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2-Heptylbenzimidazole is a chemical compound that belongs to the benzimidazole class, characterized by a benzene ring fused to an imidazole ring. It is recognized for its ability to absorb UVB radiation and convert it into less harmful infrared radiation, thus playing a crucial role in protecting the skin from the damaging effects of the sun.

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  • 5851-49-0 Structure
  • Basic information

    1. Product Name: 2-HEPTYLBENZIMIDAZOLE
    2. Synonyms: 2-Hept-1-yl-1H-benzimidazole;2-Heptylbenzimidazole;2-Heptyl-1H-benzimidazole;2-HeptylbenziMidazole 2-Heptyl-1H-benziMidazole;2-heptyl-1H-benzo[d]imidazole
    3. CAS NO:5851-49-0
    4. Molecular Formula: C14H20N2
    5. Molecular Weight: 216.32
    6. EINECS: 1308068-626-2
    7. Product Categories: N/A
    8. Mol File: 5851-49-0.mol
    9. Article Data: 22
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 392.2 °C at 760 mmHg
    3. Flash Point: 193 °C
    4. Appearance: /
    5. Density: 1.027 g/cm3
    6. Vapor Pressure: 5.28E-06mmHg at 25°C
    7. Refractive Index: 1.572
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: 2-HEPTYLBENZIMIDAZOLE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-HEPTYLBENZIMIDAZOLE(5851-49-0)
    12. EPA Substance Registry System: 2-HEPTYLBENZIMIDAZOLE(5851-49-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5851-49-0(Hazardous Substances Data)

5851-49-0 Usage

Uses

Used in Sun Care Products:
2-Heptylbenzimidazole is used as a photostabilizer in sunscreens and other cosmetic products for its capacity to safeguard the skin from UV radiation. It is valued for its photostability and safety, making it an essential ingredient in various sunscreen formulations.
Used in Cosmetic Industry:
In the cosmetic industry, 2-Heptylbenzimidazole is utilized as a UV protectant to maintain the integrity and effectiveness of the products against the sun's harmful rays. Its inclusion in formulations helps to extend the shelf life and performance of cosmetics by preventing degradation caused by UV exposure.

Check Digit Verification of cas no

The CAS Registry Mumber 5851-49-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,8,5 and 1 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5851-49:
(6*5)+(5*8)+(4*5)+(3*1)+(2*4)+(1*9)=110
110 % 10 = 0
So 5851-49-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H20N2/c1-2-3-4-5-6-11-14-15-12-9-7-8-10-13(12)16-14/h7-10H,2-6,11H2,1H3,(H,15,16)

5851-49-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-HEPTYLBENZIMIDAZOLE

1.2 Other means of identification

Product number -
Other names 2-heptyl-1H-benzimidazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5851-49-0 SDS

5851-49-0Downstream Products

5851-49-0Relevant articles and documents

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

Vasu, Amrutham,Naresh, Mameda,Krishna Sai, Gajula,Divya Rohini, Yennamaneni,Murali, Boosa,Ramulamma, Madasu,Ramunaidu, Addipilli,Narender, Nama

, p. 9439 - 9446 (2021/12/09)

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

Direct synthesis of 2-substituted benzimidazoles: Via dehydrogenative coupling of aromatic-diamine and primary alcohol catalyzed by a Co complex

Zuo, Minghui,Guo, Weihao,Pang, Yucheng,Guo, Rui,Hou, Chuanfu,Sun, Shouneng,Wu, Hongfeng,Sun, Zhizhong,Chu, Wenyi

, p. 14490 - 14495 (2020/10/03)

A Co(ii) complex with a stable structure was designed and synthesized with quinalic acid and Co (OAc)2·4H2O. The single crystal structure of the complex was characterized by X-ray diffraction. A dehydrogenative coupling of aromatic diamines and primary alcohols was developed by using the Co(ii) complex as the catalyst to synthesize 2-substituted benzimidazole. A series of 2-substituted benzimidazoles were obtained with good to excellent yields under mild reaction conditions. In addition, a compound with inhibitory Parkinson's activity was synthesized on a gram-scale by using this method. Finally, the reaction mechanism was proposed and the energy changes in the reaction process were simulated by density functional theory (DFT).

Method for preparing benzimidazole and quinazoline compounds by adopting supported nickel catalyst (by machine translation)

-

Paragraph 0054-0056; 0057; 0059, (2019/07/16)

The invention discloses a method for synthesizing benzimidazole and quinazoline compounds by oxidative coupling and dehydrogenation of a nitrogen-doped hierarchical porous biomass-based carbon material supported catalyst and a preparation method. The method comprises the following steps: adding o-phenylenediamine compound, alcohol, supported catalyst, toluene and potassium tert-butoxide as a solvent, carrying out reaction under 50~150 °C conditions, carrying out reaction 4~24 hours, cooling to room temperature, filtering the reaction liquid, and obtaining a benzimidazole compound or quinazoline compound. The method adopts "one-pot method" preparation, the intermediate can be separated and purified, energy consumption can be reduced, and the efficiency. (by machine translation)

Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly Defined Nonphosphine Manganese(I) Complex

Das, Kalicharan,Mondal, Avijit,Srimani, Dipankar

, p. 9553 - 9560 (2018/07/21)

Herein, we present a selective synthesis of 2-substituted and 1,2-disubstituted benzimidazoles by acceptorless dehydrogenative coupling of aromatic diamine with primary alcohols. The reaction is catalyzed by a phosphine-free tridentate NNS ligand-derived manganese(I) complex.

Sulfonic-acid-functionalized activated carbon made from tea leaves as green catalyst for synthesis of 2-substituted benzimidazole and benzothiazole

Goswami, Mridusmita,Dutta, Mintu Maan,Phukan, Prodeep

, p. 1597 - 1615 (2017/11/17)

Abstract: A simple and efficient procedure for synthesis of 2-substituted benzimidazole and benzothiazole has been developed by using sulfonic-acid-functionalized activated carbon as heterogeneous catalyst. The activated material was prepared from matured tea leaf in presence of phosphoric acid as activating agent. The final catalyst was prepared by anchoring –SO3H group on the surface of the activated carbon. The catalyst could be easily recovered and reused for more than three catalytic cycles without significant loss in catalytic activity. The catalytic performance of the catalyst was found to be superior to that of a similar catalyst prepared from montmorillonite K10. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis, anti-proliferative activity, SAR study, and preliminary in vivo toxicity study of substituted N,N′-bis(arylmethyl)benzimidazolium salts against a panel of non-small cell lung cancer cell lines

Shelton, Kerri L.,DeBord, Michael A.,Wagers, Patrick O.,Southerland, Marie R.,Williams, Travis M.,Robishaw, Nikki K.,Shriver, Leah P.,Tessier, Claire A.,Panzner, Matthew J.,Youngs, Wiley J.

, p. 421 - 439 (2016/12/18)

A series of N,N′-bis(arylmethyl)benzimidazolium salts have been synthesized and evaluated for their in vitro anti-cancer activity against select non-small cell lung cancer cell lines to create a structure activity relationship profile. The results indicate that hydrophobic substituents on the salts increase the overall anti-proliferative activity. Our data confirms that naphthylmethyl substituents at the nitrogen atoms (N1(N3)) and highly lipophilic substituents at the carbon atoms (C2and C5(C6)) can generate benzimidazolium salts with anti-proliferative activity that is comparable to that of cisplatin. The National Cancer Institute's Developmental Therapeutics Program tested 1, 3–5, 10, 11, 13–18, 20–25, and 28–30 in their 60 human tumor cell line screen. Results were supportive of data observed in our lab. Compounds with hydrophobic substituents have higher anti-cancer activity than compounds with hydrophilic substituents.

New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile

Obermoser, Victoria,Urban, Margarethe E.,Murgueitio, Manuela S.,Wolber, Gerhard,Kintscher, Ulrich,Gust, Ronald

, p. 138 - 152 (2016/08/30)

In previous studies, the 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid was identified as pharmacophoric core for PPARγ activation. In this structure-activity relationship study the C2-alkyl chain was elongated and the 2-COOH group was changed to a carbamide/carbonitrile or shifted to the 3- or 4-position. Furthermore, the benzo[d]imidazole was exchanged by 2,3-dihydrobenzo[d]thiazole or 1H-indole. C2-propyl derivatives showed the profile of partial agonists, while elongation of the C2-chain to that of an n-heptyl group or a 4-COOH shift changed the pharmacological profile to that of a potent full agonist. This finding can be explained by binding to the LBD in different ligand conformations. Two anchoring points (Tyr473 and Arg288) exist in the LBD, which have to be contacted to achieve receptor activation. In a crystal violet chemosensitivity assay using COS-7?cells and LNCaP cells expressing PPARγ only the carbamide derivatives influenced the cell growth, independently on the presence of the PPARγ. Therefore, receptor mediated cytotoxicity can be excluded.

Synthesis of Benzimidazoles via Iron-Catalyzed Aerobic Oxidation Reaction of Imine Derivatives with o-Phenylenediamine

Yu, Jiatao,Lu, Ming

supporting information, p. 2148 - 2157 (2015/09/01)

A simple and efficient protocol for preparing benzimidazoles via Fe(NO3)3.9H2O-catalyzed aerobic oxidation reaction of imine derivatives with o-phenylenediamine. This process uses air as an economical and green oxidant, tolerates a wide range of substrates, and affords the targeted benzimidazoles in moderate to excellent yields.

Acceptorless dehydrogenative synthesis of benzothiazoles and benzimidazoles from alcohols or aldehydes by heterogeneous Pt catalysts under neutral conditions

Chaudhari, Chandan,Siddiki, S.M.A. Hakim,Shimizu, Ken-Ichi

, p. 4885 - 4888 (2015/07/28)

Abstract Pt/Al2O3 and Pt/TiO2 were effective catalysts for the synthesis of 2-substituted benzothiazoles and benzimidazoles from 2-aminothiophenol and 1,2-phenylenediamine with alcohols or aldehydes under acceptor-free and additive-free conditions.

Iron(II) bromide-catalyzed oxidative coupling of benzylamines with ortho-substituted anilines: Synthesis of 1,3-benzazoles

Gopalaiah, Kovuru,Chandrudu, Sankala Naga

, p. 5015 - 5023 (2015/03/03)

An iron(II) bromide-catalyzed oxidative coupling of benzylamines with 2-amino/hydroxy/mercapto-anilines has been developed, allowing the synthesis of a diversity of substituted 1,3-benzazoles in good to excellent yields. This transformation is compatible with a wide range of functional groups. The method is practical, economical and employs molecular oxygen as an oxidant.

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