N-Fmoc-8-aminooctanoic acid

Base Information

• Chemical Name: N-Fmoc-8-aminooctanoic acid
• CAS No.: 126631-93-4
• Deprecated CAS: 13479-32-8,11042-58-3,511-14-8
• Molecular Formula: C23H27NO4
• Molecular Weight: 381.472
• Hs Code.: 29242990
• European Community (EC) Number: 848-538-2
• UNII: WQ3PS53E2U
• DSSTox Substance ID: DTXSID90189813
• Wikidata: Q83062026
• Mol file: 126631-93-4.mol

Synonyms:monascorubramine

Chemical Property of N-Fmoc-8-aminooctanoic acid

Chemical Property:

• Vapor Pressure: 1.9E-15mmHg at 25°C
• Melting Point: 118-119 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Refractive Index: 1.648
• Boiling Point: 597.73 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 315.296 °C
• PSA: 75.63000
• Density: 1.174 g/cm³
• LogP: 5.34120
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 381.19400834
• Heavy Atom Count: 28
• Complexity: 487

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-8-aminocaprylic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCCCCCCC(=O)O
• Description: N-Fmoc-8-aminooctanoic acid can be used as a PROTAC linker in the synthesis of PROTACs. N-Fmoc-8-aminooctanoic acid is an alkane chian with terminal Fmoc-protected amine and carboxylic acid groups. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Technology Process of N-Fmoc-8-aminooctanoic acid

There total 4 articles about N-Fmoc-8-aminooctanoic acid 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: 85.0%

8-Aminooctanoic acid (1002-57-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 8-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)octanoic acid (126631-93-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 24h; Heating;

DOI:10.1021/jm980495r

Reference yield:

C26H35NO4Si → 8-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)octanoic acid (126631-93-4)

Guidance literature:

With methanol; In dichloromethane;

DOI:10.1021/ol201404v

Reference yield:

8-Aminooctanoic acid (1002-57-9) → 8-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)octanoic acid (126631-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: dichloromethane / 3.5 h / 40 °C

2: dichloromethane / 20 °C

3: methanol / dichloromethane

With methanol; In dichloromethane;

DOI:10.1021/ol201404v

upstream raw materials:

8-Aminooctanoic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Downstream raw materials:

C₅₂H₈₂N₆O₁₂

8-Aminooctanoic acid

Refernces

• 1、 Sanchez, Laura M.,Curtis, Matthew E.,Bracamonte, Bianca E.,Kurita, Kenji L.,Navarro, Gabriel,Sparkman, O. David,Linington, Roger G.. "Versatile method for the detection of covalently bound substrates on solid supports by DART mass spectrometry". . p. 3770 - 3773. Retrieved 2011.
• 2、 -. "Novel platelet-aggregation inhibitors". . . Retrieved 2008/06/13.