4,4,5,5,5-Pentafluoro-1-pentanol
- CAS NO.:148043-73-6
- Empirical Formula: C5H7F5O
- Molecular Weight: 178.1
- MDL number: MFCD00153224
- EINECS: 421-360-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-06-07 17:47:24
What is 4,4,5,5,5-Pentafluoro-1-pentanol?
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
The Uses of 4,4,5,5,5-Pentafluoro-1-pentanol
4,4,5,5,5-Pentafluoro-1-pentanol may be used in the preparation of chlorine-capped telechelic poly(methyl methacrylate)s.
The Uses of 4,4,5,5,5-Pentafluoro-1-pentanol
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%.
Properties of 4,4,5,5,5-Pentafluoro-1-pentanol
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 | n |
Flash point: | 145 °F |
storage temp. | 2-8°C |
solubility | Chloroform |
form | Liquid |
pka | 14.77±0.10(Predicted) |
color | Clear colorless |
InChI | InChI=1S/C5H7F5O/c6-4(7,2-1-3-11)5(8,9)10/h11H,1-3H2 |
CAS DataBase Reference | 148043-73-6(CAS DataBase Reference) |
EPA Substance Registry System | 3-(Perfluoroethyl)propanol (148043-73-6) |
Safety information for 4,4,5,5,5-Pentafluoro-1-pentanol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 4,4,5,5,5-Pentafluoro-1-pentanol
InChIKey | QROUUECTKRZFHF-UHFFFAOYSA-N |
SMILES | C(O)CCC(F)(F)C(F)(F)F |
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