Pentafluorophenyl diphenylphosphinate (HCID 4652311)

Names & identifiers

Preferred name: Pentafluorophenyl diphenylphosphinate
IUPAC: 1-diphenylphosphoryloxy-2,3,4,5,6-pentafluorobenzene
English name: PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE
Molecular formula: C18H10F5O2P
Molecular weight: 384.24

Names & synonyms

Pentafluorophenyl diphenylphosphinate138687-69-1DTXSID70405265RefChem:368001DTXCID40356119873-948-3perfluorophenyl diphenylphosphinate1-diphenylphosphoryloxy-2,3,4,5,6-pentafluorobenzeneMFCD00192380FDPPPhosphinic acid, P,P-diphenyl-, 2,3,4,5,6-pentafluorophenyl ester1-diphenylphosphoryloxy-2,3,4,5,6-pentafluoro-benzene

Show more names

Pentafluorophenyl diphenyl phosphateDiphenyl phosphate of pentfluorophenylperfluorophenyl diphenylphosphinate(FDPP)Diphenylphosphinic acid pentafluorophenyl esterPENTAFLUOROPHENYL DIPHENYLPHOSPHINATE Diphenylphosphinic acid pentafluorophenyl ester

Phosphinic acid, diphenyl-, pentafluorophenyl esterC18H10F5O2PSCHEMBL863602perfluorophenyldiphenylphosphinateOOWSDKUFKGVADH-UHFFFAOYSA-NAKOS015900973CS-W009742AS-10634

Database identifiers

CAS: 138687-69-1
PubChem CID: 4652311
DTXSID: DTXSID70405265
EC Number: 873-948-3
Nikkaji: J724.117H

Properties

Computed structural properties

XLogP: 4.9
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 7
Rotatable bonds: 4
Heavy atoms: 26
Formal charge: 0
Complexity: 472

Physicochemical properties

Melting point: 47 · 47-50 °C (lit.)
Boiling point: 413.1 · 413.1±55.0 °C(Predicted)
Density: 1.45 · 1.45
storage temp.: Sealed in dry,Room Temperature
form: solid
Appearance: White to off-white Solid
InChI: InChI=1S/C18H10F5O2P/c19-13-14(20)16(22)18(17(23)15(13)21)25-26(24,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
InChIKey: OOWSDKUFKGVADH-UHFFFAOYSA-N
SMILES: P(C1=CC=CC=C1)(C1=CC=CC=C1)(OC1=C(F)C(F)=C(F)C(F)=C1F)=O
UNSPSC Code: 12352101 · 12352101
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 280 · P280-P302+P352-P304+P340
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
RIDADR: 2811 · UN2811
WGK Germany: 3 · 3
HazardClass: 6.1 · 6.1
HS Code: 29319090 · 29319090
Storage Class: 11 · 11 - Combustible Solids
Limited Quantities: 5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
ridadr: UN2811
hs_code: 29319090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
hazard_class: 6.1
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Limited Quantities: 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Precautionary statements: P280-P302+P352-P304+P340

Chemistry & industry

Applications · 3 items

UsesPentafluorophenyl Diphenylphosphinate is a reagent used as carboxyl activating group and a coupling agent in variety of amide bond formations.

UsesFDPP can be used as a coupling reagent in the: Synthesis of peptides by solid-phase and solution-phase reactions. Preparation of macrocyclic peptide cyclotheonamide B as a thrombin inhibitor. Cyclooligomerization of N-methylated-L-valine thiazole amino acid to obtain its cyclic tetramers. Macrocyclization of an intermediate for the total synthesis of ziziphine N , and for the macrolactamization of precursor in synthesizing cryptophycin D.

General DescriptionPentafluorophenyl diphenylphosphinate (FDPP) is a reagent, used as a coupling agent in the amide bond forming reactions without racemization. It can also be employed in the synthesis of dipeptides with high yields and good optical purity. FDPP can be prepared from diphenylphosphinic chloride and pentafluorophenol in the presence of imidazole.