24044-87-9

Basic information

• Product Name: Acetic acid,2-(2-benzothiazolylthio)-, methyl ester
• Synonyms: Acetic acid,2-(2-benzothiazolylthio)-, methyl ester
• CAS NO: 24044-87-9
• Molecular Formula: C₁₀H₉NO₂S₂
• Molecular Weight: 239.32
• Mol File: 24044-87-9.mol

Chemical Properties

• Melting Point: 75-76 °C
• Boiling Point: 361.3°Cat760mmHg
• Flash Point: 172.3°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 2.09E-05mmHg at 25°C
• Refractive Index: 1.658
• PKA: 0.09±0.10(Predicted)
• CAS DataBase Reference: Acetic acid,2-(2-benzothiazolylthio)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid,2-(2-benzothiazolylthio)-, methyl ester(24044-87-9)
• EPA Substance Registry System: Acetic acid,2-(2-benzothiazolylthio)-, methyl ester(24044-87-9)

Safety Data

• Hazardous Substances Data: 24044-87-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H9NO2S2/c1-13-9(12)6-14-10-11-7-4-2-3-5-8(7)15-10/h2-5H,6H2,1H3

Upstream product

• 102-77-2 4-(benzothiazole-2-sulfenyl)-morpholine 
• 105-45-3 acetoacetic acid methyl ester 
• 96-34-4 methyl chloroacetate 
• 149-30-4 2-Mercaptobenzothiazole 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 820961-77-1 C₁₅H₁₅O₃P 

Downstream Products

• 24044-91-5 [(1,3-benzothiazol-2-ylthio)acetyl]hydrazine 

Relevant articles and documents

Trisubstituted Highly Activated Benzo[ d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis

In this paper, we report the formation of highly electrophilic 1,1-deactivated olefins, their use as novel synthetic building blocks, and their transformation to structurally diverse molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPri)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular scaffolds. Overall, the obtained structures are accessed in two to four steps starting from the (mostly) commercially available aldehydes. In addition, the presence of the BT-sulfonyl group in prepared structures allows for further chemoselective functionalization/post-synthetic transformations to provide structurally diverse final compounds.

Alkyl 2-(2-benzothiazolylsulfinyl)acetates as useful synthetic reagents for alkyl 4-hydroxyalk-2-enoates by sulfinyl-Knoevenagel reaction

Isopropyl, ethyl, and methyl 2-(2-benzothiazolylsulfinyl)acetates have been found to be useful synthetic reagents for sulfinyl-Knoevenagel reaction with various aldehydes to give directly the corresponding 4-hydroxyalk-2-enoates [R′CH(OH)CHCHCO2R], which are ubiquitous structures in biologically active natural products and useful building blocks for organic synthesis of chiral compounds. From the optically pure (R)-2-(2- benzothiazolylsulfinyl)acetates (>99% ee) prepared by the enzymatic kinetic resolution of (±)-2-(2-benzothiazolylsulfinyl)acetates, optically active 4-hydroxyalk-2-enoates (up to 91% ee) have been obtained in good yields.

Continuous flow biocatalytic resolutions of methyl sulfinylacetates

Product inhibition was encountered for some substrates in the resolution of methyl sulfinylacetates mediated by lipase Amano AK, so an apparatus to continually extract the carboxylate product was devised. This was applied to resolve some sulfoxides with h

A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation

A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation was established. Various primary, secondary, and tertiary alcohols were successfully converted into the corresponding su

Electrolytic Partial Fluorination of Organic Compounds. 24.1 Highly Regioselective Anodic Monofluorination of 2-Benzothiazolyl and 5-Chloro-2-benzothiazolyl Sulfides

Electrochemical fluorination of 2-benzothiazolyl and 5-chloro-2-benzothiazolyl sulfides was successfully carried out using Et4NF·3HF as a supporting electrolyte and fluoride ion source in dimethoxyethane to provide the corresponding α-monofluorinated sulfides in good yields. Fluorination took place selectively at the position α to the sulfur atom of the sulfides, and the heterocyclic moieties were not fluorinated at all.

SYNTHESIS AND TRANSFORMATIONS OF S- AND N-SUBSTITUTED 2-MERCAPTOBENZOTHIAZOLES

2-Mercaptobenzothiazole reacts with alkyl halides and hydrazine hydrate in the thiol form, and with formaldehyde in the thione form.The alkylation of 2-mercaptobenzothiazolidin-3-yl-methanol has been performed with sulfoalkyl halides and with propan-1,3-s