19932-84-4

Basic information

• Product Name: 6-CHLORO-1,3-BENZOXAZOL-2(3H)-ONE
• Synonyms: 6-CHLORO-2-BENZOXAZOLINONE;6-CHLORO-1,3-BENZOXAZOL-2(3H)-ONE;6-CHLOROBENZOXAZOLONE;6-CHLOROBENZOXAZOL-2(3H)-ONE;6-CHLOROOXAZONE;TIMTEC-BB SBB003865;2-Benzoxazolinone, 6-chloro-;6-chloro-2(3h)-benzoxazolon
• CAS NO: 19932-84-4
• Molecular Formula: C₇H₄ClNO₂
• Molecular Weight: 169.57
• Product Categories: Oxazole&Isoxazole;AmidesAnalytical Standards;EstersMore...Close...;Alpha Sort;Analytical Standards;AromaticsVolatiles/ Semivolatiles;C;CAlphabetic;CHChemical Class;Chemical Class;ChloroAnalytical Standards;Halogenated
• Mol File: 19932-84-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 192 °C
• Appearance: Light beige/Crystalline Powder
• Density: 1.3771 (rough estimate)
• Refractive Index: 1.5557 (estimate)
• PKA: 8.34±0.70(Predicted)
• CAS DataBase Reference: 6-CHLORO-1,3-BENZOXAZOL-2(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-1,3-BENZOXAZOL-2(3H)-ONE(19932-84-4)
• EPA Substance Registry System: 6-CHLORO-1,3-BENZOXAZOL-2(3H)-ONE(19932-84-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-26/36/37/39-22-36/37/39
• WGK Germany: 3
• RTECS: DM5252000
• HazardClass: IRRITANT
• Hazardous Substances Data: 19932-84-4(Hazardous Substances Data)

Usage

Description

6-Chloro-1,3-Benzoxazol-2(3H)-One is an organic compound characterized by its light beige crystalline powder form. It is a derivative of benzoxazole, a heterocyclic compound consisting of a benzene ring fused to an oxazole ring. The presence of a chlorine atom at the 6th position provides unique chemical properties and reactivity, making it a versatile building block in the synthesis of various chemical compounds.

Uses

Used in Pharmaceutical Industry:
6-Chloro-1,3-Benzoxazol-2(3H)-One is used as a key intermediate in the synthesis of substituted triazoles, which are known as potent ABA (Abscisic Acid) receptor pan-antagonists. These ABA receptor antagonists play a crucial role in the development of novel pharmaceuticals targeting various diseases and conditions, including those related to hormonal regulation and stress response in plants and animals.
Used in Chemical Synthesis:
Due to its unique chemical structure and reactivity, 6-Chloro-1,3-Benzoxazol-2(3H)-One is also used as a building block in the synthesis of various other organic compounds. Its versatility allows it to be employed in the development of new materials, dyes, and other specialty chemicals across different industries.

InChI:InChI=1/C7H4ClNO2/c8-4-1-2-5-6(3-4)11-7(10)9-5/h1-3H,(H,9,10)

Upstream product

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• 28443-50-7 2-amino-5-chlorophenol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 19213-72-0 ethyl 1-imidazolecarboxylate 
• 66441-23-4 2-[4-(6-Chloro-benzooxazol-2-yloxy)-phenoxy]-propionic acid ethyl ester 
• 95-55-6 2-amino-phenol 
• 89-73-6 salicylhydroxamic acid 
• 131761-59-6 7-chloro-2,4-dihydroxy-2H-1,4-benzoxazin-3-one 
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Downstream Products

• 62637-25-6 [3-(3,8-dichloro-benzo[b]pyridazino[4,3-e][1,4]oxazin-5-yl)-propyl]-dimethyl-amine 
• 203862-51-5 (+/-)-6-chloro-3-[4-(4-chlorobenzyl)morpholin-2-ylmethyl]-3H-benzoxazol-2-one 
• 3621-82-7 2,6-dichloro-1,3-benzoxazole 
• 22876-20-6 6-chloro-2-mercaptobenzoxazole 
• 303098-38-6 3-benzyl-6-chlorobenzo[d]oxazol-2(3H)-one 
• 1225607-54-4 6-phenyl-1,3-benzoxazol-2(3H)-one 
• 19739-40-3 2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetic acid 
• 1609694-21-4 6-chloro-3-((2-phenylpiperidin-1-yl)methyl)benzo[d]oxazol-2(3H)-one 

Relevant articles and documents

Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone

Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahydroisoindoline-1,3-dione scaffold to provide 25 compounds (1a-1u and 2a-2d). The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X-ray single-crystal diffraction. Some of these compounds (1g, 1h, 1j, 1k) exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli at a rate of 375 g AI·ha-1. Among them, compounds 1h and 1j displayed the best post-emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha-1, respectively, which are superior to that of the commercial acifluorfen (44.3 g AI·ha-1). Field trials demonstrated that compound 1h exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound 1h could potentially be used as a post-emergence herbicide for maize fields. Two series of tetrahydroisoindoline-1,3-diones containing an alkoxycarbonyl substituted 2-benzoxazolinone moiety were designed and synthesized. Compound 1h displayed excellent herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 g AI·ha-1, and compound 1h could potentially be used as a new post-emergence herbicide for maize fields.

Metamifop on Kilogram Scale

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Iron-Catalyzed Arene C-H Amidation Using Functionalized Hydroxyl Amines at Room Temperature

Herein, we report Fe(III)(TPP)Cl as an effective catalyst for promoting arene C-H amidation through intramolecular cyclization of N-tosyloxyarylcarbamate substrates. The reaction proceeds via nitrene (outer sphere pathway) C(sp2)-H i