CAS 3602-55-9 tert-Butyl-1,4-benzoquinone (HCID 19211)

Overview

a metabolite of butylated hydroxyanisole ; structure given in first source

Names & identifiers

Preferred name: tert-Butyl-1,4-benzoquinone
IUPAC: 2-tert-butylcyclohexa-2,5-diene-1,4-dione
English name: 2-tert-Butyl-1,4-benzoquinone
Molecular formula: C10H12O2
Molecular weight: 164.2

Names & synonyms

2-tert-Butyl-1,4-benzoquinone3602-55-9tert-Butylquinonetert-Butyl-1,4-benzoquinone2-tert-Butyl-4-quinone2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-2-(1,1-Dimethylethyl)-2,5-cyclohexadiene-1,4-dioneF18QT8490SNSC-124503DTXSID701895932-t-BQ2-tert-butyl-4-benzoquinone

Show more names

TBQ2-TERT-BUTYLQUINONEtert-butylbenzoquinone2-TERT-BUTYL-1,4-QUINONETERT.-BUTYL-PARA-QUINONEBUTYL-P-QUINONE, 2-TERT-2-TERT-BUTYL-PARA-QUINONE

2-tert-butyl(1,4)para-quinoneRefChem:483640DTXCID30112084222-757-82-tert-Butyl-p-benzoquinone2-tert-butylcyclohexa-2,5-diene-1,4-dione2-tert-Butyl-p-quinonetert-Butyl-p-benzoquinone

Database identifiers

CAS: 3602-55-9
PubChem CID: 19211
DTXSID: DTXSID70189593
ChEMBL: CHEMBL2252966
UNII: F18QT8490S
EC Number: 222-757-8
Nikkaji: J60.236A

Properties

Computed structural properties

XLogP: 2
Topological polar surface area: 34.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 12
Formal charge: 0
Complexity: 287

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

Physicochemical properties

Melting point: 54 · 54-58 °C(lit.)
Boiling point: 227.8 · 227.8±15.0 °C(Predicted)
Density: 1.092 · 1.092±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform, Methanol (Slightly)
form: Solid
color: Dark Yellow
InChI: InChI=1S/C10H12O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6H,1-3H3
InChIKey: NCCTVAJNFXYWTM-UHFFFAOYSA-N
SMILES: C1(=O)C=CC(=O)C=C1C(C)(C)C
CAS DataBase Reference: 3602 · 3602-55-9(CAS DataBase Reference)
FDA UNII: 18 QT8490S · F18QT8490S
NIST Chemistry Reference: 2 · 2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-(3602-55-9)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-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
WGK Germany: 3 · 3
RTECS: 3790000 · DK3790000
HS Code: 29146990 · 29146990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (24.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-

2,5-Cyclohexadiene-1,4-dione, 2-(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.

Other Safety InformationEvaluation - Butylated hydroxyanisole and related antioxidants

Hazard Classes and CategoriesAcute Tox. 3 (24.1%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: DK3790000
hs_code: 29146990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
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: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses2-tert-Butyl-1,4-benzoquinone may be used in the synthesis of azatrioxa[8]circulene.

General Description2-tert-Butyl-1,4-benzoquinone (TBQ, TBBQ, tBQ, BuBQ, BQ , tert-butyl-p-quinone) is a 1,4-benzoquinone derivative. It is a major metabolite of the food additive, butylated hydroxyanisole (BHA). TBQ is reported to be strongly cytotoxic in human monocytic leukemia U937 cells. TBQ is an oxidation product of 2-tert-butylhydroquinone (TBHQ). Studies confirm that TBQ induces apoptosis and cell proliferation inhibition in chronic myelogenous leukemia (CML) cells. Its binding interactions with lysozyme has been examined and found to be intermediate between BHA and TBHQ. It has been reported to be synthesized by the titanium superoxide catalyzed oxidation of 2-tert-butylphenol using aq. 30% H2O2. TBQ is one of the main neoformed compounds from TBHQ decomposition in PLA-TBHQ film (Poly lactic acid).