Basic information
- Standard SMILES
CC(C)(C)c1ccc(O)c(O)c1- InChIKey
XESZUVZBAMCAEJ-UHFFFAOYSA-N- Molecular formula
- C10H14O2
- Average molar mass
- 166.22 g/mol
- Monoisotopic mass
- 166.09937969
Names & identifiers
- Preferred name
- 4-tert-Butylcatechol
- IUPAC
- 4-tert-butylbenzene-1,2-diol
- English name
- 4-tert-Butylcatechol
- Molecular formula
- C10H14O2
- Molecular weight
- 166.22
Names & synonyms
4-tert-Butylcatechol98-29-3p-tert-Butylcatecholp-tert-Butyl catecholSynox TBC1,2-Benzenediol, 4-(1,1-dimethylethyl)-4-tert-butyl catecholDTXSID5024687NSC-53109A069144KRDTXCID804687para-tert-butyl catechol
Show more names
TBC4-tbcPTBC4-TERT-BUTYL-1,2-BENZENEDIOLT-BUTYL CATECHOLP-T-BUTYLCATECHOLp-tert-Butylpyrocatechol
4-tertiary butyl catecholRefChem:858183202-653-94-(tert-butyl)benzene-1,2-diol4-tert-butylbenzene-1,2-diol4-tert-Butylpyrocatechol4-T-BUTYLCATECHOL4-t-Butylpyrocatechol
Database identifiers
- CAS
98-29-3- PubChem CID
- 7381
- DTXSID
DTXSID5024687- ChEMBL
CHEMBL220845- UNII
- 9A069144KR
- EC Number
- 202-653-9
- Nikkaji
- J21.591K
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 148
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phenols
Density1.0496 @25 °C
Flash Point130 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point285 °C @760 [mm Hg]
Melting Point52 °C
Odor ThresholdOdor Threshold = 1.0 mg/l (detection)
Vapor Pressure
0.0028 [mmHg]
0.0028 [mm Hg] @25 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description
Liquid; Dry Powder; Liquid; Other Solid; CBI
White solid; [CHEMINFO] White or tan, odorless crystalline solid; [MSDSonline]
Collision Cross Section139.3 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5024687]
Physicochemical properties
- Melting point
- 52 · 52-55 °C(lit.)
- Boiling point
- 285 °C · 285 °C(lit.)
- Density
- 1.049 · 1.049
- bulk density
- 650 · 650-700kg/m3
- vapor pressure
- 1 hPa · <1 hPa (25 °C)
- refractive index
- 20 · n20/D 1.508
- Flash point
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1 g/10 · methanol: soluble1g/10 mL, clear, colorless to slightly yellow
- pka
- 9.92 · 9.92±0.10(Predicted)
- form
- powder to lump
- color
- White to Light yellow to Light red
- Odor
- 10 %indipropylene · at 10.00%indipropylene glycol. phenolic
- Water Solubility
- 0.2 g/100 · 0.2 g/100 mL (25 ºC)
- Sensitive
- Hygroscopic
- BRN
- 2043335 · 2043335
- Exposure limits
- 5 ppm · ACGIH: TWA 5 ppm (Skin)NIOSH: TWA 5 ppm(20 mg/m3)
- InChI
- 1S/C10H14O2/c1-10(2,3)7-4-5-8(11)9(12)6-7/h4-6,11-12H,1-3H3
- InChIKey
- XESZUVZBAMCAEJ-UHFFFAOYSA-N
- SMILES
- CC(C)(C)c1ccc(O)c(O)c1
- LogP
- 1.98 at · 1.98 at 25℃
- CAS DataBase Reference
- 98 · 98-29-3(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- 4 · 4-TERT-BUTYLCATECHOL
- FDA 21 CFR
- 175.105 · 175.105; 177.2600
- EWG's Food Scores
- 1 · 1-4
- FDA UNII
- 9 A069144KR · 9A069144KR
- NIST Chemistry Reference
- 1 · 1,2-Benzenediol, 4-(1,1-dimethylethyl)-(98-29-3)
- EPA Substance Registry System
- p-tert-Butylcatechol (98-29-3)
- UNSPSC Code
- 12352104 · 12352104
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS09
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312-H314-H317-H410
- Precautionary statements
- 260 · P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C,N,T
- Risk Statements
- 22 · 22-34-43-21-51/53-21/22-39/23/24/25-20/21/22-10-50/53
- Safety Statements
- 26 · 26-36/37/39-45-61-24-60
- RIDADR
- 2923 · UN 2923 8/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 1400000 · UX1400000
- Autoignition Temperature
- 160 °C · 160 °C
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29072900 · 29072900
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1BSkin Sens. 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 815 mg/kg LD50 dermal Rat 1331 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1% (27 of 2665) of reports.
Danger
H302 (87.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2665 reports by companies from 36 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: 1,2-Benzenediol, 4-(1,1-dimethylethyl)-
1,2-Benzenediol, 4-(1,1-dimethylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenediol, 4-(1,1-dimethylethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 10-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13800
4-t-Butylpyrocatechol: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - tert-butyl catechol: Human health tier II assessment
Hazards Summary
Has corrosive effects to skin and eyes; [CHEMINFO] Danger of skin sensitization; [MAK] No mortality occurred in animals exposed to saturated concentrations (3-4 ppm); Cases of skin depigmentation have been reported in workers; [AIHA] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; Can be absorbed through skin; May cause skin sensitization; [MSDSonline]
Hazard Classes and Categories
Acute Tox. 4 (87.7%)
Acute toxicity (ingestion) - category 4
Acute toxicity (Dermal) - Category 3
Safety & protection
Protective Action Criteria (PAC)
0.18 [mg/m3]
2.0 [mg/m3]
160 [mg/m3]
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- UX1400000
- ridadr
- UN 2923 8/PG 3
- hs_code
- 29072900
- Toxicity
- LD50 orally in Rabbit: 815 mg/kg LD50 dermal Rat 1331 mg/kg
- risk_code
- 22-34-43-21-51/53-21/22-39/23/24/25-20/21/22-10-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS09
- hazard_code
- C,N,T
- safety_code
- 26-36/37/39-45-61-24-60
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H302+H312-H314-H317-H410
- Limited Quantities
- 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1BSkin Sens. 1
- Autoignition Temperature
- 160 °C
- Precautionary statements
- P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Uses & manufacturing
UsesUsed to inhibit polymerization of styrene-butadiene and other olefins; [Hawley]
U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesPigment
Industry UsesChemical reaction regulator
General Manufacturing Information
Printing Ink Manufacturing
1,2-Benzenediol, 4-(1,1-dimethylethyl)-: ACTIVE
Applications
DescriptionPara-tertiary butyl catechol is specially prepared by reacting the impure catechol fraction with tertiary butyl alcohol. Used for its various properties (inhibition of polymerization and as an antioxidizing agent) in the manufacture of rubber, plastics and paints, in the preparation of petrolatum products, and as an antioxidant in oils, it may induce vitiligo.
Uses4-tert-butylcatechol (PTBC) is used as an antioxidant in fats, oils, and mineral oils, and as a stabilizer in polyester resins and polystyrene resins. A concentration of PTBC (up to 0.005%) can be found in paints, glues, thermal paper, lubricating oil, and mineral oil products.4-tert-Butylcatechol is widely utilized as an inhibitor in polymerization of butadiene, styrene, vinyl acetate and other reactive monomers. It plays an important role in the synthesis of tungsten oxide nanoparticles by nonaqueous sol-gel process. It acts as a stabilizer in the manufacturing of polyurethane foam. It is employed as an antioxidant for synthetic rubber, polymers and oil derivatives. It is also utilized as a purification agent for aminoformate catalysts.
General Description4-tert-Butylcatechol,in the presence of O2 catalyzed by tyrosinase, yields 4-tert-butyl-o-benzoquinone. Electrochemical oxidation of 4-tert-Butylcatechol in the presence of 4-hydroxycoumarin as nucleophile has been studied using cyclic voltammetry and controlled-potential coulometry. It undergoes electrochemical trimerization via anodic oxidation and mechanism of trimerization has been studied using cyclic voltammetry and controlled-potential coulometry.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
68 records
Linked notes
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