86060-92-6

Basic information

• Product Name: FMOC-PHE-OPFP
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-PHENYLALANINE PENTAFLUORPHENYL ESTER;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PHENYLALANINE PENTAFLUOROPHENYL ESTER;N-ALPHA-FMOC-L-PHENYLALANINE PENTAFLUOROPHENYL ESTER;FMOC-PHE-OPFP;FMOC-PHENYLALANINE-OPFP;FMOC-L-PHE-OPFP;FMOC-L-PHENYLALANINE PENTAFLUOROPHENYL ESTER;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PHENYL&
• CAS NO: 86060-92-6
• Molecular Formula: C₃₀H₂₀F₅NO₄
• Molecular Weight: 553.48
• Product Categories: Amino Acids;Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 86060-92-6.mol

Chemical Properties

• Melting Point: 149-151 °C(lit.)
• Boiling Point: 674.8 °C at 760 mmHg
• Flash Point: 361.9 °C
• Appearance: White/Powder
• Density: 1.399 g/cm³
• Vapor Pressure: 4.56E-18mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: 2-8°C
• PKA: 10.28±0.46(Predicted)
• BRN: 4241247
• CAS DataBase Reference: FMOC-PHE-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-PHE-OPFP(86060-92-6)
• EPA Substance Registry System: FMOC-PHE-OPFP(86060-92-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 86060-92-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystals

InChI:InChI=1/C30H20F5NO4/c31-23-24(32)26(34)28(27(35)25(23)33)40-29(37)22(14-16-8-2-1-3-9-16)36-30(38)39-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,36,38)/t22-/m0/s1

Upstream product

• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 63-91-2 L-phenylalanine 
• 35661-40-6 N-Fmoc L-Phe 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 244633-31-6 pentafluorophenyl 4-nitrobenzenesulfonate 
• 96157-57-2 bis(pentafluorophenyl)sulfite 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 103321-57-9 2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride 

Downstream Products

• 75539-79-6 benzyloxycarbonyl-D-Phe-Phe-Gly 
• 825615-42-7 ((3R,4S)-3-{(S)-1-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-3-methyl-butyl}-2-oxo-4-phenyl-azetidin-1-yl)-acetic acid methyl ester 
• 825615-43-8 ((3S,4R)-3-{(S)-1-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-3-methyl-butyl}-2-oxo-4-phenyl-azetidin-1-yl)-acetic acid methyl ester 
• 114195-44-7 Fmoc-Phe-D-Ala-Asu(O^tBu)-D-Pro-OMe 
• 5241-71-4 Asp-Phe-NH₂ 
• 130738-23-7 Fmoc-Phe-Ala-Ser(OBzl)-Gly-Glu(OBzl)-OBzl 
• 1947-37-1 cholecystokinin-4 
• 1656305-20-2 Fmoc-FCit-PAB-OH 

Relevant articles and documents

Synthesis of aryl esters of protected amino acids from aryl sulfonates

Aryl esters of Boc- and Fmoc-protected amino acids derived from electron-deficient phenols have been prepared in good yields from aryl 4- nitrobenzenesulfonates in the presence of 1-hydroxy-benzotriazole as catalyst.

A new facile one-pot preparation of pentafluorophenyl (Pfp) and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl (Dhbt) esters of Fmoc amino acids

A new one-pot procedure for the preparation of pentafluorophenyl and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl esters of Nα-9-fluorenylmethyloxycarbonyl amino acids bearing no side chain protecting groups is described. The method gives the desired activated esters in high yield and purity without use of the highly allergenic DCC.

PREPARATION OF PENTAFLUOROPHENYL ESTERS OF FMOC PROTECTED AMINO ACIDS WITH PENTAFLUOROPHENYL TRIFLUOROACETATE

A high yield procedure for the preparation of pentafluorophenyl esters of Nα-9-fluorenylmethyloxycarbonyl protected amino acids is described.The procedure utilizes pentafluorophenyl trifluoroacetate.

Bis(pentaluorophenyl) sulfite - A new reagent for the synthesis of activated pentafluorophenyl esters of N-protected amino acids

A method was proposed for the preparation of bis(perfluorophenyl) sulfite, an effective new reagent for the synthesis of pentafluorophenyl esters of N-protected amino acids without racemization.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.