3D Mol Similar

tert-Butylhydroquinone

: Iupac Name：2-tert-butylbenzene-1,4-diol; CAS No.: 1948-33-0; Molecular Weight：166.21696; Modify Date.: 2022-11-25 02:19; Introduction: White to light tan crystalline powder or a fine beige powder. Very slight aromatic odor. View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; tert-Butylhydroquinone; 1.2 Synonyms; 1,4-Benzenediol, 2-(1,1-dimethylethyl)- 1-T-BUTYL-1,4-DIHYDROXYBENZENE 2-(1,1-Dimethylethyl)-1,4-benzenediol 2-(1,1-dimethylethyl)benzene-1,4-diol 2-(2-Methyl-2-propanyl)-1,4-benzenediol 2-T-BUTYLHYDROQUINONE 2-TERT-BUTYL-1,4-BENZENEDIOL 2-TERT-BUTYL-1,4-DIHYDROXYBENZENE 2-tert-Butylbenzene-1,4-diol 2-tert-butylhydroquinone 2-tert-butyl-hydroquinone 2-tertiary-butylhydroquinone Butylhydroquinone, t- Butylhydroquinone, tert- EINECS 217-752-2 Hydroquinone, t-butyl- Hydroquinone, tert-butyl- Hydroquinone,tert-butyl MFCD00002344 Mono-tert-butylhydroquinone MTBHQ TBHQ t-Butyl hydroquinone tert-butyl hydroquinone TERT-BUTYLHYDROCHINONE tert-Butylhydroquinone (TBHQ) TERTIARY BUTYL HYDROQUINONE; View all

1.3 CAS No.: 1948-33-0

1.4 CID: 16043

1.5 EINECS(EC#): 217-752-2

1.6 Molecular Formula: C10H14O2 (isomer)

1.7 Inchi: InChI=1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3

1.8 InChIkey: BGNXCDMCOKJUMV-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)(C)C1=C(C=CC(=C1)O)O

1.10 Isomers Smiles: CC(C)(C)C1=C(C=CC(=C1)O)O

2. Properties

2.1 Density: 295

2.1 Melting point: 125-130℃

2.1 Boiling point: 273℃

2.1 Refractive index: 1.559

2.1 Flash Point: 171℃

2.2 Precise Quality: 166.09900

2.2 PSA: 40.46000

2.2 logP: 2.39530

2.2 VaporDensity: 5.73 (Air = 1)

2.3 Appearance: tan powder

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: White, crystalline solid having a characteristic odour.

2.6 Color/Form: WHITE TO LIGHT TAN CRYSTALS

2.7 Contact Allergens: This antioxidant has seldom been reported as a sensitizer,mainly in cosmetics (lipsticks, lip-gloss, hairdyes) or in cutting oils. Simultaneous/cross-reactionshave been described to butylhydroxyanisole (BHA)and less frequently to butylhydroxytoluene (BHT), butnot to hydroquinone

2.8 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.9 Odor: Very slight aromatic odor

2.10 PH: pH = 4.56 at 25 deg C of a 1% solution of 2-tert-butylhydroquinone

2.11 pKa: 10.80±0.18(Predicted)

2.12 Water Solubility: soluble in acetone, alcohol, ethyl acetate

2.13 Spectral Properties: IR: 2:595A (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 4:141C (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)

2.14 Stability: Stable. Incompatible with strong bases, strong oxidizing agents.

2.15 StorageTemp: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.

3.2 General Description: White to light tan crystalline powder or a fine beige powder. Very slight aromatic odor.

3.3 Methods of Manufacturing: 3 parts by weight of phosphoric acid, 0.1 part by weight of water was poured into a stirring cylinder, and 6 parts by weight of hydroquinone was added to the stirring cylinder to carry out stirring;2) After stirring, the mixed solution was placed in a reaction kettle and heated to 59 ° C, and then the reaction vessel was charged with t-butanolCopies;3) heating to 81 ° C, the insulation for 2 hours to react;4) the reaction product by centrifugal separation, washing, dehydration after TBHQ crude;5) 1 part by weight of acid and 95 parts by weight of water were mixed and then heated. After heating to 81 ° C, 6.5 parts by weight of TBHQ was added and heated to 95 ° C with stirring.6) The solution of step 5) was centrifuged for the first time, the DTBHQ insoluble in water in the crude TBHQ was separated, and then the solution was cooled. When the solution was cooled to 45C or lower, the second centrifugation was carried out, and the obtained TBHQ crystal washing, dehydration, drying, that was TBHQ boutique.Wherein the drying in step 6) is carried out by pouring the wet TBHQ boutique into a vibrating screen sieve, laying the sieved TBHQ boutique on a drying tray, having a thickness of 5 cm and drying for 8 hours.The TBHQ was obtained, where the weight percentage of TBHQ was 99.9percent and the weight percentage of DTBHQ was 0.1percent.General procedure: To a Teflon stoppered tube shaped glass ampoule ～4.8mL in volume, 0.166mmol of the desired para-benzoquinone, a stir bar, and 0.25mL toluene containing 0.5mg Preparation of 2-tert-butyl-1, 4-benzoquinone A mixture of 2-t-butylphenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20percent w/w) in acetic acid (5 ml) was heated with stirring at 50-60 C under inert atmosphere. To this reaction mixture was added aq. 30percent H202 (20 mmol) drop wise over 15 min. and heated for 1 h. The catalyst was recovered by simple filtration and 2-tert-butyl-1, 4-benzoquinone formed (97percent) was separated by chromatographic purification.; View all

3.4 Purification Methods: Recrystallise the hydroquinone from H2O or MeOH and dry it in a vacuum at 70o. Store it in a dark container. [Stroh et al. Angew Chem 69 699 1957, Beilstein 6 IV 6013.] tert-Butylhydroquinone Preparation Products And Raw materials Raw materials

3.5 Usage: tert-Butylhydroquinone (TBHQ) is an antioxidant that exhibits an excellent stabilizing effect in unsaturated fats and oils. It has good solubility in fats and oils, with a maximum usage level of 0.02% based on the weight of the fat or oil or the fat content of the food product. It shows no discoloration in the presence of iron and produces no discernible flavor or odor. It can be combined with BHA and BHT. It is used in edible fats and vegetable oils to retard rancidity. It is used in potato chips and dry cereal. It is also termed butylhydroquinone and mono-tertiary-butylhydroquinone.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: S26;S28

4.1 Exposure Standards and Regulations: TBHQ is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

4.2 Packing Group: III

4.2 Fire Hazard: tert-Butylhydroquinone is combustible.

4.3 Hazard Class: 9

4.3 Hazard Declaration: H302-H315-H319-H335

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: UN3077

4.4 Caution Statement: P261-P305 + P351 + P338

4.4 Formulations/Preparations: For the most part, TBHQ is employed alone, as blends with BHT and BHA, and in conjunction with synergists such as citric acid or other metal chelating aqents.

4.5 WGK Germany: 3

4.5 RTECS: MX4375000

4.5 Report: Reported in EPA TSCA Inventory.

4.6 Safety: Safety Information about?tert-Butylhydroquinone (CAS NO.1948-33-0):
Hazard Codes:?Xn
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.; View all

4.7 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.

4.8 Toxicity

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.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H312 Harmful in contact with skin H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

IR : KBr disc

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

1948-33-0Total: 15 Synthesis Route

88-18-6 29 Suppliers

3602-55-9 39 Suppliers

1948-33-0 330 Suppliers

Literatures:
WO2005/63664 A1, ; Page/Page column 7 ;
Yield: ~1%

533-73-3 121 Suppliers

1948-33-0 330 Suppliers

Literatures:
WO2012/75053 A2, ;
Yield: null

3602-55-9 39 Suppliers

1948-33-0 330 Suppliers

Literatures:
Agricultural and Biological Chemistry, , vol. 52, # 11 p. 2843 - 2850
Yield: null

View all

8. Precursor and Product

precursor:

88-18-6

66806-57-3

3602-55-9

21112-37-8

75-65-0

4857-74-3

88-32-4

533-73-3

115-11-7

123-31-9

1634-04-4

507-19-7

121-00-6

View all

product :

844-80-4

717-47-5

143450-98-0

21112-37-8

18403-57-1

14670-48-5

192803-37-5

88-32-4

142834-55-7

114289-77-9

25441-61-6

121-00-6

25762-84-9

View all

9. Other Information

9.0 Usage: TBHQ was used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli. Environment friendly electrode materials for supercapacitors were attained by decorating the surface of graphene nanosheets with TBHQ. TBHQ is frequently used as a food preservative. Inhibition of oxidative rancidity in frozen cooked fish flakes by tert-butylhydroquinone. Nuclear factor E2-related factor 2-dependent antioxidant response element activation is by tert-butylhydroquinoneoccurring preferentially in Astrocytes conditions.

9.1 BRN: 637923

9.2 Chemical Properties: tan powder

9.3 Uses: tert-Butylhydroquinone (TBHQ) is an antioxidant that exhibits an excellent stabilizing effect in unsaturated fats and oils. It has good solubility in fats and oils, with a maximum usage level of 0.02% based on the weight of the fat or oil or the fat content of the food product. It shows no discoloration in the presence of iron and produces no discernible flavor or odor. It can be combined with BHA and BHT. It is used in edible fats and vegetable oils to retard rancidity. It is used in potato chips and dry cereal. It is also termed butylhydroquinone and mono-tertiary-butylhydroquinone.

9.4 Definition: ChEBI: A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.

9.5 General Description: White to light tan crystalline powder or a fine beige powder. Very slight aromatic odor.

9.6 Air & Water Reactions: Insoluble in water.

9.7 Reactivity Profile: Phenols, such as tert-Butylhydroquinone, 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. tert-Butylhydroquinone is incompatible with oxidizers.; View all

9.8 Fire Hazard: tert-Butylhydroquinone is combustible.

9.9 Contact allergens: This antioxidant has seldom been reported as a sensitizer, mainly in cosmetics (lipsticks, lip-gloss, hair dyes) or in cutting oils. Simultaneous/cross-reactions have been described to butylhydroxyanisole (BHA) and less frequently to butylhydroxytoluene (BHT), but not to hydroquinone

9.10 Purification Methods: Recrystallise the hydroquinone from H2O or MeOH and dry it in a vacuum at 70o. Store it in a dark container. [Stroh et al. Angew Chem 69 699 1957, Beilstein 6 IV 6013.]

9.11 Storage Conditions: 3 parts by weight of phosphoric acid, 0.1 part by weight of water was poured into a stirring cylinder, and 6 parts by weight of hydroquinone was added to the stirring cylinder to carry out stirring;2) After stirring, the mixed solution was placed in a reaction kettle and heated to 59 ° C, and then the reaction vessel was charged with t-butanolCopies;3) heating to 81 ° C, the insulation for 2 hours to react;4) the reaction product by centrifugal separation, washing, dehydration after TBHQ crude;5) 1 part by weight of acid and 95 parts by weight of water were mixed and then heated. After heating to 81 ° C, 6.5 parts by weight of TBHQ was added and heated to 95 ° C with stirring.6) The solution of step 5) was centrifuged for the first time, the DTBHQ insoluble in water in the crude TBHQ was separated, and then the solution was cooled. When the solution was cooled to 45C or lower, the second centrifugation was carried out, and the obtained TBHQ crystal washing, dehydration, drying, that was TBHQ boutique.Wherein the drying in step 6) is carried out by pouring the wet TBHQ boutique into a vibrating screen sieve, laying the sieved TBHQ boutique on a drying tray, having a thickness of 5 cm and drying for 8 hours.The TBHQ was obtained, where the weight percentage of TBHQ was 99.9percent and the weight percentage of DTBHQ was 0.1percent.General procedure: To a Teflon stoppered tube shaped glass ampoule ～4.8mL in volume, 0.166mmol of the desired para-benzoquinone, a stir bar, and 0.25mL toluene containing 0.5mg Preparation of 2-tert-butyl-1, 4-benzoquinone A mixture of 2-t-butylphenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20percent w/w) in acetic acid (5 ml) was heated with stirring at 50-60 C under inert atmosphere. To this reaction mixture was added aq. 30percent H202 (20 mmol) drop wise over 15 min. and heated for 1 h. The catalyst was recovered by simple filtration and 2-tert-butyl-1, 4-benzoquinone formed (97percent) was separated by chromatographic purification.; View all

10. Computational chemical data

Molecular Weight: 166.21696g/mol
Molecular Formula: C₁₀H₁₄O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 166.099379685
Monoisotopic Mass: 166.099379685
Complexity: 148
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 40.5
Heavy Atom Count: 12
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADgSAmAAyBoAAAgCAAiBCAAACAAAgIAAIiAAGCIgIJiKCERKAcAAkwBEImAfAwPAPgQABAAAIAAACAAIAABAAAAAAAAAAAA==

11. Question & Answer

What are the potential risks of tert-Butylhydroquinone on human health? Jul 15 2023
tert-Butylhydroquinone (4-tert-butylcatechol, abbreviated as TBC) is a common food preservative widely used in foods such as oils, nuts, and meats. Its chemical structure is shown below: tert-Butylhyd..
What are the synthesis methods and applications of tert-Butylhydroquinone in pharmaceutical chemistry? Jun 13 2023
In the field of modern organic chemistry, hydroquinone is a widely used compound with good biological activity and chemical reactivity. It is widely used in industries such as pharmaceuticals, pigment..
Is tert-Butylhydroquinone Harmful? - An Interpretation from a Scientific Perspective Jun 07 2023
Introduction In recent years, tert-Butylhydroquinone (TBHQ) has gained attention as a commonly used food additive. Some people express concerns about TBHQ, believing that it can be harmful to human he..
What is tert-Butylhydroquinone as a food additive? Jun 07 2023
tert-Butylhydroquinone (TBHQ) is a common synthetic food additive widely used for food preservation and antioxidant purposes. Its chemical name is 2-tert-butyl-4-methylphenol. TBHQ has strong antioxid..

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