2-Chlorobenzoxazole

Base Information

• Chemical Name: 2-Chlorobenzoxazole
• CAS No.: 615-18-9
• Molecular Formula: C7H4ClNO
• Molecular Weight: 153.568
• Hs Code.: 29349990
• European Community (EC) Number: 210-414-5
• NSC Number: 8439
• UNII: OFH5RW45PA
• DSSTox Substance ID: DTXSID5060643
• Nikkaji Number: J41.892G
• Wikidata: Q69756956
• ChEMBL ID: CHEMBL4575218
• Mol file: 615-18-9.mol

Synonyms:2-Chloro-1,3-benzoxazole;2-Chlorobenzo[d]oxazole;NSC 8439;

Chemical Property of 2-Chlorobenzoxazole

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.436mmHg at 25°C
• Melting Point: 7 °C(lit.)
• Refractive Index: n20/D 1.566(lit.)
• Boiling Point: 201.5 °C at 760 mmHg
• PKA: 0.62±0.10(Predicted)
• Flash Point: 85 °C
• PSA: 26.03000
• Density: 1.377 g/cm³
• LogP: 2.48120
• Storage Temp.: 2-8°C
• Water Solubility.: Not miscible in water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.9981414
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

2-Chlorobenzoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=C(O2)Cl
• General Description: 2-Chlorobenzoxazole is a chemical moiety utilized in the development of dual orexin receptor antagonists, such as MK-4305, for treating insomnia. It serves as a key structural component, replacing the fluoroquinazoline ring in earlier compounds to mitigate issues like reactive metabolite formation while maintaining potency and improving pharmacokinetic properties. Its incorporation contributed to the optimization of drug candidates with enhanced efficacy and safety profiles.

Technology Process of 2-Chlorobenzoxazole

There total 14 articles about 2-Chlorobenzoxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.5%

→ 2-chloro-1,3-benzoxazole (615-18-9)

Guidance literature:

Reference yield: 90.0%

2-sulfanyl-1,3-benzoxazole (2382-96-9,118090-08-7) → 2-chloro-1,3-benzoxazole (615-18-9)

Guidance literature:

With chlorine;

Reference yield: 89.0%

benzoxazole (273-53-0,29791-96-6) → 2-chloro-1,3-benzoxazole (615-18-9)

Guidance literature:

With tetrachloromethane; sodium t-butanolate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

upstream raw materials:

benzo[d]oxazole-2-(3H)-thione

2-sulfanyl-1,3-benzoxazole

benzoxazole

phosphorus pentachloride

Downstream raw materials:

1-benzooxazol-2-yl-4-[3-(4-methoxy-phenyl)-acryloyl]-piperazine

phenylallylbenzoxazole

2-dimethylaminobenzoxazole

N-cyclohexyl-N-methylbenzo[d]oxazol-2-amine

Refernces

Discovery of the dual orexin receptor antagonist [(7 R)-4-(5-chloro-1,3- benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2 H -1,2,3-triazol-2-yl)phenyl]methanone (MK-4305) for the treatment of insomnia

10.1021/jm100541c

The research focuses on the development of a dual orexin receptor antagonist for treating insomnia. The study began with compound 4, a diazepane-based orexin receptor antagonist, which had excellent brain penetration and potency but suffered from high clearance and low bioavailability. Efforts to improve its pharmacokinetics led to the identification of compound 10 with a 7-methyl substitution on the diazepane core, which displayed good potency, improved pharmacokinetics, and excellent in vivo efficacy. However, compound 10 formed reactive metabolites in microsomal incubations. A mechanistic hypothesis and an in vitro assay to assess bioactivation led to the replacement of the fluoroquinazoline ring of 10 with a chlorobenzoxazole to provide 3 (MK-4305), a potent dual orexin receptor antagonist that is currently being tested in phase III clinical trials for the treatment of primary insomnia. Chemicals such as 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid, 2,5-dichloro-1,3-benzoxazole, and various diazepane cores played crucial roles in the synthesis and optimization of these compounds.

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