35923-79-6

Basic information

• Product Name: PENTAFLUOROPHENYL ISOTHIOCYANATE
• Synonyms: 1,2,3,4,5-Pentafluoro-6-isothiocyanatobenzene;Benzene, pentafluoroisothiocyanato-;2,3,4,5,6-PENTAFLUOROPHENYLISOTHIOCYANATE;PENTAFLUOROPHENYL ISOTHIOCYANATE;perfluorophenyl isothiocyanate;PENTAFLUOROPHENYL ISOTHIOCYANATE 98%;Pentafluorophenylisothiocyanate,96%;Pentafluorophenylisothiocyanate98%
• CAS NO: 35923-79-6
• Molecular Formula: C₇F₅NS
• Molecular Weight: 225.14
• EINECS: 252-791-9
• Product Categories: Phenyl isocyanate&Phenyl isothiocyanate
• Mol File: 35923-79-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 38-39 °C0.2 mm Hg(lit.)
• Flash Point: 109-110°C/35mm
• Appearance: /
• Density: 1.594 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.137mmHg at 25°C
• Refractive Index: n20/D 1.540
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2736207
• CAS DataBase Reference: PENTAFLUOROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROPHENYL ISOTHIOCYANATE(35923-79-6)
• EPA Substance Registry System: PENTAFLUOROPHENYL ISOTHIOCYANATE(35923-79-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 23-26-36/37-45
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 35923-79-6(Hazardous Substances Data)

Usage

Description

PENTAFLUOROPHENYL ISOTHIOCYANATE, a chemical compound with the molecular formula C7F5NS, is an aromatic isothiocyanate derivative. It is characterized by its pentafluorophenyl group, which consists of a benzene ring with five fluorine atoms, and an isothiocyanate functional group. PENTAFLUOROPHENYL ISOTHIOCYANATE is known for its reactivity and is commonly utilized in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
PENTAFLUOROPHENYL ISOTHIOCYANATE is used as a synthetic intermediate for the preparation of 5-isopropyl-3-pentafluorophenyl-2-thiohydantoin. PENTAFLUOROPHENYL ISOTHIOCYANATE serves as a key component in the development of pharmaceuticals, particularly those with potential applications in the treatment of various medical conditions.
In the synthesis of 5-isopropyl-3-pentafluorophenyl-2-thiohydantoin, PENTAFLUOROPHENYL ISOTHIOCYANATE plays a crucial role in the formation of the thiourea moiety, which is an essential structural element in many bioactive molecules. The resulting thiohydantoin derivative may exhibit valuable pharmacological properties, making it a promising candidate for further research and development in the pharmaceutical field.

InChI:InChI=1/C7F5NS/c8-2-3(9)5(11)7(13-1-14)6(12)4(2)10

Upstream product

• 64317-34-6 N-(pentafluorophenyl)carbonimidoyl dichloride 
• 463-71-8 thiophosgene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 

Downstream Products

• 1613246-80-2 1-(perfluorophenyl)-3-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea 
• 1558465-58-9 4-(2,3,4,5,6-pentafluorophenyl)-3-thiosemicarbazide 
• 1443546-89-1 4-isobutoxy-N-(pentafluorobenzyl)-8-(pentafluorophenylthioureido)-quinoline-2-carboxamide 
• 1426059-65-5 C₂₇H₁₈F₁₅N₇S₃ 
• 1353780-14-9 C₁₃H₁₅F₅N₂S 

Relevant articles and documents

Catalytic enantioselective iodoaminocyclization of hydrazones

The first catalytic enantioselective iodoaminocyclization of β,γ-unsaturated hydrazones has been developed with the help of a trans-1,2-diaminocyclohexane-derived bifunctional thiourea catalyst and allows for the direct access to δ2-pyrazolines containing a quaternary stereogenic center in high yield with good enantioselectivity (up to 95% yield and 95:5 er).

Reactions of polyfluoroaromatic imidoyl chloride derivatives with S-nucleophilic reagents

The interactions of N-pentafluorophenylcarbonimidoyl dichloride, N-pentafluorophenylbenzimidoyl chloride and N-pentafluorophenyl (C-pentafluorophenyl) imidoyl chloride with the S-nucleophilic reagents thiourea, sodium N,N-diethyldithiocarbamate, thiocarbonyl difluoride and bis(trifluoromethyl) trithiocarbonate in the presence of CsF or AgSCF3, or thiophenol and polyfluorinated thiophenols in the presence of anhydrous K2CO3, were studied. Reactions with charged S-nucleophiles and with S-nucleophiles in the presence of a base proceeded with preservation of the N=C multiple bond in the reaction products. By varying the reaction conditions in the case of N-pentafluorophenylcarbonimidoyl dichloride it was possible to substitute one or two chlorines and obtain mono- or di-thioimidates. When C6F5 or SC6F5 groups were present at the C atom of the N=C multiple bond, preferential substitution of the para-fluorine atom occurred. Semiempirical PM3 calculation data were used to explain the direction of these reactions. N-Pentafluorophenylcarbonimidoyl dichloride reacted with sodium N,N-diethyldithiocarbamate or thiourea to give pentafluorophenylisothiocyanate. Depending on the conditions of the reactions of polyfluorinated benzimidoyl chlorides with thiourea, N-pentafluorophenylthioamides and 2-aryl-4,5,6,7-tetrafluorobenzothiazoles were formed. An attempt to produce SCF3 derivatives from AgSCF3 was unsuccessful.