35897-25-7

Basic information

• Product Name: S-(2,4-DINITROPHENYL)MERCAPTURIC ACID
• Synonyms: S-(2,4-DINITROPHENYL)MERCAPTURIC ACID;N-ACETYL-S-(2,4-DINITROPHENYL)-L-CYSTEINE;NAc-DNP-Cys
• CAS NO: 35897-25-7
• Molecular Formula: C₁₁H₁₁N₃O₇S
• Molecular Weight: 329.29
• Product Categories: Glutathione S-Transferase Agents
• Mol File: 35897-25-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 619.1 °C at 760 mmHg
• Flash Point: 328.2 °C
• Appearance: Bright Yellow Solid
• Density: 1.57 g/cm³
• Vapor Pressure: 3.45E-16mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: -20°C Freezer
• Solubility: Methanol
• CAS DataBase Reference: S-(2,4-DINITROPHENYL)MERCAPTURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: S-(2,4-DINITROPHENYL)MERCAPTURIC ACID(35897-25-7)
• EPA Substance Registry System: S-(2,4-DINITROPHENYL)MERCAPTURIC ACID(35897-25-7)

Safety Data

• Hazardous Substances Data: 35897-25-7(Hazardous Substances Data)

Usage

Chemical Properties

Bright Yellow Solid

Uses

S-(2,4-Dinitrophenyl)Mercapturic Acid can be used as a marker for low levels of exposure to benzene in industry.

InChI:InChI=1/C11H11N3O7S/c1-6(15)12-8(11(16)17)5-22-10-3-2-7(13(18)19)4-9(10)14(20)21/h2-4,8H,5H2,1H3,(H,12,15)(H,16,17)/t8-/m0/s1

Upstream product

• 616-91-1 N-acetylcystein 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 24104-92-5 O,O-diethyl O-(2,4-dinitrophenyl) thiophosphate 
• 54436-53-2 O,O-diethyl (2,4-dinitrophenyl) phosphate triester 
• 52-90-4 L-Cysteine 
• 14892-14-9 (2,3,4,5,6-pentafluorophenoxy)-acetic acid 
• 610-31-1 1,2,4-trinitrobenzene 

Relevant articles and documents

Reactivity and selectivity of the reaction of: O, O -diethyl 2,4-dinitrophenyl phosphate and thionophosphate with thiols of low molecular weight

A reactivity and selectivity study of O,O-diethyl 2,4-dinitrophenyl phosphate (1) and O,O-diethyl 2,4-dinitrophenyl thionophosphate (2) with a series of thiols of low molecular weight: N-acetyl cysteine (NAC), l-cysteine (Cys), homocysteine (Hcys), glutathione (GSH), and d-penicillamine (Pen) was conducted. Results show that (i) these nucleophiles only attack at the aromatic moiety of both triester derivatives, (ii) a kinetic control product by sulfhydryl attack of thiols was observed in the reactions of both triesters with Cys and Hcys, followed by an intramolecular amine attack leading to a thermodynamic control product. The kinetic study leads to the proposal of Meisenheimer complex formation and then proton transfer to the reaction media as the mechanism of these reactions.

1,2,4-TRINITROBENZENE AS A THIOL REAGENT

The 2,4-dinitrophenylation of thiol or amino group with 1,2,4-trinitrobenzene proceeded quantitatively at pH 8.5 and 30 deg C.The rate of S-dinitrophenylation was ca. 1E4 times faster than that of N-dinitrophenylation.So this reaction can be used for both the determination of thiol even in the presence of large excess amine and the specific modification of thiol in proteins.