Pentafluorophenol

HCID 13041CAS 771-61-9
Substructure searchFind similar structures

Basic information

Standard SMILES
Oc1c(F)c(F)c(F)c(F)c1F
InChIKey
XBNGYFFABRKICK-UHFFFAOYSA-N
Molecular formula
C6HF5O
Average molar mass
184.06 g/mol
Monoisotopic mass
183.99475546

Names & identifiers

Preferred name
Pentafluorophenol
IUPAC
2,3,4,5,6-pentafluorophenol
English name
Pentafluorophenol
Molecular formula
C6HF5O
Molecular weight
184.06

Names & synonyms

PENTAFLUOROPHENOL771-61-92,3,4,5,6-PentafluorophenolPhenol, pentafluoro-A2YCF0YUHANSC-21627DTXSID9061120RefChem:859814DTXCID1047946212-235-8PerfluorophenolC6HF5O
Show more names
PFPPFP-OHHOPFPPentaflurophenolPENTAFLUORPHENOLHPLH2)
MFCD00002156C6F5OH2,3,4,5,6-pentakis(fluoranyl)phenolpentafluorohydroxybenzeneUNII-A2YCF0YUHAEINECS 212-235-8NSC 216272,3,4,5,6-pentafluorohydroxybenzene

Database identifiers

CAS
771-61-9
PubChem CID
13041
DTXSID
DTXSID9061120
UNII
A2YCF0YUHA
EC Number
212-235-8
Nikkaji
J34.564D

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

Physical DescriptionWhite crystalline solid with an odor of phenol; mp = 32-36 deg C; [Alfa Aesar MSDS]
Ionization Efficiency · 6 items

Negative

0.91

10.5

Agilent XCT

Electrospray ionization

ammonia (10nM)

Physicochemical properties

Melting point
34 · 34-36 °C (lit.)
Boiling point
143 °C · 143 °C (lit.)
Density
1.757 · 1.757
refractive index
1.427 · 1.4270
Flash point
162 °F · 162 °F
storage temp.
30 °C · Store below +30°C.

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 6.9% (4 of 58) of reports.

Danger

H302 (24.1%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (24.1%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H314 (13.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H315 (69%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (70.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (70.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 58 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 4 of 58 reports by companies.；There are 11 notifications provided by 54 of 58 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 25-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/28416

Pentafluorophenol: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion and skin absorption; [Alfa Aesar MSDS] See 2-Fluorophenol. See Pentachlorophenol.
Hazard Classes and CategoriesAcute Tox. 4 (24.1%)；Acute Tox. 4 (24.1%)；Skin Corr. 1B (13.8%)；Skin Irrit. 2 (69%)；Eye Irrit. 2 (70.7%)；STOT SE 3 (70.7%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.；Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 25-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/28416

Pentafluorophenol: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
3
wgk
3
tsca
TSCA listed
rtecs
SM6680000
ridadr
2811
hs_code
29081000

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPhenol, 2,3,4,5,6-pentafluoro-: ACTIVE
Applications · 5 items

DescriptionPentafluorophenol 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.

UsesUsed for the preparation of pentafluorophenyl esters for peptide synthesis

UsesPentafluorophenol 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.

UsesFor the preparation of pentafluorophenyl esters for peptide synthesis.

General DescriptionPentafluorophenol 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.

Preparation methods · 1 item

PreparationPetrofluorophenyl magnesium chloride was prepared by reacting monochloropentafluorobenzene, a byproduct of the preparation of hexafluorobenzene from hexachlorobenzene, with magnesium at a reaction temperature of 45–50 °C for 2.5 h. Triisopropyl borate was used as a borizing agent to prepare dipropyl pentafluorophenylboronic acid at a reaction temperature of -10–-15 °C for 3 h. Dipropyl pentafluorophenylboronic acid was then hydrolyzed under acidic conditions to obtain pentafluorophenylboronic acid. Pentafluorophenylboronic acid was then reacted with hydrogen peroxide to obtain pentafluorophenol at a reaction temperature of 65 °C for 5 h. The resulting product had a purity of over 99.5% (GC), with a three-step yield of 60.25%.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Related reactions

3,480 records
New reaction record

Linked notes

Loading…