148043-73-6

Basic information

• Product Name: 4,4,5,5,5-Pentafluoro-1-pentanol
• Synonyms: 4,4,5,5,5-PENTAFLUOROPENTAN-1-OL;4,4,5,5,5-PENTAFLUOROPENTANOL;4,4,5,5,5-PENTAFLUORO-1-PENTANOL;Pentafluoropentanol;4,4,5,5,5-Pentafluoropentan-1-ol 96%;4,4,5,5,5-Pentafluoropentan-1-ol96%;4,4,5,5,5-Pentafluoro-1-pentanol ,97%;4,4,5,5,5-Pentafluoro-1-pentanol,95%
• CAS NO: 148043-73-6
• Molecular Formula: C₅H₇F₅O
• Molecular Weight: 178.1
• EINECS: 421-360-9
• Product Categories: Industrial/Fine Chemicals;Organic Fluorides;Alcohols;C2 to C6;Oxygen Compounds;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 148043-73-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 62-64 °C35 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless/Liquid
• Density: 1.35 g/mL at 25 °C(lit.)
• Vapor Pressure: 78mmHg at 25°C
• Refractive Index: n20/D 1.33(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• PKA: 14.77±0.10(Predicted)
• CAS DataBase Reference: 4,4,5,5,5-Pentafluoro-1-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5,5-Pentafluoro-1-pentanol(148043-73-6)
• EPA Substance Registry System: 4,4,5,5,5-Pentafluoro-1-pentanol(148043-73-6)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36-36/37/38
• Safety Statements: 26-36
• RIDADR: 1993
• WGK Germany: 2
• HazardClass: FLAMMABLE
• Hazardous Substances Data: 148043-73-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to yellow liquid

Uses

Different sources of media describe the Uses of 148043-73-6 differently. You can refer to the following data:
1. 4,4,5,5,5-Pentafluoro-1-pentanol may be used in the preparation of chlorine-capped telechelic poly(methyl methacrylate)s.
2. An intermediate in the preparation of pentafluoropentane-1-thiol: an important chain of anti-breast cancer agents.

General Description

4,4,5,5,5-Pentafluoro-1-pentanol, also known as pentafluoropentanol, is a perfluorous solvent.

InChI:InChI=1/C5H7F5O/c6-4(7,2-1-3-11)5(8,9)10/h11H,1-3H2

Synthetic route

4,4,5,5,5-pentafluoro-2-iodopent-2-en-1-ol (172032-07-4) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With hydrogen; triethylamine; platinum(IV) oxide In ethyl acetate at 25℃; for 3h;	95%

4,4,5,5,5-pentafluoropentyl acetate (148043-72-5) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With sodium hydroxide for 1h; Heating;	92%

1,1,1,2,2-pentafluoropentane → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With Cumene hydroperoxide In isopropyl alcohol at 80℃; for 2h; Reagent/catalyst; Solvent; Temperature; Autoclave;	83.3%

4,4,5,5,5-pentafluoro-2-iodopentyl acetate (148043-71-4) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / azoisobutyronitrile (AIBN), Bu3SnH / 55 - 65 °C 2: 92 percent / aq. NaOH / 1 h / Heating View Scheme

tert-butyl methyl ether (1634-04-4) + 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol (757-06-2) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With hydrogen; triethylamine; palladium

4,4,5,5,5-pentafluoro-2-iodo-1-pentanol (757-06-2) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With triethylamine; palladium In water; ethyl acetate
With 2,2'-azobis(isobutyronitrile); palladium diacetate at 60 - 70℃; Reagent/catalyst;
With hydrogen; triethylamine In acetonitrile at 50℃; under 15001.5 Torr; for 0.5h; Flow reactor;

4,4,5,5,5-pentafluoro-2-iodo-1-pentanol (757-06-2) + ethanolamine (141-43-5) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
palladium In water

4,4,5,5,5-pentafluoro-2-penten-1-ol → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
platinum (IV) oxide In ethyl acetate
platinum (IV) oxide In ethyl acetate

methanesulfonyl chloride (124-63-0) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane (252947-01-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3 - 12h; Product distribution / selectivity;	100%
With triethylamine In tetrahydrofuran at 0 - 20℃;	99%
With triethylamine In dichloromethane at 0℃; for 0.75h;	96%

thiobenzoic acid (98-91-9) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → thiobenzoic acid S-(4,4,5,5,5-pentafluoro-pentyl)ester (862700-61-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 17h;	75 g

5,10,15,20-tetrakis[2-fluoro-5-(chlorosulfonyl)phenyl]porphyrin + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 5,10,15,20-tetrakis[2-fluoro-5-(4,4,5,5,5-pentafluoropentyloxy)sulfonylphenyl]porphyrin

Conditions	Yield
In tetrahydrofuran; water at 5 - 20℃;	95%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 1,1,1,2,2-pentafluoro-5-chloro-n-pentane

Conditions	Yield
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; Solvent; Reagent/catalyst;	95%
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 2h; Solvent; Reagent/catalyst;	95%

p-(chloromethyl)benzoyl chloride (876-08-4) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C13H12ClF5O2 (1293408-08-8)

Conditions	Yield
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	93%
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	93%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + molecular sieve supported p-toluenesulfonic acid → 4,4,5,5,5-pentafluoropentyl-4-methylbenzene sulphonate (209325-64-4)

Conditions	Yield
at 65℃; for 1h; Temperature; Microwave irradiation; Molecular sieve;	91%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + thioacetic acid (507-09-5) → 1-(acetylsulfanyl)-4,4,5,5,5-pentafluoropentane (160598-75-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran 1.) 0 deg C, 30 min; 2.) 0 deg C, 30 min then 25 deg C, 1 h;	88%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → C11H10F5NO5S

Conditions	Yield
With dmap; triethylamine In dichloromethane at -10℃; for 1h; Concentration;	85%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 4,4,5,5,5-pentafluoropentanoic acid (3637-31-8)

Conditions	Yield
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%
With sodium permanganate monohydrate; tetraethylammonium hydrogen sulphate In water at 65 - 75℃; for 6.5h; Large scale;	77%
With chromium(VI) oxide; acetic acid at 0 - 20℃; for 26h;	63%

5,10,15,20-tetrakis[2,6-difluoro-3-(chlorosulfonyl)phenyl]porphyrin + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 5,10,15,20-tetrakis[2,6-difluoro-3-(4,4,5,5,5-pentafluoropentyloxy)sulfonylphenyl]porphyrin

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 5 - 20℃;	82%

C34H52N2O9S + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C39H57F5N2O9S

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; Mitsunobu reaction;	67%

4-[9-(N-t-butyloxycarbonylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 4-[9-(N-t-butyloxycarbonyl-N-4,4,5,5,5-pentafluoropentylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃;	67%

p-toluenesulfonyl chloride (98-59-9) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 4,4,5,5,5-pentafluoropentyl-4-methylbenzene sulphonate (209325-64-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 24h;	61%
With pyridine at 0 - 20℃;	53%
With pyridine at 0 - 20℃;	53%
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane
With triethylamine In dichloromethane at 20℃; for 18h;

Gly-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C32H30F5N3NiO3 + C32H30F5N3NiO3

Conditions	Yield
With cyanomethylenetributyl-phosphorane at 105℃; Inert atmosphere; Sealed tube; diastereoselective reaction;	A 50% B n/a

Gly-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C32H30F5N3NiO3 + C33H32F5N3NiO3

Conditions	Yield
With cyanomethylenetributyl-phosphorane at 105℃; Mitsunobu Displacement; Sealed tube; Inert atmosphere; diastereoselective reaction;	A 50% B n/a

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 1,1,1,2,2-pentafluoro-5-iodo-pentane (151556-31-9)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 1.5h;	45%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	45%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 2.5h;
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: sodium iodide / acetone / 12 h / Reflux View Scheme
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;

{(R)-2-[3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-5-piperazin-1-yl-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (1308375-93-0) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → (R)-tert-butyl-(2-(3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-5-(4-(4,4,5,5,5-pentafluoropentyl)-piperazin-1-yl)-2,3-dihydropyrimidin-1(6H)-yl)-1-phenylethyl)carbamate (1308380-96-2)

Conditions	Yield
With potassium carbonate; methanesulfonyl chloride; triethylamine In dichloromethane; acetonitrile at 80℃; for 7h;	21%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + 1,1'-carbonyldiimidazole (530-62-1) → imidazole-1-carboxylic acid 4,4,5,5,5-pentafluoro-pentyl ester

Conditions	Yield
In tetrahydrofuran at 20℃;
In tetrahydrofuran at 20℃; for 0.5h;

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]thiochroman

Conditions	Yield
Multi-step reaction with 3 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 76 percent / sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]thiochroman

Conditions	Yield
Multi-step reaction with 3 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 16 percent / sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 76 percent / sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]chroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 59 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: hydrogen chloride / methanol / 0.25 h / 60 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfinyl)octyl]chroman-7-ol

Conditions	Yield
Multi-step reaction with 5 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 59 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: hydrogen chloride / methanol / 0.25 h / 60 °C 5: oxone(R) / tetrahydrofuran; H2O / 0.17 h / 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → (3S,4S)-3-(4-Hydroxy-phenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-nonyl]-thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → (3R,4R)-3-(4-Hydroxy-phenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-nonyl]-thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 79 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: 74 percent / boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 11 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

Upstream product

• 172032-07-4 4,4,5,5,5-pentafluoro-2-iodopent-2-en-1-ol 
• 757-06-2 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol 
• 141-43-5 ethanolamine 
• 1634-04-4 tert-butyl methyl ether 
• 148043-71-4 4,4,5,5,5-pentafluoro-2-iodopentyl acetate 
• 148043-72-5 4,4,5,5,5-pentafluoropentyl acetate 

Downstream Products

• 3637-31-8 4,4,5,5,5-pentafluoropentanoic acid 
• 252947-01-6 1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane 
• 209325-64-4 4,4,5,5,5-pentafluoropentyl-4-methylbenzene sulphonate 
• 675847-61-7 tert-butyl {(R)-1-hydroxy-2-methyl-4-[4-(4,4,5,5,5-pentafluoro-pentyloxy)-phenyl]-but-2-yl}-carbamate 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 

Relevant articles and documents

Laboratory scale preparation of 4,4,5,5,5-pentafluoropentan-1-thiol: An important chain of antibreast cancer agents

Quantitative free radical addition of perfluoroethyl iodide to propargyl alcohol in the presence of sodium hydrosulfite gave E/Z-2-iodo-4,4,5,5,5-pentafluoro-2-penten-1-ols, which were converted to 4,4,5,5,5-pentafluoropentan-1-ol in one step in excellent yield by catalytic hydrogenation over platinum oxide in the presence of triethylamine. 4,4,5,5,5-Pentafluoropentan-1-thiol was obtained in good yield via modified Mitsunobu reaction of the alcohol.

Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate

Two efficient continuous flow iodoperfluoroalkylation methods are described: using 0.05 mol % perylene diimide (PDI) photocatalyst under 450 nm irradiation or substoichiometric triethylamine under 405 nm irradiation. These methods enable dramatically elevated productivity versus batch processes. The triethylamine-mediated method is explored mechanistically and in substrate scope. The gram-scale synthesis of an active pharmaceutical ingredient side chain is also reported in flow, via a photochemical iodoperfluoroalkylation followed by hydrogenolysis.

Process for preparing pentafluoropentanol

4,4,5,5,5-Pentafluoro-1-pentanol is prepared in a particularly advantageous manner from perfluoroethyl iodide by initially adding perfluoroethyl iodide in the presence of a radical initiator which does not carry any acyl groups to allyl alcohol and then hydrogenolytically dehalogenating the resulting 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol in the presence of a catalyst, an acid binder and a diluent.