| Identification | More | [Name]
2-Mercaptobenzoxazole | [CAS]
2382-96-9 | [Synonyms]
1,3-BENZOXAZOLE-2-THIOL
2-BENZOXAZOLETHIOL
2-MERCAPTOBENZOXAZOLE
BENZO[D]OXAZOLE-2-THIOL
BENZOOXAZOLE-2-THIOL
BENZOXAZOLE-2-THIONE
1,3-Benzoxazole-2(3H)-thione
2(3H)-Benzoxazolethione
2-benzoxazolethione
2-Benzoxazolinethione
2-benzoxazolylthiol
2-Mercapto-1,3-benzoxazole
Benzoxazole, 2-mercapto-
Benzoxazolinethione
benzoxazole-2-thiol
2-Mercatobenzoxazole
2-MERCAPTOBENZOXAZOLE 95%
2-MERCAPTOBENZOXAZOLE, 98+%
2-Mercaptobenzoxazole,>97%
2,3-Dihydrobenzoxazole-2-thione | [EINECS(EC#)]
219-191-9 | [Molecular Formula]
C7H5NOS | [MDL Number]
MFCD00005769 | [Molecular Weight]
151.19 | [MOL File]
2382-96-9.mol |
| Chemical Properties | Back Directory | [Appearance]
beige crystalline powder | [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 | [form ]
Crystalline Powder | [pka]
11.03±0.20(Predicted) | [color ]
Beige | [PH]
5 (5g/l, H2O, 20℃) | [Water Solubility ]
SLIGHTLY SOLUBLE | [BRN ]
119483 | [InChI]
1S/C7H5NOS/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H,8,10) | [InChIKey]
FLFWJIBUZQARMD-UHFFFAOYSA-N | [SMILES]
Sc1nc2ccccc2o1 | [CAS DataBase Reference]
2382-96-9(CAS DataBase Reference) | [NIST Chemistry Reference]
2(3H)-Benzoxazolethione(2382-96-9) | [EPA Substance Registry System]
2382-96-9(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P280g-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S25:Avoid contact with eyes .
S24:Avoid contact with skin .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
DM4882500
| [F ]
13 | [TSCA ]
Yes | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Toxicity]
mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04482, |
| Hazard Information | Back Directory | [Chemical Properties]
beige crystalline powder | [Uses]
2-Mercaptobenzoxazole is used in the surface treatment of materials. It is utilized for protection of metals from corrosion. | [Application]
2-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. | [Definition]
ChEBI: 2-mercapto-1,3-benzoxazole is a benzoxazole. | [Preparation]
2-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 | [Reactions]
2-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]
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 |
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