2,4-Dinitrobenzenesulfenyl chloride

Base Information

• Chemical Name: 2,4-Dinitrobenzenesulfenyl chloride
• CAS No.: 528-76-7
• Molecular Formula: C6H3 Cl N2 O4 S
• Molecular Weight: 234.62
• Hs Code.: 2930909090
• European Community (EC) Number: 208-441-2
• NSC Number: 97092
• UNII: 6XLF60A5YM
• DSSTox Substance ID: DTXSID6060181
• Nikkaji Number: J150.756G
• Wikidata: Q27265679
• Mol file: 528-76-7.mol

Synonyms:2,4-dinitrobenzenesulfenyl chloride;2,4-dinitrophenylsulfenyl chloride

Chemical Property of 2,4-Dinitrobenzenesulfenyl chloride

Chemical Property:

• Vapor Pressure: 3.34E-07mmHg at 25°C
• Melting Point: 94-97 °C(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 430.1°C at 760 mmHg
• Flash Point: 213.9°C
• PSA: 116.94000
• Density: 1.68g/cm³
• LogP: 3.79530
• Storage Temp.: Store at RT.
• Solubility.: benzene: soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 233.9502054
• Heavy Atom Count: 14
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

2,4-Dinitrobenzenesulfenyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])SCl
• Uses: 2,4-Dinitrobenzenesulfenyl chloride was used in preparation of chlorine and bromine biphenyls.

Technology Process of 2,4-Dinitrobenzenesulfenyl chloride

There total 10 articles about 2,4-Dinitrobenzenesulfenyl chloride 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:

bis(2,4-dinitrophenyl) disulphide (2217-55-2) → 2,4-dinitrobenzenesulfenyl chloride (528-76-7)

Guidance literature:

With chlorine; iron; 1,2-dichloro-ethane;

DOI:10.1021/ja01160a108

Reference yield:

2,4-dinitrothiophenol (2218-96-4) → 2,4-dinitrobenzenesulfenyl chloride (528-76-7)

Guidance literature:

With tetrachloromethane; chlorine;

DOI:10.1021/ja01149a534

Reference yield:

benzyl-(2,4-dinitro-phenyl)-sulfide (7343-61-5) → 2,4-dinitrobenzenesulfenyl chloride (528-76-7)

Guidance literature:

With sulfuryl dichloride; In 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2012.11.103

upstream raw materials:

N-chloro-succinimide

2,4-dinitrothiophenol

bis(2,4-dinitrophenyl) disulphide

S-2,4-dinitrophenyl thiobenzoate

Downstream raw materials:

2,4-dinitro-benzenesulfenic acid-(2-chloro-ethyl ester)

N-(2,4-Dinitrobenzol-sulfenyl)-piperidin

2-(2,4-dinitro-phenylsulfanyl)-thiophene

4-chloro-1-(2,6-dichloro-benzyl)-5-(2,4-dinitro-phenylsulfanyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid amide

Refernces

Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin

10.1016/j.bmcl.2011.05.083

The research focuses on the efficient synthesis of 3-O-thia-cPAs (4a–d), sulfur analogues of cyclic phosphatidic acid (cPA), with the key step being an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The synthetic route allows for the production of 4a–d in just four steps from commercially available glycidol. Preliminary biological experiments were conducted to assess the inhibitory effect of 4a–d on autotaxin (ATX), an enzyme involved in controlling the concentration of lysophosphatidic acid (LPA), which affects cell proliferation and cancer cell metastasis. The study used various reactants including glycidol, thioacetic acid, methanol, 2,4-dinitrobenzenesulfenyl chloride, and phosphite, among others, to synthesize the target compounds. The chemical structures of the synthesized compounds were confirmed using NMR (1H NMR, 31P NMR, and HH-COSY) and mass spectrometry. The biological activity was evaluated through ATX inhibition assays, which showed that 3-O-thia-cPAs exhibited a similar inhibitory effect on ATX as the original cPA, with the potency order being 2-O-ccPA 3c > 3-O-thia-cPAs 4a–d > cPA 2a.