5-Chloro-2-mercaptobenzothiazole

Base Information

• Chemical Name: 5-Chloro-2-mercaptobenzothiazole
• CAS No.: 5331-91-9
• Molecular Formula: C7H4ClNS2
• Molecular Weight: 201.7
• Hs Code.: 29342000
• European Community (EC) Number: 226-235-0
• NSC Number: 3934
• UNII: R9099U429R
• DSSTox Substance ID: DTXSID0022224
• Nikkaji Number: J20.788H
• Wikidata: Q27287987
• ChEMBL ID: CHEMBL1456330
• Mol file: 5331-91-9.mol

Synonyms:5-chloro-2-mercaptobenzothiazole

Chemical Property of 5-Chloro-2-mercaptobenzothiazole

Chemical Property:

• Appearance/Colour: Light yellow to yellow-green granular powder
• Vapor Pressure: 0.000138mmHg at 25°C
• Melting Point: 198-200 °C(lit.)
• Refractive Index: 1.785
• Boiling Point: 333.2 °C at 760 mmHg
• PKA: 8.88±0.20(Predicted)
• Flash Point: 155.3 °C
• PSA: 79.93000
• Density: 1.6 g/cm³
• LogP: 3.23840
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 200.9473692
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-2-mercaptobenzothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-37/38-36
• Safety Statements: 26-37-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)NC(=S)S2
• Uses: 5-Chloro-2-mercaptobenzothiazole (CMBZT) has been used in the analysis of lipopolysaccharide by negative-ion matrix-assisted laser desorption ionization-time of flight mass spectrometry. It has been used in the synthesis of the new mixed ligand silver(I) chloride complex with the heterocyclic thioamide CMBZT and tri(p-tolyl)phosphine. Found to be more sensitive than DHB for analysis of high mannose N-linked glycans. Used in analysis of peptidoglycan muropeptides.

Technology Process of 5-Chloro-2-mercaptobenzothiazole

There total 17 articles about 5-Chloro-2-mercaptobenzothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

carbon disulfide (75-15-0,12122-00-8) + 4-chloro-2-aminobenzenethiol (1004-00-8) → 5-chloro-2-mercaptobenzothiazole (5331-91-9)

Guidance literature:

With potassium hydroxide; In ethanol; water; Reflux;

Reference yield: 97.0%

2,5 dichloroaniline (95-82-9) + potassium ethyl xanthogenate (140-89-6) → 5-chloro-2-mercaptobenzothiazole (5331-91-9)

Guidance literature:

In dimethyl sulfoxide; at 160 ℃;

DOI:10.1021/acsinfecdis.0c00700

Reference yield: 95.0%

4-chloro-2-aminobenzenethiol (1004-00-8) + sodium dimethyldithiocarbamate (128-04-1) → 5-chloro-2-mercaptobenzothiazole (5331-91-9)

Guidance literature:

With aluminum (III) chloride; In water; N,N-dimethyl-formamide; at 120 ℃;

DOI:10.1002/ejoc.201800993

upstream raw materials:

2,5-dichloronitrobenzene

2,5 dichloroaniline

potassium ethyl xanthogenate

phenyl isothiocyanate

Downstream raw materials:

3-[(5-chloro-2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoic acid methyl ester

3-[(5-chloro-2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoic acid ethyl ester

5-chloro-3-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-3H-benzothiazole-2-thione

5-chloro-3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-3H-benzothiazole-2-thione

Refernces

• 1、 Li, Wei-wei,Zheng, Hui. "A Highly Efficient Synthesis of 2-Benzimidazolthiones and Their Congeners under Mild Conditions". . p. 175 - 181. Retrieved 2019/04/17.
• 2、 Tung, Truong-Thanh,Dao, Trong T.,Junyent, Marta G.,Palmgren, Michael,Günther-Pomorski, Thomas,Fuglsang, Anja T.,Christensen, S?ren B.,Nielsen, John. "LEGO-Inspired Drug Design: Unveiling a Class of Benzo[d]thiazoles Containing a 3,4-Dihydroxyphenyl Moiety as Plasma Membrane H+-ATPase Inhibitors". . p. 37 - 47. Retrieved 2018/01/12.