HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

2-Tert-Butylphenol

HCID 6923
New noteNew reactionRequest quotes
Print preview

Completing data — refresh the page later to see the latest

Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
27178-34-3
Standard SMILES
CC(C)(C)c1ccccc1O
InChIKey
WJQOZHYUIDYNHM-UHFFFAOYSA-N
Molecular formula
C10H14O
Average molar mass
150.22 g/mol
Monoisotopic mass
150.10446507

Overview

2-tert-Butylphenol is an alkylbenzene.

Names & identifiers

Preferred name
2-Tert-Butylphenol
IUPAC
2-tert-butylphenol
English name
tert-butylphenol
Molecular formula
C10H14O
Molecular weight
150.21756

Names & synonyms

2-TERT-BUTYLPHENOL88-18-62-t-Butylphenolo-tert-Butylphenolo-t-ButylphenolPhenol, 2-(1,1-dimethylethyl)-Phenol, o-tert-butyl-2-(1,1-Dimethylethyl)phenol2-tert-Butyl-1-hydroxybenzeneDTXSID2026525Phenol, o-(tert-butyl)-NL2FPV3N0Z
Show more names
(1,1-dimethylethyl)-Phenoltert-butyl phenol (mixed isomers)
Benzene, 1-tert-butyl-2-hydroxy-DTXCID206525RefChem:910268201-807-22-(tert-butyl)phenolTERT-BUTYLPHENOLPhenol, (1,1-dimethylethyl)-27178-34-3

Database identifiers

CAS
27178-34-3、88-18-6
PubChem CID
6923
DTXSID
DTXSID2026525
ChEMBL
CHEMBL108851
ChEBI
CHEBI:34305
UNII
NL2FPV3N0Z
EC Number
201-807-2、248-300-2
Nikkaji
J44.174K

Properties

Computed structural propertiesFilling in

XLogP
3.3
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
11
Formal charge
0
Complexity
123

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phenols
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Phenol, 2-(1,1-dimethylethyl)-) -> IFRA transparency List
LogP · 2 items

log Kow = 3.31

3.3

Density · 2 items

0.9783 @ 20 °C/4 °C

Relative density (water = 1): 0.98

Color/Form · 2 items

LIGHT YELLOW LIQUID

Amber-colored liquid

Solubility · 4 items

SOL IN ALCOHOL; VERY SOL IN ETHER; SOL IN ALKALI, CARBON TETRACHLORIDE

SOL IN ISOPENTANE, TOLUENE & ETHYL ALCOHOL

INSOL IN WATER

Solubility in water, g/100ml at 20 °C: 0.2 (poor)

Flash Point · 3 items

110 °C

230 °F OC

80 °C c.c.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H302 (99.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 798 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 5 items

Chemical: Phenol, 2-(1,1-dimethylethyl)-

Phenol, 2-(1,1-dimethylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2-(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: 21-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14446

Phenol, (1,1-dimethylethyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

2-t-Butylphenol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Propyl and butyl phenols
Fire HazardsCombustible. Above 80 °C explosive vapour/air mixtures may be formed.
Hazards Summary · 1 item

Causes somnolence, tremor, and respiratory depression in lethal-dose feeding studies of rats; [RTECS] A moderate skin and eye irritant; Emergency treatment: irritants; [HSDB] A corrosive substance that can cause injury to the skin and eyes; A respiratory tract irritant; [ICSC] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; May be absorbed through skin; Inhalation may cause chemical pneumonitis; [MSDSonline]

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as a chemical intermediate for synthetic resins, plasticizers, surface-active agents, perfumes, antioxidants, and agrochemicals; Also used as an antioxidant for aviation gasoline; [HSDB]

Petroleum Production and Refining [Category: Industry]

CHEMICAL INTERMEDIATE FOR SYNTHETIC RESINS, PLASTICIZERS, SURFACE-ACTIVE AGENTS, PERFUMES, & OTHER PRODUCTS

PERMISSIBLE ANTIOXIDANT FOR AVIATION GASOLINE

2-t-Butylphenol is a starting material for the synthesis of antioxidants and agrochemicals. Fragrance compounds are made from cis-2-t-butylcyclohexanol which is obtained by hydrogenation of 2-t-butylphenol in the presence of catalysts.

Derivatives: 2-t-butylcyclohexyl acetate; dinoterb; ethylene glycol bis(3,3-bis(3-t-butyl-4-hydroxyphenyl)butyrate); 2,2'-methylenebis(4-ethyl-6-t-butyl-phenol)

U.S. Production2023: 1,000,000 - <8,500,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 3 items

Isobutylene + phenol (orthoalkylation; coproduced with 2,6-di-t-butylphenol

2-t-Butylphenol is obtained as the main alkylation product if phenol is reacted with isobutene in the presence of sulfonated polystyrene-polydivinylbenzene ion-exchange resins. Reaction of phenol and isobutene in a 1:0.42 molar ratio at 95 °C gives a product mixture. ... 2-t-Butylphenol is obtained in a purity of 99% by distillation. 2-t-Butylphenol is formed with relatively high selectivity by reaction of phenol and isobutene over a gamma aluminum trioxide-catalyst that has been tabletted with 10% graphite and preconditioned by heating to 650 °C in an air stream. ... The selectivity for 2-t-butylphenol is 88% based on phenol conversion.

2-t-Butylphenol is formed with relatively high selectivity by reaction of phenol and isobutene over a gamma aluminum trioxide-catalyst that has been tabletted with 10% graphite and preconditioned by heating to 650 °C in an air stream. ... The selectivity for 2-t-butylphenol is 88% based on phenol conversion.

Use ClassificationFragrance Ingredients
General Manufacturing Information

Related reactions

170 records
New reaction record
HRID 2951 reaction equation
HRID 2951As reactantuspto-grants-1998_03
HRID 2953 reaction equation
HRID 2953As reactantuspto-grants-1998_03
HRID 2954 reaction equation
HRID 2954As reactantuspto-grants-1998_03
HRID 4183 reaction equation
HRID 4183As reactantuspto-grants-1988_02
HRID 19216 reaction equation
HRID 19216As reactantuspto-grants-2010_06
HRID 51092 reaction equation
HRID 51092As reactantuspto-grants-2004_03
HRID 53267 reaction equation
HRID 53267As reactantuspto-grants-1997_04
HRID 73996 reaction equation
HRID 73996As reactantuspto-grants-2014_09
Page 1 of 22

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
Boiling Point · 2 items

223 °C @ 760 mm Hg

223 °C

Melting Point · 2 items

-6.8 °C

-6.8 °C

Vapor DensityRelative vapor density (air = 1): 5.2
Vapor Pressure · 3 items

0.00015 [mmHg]

1.5X10-4 mm Hg @ 25 °C

Vapor pressure, Pa at 20 °C: 5

Physicochemical properties

Indirect Additives used in Food Contact Substances
BUTYLPHENOL, TERT-
EPA Substance Registry System
Phenol, (1,1-dimethylethyl)- (27178-34-3)
Symbol(GHS)
7 · GHS07,GHS05,GHS09
Signal word
Danger
Hazard statements
411 · H411-H314
Precautionary statements
260 · P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
TSCA
TSCA listed
UN ClassificationUN Hazard Class: 8; UN Pack Group: III
Chemical DangersReacts violently with strong oxidants, bases, acid anhydrides and acid chlorides. Attacks copper and its alloys.
Physical DangersThe vapour is heavier than air.
Packaging and LabellingDo not transport with food and feedstuffs. Marine pollutant.
Hazard Classes and Categories · 3 items

Acute Tox. 4 (100%)

Acute Tox. 4 (99.4%)

Flammable liquids - Category 4

Shipment Methods and Regulations · 3 items

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 3 items

UN 3145; Alkyl phenols, liquid, NOS

UN 2430; Alkyl phenols, solid, NOS

IMO 8.0; Alkyl phenols, liquid or solid, NOS

Safety & protection

Fire FightingUse powder, carbon dioxide, foam.
First Aid Measures · 4 items

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .

Safe StorageSeparated from strong oxidants, strong bases, acid anhydrides, acid chlorides, metals and food and feedstuffs.
Fire Fighting ProceduresIf material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Keep run-off water out of sewers and water sources. /Butyl phenols, liquid/
Disposal Methods · 1 item

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.

Spillage Disposal · 1 item

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable plastic containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 2 items

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Butyl phenols, liquid/

Personnel protection: keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material. /Butyl phenols, liquid/

Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames. Above 80 °C use a closed system and ventilation.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT GENERATION OF MISTS! IN ALL CASES CONSULT A DOCTOR!

Toxicology

InteractionsINHIBITORY EFFECTS OF 18 SYNTHETIC PHENOLIC CMPD, ADDED TO DIET, ON BENZO[A]PYRENE-INDUCED NEOPLASIA OF THE FORESTOMACH OF FEMALE MICE WERE DETERMINED. GROUP OF CMPD WITH WEAKER INHIBITORY ACTION INCLUDED 2-TERT-BUTYLPHENOL.
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1500(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 2-t-butylphenol will have low mobility in soil(SRC). Limited data, mainly derived by analogy to 4-t-butylphenol, indicate that 2-t-butylphenol may be resistant to biodegradation(SRC). 4-t-Butylphenol (at 30 mg/L) was not biodegraded over a 2 week period using an activated sludge inoculum(4); in river and sea water 4-t-butylphenol showed 11% biodegradation over 3 days(5). However, resting cells of a Pseudomonas strain obtained by selective enrichment with 4-hydroxybenzoate as the sole carbon source, were able to biodegrade 2-t-butylphenol (oxygen uptake rate 26 nmol O2/min/mg protein)(6). Volatilization of 2-t-butylphenol from moist soil surfaces would be slow(SRC) given an estimated Henry's Law constant of 1.4X10-6 atm-cu m/mole(7,SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1500(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 2-t-butylphenol would adsorb to suspended solids and sediment(SRC) in the water. 2-t-Butylphenol would volatilize slowly from water surfaces based on an estimated Henry's Law constant of 1.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 31 and 230 days, respectively(3,SRC). An estimated BCF value of 190(3,SRC), from an experimental log Kow(2), suggests that 2-t-butylphenol may bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Limited data, mainly derived by analogy to 4-t-butylphenol, indicate that 2-t-butylphenol may be resistant to biodegradation(SRC). 4-t-Butylphenol (at 30 mg/L) was not biodegraded over a 2 week period using an activated sludge inoculum(6); in river and sea water 4-t-butylphenol showed 11% biodegradation over 3 days(7).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 1.5X10-4 mm Hg at 25 °C(2) indicates that 2-t-butylphenol will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase 2-t-butylphenol is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 9.5 hours(3,SRC). Particulate-phase 2-t-butylphenol may be physically removed from the air by wet and dry deposition(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat. Shortness of breath.

Redness. Pain. Burning sensation. Skin burns.

Redness. Pain. Severe deep burns.

Burning sensation in the throat and chest. Abdominal pain. Shock or collapse.

Effluent Concentrations2-t-Butylphenol was reported in the finished water from an advanced wastewater treatment plant at Lake Tahoe, CA at unreported concentrations(1).
ICSC Environmental DataThe substance is toxic to aquatic organisms.
Soil Adsorption/Mobility · 1 item

The Koc of 2-t-butylphenol is estimated as approximately 1500(SRC), using an experimental log Kow of 3.31(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this Koc value suggests that 2-t-butylphenol has low mobility in soil(SRC).

Human Toxicity ExcerptsMODERATE IRRITANT TO EYES & SKIN.
Artificial Pollution Sources · 1 item

2-t-Butylphenol's production and use as an intermediate in the manufacture of synthetic resins, plasticizers, surface-active agents, and perfumes(1) or as a starting material for antioxidants and agrochemicals(2) may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation · 1 item

Resting cells of a Pseudomonas strain obtained by selective enrichment with 4-hydroxybenzoate as the sole carbon source, were able to biodegrade 2-t-butylphenol (oxygen uptake rate 26 nmol O2/min/mg protein)(1). 4-t-Butylphenol (at 30 mg/l) was not biodegraded over a 2 week period using an activated sludge inoculum; in river and sea water 4-t-butylphenol showed 11% biodegradation over 3 days(3). By analogy to 4-t-butylphenol, 2-t-butylphenol may be recalcitrant to biodegradation in the environment(SRC).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

tsca
TSCA listed
Signal word
Danger
Symbol(GHS)
GHS07,GHS05,GHS09
Hazard statements
H411-H314
Precautionary statements
P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
· 4 items

All Other Basic Organic Chemical Manufacturing

Phenol, 2-(1,1-dimethylethyl)-: ACTIVE

Phenol, (1,1-dimethylethyl)-: ACTIVE

2-TERT-BUTYLPHENOL WAS PREPARED AND EVALUATED AS INTRAVENOUS ANESTHETIC AGENT.

Additional notes

DefinitionChEBI: 2-tert-Butylphenol is an alkylbenzene.