22876-20-6

Basic information

• Product Name: 6-Chloro-2-benzoxazolethiol
• Synonyms: 2-MERCAPTO-6-CHLOROBENZOXAZOLE;6-CHLORO-BENZOOXAZOLE-2-THIOL;6-CHLORO-2-BENZOXAZOLETHIOL;6-CHLORO-2-MERCAPTOBENZOXAZOLE;6-chlorobenzoxazole-2(3H)-thione;6-Chloro-3H-benzoxazole-2-thione;6-Chlorbenzoxazol-2(3H)-thion;6-CHLORO-2-BENZOXAZOLETHIOL 99%
• CAS NO: 22876-20-6
• Molecular Formula: C₇H₄ClNOS
• Molecular Weight: 185.63
• EINECS: 245-282-8
• Product Categories: Oxazole&Isoxazole
• Mol File: 22876-20-6.mol

Chemical Properties

• Melting Point: 229-232 °C
• Boiling Point: 288.898 °C at 760 mmHg
• Flash Point: 128.521 °C
• Appearance: Yellow to beige/Crystalline Powder or Needles
• Density: 1.2291 (rough estimate)
• Vapor Pressure: 0.00227mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 10.23±0.20(Predicted)
• CAS DataBase Reference: 6-Chloro-2-benzoxazolethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-2-benzoxazolethiol(22876-20-6)
• EPA Substance Registry System: 6-Chloro-2-benzoxazolethiol(22876-20-6)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 22876-20-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-2-benzoxazolethiol is used as a reactant in the synthesis of disulfide bond-containing ajoene analogs. These analogs serve as quorum sensing inhibitors, which are crucial in the development of new antimicrobial agents. By inhibiting quorum sensing, these analogs can disrupt bacterial communication and prevent the formation of biofilms, thus reducing the spread of infections and enhancing the effectiveness of existing treatments.
Used in Chemical Synthesis:
As a versatile chemical compound, 6-Chloro-2-benzoxazolethiol can be employed in various chemical synthesis processes. Its unique structure allows it to be a valuable building block for the creation of new molecules with potential applications in different fields, such as materials science, pharmaceuticals, and agrochemicals.
Used in Research and Development:
Due to its unique chemical properties, 6-Chloro-2-benzoxazolethiol can be utilized in research and development for the exploration of new chemical reactions and the synthesis of novel compounds. It can serve as a starting material or an intermediate in the development of new drugs, materials, or other chemical products with potential commercial applications.

InChI:InChI=1/C7H4ClNOS/c8-4-1-2-5-6(3-4)10-7(11)9-5/h1-3H,(H,9,11)

Upstream product

• 75-15-0 carbon disulfide 
• 28443-50-7 2-amino-5-chlorophenol 
• 59-49-4 2-Benzoxazolinone 
• 95-55-6 2-amino-phenol 
• 19932-84-4 6-chlorobenzo[d]oxazol-2(3H)-one 
• 128-04-1 sodium dimethyldithiocarbamate 
• 137-26-8 Thiram 
• 140-89-6 potassium ethyl xanthogenate 
• 5910-69-0 acetic acid-(4-amino-2-hydroxy-anilide) 
• 16323-09-4 N-(4-chloro-2-hydroxyphenyl)acetamide 

Downstream Products

• 1218936-00-5 C₃₇H₃₇ClNO₅PS 
• 1218935-98-8 C₃₁H₂₅ClNO₅PS 
• 1218935-99-9 C₃₃H₂₉ClNO₅PS 
• 3621-82-7 2,6-dichloro-1,3-benzoxazole 
• 291541-06-5 2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(6-chloro-2-benzoxazolyl)thio]-pentanoic acid 
• 28443-50-7 2-amino-5-chlorophenol 
• 52112-68-2 6-chloro-1,3-benzoxazol-2-amine 
• 1374820-07-1 C₁₇H₁₆Cl₃N₃O 
• 819075-99-5 (S)-3-[(S)-2-(6-Chloro-benzooxazol-2-ylamino)-3-cyclohexyl-propionylamino]-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid tert-butyl ester 
• 819075-95-1 (S)-3-[(S)-2-(6-Chloro-benzooxazol-2-ylamino)-3-cyclohexyl-propionylamino]-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid 

Relevant articles and documents

High-efficiency low-pollution fenoxaprop-p-ethyl production process

The invention discloses a high-efficiency and low-pollution production process of fenoxaprop-p-ethyl. The production process comprises the following specific steps: (1) preparing fenoxaprop-p-ethyl; S1, preparing sulfydryl-6-chlorobenzoxazole; S2, preparing 2,6-dichlorobenzoxazole; and S3, synthesizing the fenoxaprop-p-ethyl. According to the fenoxaprop-p-ethyl, fenoxaprop-p-ethyl is finally synthesized through preparation of sulfydryl-6-chlorobenzoxazole and preparation of 2,6-dichlorobenzoxazole, the technology is simple, operation is convenient, efficiency is high, the speed is high, the production cost is saved, the income is increased, and filter residues generated in the production process can be safely treated through the technology; the waste gas enters a waste gas treatment facility for treatment and is discharged after reaching the standard; and the wastewater is desalted, removed salt is washed and dried by methanol to serve as a byproduct, and evaporated condensate water enters a factory sewage treatment station to be treated, so that the aim of protecting the environment is fulfilled, and the functions of high efficiency and low pollution are achieved.

Synthesis method of 2-mercapto-6-chlorobenzoxazole

The invention discloses a method for continuously synthesizing 2-mercapto-6-chlorobenzoxazole by a micro-channel reactor, and belongs to the technical field of organic synthesis processes. The methodcomprises the specific steps: performing ring opening on 6-chlorobenzoxazolone in a sodium hydroxide solution to obtain precursor salt, performing continuous sulfhydrylation cyclization reaction on the precursor salt and carbon disulfide in a micro-channel reactor, and performing acidification, centrifugation and drying to obtain a 2-mercapto-6-chlorobenzoxazole refined product. Compared with a traditional intermittent synthesis method of 2-mercapto-6-chlorobenzoxazole, the method has the advantages that the utilization rate of carbon disulfide is increased, the amount of three wastes is reduced, and particularly, safety accidents such as material flushing and unorganized emission of hydrogen sulfide are avoided. The method is simple to operate, high in product yield, good in quality and more beneficial to industrial production.

HMOX1 inducers

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

Method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as chlorinating agent

The invention provides a method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as a chlorinating agent. The method comprises the followingsteps: step 1, respectively preparing 2-benzoxazolone and 2-mercapto benzoxazole by taking the o-aminophenol as a raw material; step 2, preparing the 2-chlorobenzoxazole by taking the 2-mercapto benzoxazole as a raw material and the solid triphosgene as the chlorinating agent; step 3, preparing 6-chlorobenzoxazolone by taking TCCA and the 2-benzoxazolone as raw materials; step 4, preparing 2-mercapto-6-chlorobenzoxazole; step 5, preparing the 2,6-dichlorobenzoxazole by taking the 2-mercapto-6-chlorobenzoxazole as a raw material and the solid triphosgene as the chlorinating agent. The method provided by the invention is a brand-new preparation method, which has the advantages of less corrosion to equipment, high yield, less reaction time, mild reaction conditions, less by-products and reduced environmental pollution.

AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate

A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water

An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.

Selective synthesis of 2-aminobenzoxazoles and 2-mercaptobenzoxazoles by using o-aminophenols as starting material

2-Aminobenzoxazoles and 2-mercaptobenzoxazoles were selectively synthesized by treating o-aminophenols with dithiocarbamates and tetramethylthiuram disulfide (TMTD), respectively. With the promotion of NaH/CuI, the reaction of o-aminophenols with dithioca

2-sulfydryl-6-chlorobenzoxazole synthesis method

The invention relates to the field of chemical industry, and discloses a 2-sulfydryl-6-chlorobenzoxazole synthesis method. The method includes the step: (1) alkali hydrolysis: uniformly mixing 6-chlorobenzoxazolone and alkali liquor, increasing the temperature to range from 95 DEG C to 100 DEG C, performing thermal reaction to generate 2-sodium hydroxy-4-chlorobenzene sodium amino acid and reducing the temperature to range from 75 DEG C to 80 DEG C to obtain solution A; (2) sulfydryl synthesis: dripping carbon disulfide into the solution A, and performing thermal reaction at the temperature ranging from 75 DEG C to 80 DEG C after dripping to generate 2-sodium sulfydryl-6-chlorobenzoxazole and obtain solution B; (3) acidification: dripping the solution B into hydrochloric acid, performing reaction to generate 2-sulfydryl-6-chlorobenzoxazole, and performing pressure filtration and drying to obtain fine 2-sulfydryl-6-chlorobenzoxazole. Reaction system PH (potential of hydrogen) ranges from 4 to 5. Compared with the prior art, the synthesis method cannot generate a large amount of gas within a short time, punching is avoided, and safety and environmental protection accidents are avoided.