3-(4-Mercaptophenyl)acrylic acid

Base Information

• Chemical Name: 3-(4-Mercaptophenyl)acrylic acid
• CAS No.: 155378-75-9
• Molecular Formula: C₉H₈O₂S
• Molecular Weight: 180.227
• DSSTox Substance ID: DTXSID401268576
• Mol file: 155378-75-9.mol

Synonyms:3-(4-Mercaptophenyl)acrylic acid;4-MERCAPTOCINNAMIC ACID;28995-22-4;155378-75-9;(E)-3-(4-sulfanylphenyl)prop-2-enoic acid;(E)-3-(4-Mercaptophenyl)acrylic acid;2-Propenoic acid, 3-(4-mercaptophenyl)-, (2E)-;p-Mercapto-cinnamic Acid;3-(4-Mercaptophenyl)-2-propenoic Acid;g-mercaptocinnamic acid;SCHEMBL1055350;SCHEMBL1055352;DTXSID401268576;AKOS015911398;(2E)-3-(4-Mercaptophenyl)-2-propenoic acid;J-017349

Chemical Property of 3-(4-Mercaptophenyl)acrylic acid

Chemical Property:

• Melting Point: 217-218°C
• PSA: 76.10000
• LogP: 2.07310
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 180.02450067
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

4-MercaptocinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)S
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)S

Technology Process of 3-(4-Mercaptophenyl)acrylic acid

There total 5 articles about 3-(4-Mercaptophenyl)acrylic 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: 80.0%

4-chlorosulfonyl-cinnamic acid (17641-30-4) → C9H8O2S (28995-22-4,155378-75-9)

Guidance literature:

With triphenylphosphine; In toluene; for 0.166667h; chemoselective reaction; Inert atmosphere;

DOI:10.1055/s-0029-1216955

Reference yield: 60.0%

(2E)-3-[4-(chlorosulfonyl)phenyl]prop-2-enoic acid (155378-73-7) + ethanol (64-17-5) → 4-mercapto-trans-cinnamic acid (28995-22-4,155378-75-9)

Guidance literature:

With stannous chloride; In hydrogenchloride; sodium hydroxide; water;

Reference yield:

(2E)-3-[4-(chlorosulfonyl)phenyl]prop-2-enoic acid (155378-73-7) → 4-mercapto-trans-cinnamic acid (28995-22-4,155378-75-9)

Guidance literature:

With hydrogenchloride; stannous chloride dihydrate; acetic acid; In water; at 20 - 70 ℃; for 2h;

DOI:10.3184/030823408X347576

upstream raw materials:

(2E)-3-[4-(chlorosulfonyl)phenyl]prop-2-enoic acid

ethanol

4-chlorosulfonyl-cinnamic acid

Downstream raw materials:

4-acetylsulfanyl-trans-cinnamic acid

4.4'-Dithio-bis-trans-zimtsaeure

(E)-3-<4-(methylthio)phenyl>propenoic acid

Refernces

• 1、 Zhang, Wensheng,Kuang, Chunxiang,Yang, Qing. "One-pot synthesis of trans-4-alkylthio- And 4-arylthio-cinnamic acids from trans-4-chlorosulfonylcinnamic acid in an aqueous medium". experimental part. p. 546 - 548. Retrieved 2009/04/06.