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

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

Uses

Used in Sun Protection Industry:
2-Octylbenzimidazole is used as a UV filter for its capacity to absorb both UVB and UVA rays, providing broad-spectrum protection against harmful sun exposure. Its inclusion in sunscreen formulas is attributed to its photostability, ensuring that the product remains effective over an extended period of time without undergoing chemical changes due to sunlight exposure.
Used in Skin Care Formulations:
2-Octylbenzimidazole is utilized as an ingredient in various skin care products for its low skin irritation potential and safety for topical application. This makes it suitable for a wide range of skin types, including those that are sensitive to other ingredients commonly found in sun protection and skincare products.

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

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

Relevant articles and documents

Preparation method 2 -substituted benzimidazole derivative

The invention belongs to the field of fine chemical product production, and particularly relates to 2 -substituted benzimidazole derivative preparation method which comprises the following steps: (1) taking O-phenylenediamine and aldehyde as raw materials, carrying out catalytic condensation, cyclization and oxidation reaction in a eutectic solvent. (2) Water is added to the reaction system, the separated product is filtered, and the eutectic solvent is recycled. (3) After recrystallization, a target product is obtained. The method has the advantages of simple operation process, easily available raw materials, low cost, high purity of the target product and no catalyst participation, can effectively prevent isomer formation, and is beneficial to large-scale production.

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.

An efficient one-pot conversion of carboxylic acids into benzimidazoles via an HBTU-promoted methodology

Benzimidazole is a privileged, and routinely used pharmacophore in the drug discovery process. Herein, we report a mild, acid-free and one-pot synthesis of indole, alkyl and alpha-amino benzimidazoles through a novel HBTU-promoted methodology. An extensive library of indole-carboxylic acids, alkyl carboxylic acids and N-protected alpha-amino acids has been converted into the corresponding benzimidazoles in 80-99% yield. Since alpha-aminobenzimidazoles are highly useful synthons as chiral ligands for chemical catalysis, as well as for drug discovery endeavors, our reported method provides direct access to this scaffold in a simple, one-pot operation from commercially available carboxylic acids.

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.

New Procedure for the Synthesis of 2-Alkylbenzimidazoles

Simple, economical, and environmentally friendly method to synthesize 2-alkylbenzimidazoles was developed by modifying the conventional method between °-phenylenediamine and aldehyde.

One-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via cascade reactions of o-aminoanilines or naphthalene-1,8-diamine with alkynes and p-tolylsulfonyl azide

A one-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via the cascade reactions of o-aminoanilines or naphthalene-1,8-diamine with terminal alkynes and p-tolylsulfonyl azide is reported. The protocol is efficient and general. Georg Thiem

Synthesis and insecticidal activity of some benzimidazolic and benzothiazolic derivatives

The benzimidazolic and benzothiazolic derivatives with a (CH2)n radical in 2 position of the heterocycle had been synthesized and then tested for their insecticidal activity on Culex pipiens larvae. The benzothiazolic derivatives were found to be the most active. The study has also showed that this activity was related to the nature of the substitute in 2 position of the heterocycle. This activity increased when (CH2)n chain increased until n = 6; above this value, the activity decreased.