CAS 3896-11-5 Tinuvin (HCID 62531)

Overview

Bumetrizole is a small molecule drug. Bumetrizole has a monoisotopic molecular weight of 315.11 Da.

Names & identifiers

Preferred name: Tinuvin
IUPAC: 2-tert-butyl-6-(5-chlorobenzotriazol-2-yl)-4-methylphenol
English name: UV Absorber 326
Molecular formula: C17H18ClN3O
Molecular weight: 315.8

Names & synonyms

Tinuvin2-(2'-Hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazoleRefChem:570489BUMETRIZOLE3896-11-52-(tert-Butyl)-6-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-methylphenolTinuvin 3262-(5-Chloro-2-benzotriazolyl)-6-tert-butyl-p-cresolUV-326Bumetrizol2-tert-Butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenolDTXSID9036438

Show more names

2-(2-HYDROXY-3-TERT-BUTYL-5-METHYLPHENYL)-5-CHLOROBENZOTRIAZOLE2-(3-tert-Butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazoleSumisorb 300ULTRAVIOLET ABSORBENT UV-326

C17H18ClN3OMFCD00059707Phenol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl-2-tert-Butyl-6-(5-chloro-2H-benzotriazol-2-yl)-p-cresol2-tert-butyl-6-(5-chlorobenzotriazol-2-yl)-4-methylphenol7ZF18Q354W2-tert-Butyl-6-(5-chloro-2H-1,2,3-benzotriazol-2-yl)-4-methylphenolTox21_112379

Database identifiers

CAS: 3896-11-5
PubChem CID: 62531
DTXSID: DTXSID9036438
ChEMBL: CHEMBL1880325
UNII: 7ZF18Q354W
EC Number: 223-445-4
Nikkaji: J8.273B

Properties

Computed structural properties

XLogP: 5.6
Topological polar surface area: 50.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 22
Formal charge: 0
Complexity: 400

Experimental & physicochemical properties

Chemical ClassesUV filter

Polymers · 2 items

Plastics -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PC; (E)PS

Plastics -> Light stabilisers

CosmeticsUv absorber

FragrancesFragrance Ingredient (Phenol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl-) -> IFRA transparency List

Food Contact Substances · 2 items

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

Collision Cross Section183.2 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID9036438]

Physicochemical properties

Melting point: 144 · 144-147 °C(lit.)
Boiling point: 460.4 · 460.4±55.0 °C(Predicted)
Density: 1.26 · 1.26±0.1 g/cm3(Predicted)
vapor pressure: 0 Pa · 0Pa at 20℃
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form: Solid
pka: 9.31 · 9.31±0.48(Predicted)
color: Pale Yellow to Light Yellow
Water Solubility: 4 μg/L · 4μg/L at 20℃
Cosmetics Ingredients Functions: LIGHT STABILIZER
InChI: InChI=1S/C17H18ClN3O/c1-10-7-12(17(2,3)4)16(22)15(8-10)21-19-13-6-5-11(18)9-14(13)20-21/h5-9,22H,1-4H3
InChIKey: OCWYEMOEOGEQAN-UHFFFAOYSA-N
SMILES: C1(O)=C(C(C)(C)C)C=C(C)C=C1N1N=C2C=C(Cl)C=CC2=N1
LogP: 6.58 · 6.580 (est)
Substances of Very High Concern (SVHC) Candidate List: Bumetrizole (UV-326) (3896-11-5)
FDA 21 CFR: 178.201 · 178.2010
Indirect Additives used in Food Contact Substances: 2 · 2-(3'-TERT-BUTYL-2'-HYDROXY-5'-METHYL-PHENYL)-5-CHLOROBENZOTRIAZOLE
CAS DataBase Reference: 3896 · 3896-11-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 7 ZF18Q354W · 7ZF18Q354W
EPA Substance Registry System: 2 · 2-tert-Butyl-6-(5-chloro-2H-benzotriazol-2-yl)-p-cresol (3896-11-5)
UNSPSC Code: 12162002 · 12162002
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38-53
Safety Statements: 26 · 26-36-61
WGK Germany: 1 · 1
TSCA: TSCA listed
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

This chemical does not meet GHS hazard criteria for 11.4% (241 of 2118) of reports.

H413 (78.7%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2118 reports by companies from 13 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 5 items

Chemical: Phenol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl-

Hazard Traits - Bioaccumulation; Environmental Persistence

Status: Active Update: 28-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5785

Substance: Bumetrizole (UV-326)

Bumetrizole: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Phenolic benzotriazoles: Environment tier II assessment

Hazard Classes and CategoriesAquatic Chronic 4 (78.7%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 1
tsca: TSCA listed
hs_code: 29339900
risk_code: 36/37/38-53
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-61
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
REACH Registrations: Active
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Uses & manufacturing

UsesPlastics -> Typical concentration range in plastic materials -> 0.3 - 1.0%

Household ProductsCosmetics product ingredient: Bumetrizole (UV-326)

Use Classification · 4 items

Fragrance Ingredients

Cosmetics -> Uv absorber

Plastics -> Polymer Type -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PC; (E)PS

Plastics -> Light stabilisers

General Manufacturing InformationPhenol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl-: ACTIVE

Applications · 3 items

UsesUV-326 can potentially be used as a UV light filter in cosmetics and sunscreens. It may also be used as a corrosion inhibitor for the protection of building materials and automobiles.

UsesBumetrizole is an intermediate reactant in the synthesis of UV light absorbers for polyester fibers.

General Description2-tert-Butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol (UV-326) is a benzotriazole based UV absorber that can be used in the photostabilization of industrial materials. It can absorb the harmful UV radiation for the wavelength of about 290 nm.

Preparation methods · 1 item

PreparationDiazotization reaction: Weigh 6g of 98wt% H₂SO₄, 50ml of water, and 0.03mol of p-chloro-o-nitroaniline and add them to the reaction vessel. Cool to 5℃, then slowly add 15g of 20wt% NaNO₂ solution, stirring for 1 hour until the reaction is complete. Add urea to decompose residual nitrite, and filter to remove residue. Coupling reaction: Weigh 0.03mol of 2-tert-butyl-p-cresol, 50mL of water, and 0.1g of sodium dodecylbenzenesulfonate and add them to the reaction vessel, stirring to form a homogeneous white emulsion. Adjust the pH to 7-9, and under these weakly alkaline conditions, add the above diazonium salt solution dropwise over 2 hours. After the reaction is complete, filter, wash, dry, and weigh. Glucose reduction reaction: Weigh 0.015 mol of the product obtained from the diazo coupling reaction and 10 g of NaOH solution (20 wt%) and add them to the reaction vessel. When the temperature reaches 50℃, slowly add 100 ml of 30 wt% glucose solution. Continue the reaction for 1 h, cool, filter and dry to obtain the nitride intermediate. Zinc powder reduction reaction: Add 17 mL of chlorobenzene and 42 g of 14 wt% H₂SO₄ to the above nitride and heat to 90℃. Add 1.1 g of zinc powder in batches over 2 h. After the reaction is complete, add activated carbon, stir for 0.5 h, filter while hot, separate the filtrate into layers, wash the oil layer with water until neutral, and evaporate the solvent to obtain the target product. Analytical results show that the product yield is 90.9% and the purity is 99.3%.