N-Phenyl-bis(trifluoromethanesulfonimide) - ≥98% , CAS No.37595-74-7

CAS: 37595-74-7 Cat. No.: P107033 Molecular Weight: 357.25 Beilstein Registry Number: 1269141 EC Number: 609-445-0

GRADE & PURITY ≥98%

Synonyms

NSC 240874 | N-Phenylbis(trifluoromethanesulfonimide) | N-Phenyl-bis(trifluoromethanesulfonimide) | N-phenyl-bis(trifluoromethane-sulfonimide) | N-phenylbis-(trifluoromethanesulfonimide) | N-phenylbis-(trifluoromethane-sulfonimide) | trifluoro-N-phenyl-N-

Storage

Room temperature

Shipped In

Normal

Overview

Mild triflating reagent. Employed recently to convert a ketone to an enol triflate with KHMDS and thence an olefin with Pd(PPh3)4 and Bu3SnH.

Specifications

Synonyms

NSC 240874 | N-Phenylbis(trifluoromethanesulfonimide) | N-Phenyl-bis(trifluoromethanesulfonimide) | N-phenyl-bis(trifluoromethane-sulfonimide) | N-phenylbis-(trifluoromethanesulfonimide) | N-phenylbis-(trifluoromethane-sulfonimide) | trifluoro-N-phenyl-N-

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504757239
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757239
• Canonical Smiles: C1=CC=C(C=C1)N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F
• IUPAC Name: 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide
• InChIKey: DIOHEXPTUTVCNX-UHFFFAOYSA-N
• INCHI: 1S/C8H5F6NO4S2/c9-7(10,11)20(16,17)15(6-4-2-1-3-5-6)21(18,19)8(12,13)14/h1-5H
• Isomeric SMILES: C1=CC=C(C=C1)N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F
• WGK Germany: 3
• Molecular Weight: 357.25
• Beilstein: 1269141
• Reaxy-Rn: 1269141
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1269141&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Sulfanilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Sulfanilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Sulfanilides
• Alternative Parents: Organosulfonic acids and derivatives Aminosulfonyl compounds Trihalomethanes Organopnictogen compounds Organonitrogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Sulfanilide - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Trihalomethane - Alkyl fluoride - Hydrocarbon derivative - Halomethane - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organosulfur compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Alkyl halide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in methanol. Slightly soluble in chloroform and ethyl acetate
• Sensitivity: Moisture sensitive.
• Melt Point(°C): 100-103°C
• Molecular Weight: 357.300 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 356.956 Da
• Monoisotopic Mass: 356.956 Da
• Topological Polar Surface Area: 88.300 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 518.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jun Xu, Chao Peng, Bolin Yao, Hua-Jian Xu, Qiang Xie.  (2022)  Direct Deoxyfluorination of Alcohols with KF as the Fluorine Source.  JOURNAL OF ORGANIC CHEMISTRY,      [PMID:35442691] [10.1021/acs.joc.2c00388]