4,4,5,5,5-Pentafluoro-1-pentanol Chemical Properties

Boiling point:

62-64 °C35 mm Hg(lit.)

Density 

1.35 g/mL at 25 °C(lit.)

vapor pressure 

1.1-155.2hPa at 25-80.3℃

refractive index 

n20/D 1.33(lit.)

Flash point:

145 °F

storage temp. 

2-8°C

solubility 

Chloroform

pka

14.77±0.10(Predicted)

form 

Liquid

color 

Clear colorless

InChI

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

InChIKey

QROUUECTKRZFHF-UHFFFAOYSA-N

SMILES

C(O)CCC(F)(F)C(F)(F)F

LogP

1.59 at 25℃ and pH7

CAS DataBase Reference

148043-73-6(CAS DataBase Reference)

EPA Substance Registry System

3-(Perfluoroethyl)propanol (148043-73-6)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36-36/37/38

Safety Statements 

26-36

RIDADR 

1993

WGK Germany 

2

Hazard Note 

Irritant

HazardClass 

FLAMMABLE

HS Code 

29055900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4,4,5,5,5-Pentafluoro-1-pentanol Usage And Synthesis

Description

4,4,5,5,5-Pentafluoro-1-pentanol (PFP; Pentafluoropentanol) is an essential building block primarily used in the commercial manufacture of the API. It is typically activated with a sulfonate leaving group and displaced selectively by the sulfur atom in 9-mercapto-1-nonanol to make 9-[(4,4,5,5,5-pentafluoropentyl)-thio]-1-nonanol (FVS). FVS is subsequently converted into a bromide and coupled with the steroid portion to make fulvestrant. First approved by the FDA in 2002, fulvestrant is a medication used to treat hormone receptor (HR)-positive metastatic breast cancer in postmenopausal women with disease progression.

Chemical Properties

Colorless to yellow liquid

Uses

4,4,5,5,5-Pentafluoro-1-pentanol may be used in the preparation of chlorine-capped telechelic poly(methyl methacrylate)s.

Uses

4,4,5,5,5-Pentafluoro-1-pentanol (Pentafluoropentanol) is an intermediate in preparing pentafluoropentane-1-thiol: a vital chain of anti-breast cancer agents.

General Description

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

Synthesis

Pentafluoroiodoethane could used as a starting material to synthesize 4,4,5,5,5-Pentafluoro-1-pentanol. Specific steps are as follows: under an inert gas atmosphere, iron acetylacetonate, 6,6'-dimethyl-2,2'-bipyridine, and 1,2-dichloroethane were added to the reactor, reacted at RT for 0.5 h; added allyl alcohol, cesium carbonate, pentafluoroiodoethane successively, triisopropylsilane, warmed up to 80 ℃ and reacted for 24 h. Sampling and detection confirmed that the reaction of allyl alcohol was complete, stopped the reaction, and cooled to room temperature. The excess pentafluoroiodoethane was recovered, nitrogen was introduced into the system, hydrochloric acid was added to quench the reaction, washed, separated to obtain an organic phase, distilled to remove the solvent, and rectified to obtain 4,4,5,5,5-pentafluoro Amyl alcohol. Yield: 90.4%.

4,4,5,5,5-Pentafluoro-1-pentanol(148043-73-6)Related Product Information

• PERFLUOROPENTANOIC ACID
• 4,4,5,5,5-Pentafluoro-1-pentanethiol
• ETHYL PENTAFLUOROPROPIONYLACETATE
• 4,4,5,5,5-Pentafluoro-1-pentanol
• Fenipentol
• ISOAMYL ALCOHOL
• 1-Pentanol
• ALLYL PERFLUOROPENTANOATE
• 2,3,3,3-TETRAFLUORO-2-(PERFLUOROPENTOXY)PROPAN-1-OL
• (NONAFLUORO-N-BUTYL)EPOXIDE
• 1H,1H-HEPTAFLUOROBUTYL EPOXIDE
• PERFLUORO-2-TRIFLUOROMETHYL-4-OXANONANE
• ETHYL PERFLUOROPENTANOATE
• 1H,1H-PERFLUOROPENTAN-1-OL
• METHYL NONAFLUOROVALERATE
• METHYL PENTAFLUOROPROPIONYLACETATE
• 2,2,3,3,4,4,5,5,5-NONAFLUOROPENTYL 2,5,7-TRINITRO-9-OXO-9H-FLUORENE-4-CARBOXYLATE
• METHYL-3,3-DIMETHOXY-3-(PERFLUOROBUTYL)PROPANOATE