8-chlorodibenzo[b,f]thiepin-10(11H)-one

Base Information

• Chemical Name: 8-chlorodibenzo[b,f]thiepin-10(11H)-one
• CAS No.: 1469-28-9
• Molecular Formula: C14H9ClOS
• Molecular Weight: 260.744
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60356611
• Nikkaji Number: J40.687B
• Wikidata: Q72518446
• ChEMBL ID: CHEMBL1550431
• Mol file: 1469-28-9.mol

Synonyms:8-chlorodibenzo[b,f]thiepin-10(11H)-one;1469-28-9;3-chloro-6H-benzo[b][1]benzothiepin-5-one;Dibenzo[b,f]thiepin-10(11H)-one, 8-chloro-;6-Chloro-2-thiatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-9-one;MLS000543621;SCHEMBL5362218;CHEMBL1550431;DTXSID60356611;RFEQOXYRLRIDPF-UHFFFAOYSA-N;HMS2291P05;BAA46928;MFCD01411917;AKOS022172208;BS-49865;SMR000162794;CS-0217307;E77944;EN300-7353427;A854876;AE-641/30101063;2-Chloro-dibenzo[b,f][1,4]thiepin-11(10H)-one;8-chloro-10,11-dihydro-5H-dibenzo[b,f]thiepin-10-one;Z3061307163

Chemical Property of 8-chlorodibenzo[b,f]thiepin-10(11H)-one

Chemical Property:

• Melting Point: 125-126℃ (ethanol )
• Boiling Point: 425.8 °C at 760 mmHg
• Flash Point: 211.3 °C
• PSA: 42.37000
• Density: 1.359 g/cm³
• LogP: 4.23000
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 260.0062638
• Heavy Atom Count: 17
• Complexity: 307

Purity/Quality:

98% ^*data from raw suppliers

8-Chlorodibenzo[b,f]thiepin-10(11H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2SC3=C(C1=O)C=C(C=C3)Cl
• Uses: 8-Chlorodibenzo[b,f]thiepin-10(11H)-one is an intermediate in the synthesis of Zotepine-d6, which is the labeled analogue of Zotepine (Z700900), an atypical antipsychotic drug used for the treatment of acute and chronic schizophrenia, and acute bipolar mania. It acts as antagonist at dopamine and serotonin receptors. It has a high affinity for the D1 and D2 receptors.

Technology Process of 8-chlorodibenzo[b,f]thiepin-10(11H)-one

There total 4 articles about 8-chlorodibenzo[b,f]thiepin-10(11H)-one 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: 73.0%

2-[2-(4-chlorophenyl)sulfanylphenyl]acetic acid (13459-62-6) → 3-chloro-6H-benzo[b][1]benzothiepin-5-one (1469-28-9)

Guidance literature:

With polyphosphoric acid; at 135 - 140 ℃; for 2h;

DOI:10.1021/jm100652h

Reference yield:

o-iodophenylacetic acid (18698-96-9) → 3-chloro-6H-benzo[b][1]benzothiepin-5-one (1469-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide; copper / water / 24 h / 50 °C / Reflux

2: phosphorus pentoxide / 4 h / 150 °C

With phosphorus pentoxide; copper; potassium hydroxide; In water;

DOI:10.1016/j.ejmech.2016.04.058

Reference yield:

p-Chlorothiophenol (106-54-7) → 3-chloro-6H-benzo[b][1]benzothiepin-5-one (1469-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide; copper / water / 24 h / 50 °C / Reflux

2: phosphorus pentoxide / 4 h / 150 °C

With phosphorus pentoxide; copper; potassium hydroxide; In water;

DOI:10.1016/j.ejmech.2016.04.058

upstream raw materials:

2-[2-(4-chlorophenyl)sulfanylphenyl]acetic acid

o-iodophenylacetic acid

p-Chlorothiophenol

Downstream raw materials:

2-chloro-10,11-dihydrodibenzothiepin-10,11-dione

octoclothepin

4-Chlordiphenylsulfoxid-2,2'-dicarboxylic acid

Refernces

• 1、 Boudhar, Aicha,Ng, Xiao Wei,Loh, Chiew Yee,Chia, Wan Ni,Tan, Zhi Ming,Nosten, Francois,Dymock, Brian W.,Tan, Kevin S.W.. "Overcoming chloroquine resistance in malaria: Design, synthesis and structure-activity relationships of novel chemoreversal agents". . p. 231 - 249. Retrieved 2016/05/24.
• 2、 Ueda,Sato,Maeno,Umio. "Synthesis and pharmacological properties of 8-chloro-10-(2-dimethylamino-ethoxy)dibenzo[b,f]thiepin and related compounds. Neurotropic and psychotropic agents. III". . p. 3058 - 3070. Retrieved 2007/10/05.