307-30-2

Basic information

• Product Name: 1H,1H-PENTADECAFLUORO-1-OCTANOL
• Synonyms: 1H,1H-Perfluorooctan-1-ol98%;1-H,1-H-PENTADECAFLUORO-N-OCTANOL;1H,1H-Perfluoro-1-octanol,98%;1H,1H-Perfluoro-1-octanol, 98% 5GR;(Perfluorohept-1-yl)methanol, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctan-1-ol;1H,1H-Pentadecafluorooctan-1-ol 98%;(Perfluoroheptyl)carbinol;1H,1H-Pentadecafluorooctan-1-ol98%
• CAS NO: 307-30-2
• Molecular Formula: C₈H₃F₁₅O
• Molecular Weight: 400.08
• EINECS: 206-197-1
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry;Fluorous Synthesis;Rf-Tagged Building Blocks and Precursors;Specialty Synthesis
• Mol File: 307-30-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 44-47 °C(lit.)
• Boiling Point: 163-165 °C(lit.)
• Flash Point: >110°C
• Appearance: White/Crystalline Mass
• Density: 1,338 g/cm3
• Vapor Pressure: 0.681mmHg at 25°C
• Refractive Index: 1.3084
• Solubility: almost transparency in Methanol
• PKA: 12.86±0.10(Predicted)
• BRN: 1716494
• CAS DataBase Reference: 1H,1H-PENTADECAFLUORO-1-OCTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H-PENTADECAFLUORO-1-OCTANOL(307-30-2)
• EPA Substance Registry System: 1H,1H-PENTADECAFLUORO-1-OCTANOL(307-30-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 307-30-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline mass

InChI:InChI=1/C8H3F15O/c9-2(10,1-24)3(11,12)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)23/h24H,1H2

Synthetic route

isopropyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate (106608-82-6) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With RuCl2(DPPEA)(±DAIPEN); hydrogen; sodium methylate In isopropyl alcohol; benzene at 100℃; under 750.075 - 45004.5 Torr; for 40h; Autoclave;	95%

Perfluorooctanoic acid (335-67-1) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With diethyl ether; pyrographite; ruthenium at 175℃; under 257428 Torr; Hydrogenation;
Multi-step reaction with 2 steps 1: 90 percent / thionyl chloride, N,N-dimethylformamide / 4 h / Heating 2: 77 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether; toluene / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: chloroform 2: lithium alanate; diethyl ether View Scheme

pentadecafluorooctanoyl chloride (335-64-8) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether; toluene for 0.5h; Heating;	77%
With lithium aluminium tetrahydride; diethyl ether

Perfluorooctanoic acid (335-67-1) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol-d2 + 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With formic acid; water-d2; ruthenium trichloride; triphenylphosphine at 200℃; for 8h;
With hydrogen; water-d2; 5 wt% Ru/C at 160℃; under 44134.3 Torr; for 8h;

ethyl perfluorooctanoate (3108-24-5) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With lithium aluminium tetrahydride

methyl perfluorooctanoate (376-27-2) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With lithium aluminium tetrahydride

pentadecafluoro-octanoic acid butyl ester (307-96-0) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + 2-bromoisobutyric acid bromide (20769-85-1) → 2-bromo-2-methylbutyrylic acid-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl) ester

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃;	97%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + 1-Hexadecanol (36653-82-4) → 1-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-octyloxy)-hexadecane

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 65℃; for 2h;	96%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + 3-chloroprop-1-ene (107-05-1) → 8-(allyloxyl)-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluorooctane (812-72-6)

Conditions	Yield
With sodium hydroxide; tetramethylammonium hydrogen sulfate at 40℃; for 12h;	96%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + Nonafluorobutanesulfonyl fluoride (375-72-4) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyl nonafluorobutanesulfonate (187039-77-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	96%
With triethylamine In diethyl ether	95%
With triethylamine In diethyl ether at 0 - 20℃; for 24h;	95%
With triethylamine In dichloromethane at -15℃;	49%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + bromoacetic acid (79-08-3) → 1H,1H-perfluorooctyloxyacetic acid (287411-18-1)

Conditions	Yield
Stage #1: 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol With sodium hydride In tetrahydrofuran at 20℃; for 1.5h; deprotonation; Stage #2: bromoacetic acid In tetrahydrofuran at 20℃; for 24h; Alkylation;	96%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + Farnesol (106-28-5) → (2E,6E)-3,7,11-Trimethyl-1-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-octyloxy)-dodeca-2,6,10-triene

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene for 2h; Ambient temperature;	95%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + trifluoromethylsulfonic anhydride (358-23-6) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-n-octyl trifluoromethanesulfonate (17352-09-9)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	91.5%
With triethylamine In diethyl ether at -50 - 0℃; for 0.333333h;
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With pyridine In dichloromethane

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + trifluoromethane sulfonyl chloride (421-83-0) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-n-octyl trifluoromethanesulfonate (17352-09-9)

Conditions	Yield
With triethylamine In dichloromethane for 6h; Ambient temperature;	90%
With triethylamine In dichloromethane for 1h; Ambient temperature;	85%
With triethylamine In dichloromethane

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + Hexamethylphosphorous triamide (1608-26-0) → hexafluorophosphate de 1H,1H-perfluoro-octyloxy(trisdimethylamino) phosphonium

Conditions	Yield
With potassium hexafluorophosphate; tetrachloromethane In tetrahydrofuran at -30℃; for 0.5h;	90%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + <(4-nitrophenyl)oxy>sulfonyl isocyanate (73748-48-8) → Perfluoroheptylmethyl-N-(4-nitrophenoxysulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	90%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + 4-Vinylbenzyl chloride (1592-20-7) → 4-vinylbenzyl(1H,1H-pentadecafluorooctyl)ether

Conditions	Yield
With sodium hydroxide; tert-butyl alcohol at 65 - 70℃; for 7h;	90%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + isocyanate de chloro-4 phenoxysulfonyle (14793-41-0) → Perfluoroheptylmethyl-N-(4-chlorosulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	89%

para-dinitrobenzene (100-25-4) + 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) → 4-nitro-1-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyloxy)benzene (142706-75-0)

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 2h;	89%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + Thioctic acid (1077-28-7, 62-46-4) → C16H15F15O2S2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice;	88%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → Trimethyl-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-octyloxy)-silane

Conditions	Yield
With saccharin sodium salt at 80 - 90℃; for 2h;	87.5%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + isocyanatosulfuric acid 2,6-dimethyl-phenyl ester (14754-44-0) → Perfluoroheptylmethyl-N-(2,6-dimethylphenoxysulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.416667h; Addition;	87%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + tetrakis(pentafluorophenyl)porphyrin (25440-14-6) → 5,10,15,20-tetrakis[2,3,5,6-tetrafluoro-4-(1H,1H-perfluorooctyloxy)phenyl]porphyrin

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; regioselective reaction;	87%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + malonoyl dichloride (1663-67-8) → bis (1.1-dihydroperfluorooctyl) malonate (24120-25-0)

Conditions	Yield
In toluene	86.5%
In toluene	86.5%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) → Fluorosulfuric acid pentadecafluoroheptyl ester (75668-23-4)

Conditions	Yield
With potassium fluorosulfonate; fluorosulphonic acid at 25℃; anodic oxidation; 6.5 F/mol;	85%

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + propargyl bromide (106-96-7) → 3-((1-perfluoroheptyl)methoxy)prop-1-yne (1334419-25-8)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; Cooling with ice;	85%
With sodium hydroxide In tetrahydrofuran at 20℃;

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (307-30-2) + p-toluenesulfonyl chloride (98-59-9) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octyl 4-toluenesulfonate (24962-65-0)

Conditions	Yield
With potassium hydroxide In diethyl ether at -4℃; for 24h;	85%
With triethylamine In dichloromethane at 0 - 20℃;	77%

Upstream product

• 335-64-8 pentadecafluorooctanoyl chloride 
• 335-67-1 Perfluorooctanoic acid 
• 307-96-0 pentadecafluoro-octanoic acid butyl ester 
• 376-27-2 methyl perfluorooctanoate 
• 106608-82-6 isopropyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate 
• 3108-24-5 ethyl perfluorooctanoate 

Downstream Products

• 307-98-2 1H,1H-perfluoro-n-octyl acrylate 
• 812-72-6 1H,1H-pentadecafluorooctyl allyl ether 
• 3934-23-4 1,1-dihydroperfluorooctyl methacrylate 
• 17352-09-9 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-n-octyl trifluoromethanesulfonate 
• 142706-75-0 4-nitro-1-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyloxy)benzene 
• 137677-91-9 4-trifluoromethyl-2,6-diaminophenyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl ether 
• 23588-89-8 triethylamine hydrofluoride 
• 5577-62-8 2,4,6-tris(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy)-1,3,5-triazine 
• 137677-90-8 1,3-Dinitro-2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-octyloxy)-5-trifluoromethyl-benzene 
• 31185-69-0 Perfluorooctanal hydrate 

Relevant articles and documents

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METHOD FOR PRODUCING PERFLUOROALCOHOL AND DEUTERATED PERFLUOROALCOHOL

PROBLEM TO BE SOLVED: To provide a method for efficiently synthesizing a perfluoroalcohol at a low coat. SOLUTION: This method for producing the perfluoroalcohol expressed by general formula (I) (Rf is a perfluoroalkyl; and YA and YB are each independently hydrogen or deuterium) comprises reducing a perfluorocarboxylic acid expressed by general formula (II) in water and/or heavy water in the presence of a transition metal catalyst by using a hydrogen donor.

Hydrophobic Effects on Photochemical and Photophysical Processes: Evidence for Aggregation of Perfluorocarbon in Aqueous-Organic Solvents

The emission spectra and photodimerization of fluorinated alkyl 2-naphthoates (NpFCn) and 9-anthrylmethyl perfluoroalkanoates (AnFCn) in aqueous-organic binary solvents have been investigated.The fluorescence spectra of NpFCn in dimethyl sulfoxide-water (DMSO-H2O) are dominated by excimer emission.Addition of long chain fluorocarbon compounds to the solution results in a reduction in the excimer emission and an enhancement of monomer emission.Selective excitation of the naphthalene moiety in the mixture solution of NpFCn and AnFCn leads to strong emission from AnFCn.Photoirradiation of NpFCn yields a 'cubane-like' photodimer with a relatively high quantum yield.All these observations suggest that hydrophobic interactions force molecules with long fluorocarbon chains to form aggregates in aqueous-organic binary solvents.