9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one

Base Information

• Chemical Name: 9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one
• CAS No.: 1622-55-5
• Molecular Formula: C13H10OS
• Molecular Weight: 214.288
• Hs Code.: 2934999090
• European Community (EC) Number: 605-282-4
• DSSTox Substance ID: DTXSID80354311
• Nikkaji Number: J1.184.495B
• Wikidata: Q82132372
• Mol file: 1622-55-5.mol

Synonyms:1622-55-5;9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one;9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)thiophen-4-one;4-Oxo-9,10-dihydro-4H-benzo(4,5)-cyclohepta-(1,2b)thiophene;4-Oxo-9,10-dihydro-4H-benzo-(4,5)-cyclohepta-(1,2b)thiophene;6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-2-one;9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one (90per cent);SCHEMBL3036634;DTXSID80354311;HMS1608A08;MFCD00808048;AKOS001484793;9,10-dihydro-1-thiabenzo[f]azulen-4-one;9,10-Dihydro-1-thia-benzo[f]azulen-4-one;9,10-dihydro-1-thia-benzo[f]azulene-4-one;CS-0447702;EU-0034727;FT-0666903;A852223;SR-01000400070;A1-00138;J-009913;J-515912;SR-01000400070-1;4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-one;9,10-Dihydro-4H-benzo[4,5]cyclohepta[b] -thiophen-4-one;9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene-4-one;9, 10-Dihydro-4H-benzo[4, 5]cyclohepta[1, 2-b]thiophen-4-one

Chemical Property of 9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one

Chemical Property:

• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.644
• Boiling Point: 371.1 °C at 760 mmHg
• Flash Point: 178.2 °C
• PSA: 45.31000
• Density: 1.262 g/cm³
• LogP: 3.07770
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 214.04523611
• Heavy Atom Count: 15
• Complexity: 263

Purity/Quality:

99.9% ^*data from raw suppliers

9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CS2)C(=O)C3=CC=CC=C31
• Uses: Intermediate in the preparation of Ketotifen.

Technology Process of 9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one

There total 10 articles about 9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-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: 60.0%

2-[2-(thienyl)ethyl] benzoic acid (1622-54-4) → 9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-4-one (1622-55-5)

Guidance literature:

With PPA; In xylene; at 120 - 130 ℃; for 2h;

DOI:10.1515/HC.2001.7.5.449

Reference yield: 33.0%

2-(2-phenylethyl)thiophene-3-carboxylic acid (125790-51-4) → 9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-4-one (1622-55-5)

Guidance literature:

With methanesulfonic acid; at 110 ℃; for 2h;

DOI:10.1002/hlca.19900730507

Reference yield:

2-Methyl-benzoic acid methyl ester (89-71-4) → 9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-4-one (1622-55-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / N-bromosuccinimide; benzoylperoxide / CCl₄ / 2 h / Heating

2: 80 percent / 5 h / 150 °C

3: 80 percent / potassium hydroxide / tetrahydrofuran / 0.25 h / 20 °C

4: 80 percent / aq. sodium hydroxide; hydrogen / Pd/C / 12 h / 100 °C / 15200 Torr

5: 60 percent / polyphosphoric acid / xylene / 2 h / 120 - 130 °C

With potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; PPA; hydrogen; dibenzoyl peroxide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; xylene; 3: Wittig-Horner reaction;

DOI:10.1515/HC.2001.7.5.449

upstream raw materials:

2-(2-phenylethyl)thiophene-3-carboxylic acid

2-[2-(thienyl)ethyl] benzoic acid

thiophene-2-carbaldehyde

methyl 2-bromomethylbenzoate

Downstream raw materials:

sulfure de pentamethylene

4-(4-tetrahydrothiopyranyl)-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophene-4-ol

4,4'-bis(tetrahydrothiopyranyl)

4-hydroxy-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophene

Refernces

• 1、 Bollinger,Cooper,Gubler,Leutwiler,Payne. "116. (Benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)acetic Acids: Novel non-ulcerogenic antiinflammatory agents". . p. 1197 - 1204. Retrieved 2007/10/02.