HuagongsheHuagongshe Chemistry Print Report · For research reference only
Drometrizole
UV-P · TINUVIN P · 2-(2-HYDROXY-5-METHYLPHENYL)BENZOTRIAZOLE · UV-71 · 2-(2H-BENZOTRIAZOL-2-YL)-P-CRESOL · 2-(2H-BENZOTRIAZOL-2-YL)-4-METHYLPHENOL · 2-(2H-1,2,3-Benzotriazol-2-yl)-4-methylphenol · Benazol P
Identifiers & Physical Properties
| CAS No. | 2440-22-4 |
|---|---|
| Molecular formula | C13H11N3O |
| Average molar mass | 225.25 g/mol |
| Monoisotopic mass | 225.09021198 g/mol |
| SMILES | Cc1ccc(O)c(-n2nc3ccccc3n2)c1 |
| InChIKey | MCPKSFINULVDNX-UHFFFAOYSA-N |
| PubChem CID | 17113 |
| ChEMBL | CHEMBL1564747 |
| ChEBI | CHEBI:134926 |
| EC No. | 219-470-5 |
| DTXSID | DTXSID1027479 |
Chemical & Physical Properties
| XLogP | 4.3 |
|---|---|
| Topological polar surface area | 50.9 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 17 |
| Formal charge | 0 |
| Complexity | 259 |
| Physical Description | Dry PowderOther SolidLarge Crystals |
| Collision Cross Section | 155.4 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID1027479] |
| Melting point | 125.5-129.5 °C(lit.) |
| Boiling point | bp10 225° |
| Density | 1.38 |
| Vapor pressure | 0Pa at 20℃ |
| Refractive index | 1.5600 (estimate) |
| Flash point | 54°C |
| Storage conditions | 15-25°C |
| Solubility | DMSO (Slightly), Methanol (Slightly)173μg/L at 20℃ |
| Physical state | Solid |
| pKa (acidity coefficient) | 8.15±0.43(Predicted) |
| Color | Off-White to Pale Yellow |
| Merck | 14,3447 |
| Stability | Hygroscopic |
| Cosmetics Ingredients Functions | UV ABSORBER |
| Cosmetic Ingredient Review (CIR) | Drometrizole (2440-22-4) |
| InChI | 1S/C13H11N3O/c1-9-6-7-13(17)12(8-9)16-14-10-4-2-3-5-11(10)15-16/h2-8,17H,1H3 |
| InChIKey | MCPKSFINULVDNX-UHFFFAOYSA-N |
| SMILES | Cc1ccc(O)c(c1)-n2nc3ccccc3n2 |
| LogP (partition coefficient) | 4.2 at 25℃ |
| CAS DataBase Reference | 2440-22-4(CAS DataBase Reference) |
| Indirect Additives used in Food Contact Substances | 2-(2'-HYDROXY-5'-METHYLPHENYL)BENZOTRIAZOLE |
| FDA 21 CFR | 178.2010 |
| EWG's Food Scores | 1-2 |
| FDA UNII | 5X93W9OFZL |
| NIST Chemistry Reference | Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-(2440-22-4) |
| EPA Substance Registry System | 2-(2H-Benzotriazol-2-yl)-p-cresol (2440-22-4) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H317-H410 |
| GHS precautionary statements | P261-P272-P273-P280-P302+P352-P333+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38-53-43 |
| Safety statements (S) | 22-24/25-36/37 |
| Water hazard class (WGK) | 1 |
| RTECS number | GO6860000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29339900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Aquatic Chronic 1Skin Sens. 1B |
| Toxicity | LD50 oral in mouse: 6500mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.8% (7 of 885) of reports.WarningH317 (97.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]H410 (47%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]H413 (46%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 885 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 7 of 885 reports by companies.There are 18 notifications provided by 878 of 885 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl- 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: 31-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13300Drometrizole: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Phenolic benzotriazoles: Environment tier II assessment |
| Hazard Classes and Categories | Skin Sens. 1 (97.1%)Aquatic Chronic 1 (47%)Aquatic Chronic 4 (46%)Skin sensitization - Category 1BSpecific target organ toxicity - Single exposure - Category 1 (respiratory organs)Specific target organ toxicity - Repeated exposure - Category 2 (kidney)Hazardous to the aquatic environment (Long-term) - Category 1 |
| Toxicity summary | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | GO6860000 |
| Customs code | 29339900 |
| Toxicity | LD50 oral in mouse: 6500mg/kg |
| Risk statements (R) | 36/37/38-53-43 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS09 |
| Hazard symbols | Xi |
| Safety statements (S) | 22-24/25-36/37 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317-H410 |
| REACH registrations | Active |
| Hazard class | Aquatic Chronic 1Skin Sens. 1B |
| GHS precautionary statements | P261-P272-P273-P280-P302+P352-P333+P313 |
Applications & Uses
Uses
An ultraviolet light absorber for stabilizing plastics and other organic materials against discoloration and deterioration.
Uses
2(2-Hydroxy-5-methylphenyl)benzotriazol is an UV adsorber for use in plastics, cosmetics, dental materials, acrylic materials, dyes, etc.
Uses
Drometrizole is an intermediate reactant in the synthesis of UV light absorbers for polyester fibers.
Preparation & Synthesis
Preparation
First, p-toluenesulfonyl chloride was reacted with pyridine in the presence of sodium carbide to give N-p-toluenesulfonylpyridinone (1). Then, N-p-toluenesulfonylpyridinone (1) was condensed with p-hydroxybenzoic acid in the presence of zinc chloride to give the UV-P intermediate 2-(2-(p-toluenesulfonyl)-4-methoxyphenyl)-5-(2-hydroxyphenyl)-1,3,4-thiadiazole (2). Finally, the intermediate 2-(2-(p-toluenesulfonyl)-4-methoxyphenyl)-5-(2-hydroxyphenyl)-1,3,4-thiadiazole (2) was hydrolyzed in the presence of sodium hydroxide to give the final product 2-(2-(p-toluenesulfonyl)-4-hydroxyphenyl)-5-(2-hydroxyphenyl)-1,3,4-thiadiazole (UV-P).