[2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid

Base Information

• Chemical Name: [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid
• CAS No.: 166108-71-0
• Molecular Formula: C21H23NO6
• Molecular Weight: 385.417
• Hs Code.: 29189900
• European Community (EC) Number: 805-205-6
• DSSTox Substance ID: DTXSID50373231
• Nikkaji Number: J2.173.030K
• Wikidata: Q72477838
• Mol file: 166108-71-0.mol

Synonyms:166108-71-0;[2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid;Fmoc-NH-PEG2-CH2COOH;1-(9H-FLUOREN-9-YL)-3-OXO-2,7,10-TRIOXA-4-AZADODECAN-12-OIC ACID;Fmoc-8-amino-3,6-dioxaoctanoic acid;8-(Fmoc-amino)-3,6-dioxaoctanoic acid;{2-[2-(Fmoc-amino)ethoxy]ethoxy}acetic acid;2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]acetic Acid;FMOC-AEEAC-OH;MFCD01321015;FMOC-AMINO-3,6 DIOXAOCTANOIC ACID;FMOC-AEEA;2,7,10-Trioxa-4-azadodecan-12-oic acid, 1-(9H-fluoren-9-yl)-3-oxo-;8-(9-FLUORENYLMETHYLOXYCARBONYL-AMINO)-3,6-DIOXAOCTANOIC ACID;3,6,11-TRIOXA-9-AZADODECANOIC ACID, 12-(9H-FLUOREN-9-YL)-10-OXO-;Fmoc-Adoa-OH;8-(Fmoc-amino)-3,6-dioxa-octanoic acid;{2-[2-(Fmoc-amino)-ethoxy]-ethoxy}-acetic acid;Fmoc-8-amino-3,6-dioxa-octanoic acid;[2-(2-(Fmoc-amino)ethoxy)ethoxy]acetic acid;Fmoc-mini-PEG;Fmoc-AEEA-OH;FMOC-ADOA;8-[(9H-Fluoren-9-ylmethoxy)carbonylamino]-3,6-dioxa-n-octanoic Acid;[2-[2-[(Fmoc-amino)ethoxy]ethoxy]acetic Acid;SCHEMBL259018;DTXSID50373231;BCP11185;TD8147;AKOS015840985;AB09039;CS-W007713;HY-W007713;AC-26584;AM808139;AS-17641;BP-22044;SY017426;8-(Fmoc-amino)-3,6-dioxa-n-octanoic Acid;F0719;FT-0645528;EN300-1556421;Fmoc-NH-PEG2-CH2COOHFmoc-NH-PEG2-CH2COOH;A810696;8-(9-Fluorenylmethoxycarbonylamino)-3,6-dioxaoctanoic acid;{2-[2-(Fmoc-amino)ethoxy]ethoxy}acetic acid, >=95.0% (HPLC);(2-(2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy)ethoxy)acetic acid;[2-[2-(9H-Fluorene-9-ylmethoxycarbonylamino)ethoxy]ethoxy]acetic acid;[2-[2-[(9H-Fluoren-9-ylmethoxy)carbonylamino]ethoxy]ethoxy]acetic Acid;2-[2-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)ethoxy]acetic acid;2-{2-[2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)ETHOXY]ETHOXY}ACETIC ACID;2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]acetic acid;1-(9H-Fluoren-9-yl)-3-oxo-2,7,10-trioxa-4-azadodecan-12-oic acid

Chemical Property of [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 8.27E-17mmHg at 25°C
• Melting Point: 90-92℃
• Refractive Index: 1.579
• Boiling Point: 631.4 °C at 760 mmHg
• PKA: 3.40±0.10(Predicted)
• Flash Point: 335.6 °C
• PSA: 94.09000
• Density: 1.265 g/cm³
• LogP: 3.03380
• Storage Temp.: -15°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 385.15253745
• Heavy Atom Count: 28
• Complexity: 491

Purity/Quality:

99%, ^*data from raw suppliers

8-(Fmoc-amino)-3,6-dioxaoctanoicAcid ^*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)NCCOCCOCC(=O)O
• Uses: [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid is a hydrophilic, heterobifunctional spacer. Hydrophillic spacer group. 8-(Fmoc-amino)-3,6-dioxaoctanoic Acid is a hydrophilic, heterobifunctional spacer.
• Description: Fmoc-NH-PEG2-CH2COOH is a PEG linker containing an Fmoc-protected amine and a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. 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 [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid

There total 12 articles about [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic 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: 100.0%

8-(9-fluorenylmethoxycarbonylamino)-3,6-dioxaoctanoic acid tert-butyl ester → 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid (166108-71-0,675606-79-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h;

Reference yield:

2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol (6338-55-2) → 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid (166108-71-0,675606-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / water / Inert atmosphere

2: sodium hypochlorite; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1021/ja204488p

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + [2-(N-2-amino ethoxy)ethoxy] acetic acid (134978-97-5,139729-28-5) → 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid (166108-71-0,675606-79-8)

Guidance literature:

With potassium carbonate; In water; for 16h;

DOI:10.1021/ol0502578

upstream raw materials:

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

[2-(N-2-amino ethoxy)ethoxy] acetic acid

[2-(2-dibenzylaminoethoxy)ethoxy]acetic acid

[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester

Downstream raw materials:

[2-(2-{2-[2-(2-{[2'-(4-hydroxy-phenyl)-6-(4-methyl-piperazin-1-yl)-1H,3'H-[2,5']bibenzoimidazolyl-4-carbonyl]-amino}-ethoxy)-ethoxy]-acetylamino}-ethoxy)-ethoxy]-acetic acid

2'-(4-hydroxy-phenyl)-6-(4-methyl-piperazin-1-yl)-1H,3'H-[2,5']bibenzoimidazolyl-4-carboxylic acid (2-{2-[(2-{2-[(2-{2-[(2-mercapto-ethylcarbamoyl)-methoxy]-ethoxy}-ethylcarbamoyl)-methoxy]-ethoxy}-ethylcarbamoyl)-methoxy]-ethoxy}-ethyl)-amide

C₅₀H₇₈N₆O₁₄

Refernces

• 1、 -. "Novel linker compound and Site-Specific compounds of Antibody-Drug Conjugate Comprising the Same". . . Retrieved 2020/02/07.
• 2、 Visintin, Cristina,Aliev, Abil E.,Riddall, Dieter,Baker, David,Okuyama, Masahiro,Hoi, Pui Man,Hiley, Robin,Selwood, David L.. "Membrane receptor probes: Solid-phase synthesis of biotin-Asp-PEG-arvanil derivatives". . p. 1699 - 1702. Retrieved 2007/10/03.