52112-68-2

Basic information

• Product Name: 6-CHLOROBENZO[D]OXAZOL-2-AMINE
• Synonyms: 6-CHLOROBENZO[D]OXAZOL-2-AMINE;2-Amino-6-chlorobenzoxazole;6-Chloro-1,3-benzoxazol-2-amine;(6-chloro-1,3-benzoxazol-2-yl)amine;2-Benzoxazolamine, 6-chloro-;2-Benzoxazolamine, 6-chloro- (9CI);6-Chloro-2-benzoxazolamine;BENZOXAZOLE, 2-AMINO-6-CHLORO-
• CAS NO: 52112-68-2
• Molecular Formula: C₇H₅ClN₂O
• Molecular Weight: 168.58
• Mol File: 52112-68-2.mol

Chemical Properties

• Melting Point: 184 °C
• Boiling Point: 316.8ºC at 760 mmHg
• Flash Point: 145.4ºC
• Appearance: /
• Density: 1.4369 (rough estimate)
• Vapor Pressure: 0.000401mmHg at 25°C
• Refractive Index: 1.5618 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.17±0.30(Predicted)
• CAS DataBase Reference: 6-CHLOROBENZO[D]OXAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROBENZO[D]OXAZOL-2-AMINE(52112-68-2)
• EPA Substance Registry System: 6-CHLOROBENZO[D]OXAZOL-2-AMINE(52112-68-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 52112-68-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLOROBENZO[D]OXAZOL-2-AMINE is used as a key intermediate for the synthesis of various pharmaceuticals due to its unique core structure and reactivity. It contributes to the development of new drugs and biologically active compounds, enhancing the therapeutic potential of medications.
Used in Agrochemical Industry:
In the agrochemical sector, 6-CHLOROBENZO[D]OXAZOL-2-AMINE is utilized as a building block for the preparation of agrochemicals. Its structural features allow for the creation of compounds that can be used in pest control and crop protection, thereby improving agricultural productivity.
Used in Organic Synthesis:
6-CHLOROBENZO[D]OXAZOL-2-AMINE is employed as a versatile building block in organic synthesis for the preparation of a wide range of functional materials. Its unique structure facilitates the synthesis of complex organic compounds, broadening the scope of applications in various industries.
Used in Medicinal Chemistry Research:
6-CHLOROBENZO[D]OXAZOL-2-AMINE is used as a research compound in medicinal chemistry to explore its potential in the development of new therapeutic agents. Its presence in the molecular structure of various compounds can influence their biological activity, making it a valuable tool in drug discovery and design.

InChI:InChI=1/C7H5ClN2O/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H2,9,10)

Upstream product

• 2420-26-0 4-chlorosalicylaldehyde 
• 506-68-3 bromocyane 
• 28443-50-7 2-amino-5-chlorophenol 
• 44830-55-9 3-cyano-1-isopropylguanidine 
• 557-21-1 zinc(II) cyanide 
• 22876-20-6 6-chloro-2-mercaptobenzoxazole 
• 127099-85-8 N-Cyanoguanidine 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 104619-51-4 di(1H-imidazol-1-yl)methanimine 
• 140-38-5 N-(4-chlorophenyl)urea 
• 106-47-8 4-chloro-aniline 
• 58696-59-6 7-Chloro-2H-benzo[1,2,4]oxadiazine-3-carboxylic acid ethyl ester 
• 4570-41-6 1,3-benzoxazol-2-amine 
• 30818-28-1 5-chloro-2-cyanophenol 

Relevant articles and documents

Design, synthesis, and evaluation of substituted 2-acylamide-1,3-benzo[d]zole analogues as agents against MDR- and XDR-MTB

N-(5-Chlorobenzo[d]oxazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamideox-amide has been identified as a potent inhibitor of Mtb H37Rv, with a minimum inhibitory concentration (MIC) of 0.42 μM. In this study, a series of substituted 2-acylamide-1,3-zole analogues were designed and synthesized, and their anti-Mtb activities were analyzed. In total, 17 compounds were found to be potent anti-Mtb agents, especially against the MDR- and XDR-MTB strains, with MIC values 10 μM. These analogues can inhibit both drug-sensitive and drug-resistant Mtb. Four representative compounds were selected for further profiling, and the results indicate that compound 18 is acceptably safe and has favorable pharmacokinetic (PK) properties. In addition, this compound displays potent activity against Gram-positive bacteria, with MIC values in the range of 1.48–11.86 μM. The data obtained herein suggest that promising anti-Mtb candidates may be developed via structural modification, and that further research is needed to explore other compounds.

Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1–2 μM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines

An operationally simple oxidation-cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.

Cyanoguanidine as a versatile, eco-friendly and inexpensive reagent for the synthesis of 2-aminobenzoxazoles and 2-guanidinobenzoxazoles

An effective, easy-to-handle, safe and inexpensive protocol is reported for the synthesis of 2-aminobenzoxazoles under Lewis acid activation, utilising cyanoguanidine as the cyanating reagent. An optimized procedure for the synthesis of 2-guanidinobenzoxazole and novel derivatives is also described.

Substituted benzo - 1, 3 - [...] compound, its preparation and use

The invention relates to a substituted benzo-1, 3-miscellaneous azole compound shown in the general formula I, and further relates to a preparation method of the compound and application to the preparation of antituberculosis drugs. The compound provided by the invention has effect not only on mycobacterium tuberculosis sensitive strains, but also on resistant strains which have drug resistance to isoniazid, rifampicin, and other traditional frontline antituberculosis drugs, and is a novel antimycobacterium tuberculosis compound.

A facile synthesis of 2-aminobenzoxazoles and 2-aminobenzimidazoles using N -cyano- N -phenyl- P -toluenesulfonamide (NCTS) as an efficient electrophilic cyanating agent

A facile synthesis of 2-aminobenzoxazole and 2-aminobenzimidazole derivatives employing a nonhazardous electrophilic cyanating agent: N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) with various substituted 2-aminophenols and benzene-1,2-diamine derivatives in the presence of lithium hexamethyldisilazide (LiHMDS) is described. This novel protocol boasts operational simplicity, shorter reaction time, and simple workup.

2-Aminobenzoxazole ligands of the hepatitis C virus internal ribosome entry site

2-Aminobenzoxazoles have been synthesized as ligands for the hepatitis C virus (HCV) internal ribosome entry site (IRES) RNA. The compounds were designed to explore the less basic benzoxazole system as a replacement for the core scaffold in previously discovered benzimidazole viral translation inhibitors. Structure-activity relationships in the target binding of substituted benzoxazole ligands were investigated.

Poly (ethylene glycol)-bound sulphonic acid as a novel catalyst for synthesis of benzoxazoles

ABSTRACT Ahighly efficient, simple and rapid method for the preparation of various 2-aminobenzoxazoles and other benzoxazole derivatives using a catalytic amount of poly (ethylene glycol)-bound sulphonic acid (PEG-SO3H) is described. PEG-SO3H is found to be economical and reusable catalyst with low catalytic loading. The percentage yield was found to be satisfactory, experimental set-up and purification of final products is facile and easy. GRAPHICAL ABSTRACT.

Ring Contraction of 1,2,4-Benzoxadiazines to Benzoxazoles

1,2,4-Benzoxadiazines (1) undergo a ring contraction to benzoxazoles (2) on heating.Other products of the reaction have been identified as nitrogen and ammonia.A mechanism is suggested for this reaction which involves (i) electrocyclic ring opening to an o-benzoquinone imine, (ii) recyclisation to a diaziridine, and (iii) extrusion of a nitrene fragment.Evidence is presented which is consistent with this proposal: thus, the benzoxazole (7) is produced on heating 3,5-di-t-butyl-o-benzoquinone with benzamidine and 4-nitrobenzoylnitrene is intercepted as the ylide (11) from the thermolysis of the substituted benzoxadiazine (10).