24933-57-1

Basic information

• Product Name: 4-(DIFLUOROMETHYLTHIO)NITROBENZENE
• Synonyms: 4-(DIFLUOROMETHYLTHIO)NITROBENZENE;(difluoromethyl)(4-nitrophenyl)sulfane;(difluoromethyl)(4-nitrophenyl)sulfane(WXC06666)
• CAS NO: 24933-57-1
• Molecular Formula: C₇H₅F₂NO₂S
• Molecular Weight: 205.18
• Mol File: 24933-57-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 40 °C
• Boiling Point: 252.1°C at 760 mmHg
• Flash Point: 106.3°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.0314mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 4-(DIFLUOROMETHYLTHIO)NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIFLUOROMETHYLTHIO)NITROBENZENE(24933-57-1)
• EPA Substance Registry System: 4-(DIFLUOROMETHYLTHIO)NITROBENZENE(24933-57-1)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 24933-57-1(Hazardous Substances Data)

Usage

General Description

4-(Difluoromethylthio)nitrobenzene is a chemical compound often used in organic and chemical synthesis. Its primary elements include carbon, hydrogen, nitrogen, sulfur, oxygen and fluorine with a molecular weight of about 215.14. 4-(DIFLUOROMETHYLTHIO)NITROBENZENE typically appears as a colorless to light yellow liquid. It has a specific melting point, boiling point and flash point and is typically stored in cool, ventilated areas. Like many other chemicals, it requires careful handling as it may trigger eye, skin, or respiratory irritation, and is harmful if inhaled, ingested, or in contact with skin. Its CAS number is 32907-41-4. It doesn't have known uses in everyday products and is predominantly utilized in laboratory settings and for research purposes.

InChI:InChI=1/C7H5F2NO2S/c8-7(9)13-6-3-1-5(2-4-6)10(11)12/h1-4,7H

Upstream product

• 353-59-3 halon-1211 
• 1849-36-1 para-nitrobenzenethiol 
• 75-61-6 dibromodifluoromethane 
• 75-45-6 Chlorodifluoromethane 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 1097192-99-8 N-toluylsulfonyl S-difluoromethyl S-phenyl sulfoximine 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 115262-01-6 [bromo(difluoro)methyl]-trimethyl-silane 
• 2137-92-0 4-nitrophenyl thiocyanate 
• 65864-64-4 trimethyl(difluoromethyl)silane 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 100-01-6 4-nitro-aniline 
• 24067-17-2 4-nitrophenylboronic acid 
• 100-32-3 di(p-nitrophenyl) disulfide 

Downstream Products

• 55384-52-6 5-difluoromethylsulfanyl-3-phenyl-benzo[c]isoxazole 
• 24933-60-6 4-difluoromethylsulfanylaniline 
• 24933-67-3 1-((difluoromethyl)sulfinyl)-4-nitrobenzene 
• 24906-74-9 1-((difluoromethyl)sulfonyl)-4-nitrobenzene 
• 24906-81-8 Difluormethyl-<4-hydroxy-phenyl>-sulfon 
• 24906-88-5 (4-Amino-phenyl)-difluormethyl-sulfoxid 
• 24906-77-2 4-((difluoromethyl)sulfonyl)aniline 
• 55384-49-1 2-Amino-5-difluoromethylthiobenzophenone 

Relevant articles and documents

Difluoromethylation of Phenols and Thiophenols with the S-(Difluo-romethyl)sulfonium Salt: Reaction, Scope, and Mechanistic Study

A facile and practical approach for the difluoromethylation of phenols and thiophenols was described. Making use of the recently developed bench-stable S-(difluoromethyl)sulfonium salt as the difluorocarbene precursor, a wide variety of diversely functionalized phenols and thiophenols were readily converted to their corresponding aryl difluoromethyl ethers in good to excellent yields in the presence of lithium hydroxide. Chemoselectivity of various O,S-nucleophiles toward difluorocarbene was systematically studied, suggesting the reactivity order ArS- > RS-, ArO- > ROH > RO-, ArSH, ArOH, RSH.

Difluoromethyl bioisostere: Examining the lipophilic hydrogen bond donor concept

There is a growing interest in organic compounds containing the difluoromethyl group, as it is considered a lipophilic hydrogen bond donor that may act as a bioisostere of hydroxyl, thiol, or amine groups. A series of difluoromethyl anisoles and thioanisoles was prepared and their druglike properties, hydrogen bonding, and lipophilicity were studied. The hydrogen bond acidity parameters A (0.085-0.126) were determined using Abraham's solute 1H NMR analysis. It was found that the difluoromethyl group acts as a hydrogen bond donor on a scale similar to that of thiophenol, aniline, and amine groups but not as that of hydroxyl. Although difluoromethyl is considered a lipophilicity enhancing group, the range of the experimental Δlog P(water-octanol) values (log P(XCF2H) - log P(XCH3)) spanned from -0.1 to +0.4. For both parameters, a linear correlation was found between the measured values and Hammett σ constants. These results may aid in the rational design of drugs containing the difluoromethyl moiety.

PhSO2SCF2H: A Shelf-Stable, Easily Scalable Reagent for Radical Difluoromethylthiolation

A new shelf-stable and easily scalable difluoromethylthiolating reagent S-(difluoromethyl) benzenesulfonothioate (PhSO2SCF2H) was developed. PhSO2SCF2H is a powerful reagent for radical difluoromethylthiolation of aryl and alkyl boronic acids, decarboxylative difluoromethylthiolation of aliphatic acids, and a phenylsulfonyl-difluoromethylthio difunctionalization of alkenes under mild reaction conditions.