2-Phenylethynesulfonamide

Base Information

• Chemical Name: 2-Phenylethynesulfonamide
• CAS No.: 64984-31-2
• Molecular Formula: C8H7NO2S
• Molecular Weight: 181.215
• Hs Code.: 2935009090
• European Community (EC) Number: 636-240-3
• NSC Number: 303580
• DSSTox Substance ID: DTXSID40316450
• Nikkaji Number: J2.619.793G
• Wikidata: Q27165400
• ChEMBL ID: CHEMBL1241268
• Mol file: 64984-31-2.mol

Synonyms:2-phenylacetylenesulfonamide;2-phenylethynesulfonamide;PES derivative PESA;PFT-mu;PFTmu;pifithrin mu;pifithrin-mu

Chemical Property of 2-Phenylethynesulfonamide

Chemical Property:

• Vapor Pressure: 4.03E-05mmHg at 25°C
• Melting Point: 135.0 to 139.0 °C
• Refractive Index: 1.633
• Boiling Point: 351.7 °C at 760 mmHg
• PKA: 7.96±0.60(Predicted)
• Flash Point: 166.5 °C
• PSA: 68.54000
• Density: 1.39 g/cm³
• LogP: 2.06520
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble >10mg/mL, clear
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 181.01974964
• Heavy Atom Count: 12
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

Phenylethynsulfonic Acid Amide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CS(=O)(=O)N
• Description: In addition to its transactivational functions, p53 mediates apoptosis by binding with the anti-apoptotic proteins Bcl-xL and Bcl-2 at the mitochondrial surface. Pifithrin-μ (PFT-μ) is an inhibitor of p53-mediated apoptosis, preventing p53 binding to Bcl-xL and Bcl-2 at the mitochondria without affecting p53 transactivational activities In vitro, PFT-μ binds both p53 (Kd = 0.82 mM) and Bcl-xL (Kd = 0.80 mM). PFT-μ reduces p53-mediated apoptosis induced by γ-radiation in mouse thymocytes in vitro and protects mice from doses of radiation that cause lethal hematopoietic syndrome. At 25 μM, PFT-μ reduces apoptosis triggered by nutlin-3, which inhibits MDM2/p53 binding and potentiates p53-mediated growth arrest and apoptosis. PFT-μ also interacts selectively with heat shock protein 70 (Hsp70), leading to disruption of the association between Hsp70 and many of its co-chaperones and substrate proteins.
• Uses: A small molecule inhibitor of p53 binding to mitochondria protects mice from gamma radiation Pifithrin-μ has been used:to treat microglial cell line to analyse its neuroprotective effect on M1-like and M2-like phenotypeas heat shock protein (HSP)-70 inhibitor, to treat transfected Marc-145 cellsto inhibit heat shock cognate 70 (Hsc70) to elucidate heat shock chaperones mouse embryonic stem cells

Technology Process of 2-Phenylethynesulfonamide

There total 3 articles about 2-Phenylethynesulfonamide 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: 68.0%

phenylacetylene (536-74-3) → 2-phenylethynesulfonamide (64984-31-2)

Guidance literature:

phenylacetylene; With lithium hexamethyldisilazane; In tetrahydrofuran; acetone; at -78 ℃; for 0.166667h; Cooling with liquid nitrogen;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; acetone; for 0.166667h;

With sulphamoyl chloride; In tetrahydrofuran; acetone; at -78 ℃; for 1h;

DOI:10.3390/molecules21070949

Reference yield:

(Z)-2-chloro-2-phenyl-ethenesulfonic acid amide (64984-30-1) → 2-phenylethynesulfonamide (64984-31-2)

Guidance literature:

With sodium hydroxide;

DOI:10.1246/bcsj.50.2346

Reference yield:

α-acetophenonesulfonic acid sodium salt (63738-92-1) → 2-phenylethynesulfonamide (64984-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) PCl₅, (ii) aq. NH₃

2: aq. NaOH

With sodium hydroxide;

DOI:10.1246/bcsj.50.2346

upstream raw materials:

(Z)-2-chloro-2-phenyl-ethenesulfonic acid amide

α-acetophenonesulfonic acid sodium salt

phenylacetylene

Downstream raw materials:

(4,4-dioxo-6-phenyl-4H-4λ⁶-[1,4,3]oxathiazin-2-yl)-phenyl-amine

(4,4-dioxo-6-phenyl-4H-4λ⁶-[1,4,3]oxathiazin-2-yl)-phenyl-amine

(1,1-dioxo-5-phenyl-1H-1λ⁶-[1,4,2]dithiazin-3-yl)-ethyl-amine

(1,1-dioxo-5-phenyl-1H-1λ⁶-[1,4,2]dithiazin-3-yl)-methyl-amine

Refernces

• 1、 -. "Near-infrared multifunctional photo-thermal agent as well as preparation method and application thereof". Paragraph 0024; 0029; 0031; 0036. . Retrieved 2021/09/22.