2,5-Di-tert-butylhydroquinone

HCID 2374CAS 1322-72-1
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(C)(C)c1cc(O)c(C(C)(C)C)cc1O
InChIKey
JZODKRWQWUWGCD-UHFFFAOYSA-N
Molecular formula
C14H22O2
Average molar mass
222.32 g/mol
Monoisotopic mass
222.16197994

Overview

2,5-di-tert-butylbenzene-1,4-diol is a member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.

Names & identifiers

Preferred name
2,5-Di-tert-butylhydroquinone
IUPAC
2,5-ditert-butylbenzene-1,4-diol
English name
2,5-Di-tert-butylhydroquinone
Molecular formula
C14H22O2
Molecular weight
222.32

Names & synonyms

2,5-Di-tert-butylhydroquinone88-58-42,5-Di-tert-butylbenzene-1,4-diolDTBHQDibugDi-t-butylhydroquinoneDybugSantovar O2,5-Di-tert-butylquinolNonflex AlbaNaugard 451Antage DBH
Show more names
BHQDBHQBlack Hole QuencherProbesANTIOXIDANT DTBHQDibutylhydroquinone2,5-ditertiary butyl hydroquinone2-carbamoyl-2-propylpentanoic acid
Nocrac NS 71,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-2,5-Di-tert-butyl-1,4-benzenediol2,5-Di-tert-butyl-1,4-hydroquinonedi-tert-butylhydroquinone1,4-Dihydroxy-2,5-di-tert-butylbenzene2,5-Di-tert-butyl-1,4-benzohydroquinoneDTXSID8041248

Database identifiers

CAS
1322-72-1、88-58-4
PubChem CID
2374
DTXSID
DTXSID8041248
ChEMBL
CHEMBL480626
ChEBI
CHEBI:41094
UNII
26XK13B61B
EC Number
201-841-8
Nikkaji
J3.545I

Properties

Computed structural properties

XLogP
4.6
Topological polar surface area
40.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
16

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phenols
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 items

Cosmetic ingredients (Di-t-Butylhydroquinone) -> CIR (Cosmetic Ingredient Review)

Antioxidant

Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 2 items

CBI

Off-white crystalline powder; [Alfa Aesar MSDS]

Collision Cross Section155.1 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8041248]

Physicochemical properties

Melting point
216 · 216-218 °C(lit.)
Boiling point
321 °C · 321°C
Density
1 · 1,07 g/cm3
refractive index
1.4576 · 1.4576 (estimate)
Flash point
216 °C · 216 °C
storage temp.
30 °C · Store below +30°C.

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.7% (2 of 279) of reports.

Danger

H301 (46.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 279 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-

1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediol, 2,5-bis(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: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24124

2,5-Di-tert-butylhydroquinone: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Causes lung and liver changes in 2-day intermittent oral studies of mice; Causes changes in clotting factors in 3-week constant oral studies rats; [RTECS] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS] See t-Butylhydroquinone. See 2,5-Di-t-pentylhydroquinone.

Hazard Classes and CategoriesAcute Tox. 3 (46.6%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

3.0 [mg/m3]

32 [mg/m3]

190 [mg/m3]

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity Summary · 2 items

The Expert Panel concludes that the available data are insufficient to support the safety of Di-t-Butylhydroquinone for use in cosmetic products.

The available data are insufficient to support safety, but the ingredient is not used

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
MX5160000
hs_code
29072900
risk_code
36/37/38-22

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Uses & manufacturing

Uses · 2 items

CIR ingredient: Di-t-Butylhydroquinone

Ca2+-ATPase antagonist. [ChemIDplus]

U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Use ClassificationCosmetics -> Antioxidant
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-: ACTIVE

Applications · 3 items

Description2,5-Di-tert-butylhydroquinone, also known as 2,5-TBHQ or DTBHQ, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. It is a phenol derivative containing 2 phenol groups and 2 alkyl groups, each consisting of three methyl groups.

Uses2,5-Di-tert-butylhydroquinone is the oxidation substrate used to measure the catalytic activity of the copper(II) enzyme-like catalysts.

General DescriptionMobilizes Ca2+ specifically from the Ins(1,4,5)P3-sensitive Ca2+ stores by inhibiting microsomal and sarcoplasmic reticulum Ca2+-ATPase activity. Does not affect mitochondrial Ca2+ fluxes or plasma membrane Ca2+/Mg2+ ATPase activity. Useful for the study of endomembrane Ca2+ stores and plasma membrane Ca2+ permeability pathways.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.

Related reactions

22 records
New reaction record

Linked notes

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