CAS 375-72-4 Perfluoro-1-butanesulfonyl fluoride (HCID 67814)

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Basic information

CAS: 375-72-4
Standard SMILES: O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
InChIKey: LUYQYZLEHLTPBH-UHFFFAOYSA-N
Molecular formula: C4F10O2S
Average molar mass: 302.09 g/mol
Monoisotopic mass: 301.94593244

Names & identifiers

Preferred name: Perfluoro-1-butanesulfonyl fluoride
IUPAC: 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride
English name: Nonafluorobutanesulfonyl fluoride
Molecular formula: C4F10O2S
Molecular weight: 302.09

Names & synonyms

375-72-4Perfluorobutanesulfonyl fluoridePerfluoro-1-butanesulfonyl fluorideNonafluoro-1-butanesulfonyl fluorideperfluorobutane-1-sulphonyl fluoride1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro-WC4FPA9BCMDTXSID20861913n-Nonafluorobutanesulfonyl fluoride1,1,2,2,3,3,4,4,4-Nonafluoro-1-butanesulfonyl fluorideEINECS 206-792-61,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulphonyl fluoride

Show more names

PBSFFC-4Perfluoro n-butylsulfonyl fluorideNonaflylfluorideFX-450KGS/DRUM

EC 206-792-61,1,2,2,3,3,4,4,4-Nonafluorobutan-1-sulfonyl fluorideRefChem:860215DTXCID80810765Nonafluorobutanesulfonyl fluoride1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoridenonafluorobutane-1-sulfonyl fluorideMFCD00007422

Database identifiers

CAS: 375-72-4
PubChem CID: 67814

Properties

Computed structural properties

XLogP: 3.4
Topological polar surface area: 42.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 12
Rotatable bonds: 3
Heavy atoms: 17
Formal charge: 0
Complexity: 386

Experimental & physicochemical properties

PFAS · 6 items

PFAS -> Other/unspecified

PFAS -> Perfluoroalkane sulfonyl fluoride (PASF)-based substances

PFAS -> OECD Category

PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

PFAS -> Other/unspecified

PFAS

Physicochemical properties

Melting point: -110 °C · -110°C
Boiling point: 64 °C · 64 °C (lit.)
Density: 1.682 g/mL · 1.682 g/mL at 25 °C (lit.)
vapor pressure: 16.665 kPa · 16.665kPa at 20℃
refractive index: 20 · n20/D 1.3(lit.)
Flash point: 65 · 65-66°C
storage temp.: -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility: Chloroform (Sparingly), Methanol (Sparingly)
form: Liquid
color: Colorless to yellow

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 22.8% (38 of 167) of reports.

Danger

H314 (76.6%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 167 reports by companies from 14 notifications to the ECHA C&L Inventory.

Warning

Hazard information

Regulatory Information · 3 items

Chemical: 1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro-

1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 12-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10698

Other Safety InformationIMAP assessments - Perfluorobutanesulfonic acid and its direct precursors: Environment tier II assessment

Hazard Classes and Categories · 2 items

Skin Corr. 1B (76.6%)

Eye irritation - category 2A

Safety data

F: 10-21
PPE: Faceshields, Gloves, Goggles
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 2
hs_code: 29049090
risk_code

Chemistry & industry

Uses & manufacturing

U.S. Production2023: <75,000 lb

Use ClassificationPFAS (per- and polyfluoroalkyl substances) -> OECD Category

General Manufacturing Information1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro-: ACTIVE

Applications · 3 items

Description1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl fluoride (NfF) also called Nonafluorobutanesulfonyl fluoride is a versatile compound in organic synthesis. It can be used as a fluoride source for the nucleophilic introduction of fluorine, but it is also frequently applied as sulfonylation reagent generating intermediates with strong electron withdrawing perfluorinated alkyl substituents.

UsesBenzynes were generated from o-(trimethylsilyl) phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process.Nonafluorobutanesulfonyl fluoride (nonaflyl fluoride, C 4 F 9 SO 2 F, NfF) is the most widely used commercially available reagent for the synthesis of nonaflates.

UsesNonafluorobutanesulfonyl fluoride (NfF, NBSF, PBSF) can be used as a general-purpose diazotransfer reagent with high efficiency, wide substrate range, good shelf stability, relatively low cost, and easy purification. It is a favourable alternative to other commonly used diazotransfer reagents[1]. In addition, Nonafluorobutanesulfonyl fluoride was used in the formation of a new dehydrated glycosylation scheme. In contrast to the main classical glycosylation reactions, this scheme glycosylation reaction is carried out under mildly alkaline conditions. In the absence of an external acceptor, the glycosyl hemiacetal undergoes self-condensation, providing the corresponding symmetric 1,1'- disaccharide in high yield[2].