20600-44-6

Basic information

• Product Name: 5-CHLORO-2-BENZOTHIAZOLINONE
• Synonyms: 5-CHLORO-2-BENZOTHIAZOLINONE;5-CHLORO-2-BENZOTHIAZOLONE;5-CHLOROBENZOTHIAZOLONE;Chlorobenzothiazolinone;2(3H)-Benzothiazolone,5-chloro-(9CI);5-CHLORO-2-BENZOTHIAZOLINONE 95+%;5-Chloro-2-benzothiazolinone ,98%;5-Chlorobenzothiazol-2-ol
• CAS NO: 20600-44-6
• Molecular Formula: C₇H₄ClNOS
• Molecular Weight: 185.63
• Product Categories: BENZOTHIAZOLE
• Mol File: 20600-44-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 234.0 to 238.0 °C
• Appearance: /
• Density: 1.515g/cm³
• Refractive Index: 1.669
• PKA: 9.57±0.20(Predicted)
• CAS DataBase Reference: 5-CHLORO-2-BENZOTHIAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-BENZOTHIAZOLINONE(20600-44-6)
• EPA Substance Registry System: 5-CHLORO-2-BENZOTHIAZOLINONE(20600-44-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-24/25
• Hazardous Substances Data: 20600-44-6(Hazardous Substances Data)

Usage

Chemical Properties

White to gray solid

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

Upstream product

• 5331-91-9 5-chloro-1,3-benzothiazole-2(3H)-thione 
• 29203-75-6 5-chloro-2-(methylsulfonyl)benzothiazole 
• 201230-82-2 carbon monoxide 
• 89-61-2 2,5-dichloronitrobenzene 
• 103-71-9 phenyl isocyanate 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 1202680-24-7 phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate 
• 81782-43-6 5-chloro-benzothiazole-2-sulfonamide 
• 29124-55-8 2-amino-4-chlorophenyl disulfide 
• 463-58-1 carbon oxide sulfide 
• 3507-41-3 5-Chloro-2-(methylthio)benzothiazole 

Downstream Products

• 54769-25-4 2-(5-chloro-2-oxo-2,3-dihydro-1,3-benzothiazol-3-yl)acetic acid 
• 102749-64-4 [2-(6-chloro-3-phenyl-benzo[1,4]thiazin-4-yl)-ethyl]-dimethyl-amine 
• 95476-09-8 4-chloro-2-methylamino-thiophenol 
• 95476-13-4 4-chloro-2-(2-dimethylamino-ethylamino)-thiophenol 
• 100375-25-5 5-chloro-N-methyl-2-(2-nitro-phenylsulfanyl)-aniline 
• 1234055-97-0 5-chloro-3-[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl]-3H-benzothiazol-2-one 
• 33354-22-2 5-chloro-3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2(3H)-one 
• 72680-46-7 2-(5-Chloro-2-oxo-benzothiazol-3-yl)-N-(3-trifluoromethyl-phenyl)-acetamide 
• 33353-25-2 1-benzyl-4-[(5-chloro-2-oxo-benzothiazol-3-yl)-acetyl]-piperazine 
• 36857-46-2 3-(4-Hydroxypiperidino)carbonylmethyl-5-chlor-2-benzothiazolinon 
• 36857-73-5 1-[(5-chloro-2-oxo-benzothiazol-3-yl)-acetyl]-4-phenyl-piperazine 
• 85750-08-9 ethyl (5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)acetate 

Relevant articles and documents

Method for synthesizing benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials

The invention discloses a method for synthesizing a benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials. The method comprises the following steps: mixing disulfide,inorganic sulfide and an organic solvent, introducing sufficient COS to implement a reaction, and concentrating and purifying a reaction liquid, thereby obtaining the benzothiazole-2-ketone derivative. The inorganic sulfide used in the method is adopted as an activation catalyst and is low in price and easy to obtain; a catalysis system is relatively simple, and no other catalyst promoter is addedexcept reactants and inorganic sulfide; direct dehydration is implemented in the reaction process, no other dehydration agent is used, and thus the atom economy is improved; the catalysis system is good in applicability, is applicable to synthesis of fine chemicals with high additional values, and is very good in substrate applicability to each fine chemical with high additional values; reactionsare implemented at normal temperatures, normal pressure or low pressure, and thus danger coefficients can be reduced; the reaction time is short, and the efficiency can be improved.

Method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2

The present invention relates to a method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2. According to the present invention, an inexpensive and easily-available sulfur-containing metal salt compound is first used as an activation catalyst for CO2, and a reaction raw material and CO2 are converted into a corresponding target compound at a low reaction temperature under a low CO2 pressure; and the method has high atomic economy, can reduce the generation of by-products, meets the standards of environmental friendliness and environmentally friendly chemistry, and is the effective way capable of completely utilizing CO2 as the renewable resource, developing new energy and achieving the beneficial cycle of carbon in nature.

Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions

Carbonyl sulfide (COS), whose molecular structure is similar to CO2 and CS2, could be used as a better alternative carbonyl reagent due to its high chemical activity. However, the unfriendly by-product H2S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o-aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H2S generation and S–S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S–S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodology provided a promising process for the utilization of COS.

Facile Synthesis of Benzo[ d ]azol-2(3 H)-ones Using 2-Phenoxycarbonyl-4,5-dichloropyridazin-3(2 H)-one as Green CO Source

Developing eco-friendly, stable, and easy-to-handle acyl sources is of great importance in synthetic and green chemistry. This study describes the synthesis of benzo[d]azol-2(3H)-ones such as benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and benzo[d]imidazol-2(3H)-ones using 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one in one pot. The reaction reported is carried out under neutral or acidic conditions in the presence of zinc or sodium bicarbonate to give the corresponding heterocycles in good to excellent yields. The reaction uses a solid stable carbonyl source that is a recyclable functional-group carrier, pyridazin-3(2H)-one.

Lanthanide-catalyzed cyclocarbonylation and cyclothiocarbonylation: A facile synthesis of benzannulated 1,3-diheteroatom five- and six-membered heterocycles

La[N(SiMe3)2]3 proves to be an efficient catalyst system for the cyclocarbonylation of 1,2-disubstituted benzenes with isocyanates. In this approach, aryl/alkyl isocyanates react with o-phenylenediamine, o-aminophenol, o-aminothiophenol, catechols and anilines ortho-substituted by CH2NH2 and CONH2 to form, respectively, the corresponding benzimidazolones, benzoxazolones, benzothiazolones, benzodioxolones, 3,4-dihydroquinazolin-2(1H)-one, and quinazolinediones. These results represent the first example of lanthanide-catalyzed carbonylation. This methodology is also applicable for the preparation of various benzannulated 1,3-diheteroatom cyclic thioketones starting from aryl/alkyl isothiocyanates or CS2 in good to excellent yields. Based on the results of experiments performed using an o-aminobenzamido dianion lanthanide complex, a general mechanism, involving the tandem reaction of two lanthanide-ligand bonds with one heterocumulene molecule, is proposed as well.

Hydroxylamine as an oxygen nucleophile: Substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure-reactivity relationships, oxygen labeling experiments, and (in)direct detection of intermediates and products reveal that the reaction proceeds via oxygen attack, and that oxygen incorporated in the 2-hydroxybenzothiazole product derives from hydroxylamine. The reaction, which is performed under mild conditions, can be used as a deprotection method for cleavage of benzothiazole-2-sulfonyl-protected amino acids.

Synthesis of 2-Oxo-3-benzothiazolineacetyl Chloride (7), 5-Chloro-2-oxo-3-benzothiazolineacetyl Chloride (8) and Derivatives

The reaction of 2-oxo-3-benzothiazolineacetic acid (5) and the 5-chloro analogue 6 with thionyl chloride afforded the titled compounds 7 and 8.The reaction of 7 or 8 with substituted hydrazines, amines or substituted anilines, alcohols and mercaptans furnished the hydrazides 9-14, acetamides and acetanilides 16-21, esters 26-30 and thiolesters 31-37, respectively.Alternate routes for the synthesis of hydrazide 15, acetamides and acetanilides 22-25 and thiolesters 35-36 are described.The reaction of 2-oxo-3(2H)-benzothiazolineacetonitrile with thioacetic acid under acidic conditions afforded 2-oxo-3-benzothiazolineethanethioamide (38).

Synthesis of 2-Oxo and 2-Thioxo-3(2H)-benzothiazoleethanimic Acid Anhydride with Acetic Acid and Related Products

The reaction of the appropriate 2-benzothiazolinone with 2-chloroacetamide under basic conditions afforded the 2-oxo-3(2H)-benzothiazolineacetamides 6-9.The 2-thioxo-3(2H)-benzothiazolineacetamide (10) was prepared by the reaction of 3-(carbethoxymethyl)benzothiazoline-2-thione with ammonium hydroxide.The reaction of acetamides 6-10 with the appropriate anhydride containing a catalytic amount of the sodium salt of the acid corresponding to the anhydride afforded the titled compounds 11-18 in excellent yields.The omission of the catalyst in the same reaction furnished a mixture containing 57percent of the titled compound, 37percent of the nitrile and 6percent of an unknown.Possible mechanism and supporting nmr, ir and mass spectral data are discussed.