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2-Mercaptobenzoxazole

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CAS:2382-96-9
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2-Mercaptobenzoxazole Basic information
Product Name:2-Mercaptobenzoxazole
Synonyms:benzoxazole-2-thiol;2-Mercatobenzoxazole;2-MERCAPTOBENZOXAZOLE 95%;2-MERCAPTOBENZOXAZOLE, 98+%;2-Mercaptobenzoxazole,>97%;BENZO[D]OXAZOLE-2-THIOL;BENZOXAZOLE-2-THIONE;BENZOOXAZOLE-2-THIOL
CAS:2382-96-9
MF:C7H5NOS
MW:151.19
EINECS:219-191-9
Product Categories:Isoxazoles, Oxadiazoles, Oxazoles;Oxazole&Isoxazole;J's
Mol File:2382-96-9.mol
2-Mercaptobenzoxazole Structure
2-Mercaptobenzoxazole Chemical Properties
Melting point 192-195 °C(lit.)
Boiling point 360°C (rough estimate)
density 1.2170 (rough estimate)
refractive index 1.5500 (estimate)
storage temp. Sealed in dry,Room Temperature
pka11.03±0.20(Predicted)
form Crystalline Powder
color Beige
PH5 (5g/l, H2O, 20℃)
Water Solubility SLIGHTLY SOLUBLE
BRN 119483
InChIKeyFLFWJIBUZQARMD-UHFFFAOYSA-N
CAS DataBase Reference2382-96-9(CAS DataBase Reference)
NIST Chemistry Reference2(3H)-Benzoxazolethione(2382-96-9)
EPA Substance Registry System2-Mercaptobenzoxazole (2382-96-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-25-24-36-26
WGK Germany 3
RTECS DM4882500
13
TSCA Yes
HS Code 29349990
Toxicitymouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04482,
MSDS Information
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2-Mercaptobenzoxazole English
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2-Mercaptobenzoxazole Usage And Synthesis
Chemical Propertiesbeige crystalline powder
Uses2-Mercaptobenzoxazole is used in the surface treatment of materials. It is utilized for protection of metals from corrosion.
Preparation2-Mercaptobenzoxazole has already been described in 1876 by Dunner (Ber. 9, (1876) page 465). 2-Mercaptobenzoxazole and its derivatives are prepared by processes which are based in principle on the reaction between o-aminophenol and alkali metal alkylxanthates. The alkali metal alkylxanthate here can either be employed as such, or it can be produced in the reaction mixture itself from an alkali, a lower alkanol and carbon disulphide.
https://patents.google.com/patent/US4677209A/en
Application2-Mercaptobenzoxazole is a widely used organic scaffold in medicinal chemistry.
2-Mercaptobenzoxazole and their derivatives are known to posses several biological activities such as antibacterial, antifungal, antiinflammatory, insecticidal and herbicidal. 4-0xo-thiazolidines have also played an important activities as analgesic, anti-HIV, antitubercular, anthelmentic, dye-stuffs, fluorescent and as a photosensitizer. The incorporation of 4-oxothiazolidine and their 5-arylidene moieties in 2-mercaptobenzoxazole frame work has been found to enhance the activity.
DefinitionChEBI: 2-mercapto-1,3-benzoxazole is a benzoxazole.
Reactions2-Mercaptobenzoxazole with ethyl chloroacetate and anhydrous K2C03 in the presence of dry acetone was refluxed on water bath to give ethyl-2-(mercaptobenzoxazolo)acetate.
Synthesis
Carbon disulfide

75-15-0

2-Aminophenol

95-55-6

2-Mercaptobenzoxazole

2382-96-9

1. 15 mL of ethanol, 3 mL of water, 10 mmol of o-aminophenol, 10 mmol of carbon disulfide, and 10 mmol of potassium hydroxide were sequentially added to the reaction flask. 2. The reaction mixture was heated to 80 °C and stirred at reflux for 3 hours at this temperature. 3. Upon completion of the reaction, a small amount of zeolite was added to the mixture and filtered while hot. 4. Warm the filtrate to 70 °C and slowly pour it into a beaker containing 10 mL of warm water (preheated to 60-70 °C). 5. cool the beaker in an ice-water bath to induce precipitation of the product. 6. The precipitated white transparent needle-like crystals were collected by filtration and dried to give 1.23 g of 2-mercaptobenzoxazole in 81% yield.

References[1] Patent: CN108794421, 2018, A. Location in patent: Paragraph 0024; 0025; 0027
[2] Heteroatom Chemistry, 2001, vol. 12, # 3, p. 151 - 155
[3] Letters in Organic Chemistry, 2010, vol. 7, # 7, p. 519 - 527
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5374 - 5379
[5] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 913 - 923
2-Mercaptobenzoxazole Preparation Products And Raw materials
Raw materialsCarbon disulfide-->Benzoxazole-->Tetramethylthiuram Disulfide-->2-Aminophenol-->Ethanol-->Water-->Potassium hydroxide
Preparation Products6-NITRO-BENZOOXAZOLE-2-THIOL
Tag:2-Mercaptobenzoxazole(2382-96-9) Related Product Information
ISOXAFLUTOLE Isoxazole Sulfamethoxazole Fenoxaprop-P Benzoxazole Famoxadone 2-Hydroxybenzimidazole 2-Mercaptobenzimidazole 5-CHLORO-2-MERCAPTOBENZOXAZOLE 2-Methylthio Benzoxazole 7-CHLORO-2-MERCAPTOBENZOXAZOLE 97 4,5-DIPHENYL-2-MERCAPTOBENZOXAZOLE 6-CHLORO-2-BENZOXAZOLETHIOL 99%,6-CHLORO-2-MERCAPTOBENZOXAZOLE,6-CHLORO-2-BENZOXAZOLETHIOL 6-METHYL-1,3-BENZOXAZOLE-2-THIOL 2-MERCAPTO-5-PHENYLBENZOXAZOLE 6-NITRO-2-BENZOXAZOLETHIOL,6-Nitro-2-benzoxazolethiol 2-Benzoxazolethiol 2-Mercaptobenzoxazole ETHYL 2-[(5-CHLORO-1,3-BENZOXAZOL-2-YL)SULFANYL]ACETATE

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