2,4-Dicumylphenol (HCID 76013)

Overview

an antihistaminic agent; structure in first source

Names & identifiers

Preferred name: 2,4-Dicumylphenol
IUPAC: 2,4-bis(2-phenylpropan-2-yl)phenol
English name: 2,4-Bis(alpha,alpha-dimethylbenzyl)phenol
Molecular formula: C24H26O
Molecular weight: 330.46

Names & synonyms

2772-45-42,4-Bis(alpha,alpha-dimethylbenzyl)phenol2,4-Bis(1-methyl-1-phenylethyl)phenol2,4-DicumylphenolPhenol, 2,4-bis(1-methyl-1-phenylethyl)-DTXSID70292419U10Z6U3JPDTXCID909241AH5 phenol cpdRefChem:82218220-466-02,4-bis(2-phenylpropan-2-yl)phenol

Show more names

2,4-Bis(2,4-dibutanol2,4 DI-CUMYLPHENOL2,4-Bis(α,α-dimethyL2,4-bis(α,α-dimethylbenzyl)phenol2,4-Bis(α,α-dimethylbenzyl)phenol2,4-BIS(ALPHA,ALPHA-DIMETHYLBENZYL)

2,4-Di-alpha-cumylphenolMFCD001912422,4-Bis(|A,|A-dimethylbenzyl)phenolAKOS001017927NCGC00247990-02NCGC00247990-03Z56812043CAS-2772-45-4

Database identifiers

CAS: 2772-45-4
PubChem CID: 76013
DTXSID: DTXSID7029241
ChEMBL: CHEMBL3183863
UNII: 9U10Z6U3JP
EC Number: 220-466-0
Nikkaji: J299.227B

Properties

Computed structural properties

XLogP: 7.2
Topological polar surface area: 20.2 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 4
Heavy atoms: 25
Formal charge: 0
Complexity: 412

Experimental & physicochemical properties

Chemical ClassesUV filter

Endocrine DisruptorsPotential endocrine disrupting compound

Physical DescriptionOther Solid; Liquid

Collision Cross Section171.9 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7029241]

Physicochemical properties

Melting point: 63 · 63-65 °C(lit.)
Boiling point: 206 °C15 · 206 °C15 mm Hg(lit.)
Density: 1.063 · 1.063
refractive index: 1.638 · 1.6380 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: soluble in Methanol
form: powder to crystal
pka: 10.71 · 10.71±0.10(Predicted)
color: White to Light yellow
InChI: InChI=1S/C24H26O/c1-23(2,18-11-7-5-8-12-18)20-15-16-22(25)21(17-20)24(3,4)19-13-9-6-10-14-19/h5-17,25H,1-4H3
InChIKey: FMUYQRFTLHAARI-UHFFFAOYSA-N
SMILES: C1(O)=CC=C(C(C)(C2=CC=CC=C2)C)C=C1C(C)(C1=CC=CC=C1)C
CAS DataBase Reference: 2772 · 2772-45-4(CAS DataBase Reference)
FDA UNII: 9 U10Z6U3JP · 9U10Z6U3JP
EPA Substance Registry System: 2 · 2,4-Bis(1-methyl-1-phenylethyl)phenol (2772-45-4)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H413
Precautionary statements: 305 · P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes: Xi
Risk Statements: 26 · 26-27-36/39-36
Safety Statements: 26 · 26-27-28-36/39
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 2907.19 · 2907.19.8000
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2
REACH Registrations: Inactive

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.4% (1 of 42) of reports.

Warning

H319 (95.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P351+P338, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Phenol, 2,4-bis(1-methyl-1-phenylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,4-bis(1-methyl-1-phenylethyl)- 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: 08-04-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17219

Phenol, 2,4-bis(1-methyl-1-phenylethyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesEye Irrit. 2 (95.2%)

Safety data

wgk: 3
tsca: TSCA listed
hs_code: 2907.19.8000
risk_code: 26-27-36/39-36
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-27-28-36/39
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H413
REACH Registrations: Inactive
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2
Precautionary statements: P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 1,000,000 - <8,500,000 lb

Consumer UsesAntioxidant

Industry UsesUV stabilizer

General Manufacturing Information · 2 items

Plastics Material and Resin Manufacturing

Phenol, 2,4-bis(1-methyl-1-phenylethyl)-: ACTIVE

Applications · 4 items

UsesUV Stabilizer and Antioxidant Intermediate

Uses2,4-bis(2-Phenylpropan-2-yl)phenol is used as a reagent in ring opening polymerization reactions of cyclic esters. It is an intermediate in the synthesis of Benzotriazole BT (B206990), a low volatile benzotriazole UV light absorber and stabilizer.

Uses2,4-Bis(α,α-dimethylbenzyl)phenol may be used in the preparation of a novel ligand, 2,2′-methylenebis(4,6-di(1-methyl-1-phenylethyl)phenol) (MMPEP-H2).

General Description2,4-Bis(α,α-dimethylbenzyl)phenol is reported to possess antihistaminic activity. Structure of 2,4-bis(α,α-dimethylbenzyl)phenol is reported to have a torsion angle of 129.95(13)° for the C-C bond that connects the benzyl carbon to the phenol ring ortho to the OH group.