139175-50-1

Basic information

• Product Name: 3-(PERFLUOROOCTYL)PROPYLAMINE
• Synonyms: 1H,1H,2H,2H,3H,3H-PERFLUOROUNDECYLAMINE;4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-HEPTADECAFLUOROUNDECYLAMINE;3-(PERFLUOROOCTYL)PROPYLAMINE;3-(Perfluorooctyl)propylamine, 1H,1H,2H,2H,3H,3H-Perfluoroundecylamine
• CAS NO: 139175-50-1
• Molecular Formula: C₁₁H₈F₁₇N
• Molecular Weight: 477.16
• Mol File: 139175-50-1.mol

Chemical Properties

• Boiling Point: 205.132°C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.602 g/mL at 25 °C
• Vapor Pressure: 0.254mmHg at 25°C
• Refractive Index: n20/D 1.326
• PKA: 9.61±0.10(Predicted)
• CAS DataBase Reference: 3-(PERFLUOROOCTYL)PROPYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(PERFLUOROOCTYL)PROPYLAMINE(139175-50-1)
• EPA Substance Registry System: 3-(PERFLUOROOCTYL)PROPYLAMINE(139175-50-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-45-36/37/39
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 139175-50-1(Hazardous Substances Data)

Usage

Uses

Used in the Production of Fluorocarbon Surfactants:
3-(Perfluorooctyl)propylamine is used as a key ingredient in the production of fluorocarbon surfactants due to its low surface tension and chemical stability. These surfactants are essential in the manufacturing of coatings, polymers, and lubricants, enhancing the performance and durability of these products.
Used in Aerospace Industry:
In the aerospace industry, 3-(Perfluorooctyl)propylamine is utilized for its ability to reduce surface tension, which is crucial for the performance of aircraft components. Its resistance to harsh environmental conditions makes it a valuable ingredient in aerospace applications.
Used in Electronics Industry:
3-(Perfluorooctyl)propylamine is employed in the electronics industry to improve the performance of electronic components. Its low surface tension and chemical stability contribute to the efficiency and reliability of electronic devices.
Used in Automotive Industry:
The automotive industry also benefits from the use of 3-(Perfluorooctyl)propylamine, particularly in the development of high-performance lubricants and coatings. Its properties enhance the durability and performance of automotive components, contributing to the overall efficiency and longevity of vehicles.
However, it is important to note that due to the potential environmental and health impacts of 3-(Perfluorooctyl)propylamine, including bioaccumulation and toxicity, regulations and restrictions on its use and handling have been implemented in some regions. This highlights the need for responsible and sustainable practices in the application of this chemical compound.

InChI:InChI=1/C11H8F17N/c12-4(13,2-1-3-29)5(14,15)6(16,17)7(18,19)8(20,21)9(22,23)10(24,25)11(26,27)28/h1-3,29H2

Upstream product

• 296233-86-8 benzyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl)-amine 
• 150225-20-0 2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-iodo-undecyl)-isoindole-1,3-dione 
• 26649-26-3 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanenitrile 
• 42028-44-4 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecan-1-al 
• 1651-41-8 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecan-1-ol 
• 200112-75-0 3-(perfluorooctyl)propyl iodide 
• 150225-29-9 2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-isoindole-1,3-dione 

Downstream Products

• 1020667-97-3 4-azido-2,3,5,6-tetrafluoro-N-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadeca fluoroundecyl) benzamide 
• 1318213-27-2 C₂₉H₂₄F₁₇NO₄ 

Relevant articles and documents

Convenient syntheses and characterization of fluorophilic perfluorooctyl-propyl amines and ab initio calculations of proton affinities of related model compounds

A convenient and effective method for the preparation of perfluorooctyl-propyl amines ([Rf8(CH2)3]nNH3-n (1-3), n=1,2,3; Rf8(CH2)3NHMe (4); [Rf8(CH2)3]2NMe (5); Rf8(CH2)3NMe2 (6); Rf8=F(CF2)8) via a step by step alkylation with Rf8(CH2)3I is described. The fluorophilicity values of 1-6 were determined by GC and range from 0.79±0.07 (1) to 5.3±0.2 (3). Systematic ab initio calculations of proton affinities of model compounds (7a-j) using Hartree-Fock and density functional theory imply that the inserted trimethylene spacer unit efficiently reduces the electron-withdrawing effect of the perfluorinated segment. All structures were verified by multinuclear one- and two-dimensional NMR experiments involving both homo- (19F-19F) and hetero-nuclear (1H-13C, 1H-15N, 19F-13C) correlations based on the GMQFCOPS and inverse 1H and/or 19F detected GHSQC, GHMQC sequences with broadband adiabatic 13C-decoupling.

Improved synthesis of perfluorooctylpropyl amine

Hydrazinolysis of N-perfluorooctylpropyl phthalimide is an easy route to scale up for the title compound. Both the alkylation of potassium phthalimide with perfluorooctylpropyl iodide and the hydrogenolysis of the adduct of perfluoroctyl iodide to N-allyl-phthalimide provide this amine precursor in good yields. The latter procedure, however, has a better atom economy, since it requires only three steps from perfluorooctyl iodide.

Convenient syntheses of a family of easily recoverable fluorous primary, secondary and tertiary aliphatic amines NH(3-x[(CH2)(m)(CF2)7CF3](x) (m = 3-5; x = 1-3) - Fine tuning of basicities and fluorous phase aff

The alcohols HOCH2(CH2)(m-1)(CF2)7CF3 [m = 3-5; (CF2)7CF3 = R(f8)] are oxidized to aldehydes O=CH(CH2)(m-1)R(f8) (Dess-Martin reagent, 90-96%), which are co

Lubricants and new polyfluorinated compounds which can be used as additives

In order to improve the wear resistance properties of lubricants, at least one compound of the following formula is incorporated therein: STR1 Rf is a perfluorinated radical, a=0 to 10, b=0 or 1 (if a=o and c=1), c=1 to 4 (2 if a≠0), m=0 or 1, n=0 or 1, X