperitoneal route. Moderately toxic by ingestion and inhalation. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

tert-Butylhydroquinone Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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