N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Base Information

• Chemical Name: N-(9-Fluorenylmethoxycarbonyloxy)succinimide
• CAS No.: 82911-69-1
• Molecular Formula: C19H15NO5
• Molecular Weight: 337.332
• Hs Code.: 2925.19
• European Community (EC) Number: 433-520-5,617-400-1
• UNII: AD7AUS3GKT
• DSSTox Substance ID: DTXSID90232090
• Nikkaji Number: J208.522D
• Wikidata: Q72478709
• Mol file: 82911-69-1.mol

Synonyms:9-fluorenylmethylsuccinimidyl carbonate;Fmoc-ONSu

Chemical Property of N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 6.55E-10mmHg at 25°C
• Melting Point: 150-153 °C(lit.)
• Refractive Index: 1.661
• Boiling Point: 494.3 °C at 760 mmHg
• Flash Point: 252.7 °C
• PSA: 72.91000
• Density: 1.42 g/cm³
• LogP: 2.95400
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in dimethyl sulfoxide and dimethyl formamide.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 337.09502258
• Heavy Atom Count: 25
• Complexity: 524

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-OSu ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-51/53-43-22
• Safety Statements: 22-24/25-26/37/39-26-61-37-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: N-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides. N-protecting reagent for oligonucleotide and peptide syntheses Reagent for the preparation of pure Fmoc amino acids free from contamination by Fmoc-dipeptides.

Technology Process of N-(9-Fluorenylmethoxycarbonyloxy)succinimide

There total 6 articles about N-(9-Fluorenylmethoxycarbonyloxy)succinimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; for 1h; Ambient temperature;

DOI:10.1055/s-1983-30468

Reference yield: 90.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + dicyclohexylamine salt of N-hydroxysuccinimide (82911-72-6) → N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1)

Guidance literature:

In chloroform;

DOI:10.1139/v82-146

Reference yield: 90.0%

C16H26N2O3 + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1)

Guidance literature:

In chloroform;

DOI:10.2174/092986610791306625

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

(fluorenylmethoxy)carbonyl chloride

2,5-dioxopyrrolidin-1-yl carbonochloridate

9-Fluorenylmethanol

Downstream raw materials:

N-α-9-fluorenylmethoxycarbonyl-aspartic acid

(S)-2-(N-fluorenylmethoxycarbonylamino)propanol

(S)-(9H-fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate

Fmoc-m-Nip(Bn)

Refernces

Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives

10.1016/j.tetlet.2003.11.133

The study presents a concise synthesis method for a novel class of homochiral aromatic amino acid surrogates, featuring tetrahydroindazole or benzisoxazole systems. These surrogates were synthesized through the acylation of cyclic 1,3-diketone by the side-chain carboxyl functionality of specific amino acid precursors, followed by a regioselective condensation with hydrazine, N-benzylhydrazine, and hydroxylamine. The synthetic strategy is versatile, allowing for the creation of structurally diverse derivatives. These novel amino acids can be efficiently incorporated into proteins and have potential applications in imparting unique properties to biological peptides. The study also includes the synthesis of Na-Fmoc-protected derivatives, which are useful for solid-phase peptide assembly, and the exploration of the stereochemistry integrity of the homochiral starting material through chemical transformations. The synthesized amino acids offer opportunities as structural surrogates of tryptophan and as building blocks for designing molecular probes.