2-Hydroxy-4-(2-(tosyloxy)acetamido)benzoic acid

Base Information

• Chemical Name: 2-Hydroxy-4-(2-(tosyloxy)acetamido)benzoic acid
• CAS No.: 501919-59-1
• Molecular Formula: C16H15NO7S
• Molecular Weight: 365.364
• Hs Code.: 2924299090
• NSC Number: 74859
• UNII: JG1E8503OI
• DSSTox Substance ID: DTXSID00198234
• Nikkaji Number: J2.466.753G
• Wikidata: Q27163139
• ChEMBL ID: CHEMBL477936
• Mol file: 501919-59-1.mol

Synonyms:NSC 74859;NSC-74859;NSC74859;S3I 201;S3I-201;S3I201

Chemical Property of 2-Hydroxy-4-(2-(tosyloxy)acetamido)benzoic acid

Chemical Property:

• Boiling Point: 654.7 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 349.8 °C
• PSA: 138.38000
• Density: 1.507 g/cm³
• LogP: 2.89660
• Storage Temp.: ?20°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 365.05692299
• Heavy Atom Count: 25
• Complexity: 578

Purity/Quality:

99% ^*data from raw suppliers

NSC 74859 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC(=O)NC2=CC(=C(C=C2)C(=O)O)O
• Uses: A chemical probe inhibitor of STAT3 with an IC50 of 86 μM. S2I-201 is a small molecule inhibitor that provides a pathway to rational combination therapies for Melanoma. S3I-201 has been used as a signal transducer and activator of transcription 3 (STAT3) inhibitor: to confirm the role of STAT3 phosphorylation in interleukin (IL)-33 production in lung epithelial cells and IL-22 mRNA expression in sorted group 3 innate lymphoid cells (ILC3s) to study the cellular response of STAT3 triggered by β-hexaclorocyclohexane (β-HCH) in various cell linesto examine the influence of STAT3 in response to angiotensin II (ang II) on induction of fibrotic proteins in kidney epithelial cells

Technology Process of 2-Hydroxy-4-(2-(tosyloxy)acetamido)benzoic acid

There total 4 articles about 2-Hydroxy-4-(2-(tosyloxy)acetamido)benzoic 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: 63.0%

2-chloro-2-oxoethyl 4-methylbenzenesulfonate (54150-49-1) → 2-hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]benzoic acid (501919-59-1)

Guidance literature:

4-Aminosalicylic acid; With sodium hydroxide; In water; at 20 ℃; for 0.166667h;

2-chloro-2-oxoethyl 4-methylbenzenesulfonate; With sodium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;

Reference yield:

ethyl α-p-toluenesulfonyloxyacetate (39794-75-7) → 2-hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]benzoic acid (501919-59-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

2.1: thionyl chloride / 1.5 h / Heating / reflux

3.1: sodium hydroxide / water / 0.17 h / 20 °C

3.2: 2 h / 0 - 20 °C

With sodium hydroxide; thionyl chloride; water; In ethanol; water;

Reference yield:

2-(4-methylphenyl)sulfonyloxyacetic acid (39794-77-9) → 2-hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]benzoic acid (501919-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / 1.5 h / Heating / reflux

2.1: sodium hydroxide / water / 0.17 h / 20 °C

2.2: 2 h / 0 - 20 °C

With sodium hydroxide; thionyl chloride; In water;

upstream raw materials:

2-chloro-2-oxoethyl 4-methylbenzenesulfonate

ethyl α-p-toluenesulfonyloxyacetate

2-(4-methylphenyl)sulfonyloxyacetic acid

p-toluenesulfonyl chloride

Refernces