Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide

• CAS: 39847-39-7
• Catalog Number: ACM39847397
• Category: Main Products
• Molecular Weight: 581.2
• Molecular Formula: C₈HF₁₈NO₄S₂
• Synonyms: 1,1,2,2,3,3,4,4,4-nonafluoro-N-[(nonafluorobutyl)sulfonyl]-1-Butanesulfonamide;BIS(1,1,2,2,3,3,4,4,4-NONAFLUORO-1-BUTANESULFONYL)IMIDE;Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butaneulfonyl)imide
• IUPAC Name: 1,1,2,2,3,3,4,4,4-nonafluoro-N-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane-1-sulfonamide
• Canonical SMILES: C(C(C(F)(F)S(=O)(=O)NS(=O)(=O)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)(F)F
• InChI Key: KZJUHXVCAHXJLR-UHFFFAOYSA-N
• EC Number: 609-746-7
• Exact Mass: 580.90600

Case Study

Nf2NH-Catalyzed Polyester Synthesis via Sublimatable Brønsted Acid Catalysis

Moyori, Takaya, et al. Biomacromolecules 13.5 (2012): 1240-1243.

Industrial polyester synthesis faces limitations in residual metal contamination (critical for electronics/biomedical applications) and energy-intensive reaction conditions. This study evaluated bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide (Nf2NH) as an organic Brønsted acid catalyst for low-temperature dehydration polycondensation of dicarboxylic acids and diols, enabling metal-free polyester synthesis with catalyst recovery via sublimation.
Polycondensation Approach:
Polycondensation reactions were conducted under mild conditions (60-80°C, 0.3-3 mmHg pressure). Nf2NH (0.1 mol%) catalyzed reactions of diols (e.g., 3-methylpentanediol) and dicarboxylic acids (e.g., adipic acid). Catalytic performance was compared with trifluoromethanesulfonylimide (Tf2NH), nonafluorobutanesulfonic acid (NfOH), and triflic acid (TfOH). Polyesters were purified by reprecipitation (chloroform/hexane), and catalyst recovery was achieved via sublimation during reactions.
Key Findings:
· Superior Catalytic Activity: Nf2NH outperformed all reference catalysts (including Tf2NH and p-toluenesulfonic acid) at 60°C, synthesizing aliphatic polyesters with Mn > 19,000 and aromatic polyesters with Mn > 7,000.
· Sublimation-Driven Recovery: Nf2NH sublimated from reaction mixtures during polycondensation, yielding extra-pure catalyst suitable for immediate reuse without activity loss (>99% reaction yield after purification).

Bis(1,1,2,2,3,3,4,4,4-Nonafluoro-1-Butanesulfonyl)Imide Used in Aerobic Olefin Reduction

Arakawa, Yukihiro, et al. SynOpen 1.01 (2017): 0011-0014.

Aerobic olefin reduction requires efficient catalysts to achieve high yields and chemoselectivity under mild conditions. This study reported bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide [(C4F9SO2)2NH] as an ultra-strong Brønsted acid catalyst (pKa = 0.0 in CH3CN) for the aerobic reduction of olefins using hydrazine-generated diimide, benchmarking its efficacy against commercial acids (TsOH·H2O, MsOH, DPP, AcOH).
Experimental Approach:
Catalytic activity was tested in the reduction of 4-phenyl-1-butene (1a) to butylbenzene (2a) under 1 atm O2 at 35°C in acetonitrile. Reactions used 5 mol% catalyst, 2 equivalents hydrazine monohydrate, and were monitored by GC for 60 minutes. Kinetic performance was quantified via k_obs/k₀ ratios (observed rate with catalyst vs. uncatalyzed control).
Key Findings:
· (C4F9SO2)2NH achieved near-quantitative yield (≈99%) of 2a within 60 minutes, matching the performance of TsOH·H2O and surpassing weaker acids (DPP: 50%; AcOH: 17%; uncatalyzed: 5%).
· (C4F9SO2)2NH exhibited the highest reaction acceleration among tested catalysts, with k_obs/k₀ = 215 (vs. TsOH·H2O: 185; DPP: 70; AcOH: 20; MsOH: 4).
· Its ultra-low pKa enabled superior catalytic behavior over weaker acids. However, the kinetic improvement over TsOH·H2O (pKa = 8.6) was less pronounced than expected from the pKa difference.

Custom Q&A

What is the molecular formula of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The molecular formula is (C4F9SO2)2NHC8HF18NO4S2.

What are the synonyms of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The synonyms are 39847-39-7, BIS(1,1,2,2,3,3,4,4,4-NONAFLUORO-1-BUTANESULFONYL)IMIDE, 1,1,2,2,3,3,4,4,4-nonafluoro-N-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane-1-sulfonamide, SCHEMBL899196, Bis(perfluorobutanesulfonyl)imide.

What is the molecular weight of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The molecular weight is 581.2 g/mol.

When was Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide created?

It was created on October 25, 2006.

When was Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The IUPAC name is 1,1,2,2,3,3,4,4,4-nonafluoro-N-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane-1-sulfonamide.

What is the InChI of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The InChI is InChI=1S/C8HF18NO4S2/c9-1(10,5(17,18)19)3(13,14)7(23,24)32(28,29)27-33(30,31)8(25,26)4(15,16)2(11,12)6(20,21)22/h27H.

What is the InChIKey of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The InChIKey is KZJUHXVCAHXJLR-UHFFFAOYSA-N.

What is the Canonical SMILES of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The Canonical SMILES is C(C(C(F)(F)S(=O)(=O)NS(=O)(=O)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)(F)F.

What is the CAS number of Bis(1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonyl)imide?

The CAS number is 39847-39-7.