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2,6-Di-t-butyl-p-benzoquinone

HCID 12867
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
719-22-2
Standard SMILES
CC(C)(C)C1=CC(=O)C=C(C(C)(C)C)C1=O
InChIKey
RDQSIADLBQFVMY-UHFFFAOYSA-N
Molecular formula
C14H20O2
Average molar mass
220.31 g/mol
Monoisotopic mass
220.14632988

Overview

2,6-Di-tert-butylbenzoquinone is a member of 1,4-benzoquinones.

Names & identifiers

Preferred name
2,6-Di-t-butyl-p-benzoquinone
IUPAC
2,6-ditert-butylcyclohexa-2,5-diene-1,4-dione
English name
2,6-Di-tert-butyl-p-benzoquinone
Molecular formula
C14H20O2
Molecular weight
220.31

Names & synonyms

719-22-22,6-Di-tert-butyl-P-benzoquinone2,6-Di-tert-butylcyclohexa-2,5-diene-1,4-dione2,6-Di-tert-butyl-1,4-benzoquinone2,6-Di-tert-butylbenzoquinone2,6-DI-T-BUTYL-P-BENZOQUINONE2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-2,6-Bis(1,1-dimethylethyl)-2,5-cyclohexadiene-1,4-dionep-Benzoquinone, 2,6-di-tert-butyl-2,6-Di-t-butyl-1,4-benzoquinoneNSC 14448CCRIS 7070
Show more names
DBQBHT-QBHT-quinone2,6-Di-tert-butylquinoneDibutylpbenzoquinone
HSDB 27753,5-di-tert-butylquinoneEINECS 211-946-0NSC-144484C9D8L0Y0TAI3-610492,6-di-tert-butylbenzo-1,4-quinone3,5-DI-TERT-BUTYL-P-BENZOQUINONE

Database identifiers

CAS
719-22-2
PubChem CID
12867
DTXSID
DTXSID7021493
ChEMBL
CHEMBL3185121
ChEBI
CHEBI:89187
UNII
4C9D8L0Y0T
EC Number
211-946-0
Nikkaji
J65.911H

Properties

Computed structural propertiesFilling in

XLogP
3.4
Topological polar surface area
34.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
16
Formal charge
0
Complexity
359

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Aromatic Ketones

Antioxidant

SpringerMaterials PropertiesChemical shift
LogP · 2 items

log Kow = 4.42

4.42

Color/FormYellow crystals
Melting Point · 2 items

65-67 °C

65-67 °C

Vapor Pressure0.000411 [mmHg]
Physical Description · 2 items

Yellow solid; [HSDB] Orange crystalline powder; [MSDSonline]

Solid

Physicochemical properties

Melting point
65 · 65-67 °C(lit.)
Boiling point
75 · 75-80 °C (0.7 mmHg)

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 · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryAn irritant; Effects in high-dose animal studies include ulceration of the nasal septum and hemorrhage; [MSDSonline] See Quinone.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety & protection

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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(3), an estimated Koc value of 6000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that suggests that 2,6-di-t-butyl-p-benzoquinone will be essentially immobile in soil(3). In an unconfined aquifer, however, 2,6-di-t-butyl-p-benzoquinone was transported an estimated 2710 meters over a 43 year period(2,4). 2,6-Di-t-butyl-p-benzoquinone is not expected to volatilize from moist soil surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(5,SRC). It may, however, volatilize from the surface of dry soils given an estimated vapor pressure of 4.1X10-4 mm Hg(6,SRC). Incomplete information is available regarding the biodegradation potential of 2,6-di-t-butyl-p-benzoquinone; Rhine River water which was subjected to bank filtration had lower concentrations of 2,6-di-t-butyl-p-benzoquinone than the original water(7). Adsorption to soil however, was not measured(7,SRC)).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

THE URINARY & FECAL EXCRETION OF 3 NEW METABOLITES OF BUTYLATED HYDROXYTOLUENE (BHT, 3,5-DI-TERT-BUTYL-4-HYDROXYTOLUENE) WERE REVEALED BY GAS CHROMATOGRAPHY AFTER IP ADMIN TO MALE WISTAR RATS. THE STRUCTURES OF THESE METABOLITES, 2,6-DI-TERT-BUTYL-P-BENZOQUINONE, 2,6-DI-TERT-BUTYLHYDROQUINONE, & 2,6-DI-TERT-BUTYL-4-((METHYLTHIO)METHYL)PHENOL WERE IDENTIFIED BY COMPARISON OF GAS CHROMATOGRAPHIC & MASS SPECTRAL DATA WITH THOSE OF AUTHENTIC SAMPLES.

Quinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of oxygen radicals and semiquinone radicals. /Quinones/

Cellular LocationsMembrane

Uses & manufacturing

Uses · 2 items

Used as an oxidant and polymerization catalyst; [HSDB]

Oxidant, polymerization catalyst

General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-: ACTIVE
Applications · 2 items

Uses2.6-Di-tert-butyl-p-benzoquinone was used as a treatment agent to improve germination, plant health and yield.

Uses2,6-Di-tert-butyl-1,4-benzoquinone was used as an antioxidant to study the elimination rate of micro pollutant from storm and waste water. It was also used as a metabolite of butylated hydroxytoluene. It is used as a treatment agent to improve germination and plant health.

Upstream & downstream products

Upstream raw materials

2,6-DI-TERT-BUTYL-4-METHOXYPHENOL

Related reactions

47 records
New reaction record
HRID 23804 reaction equation
HRID 23804As reactantuspto-grants-2005_02
HRID 23809 reaction equation
HRID 23809As reactantuspto-grants-2005_02
HRID 36723 reaction equation
HRID 36723As reactantuspto-grants-1995_05
HRID 36725 reaction equation
HRID 36725As reactantuspto-grants-1995_05
HRID 36731 reaction equation
HRID 36731As reactantuspto-grants-1995_05
HRID 36733 reaction equation
HRID 36733As reactantuspto-grants-1995_05
HRID 124673 reaction equation
HRID 124673As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 260367 reaction equation
HRID 260367As reactantuspto-grants-1996_06
Page 1 of 6

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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Density
1.0106 · 1.0106 (rough estimate)
refractive index
1.497 · 1.4970 (estimate)
Flash point
110 ° · >110°(230°F)
storage temp.
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Crystals or Crystalline Powder
color
Orange to brown
Water Solubility
Insoluble in water.
BRN
1911512 · 1911512
Henry's Law Constant
6.2 · 6.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Light sensitive
InChI
1S/C14H20O2/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8H,1-6H3
InChIKey
RDQSIADLBQFVMY-UHFFFAOYSA-N
SMILES
CC(C)(C)C1=CC(=O)C=C(C1=O)C(C)(C)C
CAS DataBase Reference
719 · 719-22-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
4 C9D8L0Y0T · 4C9D8L0Y0T
NIST Chemistry Reference
2 · 2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-(719-22-2)
EPA Substance Registry System
2 · 2,6-Di-tert-butylbenzoquinone (719-22-2)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
302 · P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36-36/37/39-22
WGK Germany
3 · 3
RTECS
3970000 · DK3970000
TSCA
TSCA listed
HS Code
29146990 · 29146990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
719 · 719-22-2(Hazardous Substances Data)

AQUATIC FATE: 2,6-Di-t-butyl-p-benzoquinone should adsorb to suspended solids and organic matter in the water column based on an estimated Koc of 6100(1,SRC) from an experimental log Kow(2) and a suggested classification scheme(3). 2,6-Di-t-butyl-p-benzoquinone (at 0.3 ug/L) had a half-life in Rhine River water of 3.4 days; measurements were made at Lobith and 24.5 hours later at Gorinchem(4). Loss of this compound during this stretch of river may have been due to adsorption to particulates or to biodegradation(4,SRC). An estimated BCF value of 1400(1,SRC), from an experimental log Kow(2), suggests that 2,6-di-t-butyl-p-benzoquinone will bioconcentrate in aquatic organisms. This compound has been detected in fish from the Great Lakes(5). 2,6-Di-t-butyl-p-benzoquinone is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(6).

ATMOSPHERIC FATE: Based on an estimated vapor pressure of 4.1X10-4 mm Hg at 25 °C(1,SRC), 2,6-di-t-butyl-p-benzoquinone should exist in both the vapor phase and particulate phase in the ambient atmosphere(2,SRC). 2,6-Di-t-butyl-p-benzoquinone should degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 17 hours(3,SRC). Particulate-phase 2,6-di-t-butyl-p-benzoquinone may be physically removed from the air by wet and dry deposition(SRC).

Effluent Concentrations1 of 21 samples of wastewater from the photographic industry contained unreported concentrations of 2,6-di-t-butyl-p-benzoquinone(1). 1 of 10 POTW plants sampled contained 2,6-di-t-butyl-p-benzoquinone in the final effluent(2).
Soil Adsorption/Mobility · 1 item

Based on an experimental log Kow of 4.42(1), the Koc of 2,6-di-t-butyl-p-benzoquinone is estimated as approximately 6100 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that 2,6-di-t-butyl-p-benzoquinone will be immobile in soil(SRC). Sewage which had been through secondary treatment was subjected to rapid infiltration; the concentration of 2,6-di-t-butyl-p-benzoquinone in the initial sewage was from 0.022-0.037 ug/L and ranged from barely detected to 0.005 ug/L in the groundwater below the rapid infiltration beds(4). It was believed that the loss of this compound was due to adsorption as the sewage had already been through secondary treatment(4). In an unconfined aquifer, however, 2,6-di-t-butyl-p-benzoquinone was shown to have been transported for a considerable distance(between 1940-1983, estimated 2710 m)(1,5).

Atmospheric ConcentrationsURBAN/SUBURBAN: 2,6-Di-t-butyl-p-benzoquinone was detected in the personal air (1 of 8 samples total) of 12 people located either in New Jersey or North Carolina(1).
Human Toxicity ExcerptsChronic neurotoxic effects include vision disturbances. /From table/ /Quinones/
Fish/Seafood ConcentrationsComposite fish samples (lake trout, walleye) were found to contain 2,6-di-t-butyl-p-benzoquinone in 3 of 8 locations in the Great Lakes (two sites in Lake Erie, one site in Lake Michigan)(1).
Artificial Pollution Sources · 2 items

VOLATILE POLLUTANTS, INCLUDING 2,6-DI-T-BUTYL-P-BENZOQUINONE, WERE PRODUCED FROM SEVERAL RUBBER GOODS MANUFACTURING PROCESSES & ANALYZED BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY. THEIR CUMULATIVE CONCN RANGED FROM 25-27,000 UG/CU M.

2,6-Di-t-butyl-p-benzoquinone's production and subsequent use as an oxidant and polymerization catalyst(1), may result in its release to the environment through various waste streams(SRC). 2,6-Di-t-butyl-p-benzoquinone is also an environmental product of the oxidation of 2,6-di-t-butyl phenol, a common antioxidant additive(2,3).

Environmental Biodegradation · 1 item

2,6-Di-t-butyl-p-benzoquinone (at 0.3 ug/l) had a half-life in Rhine River water of 3.4 days; measurements were made at Lobith and 24.5 hours later at Gorinchem(1). Degradation of this compound was believed due to aerobic and anaerobic biodegradation(1); however, adsorption to suspended solids and organic matter in the water column was not measured(1,SRC). 2,6-di-t-butyl-p-benzoquinone (at 2 ug/L) initially present in Rhine River water was not detected once the water was passed through a bank filtration process(2). It was not specified whether the loss of this compound was due to biodegradation or adsorption(2,SRC).

Sediment/Soil Concentrations · 1 item

2,6-Di-t-butyl-p-benzoquinone was present in Pawtuxet River sediment located downstream of a plant which produced antioxidants (at concentrations of 1 ppm to 80 ppm(1). 2,6-Di-t-butyl-p-benzoquinone was present in sediment (0.1-40 ppm) located downstream from a specialty chemicals manufacturing plant(2).

Environmental Bioconcentration · 1 item

An estimated BCF value of 1400 was calculated for 2,6-di-t-butyl-p-benzoquinone, using a measured log Kow of 4.42(1) and a recommended regression-derived equation(2,SRC). This BCF value suggests that 2,6-di-t-butyl-p-benzoquinone will bioconcentrate in aquatic organisms(2,SRC).This compound was detected in fish in the Great Lakes(3) suggesting that bioconcentration may occur(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 2,6-di-t-butyl-p-benzoquinone is estimated as 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This indicates that 2,6-di-t-butyl-p-benzoquinone will essentially not volatilize from water surfaces(2,SRC).

Non-Human Toxicity ExcerptsAcute neurotoxic effects reported in animals include convulsions; medullary paralysis. /From table/ /Quinones/

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DK3970000
hs_code
29146990
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36-36/37/39-22
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H315-H319-H335
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P302+P352-P305+P351+P338
Hazardous Substances Data
719-22-2(Hazardous Substances Data)
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
1,4-Benzenediol, 2,6-bis(1,1-dimethylethyl)-, 4-acetate
2,4,6-Tri-tert-butylphenol
3,3',5,5'-Tetra-tert-butyldiphenoquinone
2,6-Di-tert-butylphenol

Downstream products

3,3',5,5'-TETRA(TERT-BUTYL)[1,1'-BIPHENYL]-4,4'-DIOL2,6-di-tert-butylhydroquinone

Additional notes

DefinitionChEBI: 2,6-Di-tert-butylbenzoquinone is a member of 1,4-benzoquinones.