N-(Phenylthio)phthalimide

Base Information

• Chemical Name: N-(Phenylthio)phthalimide
• CAS No.: 14204-27-4
• Molecular Formula: C14H9 N O2 S
• Molecular Weight: 255.297
• Hs Code.: 29309090
• DSSTox Substance ID: DTXSID50408577
• Nikkaji Number: J37.057F
• Wikidata: Q82214096
• Mol file: 14204-27-4.mol

Synonyms:N-(Phenylthio)phthalimide;14204-27-4;2-(Phenylthio)isoindoline-1,3-dione;2-phenylsulfanylisoindole-1,3-dione;1H-Isoindole-1,3(2H)-dione, 2-(phenylthio)-;Oprea1_026778;Oprea1_393002;SCHEMBL809458;2-(phenylsulfanyl)-2,3-dihydro-1H-isoindole-1,3-dione;DTXSID50408577;N-(Phenylthio)phthalimide, 98%;NMHKBABHRKQHOL-UHFFFAOYSA-N;MFCD00192396;2-Phenylsulfanyl-isoindole-1,3-dione;AKOS003619181;SB64068;AS-65777;CS-0085394;A12040;J-007584

Chemical Property of N-(Phenylthio)phthalimide

Chemical Property:

• Vapor Pressure: 1.13E-07mmHg at 25°C
• Melting Point: 160-163 °C(lit.)
• Refractive Index: 1.723
• Boiling Point: 432.2°C at 760 mmHg
• PKA: -3.05±0.20(Predicted)
• Flash Point: 215.2°C
• PSA: 62.68000
• Density: 1.42g/cm³
• LogP: 2.92780
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO: soluble25mg/mL, clear, yellow
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 255.03539970
• Heavy Atom Count: 18
• Complexity: 328

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-(Phenylthio)phthalimide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SN2C(=O)C3=CC=CC=C3C2=O

Technology Process of N-(Phenylthio)phthalimide

There total 14 articles about N-(Phenylthio)phthalimide 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: 86.0%

phthalimide (136918-14-4,85-41-6) + thiophenol (108-98-5) → N-phenylthiophthalimide (14204-27-4)

Guidance literature:

phthalimide; thiophenol; With pyridine; In acetonitrile; at 20 ℃; Heating;

With bromine; In acetonitrile; at 20 ℃;

In methanol; acetonitrile; for 0.5h;

DOI:10.1039/c6cc02641a

Reference yield: 81.0%

bromobenzene (108-86-1,52753-63-6) + phthalimidesulfenyl chloride (54974-07-1) → N-phenylthiophthalimide (14204-27-4)

Guidance literature:

bromobenzene; With iodine; magnesium; lithium chloride; In tetrahydrofuran; at 55 ℃; for 2.5h; Inert atmosphere; Schlenk technique;

With zinc(II) chloride; In tetrahydrofuran; at 0 - 25 ℃; for 1h; Inert atmosphere; Schlenk technique;

phthalimidesulfenyl chloride; In tetrahydrofuran; dichloromethane; at 0 - 25 ℃; for 0.833333h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.202009699

Reference yield: 78.0%

N-chlorophthalimide (3481-09-2) + thiophenol (108-98-5) → N-phenylthiophthalimide (14204-27-4)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/d1cc05835e

upstream raw materials:

S-Phenyl benzenethiosulfonate

phenyl 4-chlorobenzenethiosulfonate

p-methoxyphenylsulfonothioic phenyl ester

phthalimide

Downstream raw materials:

1-(4-chlorophenyl)-4-(phenylthio)piperazine

1-phenylsulfanyl-4-o-tolyl-piperazine

Phenyl(phenylthio)acetaldehyd

α-(phenylthio)butanal

Refernces

• 1、 Wei, Zhaoxin,Wang, Renjie,Zhang, Yonghong,Wang, Bin,Xia, Yu,Abdukader, Ablimit,Xue, Fei,Jin, Weiwei,Liu, Chenjiang. "Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides". supporting information. p. 4728 - 4732. Retrieved 2021/09/10.
• 2、 Yang, Zhen,Guo, Yujing,Koenigs, Rene M.. "Photochemical, Metal-Free Sigmatropic Rearrangement Reactions of Sulfur Ylides". supporting information. p. 6703 - 6706. Retrieved 2019/05/10.