13060-24-7

Basic information

• Product Name: 2-Octylbenzimidazole
• Synonyms: 2-Octyl-1H-benzimidazole;2-octylbenzimidazole;2-Octylbenzoimidazol;1H-BenziMidazole,2-octyl-;2-octylbenzIMIDAZOLE:2-octyl-1h-benzIMIDAZOLE;2-octyl-1H-benzo[d]imidazole
• CAS NO: 13060-24-7
• Molecular Formula: C₁₅H₂₂N₂
• Molecular Weight: 230.35
• Mol File: 13060-24-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 144°C
• Boiling Point: 404°C
• Flash Point: 198°C
• Appearance: /
• Density: 1.014
• Vapor Pressure: 2.24E-06mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.99±0.10(Predicted)
• CAS DataBase Reference: 2-Octylbenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Octylbenzimidazole(13060-24-7)
• EPA Substance Registry System: 2-Octylbenzimidazole(13060-24-7)

Safety Data

• Hazardous Substances Data: 13060-24-7(Hazardous Substances Data)

Usage

General Description

2-Octylbenzimidazole is an organic compound that is commonly used in sunscreen formulas as a UV filter. It is an effective absorber of both UVB and UVA rays, providing broad-spectrum protection against harmful sun exposure. 2-Octylbenzimidazole is known for its photostability, meaning it does not undergo chemical changes when exposed to sunlight, making it an ideal ingredient for long-lasting sun protection products. Additionally, it has low skin irritation potential and is considered safe for topical application, enhancing its popularity as an ingredient in sunscreen and other skin care formulations.

InChI:InChI=1/C15H22N2/c1-2-3-4-5-6-7-12-15-16-13-10-8-9-11-14(13)17-15/h8-11H,2-7,12H2,1H3,(H,16,17)

Synthetic route

C15H24N2O → 2-octyl-1H-benzoimidazole (13060-24-7)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In toluene for 3h; Reflux;	90%

nonan-1-al (124-19-6) + 2-amino-1-benzylamine (4403-69-4) → 2-octyl-1H-benzoimidazole (13060-24-7)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 20℃; for 1h; chemoselective reaction;	84%

nonanoic acid (112-05-0) + 1,2-diamino-benzene (95-54-5) → 2-octyl-1H-benzoimidazole (13060-24-7)

Conditions	Yield
Heating;	80%

1-nonyne (3452-09-3) + 1,2-diamino-benzene (95-54-5) → 2-octyl-1H-benzoimidazole (13060-24-7)

Conditions	Yield
Stage #1: 1-nonyne; 1,2-diamino-benzene With copper(l) iodide; 4-toluenesulfonyl azide; triethylamine In acetonitrile at 20℃; for 6h; Inert atmosphere; Stage #2: With sulfuric acid In acetonitrile for 4h; Reflux;	74%

nonan-1-al (124-19-6) + 1,2-diamino-benzene (95-54-5) → 2-octyl-1H-benzoimidazole (13060-24-7)

Conditions	Yield
With sodium hydrogensulfite In N,N-dimethyl acetamide at 100℃; for 2h;	51.7%

Upstream product

• 112-05-0 nonanoic acid 
• 95-54-5 1,2-diamino-benzene 
• 124-19-6 nonan-1-al 
• 3452-09-3 1-nonyne 
• 4403-69-4 2-amino-1-benzylamine 
• 500542-69-8 1,1,1-trimethoxynonane 

Relevant articles and documents

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Anodic oxidation of dithiane carboxylic acids: A rapid and mild way to access functionalized orthoesters

A new electrochemical methodology has been developed for the preparation of a wide variety of functionalized orthoesters under mild and green conditions from easily accessible dithiane derivatives. The new methodology also offers an unprecedented way to access tri(fluorinated) orthoesters, a class of compound that has never been studied before. This provides the community with a rapid and general method to prepare libraries of functionalized orthoesters from simple and readily available starting materials.

Practical application of PhI(OAc)2/I2 combination to synthesize benzimidazoles from 2-aminobenzylamine through ring distortion strategy

In this present work the combination of iodobenzenediacetate (PIDA)/iodine has been established as a promising reagent to promote the construction of 2-substituted benzimidazoles from 2-aminobenzylamine and a variety of easily available aldehydes/arylamines through a ring distortion strategy. The present protocol offers mild, metal free, robust conditions to synthesize 2-substituted benzimidazoles in good to excellent yields. In addition, the oxidation prone functional groups show tolerance during the reaction and after completion of the reaction pure products can be easily obtained applying hassle free filtration of the reaction mixture through silica gel bed.