Oxybenzone

Base Information

• Chemical Name: Oxybenzone
• CAS No.: 131-57-7
• Deprecated CAS: 14375-37-2,153859-73-5,58392-15-7,58392-22-6,897050-18-9,138464-23-0,2216794-47-5,138464-23-0,153859-73-5,58392-15-7,58392-22-6,897050-18-9
• Molecular Formula: C14H12O3
• Molecular Weight: 228.247
• Hs Code.: 29145000
• European Community (EC) Number: 205-031-5
• NSC Number: 757260,7778
• UNII: 95OOS7VE0Y
• DSSTox Substance ID: DTXSID3022405
• Nikkaji Number: J5.562J
• Wikipedia: Oxybenzone
• Wikidata: Q518114
• NCI Thesaurus Code: C47646
• RXCUI: 32673
• Pharos Ligand ID: AW7TJY78RCN8
• Metabolomics Workbench ID: 43557
• ChEMBL ID: CHEMBL1625
• Mol file: 131-57-7.mol

Synonyms:2-hydroxy-4-methoxybenzone;2-hydroxy-4-methoxybenzophenone;benzophenone-3;Eusolex 4360;Eusolex-4360;HMBP cpd;oxybenzone;Solbar

Chemical Property of Oxybenzone

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 5.26E-06mmHg at 25°C
• Melting Point: 62-64 °C(lit.)
• Refractive Index: 1.595
• Boiling Point: 370.3 °C at 760 mmHg
• PKA: 7.56±0.35(Predicted)
• Flash Point: 140.5 °C
• PSA: 46.53000
• Density: 1.201 g/cm³
• LogP: 2.63180
• Storage Temp.: 2-8°C
• Solubility.: 95% ethanol: soluble50mg/mL, clear, colorless
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.078644241
• Heavy Atom Count: 17
• Complexity: 258

Purity/Quality:

Oxybenzone- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Sunscreens
• Canonical SMILES: COC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
• Chemical Properties and Functionality: Oxybenzone (benzophenone-3) is an organic UV protectant added to many sunscreen products. It absorbs UV photons and dissipates their energy as harmless heat, protecting against the damaging effects of ultraviolet light. Found in approximately 3,500 sunscreen products worldwide.
• Safety and Regulatory Approval: Approved for use in sunscreen products by regulatory authorities in the United States, Canada, and the European Union.; Considered safe and effective when used in concentrations less than 6%.; No adverse reactions reported over 20 years of use, according to the American Skin Cancer Foundation.; Safety research requested by the FDA due to potential absorption by the body, especially with daily use.
• Skin Sensitivity Concerns: Oxybenzone can induce photosensitivity dermatitis, characterized by skin redness, rash, and itching after sun exposure. Severe cases may result in facial swelling, requiring medical treatment.
• Environmental Impact: Oxybenzone can contribute to coral reef damage, affecting coral growth and causing coral bleaching. Some areas have phased out oxybenzone-containing sunscreens due to concerns about coral reef health.

Technology Process of Oxybenzone

There total 49 articles about Oxybenzone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-hydroxy-4-methoxybenzhydrol (926236-29-5) → Benzophenone-3 (131-57-7,897050-18-9)

Guidance literature:

With bismuth (III) nitrate pentahydrate; cellulose supported copper⁽⁰⁾; oxygen; In acetonitrile; at 60 ℃; for 0.5h;

DOI:10.1016/j.catcom.2016.01.003

Reference yield: 94.0%

2.4-dihydroxybenzophenone (131-56-6) + carbonic acid dimethyl ester (616-38-6) → Benzophenone-3 (131-57-7,897050-18-9)

Guidance literature:

With sodium carbonate; at 160 - 170 ℃; for 10h;

Reference yield: 91.0%

2.4-dihydroxybenzophenone (131-56-6) + methylene chloride (74-87-3) → Benzophenone-3 (131-57-7,897050-18-9)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium carbonate; In tert-butyl methyl ether; water; chlorobenzene; at 100 ℃; for 2h; under 2250.23 Torr; Temperature; Solvent; Reagent/catalyst; Pressure; Autoclave;

upstream raw materials:

2,4-dimethoxybenzophenone

benzoyl chloride

1,3-Dimethoxybenzene

2.4-dihydroxybenzophenone

Downstream raw materials:

(2,5-dihydroxy-4-methoxyphenyl)phenylmethanone

7-methoxy-4-phenyl-2H-chromen-2-one

4-Methoxy-6-hydroxy-3-morpholinomethylbenzophenon

4-Methoxy-2-hydroxy-3-morpholinomethylbenzophenon

Refernces

• 1、 -. "Preparation method of sun-screening agent 2-hydroxy-4-methoxy-5-sulfo benzophenone". Paragraph 0052-0053. . Retrieved 2021/02/06.
• 2、 Du, Jihong,Duan, Baogen,Liu, Kun,Liu, Renhua,Yu, Feifei,Yuan, Yongkun,Zhang, Chenyang,Zhang, Jin. "Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water". supporting information. . Retrieved 2022/02/09.