Pentafluorophenol Chemical Properties

Melting point:

34-36 °C (lit.)

Boiling point:

143 °C (lit.)

Density 

1.757

refractive index 

1.4270

Flash point:

162 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Low Melting Crystalline Solid

pka

5.50±0.33(Predicted)

Specific Gravity

1.757

color 

White to almost white

Water Solubility 

soluble

BRN 

1912584

Stability:

Stable. Incompatible with strong oxidizing agents, bases, acid chlorides, acid anhydrides.

InChIKey

XBNGYFFABRKICK-UHFFFAOYSA-N

CAS DataBase Reference

771-61-9(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, pentafluoro-(771-61-9)

EPA Substance Registry System

Pentafluorophenol (771-61-9)

Safety Information

Hazard Codes 

Xi,T,C,Xn

Risk Statements 

36/37/38-34-20/21/22-63-43-23/24/25-45-67-40

Safety Statements 

26-36-45-36/37/39-36/37-24/25-23-53

RIDADR 

2811

WGK Germany 

3

RTECS 

SM6680000

F 

3

Hazard Note 

Toxic/Irritant

TSCA 

T

HazardClass 

8

PackingGroup 

III

HS Code 

29081000

Toxicity

LD50 scu-rat: 322 mg/kg IZSBAI 3,91,65

MSDS

• Language:English Provider:Pentafluorophenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pentafluorophenol Usage And Synthesis

Description

Pentafluorophenol can be used for the preparation of penta-fluorophenyl esters for peptide synthesis. It is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids. It can be used for synthesizing novel reagents which can achieve highly diastereoselective acetal cleavage.

Reference

3. Ishihara, Kazuaki, N. Hanaki, and H. Yamamoto. "Highly diastereoselective acetal cleavages using novel reagents prepared from organoaluminum and pentafluorophenol" Cheminform 25.9(2010):no-no.

Chemical Properties

White solid

Uses

Used for the preparation of pentafluorophenyl esters for peptide synthesis

Uses

Pentafluorophenol is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids.

Uses

For the preparation of pentafluorophenyl esters for peptide synthesis.

Application

Pentafluorophenol can be used as a reactant to synthesize pentafluorophenyl esters from:

• N-protected amino acid in the presence of dicyclohexylcarbodiimide and ethyl acetate.
• t-Butoxycarbonyl-L-alanylglycinein the presence of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride.
• Aliphatic dicarboxylic acids in the presence of pyridine, diisopropylcarbodiimide, and acetonitrile.

It can also be used as a reactant to synthesize pentafluorophenyl formate which can be used as a formylating agent in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 5502, 1989 DOI: 10.1021/jo00284a022

General Description

Pentafluorophenol is widely used as a precursor in both solution and solid-phase peptide synthesis. It is also involved in the preparation of aromatic fluoro derivatives.

Safety Profile

scu-rat LD50:322 mg/kg IZSBAI 3,91,65

Purification Methods

Pentafluorophenol is a hygroscopic low melting solid not freely soluble in H2O. Purify it by distillation, preferably in a vacuum [Forbes et al. J Chem Soc 2019 1959, IR and pKa: Birchall & Haszeldine J Chem Soc 13 1959]. IRofafilmhas max 3600 (OH) and 1575 (fluoroaromatic breathing) cm-1 . The benzoyl derivative has m 74-75o, 3,4-dinitrobenzoyl derivative has m 107o, the tosylate has m 64-65o (from EtOH) and the K salt crystallises from Me2CO, m 242o(dec), with 1H2O-salt the m is 248o(dec) and the 2H2O-salt has m 245o(dec). [Beilstein 6 IV 782.]

Pentafluorophenol(771-61-9)Related Product Information

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• 2-Phenylphenol
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• PENTAFLUOROPHENYL ISOTHIOCYANATE
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• 9-FLUORENYLMETHYL PENTAFLUOROPHENYL CARBONATE
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