2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid

Base Information

• Chemical Name: 2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid
• CAS No.: 32004-67-4
• Molecular Formula: C₂₀H₁₇FO₂S
• Molecular Weight: 340.418
• European Community (EC) Number: 250-892-2
• Nikkaji Number: J278.220K,J319.992D
• Mol file: 32004-67-4.mol

Synonyms:32004-67-4;SULINDACSULFIDE;2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid;cis-Sulindac sulfide;C20-H17-F-O2-S;SFI;MFCD00869764;J-018597;{5-Fluoro-2-methyl-1-[4-(methylsulphanyl)benzylidene]-1H-inden-3-yl}acetic acid

Chemical Property of 2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid

Chemical Property:

• Appearance/Colour: Yellow-orange solid
• Vapor Pressure: 6.6E-12mmHg at 25°C
• Melting Point: 189-191°C
• Refractive Index: 1.653
• Boiling Point: 526.3 °C at 760 mmHg
• PKA: 4.26±0.10(Predicted)
• Flash Point: 272.1 °C
• PSA: 62.60000
• Density: 1.3 g/cm³
• LogP: 5.35000
• Storage Temp.: +15C to +30C
• Solubility.: DMSO: >22 mg/mL
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 340.09332912
• Heavy Atom Count: 24
• Complexity: 546

Purity/Quality:

99.9% ^*data from raw suppliers

Sulindac Sulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-42/43-63

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C2=C(C1=CC3=CC=C(C=C3)SC)C=CC(=C2)F)CC(=O)O
• Isomeric SMILES: CC\1=C(C2=C(/C1=C/C3=CC=C(C=C3)SC)C=CC(=C2)F)CC(=O)O
• Description: Sulindac sulfide is an aryl sulfide that is a metabolite of sulindac. A non-steroidal anti-inflammatory drug, which also has anticancer activity. It has a role as a non-steroidal anti-inflammatory drug, an apoptosis inducer and an antineoplastic agent. It is an aryl sulfide, an organofluorine compound and a monocarboxylic acid. It derives from a sulindac.
• Uses: Sulindac sulfide is an active metabolite of Sulindac that inhibits for COX. Sulindac is a non-steroidal anti-inflammatory drug. Inhibits cyclooxygenase, but induces apoptosis by a cyclooxygenase-independent mechanism. Inhibition of Ras activation of Ref-1. Impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP b.

Technology Process of 2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid

There total 5 articles about 2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid 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:

4-methylthiobenzaldehyde (146857-81-0) + 5-fluoro-2-methyl-1H-indene-3-acetic acid (32004-66-3) → 5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4)

Guidance literature:

With sodium methylate; In methanol;

Reference yield:

C21H16FNO2S → 5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4)

Guidance literature:

With sodium hydroxide; In water; for 30h; Reflux;

Reference yield:

6-fluoro-2-methylindanone (37794-19-7) → 5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium acetate; sodium methylate / methanol / 26 h / Inert atmosphere; Reflux

2: methanol / 5 h / Inert atmosphere; Reflux

3: sodium hydroxide / water / 30 h / Reflux

With ammonium acetate; sodium methylate; sodium hydroxide; In methanol; water;

upstream raw materials:

4-methylthiobenzaldehyde

5-fluoro-2-methyl-1H-indene-3-acetic acid

6-fluoro-2-methylindanone

Downstream raw materials:

5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acid

Sulindac

2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid

Refernces

• 1、 -. "Method for treating patients with diabetic retinopathy by administering substituted sulfonyl indenyl acetic acids and alcohols". . . Retrieved 2008/06/13.
• 2、 -. "Method for treating patients with acne by administering a CGMP-specific PDE inhibitor". . . Retrieved 2008/06/13.