CAS 133745-75-2 N-Fluorobenzenesulfonimide (HCID 588007)

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Basic information

CAS: 133745-75-2
Standard SMILES: O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1
InChIKey: RLKHFSNWQCZBDC-UHFFFAOYSA-N
Molecular formula: C12H10FNO4S2
Average molar mass: 315.3 g/mol
Monoisotopic mass: 315.00352831

Names & identifiers

Preferred name: N-Fluorobenzenesulfonimide
IUPAC: N-(benzenesulfonyl)-N-fluorobenzenesulfonamide
English name: N-Fluorobenzenesulfonimide
Molecular formula: C12H10FNO4S2
Molecular weight: 315.34

Names & synonyms

N-Fluorobenzenesulfonimide133745-75-2N-Fluoro-N-(phenylsulfonyl)benzenesulfonamideNFSIACCUFLUOR NFSINFBS(Phso2)2NFBENZENESULFONAMIDE, N-FLUORO-N-(PHENYLSULFONYL)-38TGL3A00IDTXSID10343177RefChem:830032DTXCID70294257

Show more names

N-FLUOROBENZENESULFONAMIDEN-FluorobenzenesulfonmideN-fluorobisbenzenesulfonamideN-(benzenesulfonyl)-S-phenylfluoranesulfonamido

431-940-3603-762-8N-Fluorodibenzenesulfonimiden-fluorobenzenesulphonimidebis(phenylsulfonyl)fluoroamineN-(benzenesulfonyl)-N-fluorobenzenesulfonamideN-Fluorobis(phenylsulfonyl)amineMFCD00144885

Database identifiers

CAS: 133745-75-2
PubChem CID: 588007
DTXSID: DTXSID10343177
ChEMBL: CHEMBL1338788
UNII: 38TGL3A00I
EC Number: 431-940-3、603-762-8
Nikkaji: J456.242I

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 88.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 6
Rotatable bonds: 4
Heavy atoms: 20
Formal charge: 0
Complexity: 461

Physicochemical properties

Melting point: 114 · 114-116 °C
Boiling point: 471.4 · 471.4±28.0 °C(Predicted)
Density: 1.4466 · 1.4466 (estimate)
Flash point: 110 ℃ · 110℃
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.
form: solid
pka: -32.45 · -32.45±0.70(Predicted)
color: white
BRN: 5348902 · 5348902
InChI: InChI=1S/C12H10FNO4S2/c13-14(19(15,16)11-7-3-1-4-8-11)20(17,18)12-9-5-2-6-10-12/h1-10H
InChIKey: RLKHFSNWQCZBDC-UHFFFAOYSA-N
SMILES: C1(S(N(F)S(C2=CC=CC=C2)(=O)=O)(=O)=O)=CC=CC=C1
CAS DataBase Reference: 133745 · 133745-75-2(CAS DataBase Reference)
FDA UNII: 38 TGL3A00I · 38TGL3A00I

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.9% (1 of 52) of reports.

Warning

H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (98.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (94.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 52 reports by companies.；There are 11 notifications provided by 51 of 52 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 23-10-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/10371

Benzenesulfonamide, N-fluoro-N-(phenylsulfonyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)

Skin Irrit. 2 (96.2%)；Eye Irrit. 2 (98.1%)；STOT SE 3 (94.2%)

Regulatory information

Regulatory Information · 2 items

Chemistry & industry

Applications · 3 items

UsesVersatile fluorinating reagent used in the fluorination of aryls, enolates, carbanions, organolithiums, etc.

UsesN-Fluorobenzenesulfonimide fluorinates aromatics, enolates, azaenolates and carbanions in high yield. It is used for diastereoselective fluorination of Li enolates of chiral carboximides, for directed fluorination of ortho-lithiated aromatics and for a review of electrophilic N-F fluorinating agents. Asymmteric fluorinations is effected in the presence of a Pd-BINAP catalyst system at room temperature in an ionic liquid. It is a reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams. It is also used in the electrophilic difluorination of dihalopyridines with butyl lithium and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.

General DescriptionN-Fluorobenzenesulfonimide (NFSi) is a commonly used electrophilic fluorinating agent in organic synthesis to introduce fluorine into neutral organic molecules. It is also used to fluorinate nucleophilic substrates such as reactive organometallic species and malonate anions.NFSi can be synthesized by the reaction of benzenesulfonimide with fluorine.