2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol

Base Information

• Chemical Name: 2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol
• CAS No.: 63676-22-2
• Molecular Formula: C14H10O2S
• Molecular Weight: 242.298
• European Community (EC) Number: 691-840-2
• UNII: 8ZK5PJ1CM3
• DSSTox Substance ID: DTXSID70332204
• Nikkaji Number: J2.310.147E
• Wikidata: Q27097953
• Pharos Ligand ID: JJQL7DALFB3A
• Metabolomics Workbench ID: 151888
• ChEMBL ID: CHEMBL431698
• Mol file: 63676-22-2.mol

Synonyms:63676-22-2;2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol;RALOXIFENE CORE;2-(4-Hydroxyphenyl)benzo[b]thiophene-6-ol;Estrogen receptor modulator 1;2-(4-hydroxyphenyl)-1-benzothiophen-6-ol;2-(4-HYDROXYPHENYL)-BENZO[B]THIOPHENE-6-OL;8ZK5PJ1CM3;CHEMBL431698;2-(4-hydroxyphenyl)-1-benzothiophene-6-ol;2-(4-Hydroxyphenyl)benzo(b)thiophene-6-ol;Benzo[b]thiophene-6-ol, 2-(4-hydroxyphenyl)-;EC 691-840-2;6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene;6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thiophene;6-HYDROXY-2-(4-HYDROXYPHENYL)-BENZO(B)THIOPHENE;benzthiophene compound, 3;UNII-8ZK5PJ1CM3;ZTW;SCHEMBL2567321;BDBM20628;DTXSID70332204;MFCD16619490;AKOS016003276;AC-8398;DB08773;AS-64856;HY-110201;2-(4-hydroxyphenyl)-6-hydroxybenzothiophene;CS-0033065;FT-0709145;H1628;F16052;2-(4-Hydroxyphenyl)-6-Hydroxybenzo[b]thiophene;Q27097953

Chemical Property of 2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol

Chemical Property:

• Vapor Pressure: 1.01E-09mmHg at 25°C
• Melting Point: 295 °C(dec.)
• Refractive Index: 1.742
• Boiling Point: 477 °C at 760 mmHg
• PKA: 9.32±0.15(Predicted)
• Flash Point: 242.3 °C
• PSA: 68.70000
• Density: 1.383 g/cm³
• LogP: 3.97950
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 242.04015073
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC3=C(S2)C=C(C=C3)O)O
• Uses: 2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol is used in the synthesis of Raloxifene (R100000) an estrogen receptor modulator.

Technology Process of 2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol

There total 8 articles about 2-(4-Hydroxyphenyl)benzo[b]thiophen-6-ol 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: 89.3%

2-(4'-methoxyphenyl)-6-methoxybenzothiophene (63675-74-1) → 6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene (63676-22-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 5 ℃;

Reference yield:

3-methoxybenzenethiol (15570-12-4) → 6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene (63676-22-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: K₂CO₃ / acetone

1.2: BF₃*Et₂O

2.1: BuLi

2.2: B(OiPr)3

2.3: HCl

3.1: Na₂CO₃; Pd(PPh₃)4

4.1: BBr₃

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; boron tribromide; sodium carbonate; potassium carbonate; In acetone; 3.1: Suzuki coupling reaction;

DOI:10.1021/jm015577l

Reference yield:

3-methoxybenzenethiol (15570-12-4) → 6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene (63676-22-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80.4 percent / KOH / ethanol; H₂O; ethyl acetate / Ambient temperature

2: 69 percent / PPA / 1 h / 85 - 90 °C

3: 71 percent / pyridine hydrochloride / 6 h / 220 °C

With potassium hydroxide; pyridine hydrochloride; In ethanol; water; ethyl acetate;

DOI:10.1021/jm00374a021

upstream raw materials:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene

6-methoxy-benzo[b]thiophene

3-methoxybenzenethiol

6-methoxy-benzo[b]thiophen-2-yl boronic acid

Downstream raw materials:

<6-(benzoyloxy)-2-<4-(benzoyloxy)phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride

6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-hexamethyleneiminoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Refernces

• 1、 -. "Phenyl benzothiophene rod-like liquid crystal compounds and preparation method thereof". Paragraph 0049-0051; 0054; 0057. . Retrieved 2020/07/02.
• 2、 -. "Polymerizable compound containing benzothiophene". Paragraph 0084; 0085; 0086; 0087; 0088. . Retrieved 2016/10/27.