Chlormezanone

Base Information

• Chemical Name: Chlormezanone
• CAS No.: 80-77-3
• Deprecated CAS: 102818-65-5
• Molecular Formula: C₁₁H₁₂ClNO₃S
• Molecular Weight: 273.74
• European Community (EC) Number: 201-307-4
• NSC Number: 759569,169108
• UNII: C14WB33Y0S,GP568V9G19,4BU37OM8KL
• DSSTox Substance ID: DTXSID3022798
• Nikkaji Number: J3.854G
• Wikipedia: Chlormezanone
• Wikidata: Q5102983
• NCI Thesaurus Code: C65316
• Metabolomics Workbench ID: 145900
• ChEMBL ID: CHEMBL1200714
• Mol file: 80-77-3.mol

Synonyms:Chlormethazanone;Chlormezanone

Chemical Property of Chlormezanone

Chemical Property:

• Vapor Pressure: 1.68E-11mmHg at 25°C
• Melting Point: 114 °C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 534.5oC at 760 mmHg
• PKA: -2.37±0.40(Predicted)
• Flash Point: 277.1oC
• PSA: 62.83000
• Density: 1.391g/cm3
• LogP: 2.63420
• Storage Temp.: Store at RT
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 273.0226421
• Heavy Atom Count: 17
• Complexity: 395

Purity/Quality:

99% ^*data from raw suppliers

Chlormezanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(S(=O)(=O)CCC1=O)C2=CC=C(C=C2)Cl
• Uses: Chlormezanone improves the emotional state of the patient, relieving moderate anxiety and stress. However, it has a number of side effects, and because it does not have any advantage over other anxiolytics, it is rarely used in practice. The use of chlormezanone is associated with large increases in the risk of Stevens-Johnson syndrome or toxic epidermal necrolysis.
• Therapeutic Function: Tranquilizer

Technology Process of Chlormezanone

There total 5 articles about Chlormezanone 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: 96.0%

2-(4-chloro-2,3-dihydroxyphenyl)-3-methyl-1,3-thiazinan-4-one → chlormezanone (102818-66-6,102818-67-7,80-77-3)

Guidance literature:

With 2-methyl-2,4-pentanediol; potassium ruthenate; chloromethyl methyl ether; at 30 ℃; for 2.16667h; Temperature;

Reference yield: 68.0%

2-(4-Chlorophenyl)-3-methyl-3,4,5,6-tetrahydro-2H-1,3-thiazin-4-on (30897-26-8) → chlormezanone (102818-66-6,102818-67-7,80-77-3)

Guidance literature:

With sodium perborate; In acetic acid; at 45 - 50 ℃; for 8h;

DOI:10.1016/S0040-4020(01)81008-5

Reference yield:

(+)-2-(4-Chlorphenyl)-3-methyl-1,3-thiazinan-4-on-1,1-dioxid (102818-66-6) → chlormezanone (102818-66-6,102818-67-7,80-77-3)

Guidance literature:

With phosphate buffer; at 37 ℃; for 48h; pH=7.4; Further Variations:; pH-values; Temperatures; Kinetics;

upstream raw materials:

2-(4-Chlorophenyl)-3-methyl-3,4,5,6-tetrahydro-2H-1,3-thiazin-4-on

(+)-2-(4-Chlorphenyl)-3-methyl-1,3-thiazinan-4-on-1,1-dioxid

(-)-2-(4-Chlorphenyl)-3-methyl-1,3-thiazinan-4-on-1,1-dioxid

Downstream raw materials:

(+)-2-(4-Chlorphenyl)-3-methyl-1,3-thiazinan-4-on-1,1-dioxid

(-)-2-(4-Chlorphenyl)-3-methyl-1,3-thiazinan-4-on-1,1-dioxid

3-sulfinopropionic acid

4-chlorobenzaldehyde

Refernces

• 1、 Seeling,Oelschlaeger,Rothley. "Important pharmaceutical-chemical characteristics of the centrally acting muscle relaxant chlormezanone". . p. 293 - 296. Retrieved 2007/10/03.
• 2、 McKillop, Alexander,Kemp, Duncan. "FURTHER FUNCTIONAL GROUP OXIDATIONS USING SODIUM PERBORATE". . p. 3299 - 3306. Retrieved 2007/10/02.