Fmoc-Phe(4-CN)-OH

Base Information

• Chemical Name: Fmoc-Phe(4-CN)-OH
• CAS No.: 173963-93-4
• Molecular Formula: C25H20N2O4
• Molecular Weight: 412.445
• Hs Code.: 2926 90 70
• European Community (EC) Number: 812-307-4
• DSSTox Substance ID: DTXSID10426257
• Nikkaji Number: J1.362.567K
• Wikidata: Q72478219
• Mol file: 173963-93-4.mol

Synonyms:173963-93-4;Fmoc-Phe(4-CN)-OH;Fmoc-L-4-Cyanophenylalanine;Fmoc-4-cyano-L-phenylalanine;fmoc-dl-4-cyanophenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-cyanophenyl)propanoic acid;Fmoc-D-4-Cyanophenylalanine;L-Phenylalanine, 4-cyano-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2S)-3-(4-cyanophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;MFCD00672559;fmoc-p-cyano-l-phenylalanine;SCHEMBL178773;DTXSID10426257;AKOS005137956;AKOS015889883;AC-9895;AM82778;CS-W008527;HY-W008527;DS-15201;A50200;Fmoc-Phe(4-CN)-OH, >=98.0% (HPLC);EN300-1168570;A811587;J-010954;Fmoc-L-4-Cyanophenylalanine (Fmoc-L-Phe(4-CN)-OH);4-Cyano-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine;N-(9H-Fluorene-9-ylmethoxycarbonyl)-4-cyano-L-phenylalanine;(2S)-3-(4-cyanophenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(s)-2-(((9h-fluoren-9-yl)methoxy)carbonylamino)-3-(4-cyanophenyl)propanoic acid;N-Fmoc-4-cyano-L-phenylalanine

Chemical Property of Fmoc-Phe(4-CN)-OH

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.38E-19mmHg at 25°C
• Melting Point: 189 °C
• Refractive Index: 1.672
• Boiling Point: 678.7 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 364.3 °C
• PSA: 99.42000
• Density: 1.35 g/cm³
• LogP: 4.48358
• Storage Temp.: 2-8°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 412.14230712
• Heavy Atom Count: 31
• Complexity: 671

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-4-cyano-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)C#N)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)C#N)C(=O)O
• Uses: Fmoc-L-4-cyanophenylalanine can be used as neuroprotective compounds.

Technology Process of Fmoc-Phe(4-CN)-OH

There total 4 articles about Fmoc-Phe(4-CN)-OH 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: 89.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-4-Cyanophenylalanine (167479-78-9) → Fmoc-L-4-cyanophenylalanine (173963-93-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jm950112e

Reference yield:

N-acetyl-4-cyano-α-(ethoxycarbonyl)phenylalanine ethyl ester (52117-01-8) → Fmoc-L-4-cyanophenylalanine (173963-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaOH, 2.) 6 M aq. HCl / 1.) EtOH, reflux, 18 h, 2.) EtOH

2: 70.7 percent / aq. LiOH / 56 h / porcine kidney acylase, pH 7.2-7.5

3: 89 percent / aq. Na₂CO₃ / dioxane / 1.5 h / 0 - 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; sodium carbonate; In 1,4-dioxane;

DOI:10.1021/jm950112e

Reference yield:

4-cyanobenzyl bromide (17201-43-3) → Fmoc-L-4-cyanophenylalanine (173963-93-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) EtONa / 1.) EtOH, 0-5 deg C, 45 min, 2.) EtOH, reflux, 2.5 h

2: 1.) NaOH, 2.) 6 M aq. HCl / 1.) EtOH, reflux, 18 h, 2.) EtOH

3: 70.7 percent / aq. LiOH / 56 h / porcine kidney acylase, pH 7.2-7.5

4: 89 percent / aq. Na₂CO₃ / dioxane / 1.5 h / 0 - 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; sodium ethanolate; sodium carbonate; In 1,4-dioxane;

DOI:10.1021/jm950112e

upstream raw materials:

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

(S)-4-Cyanophenylalanine

N-acetyl-4-cyano-α-(ethoxycarbonyl)phenylalanine ethyl ester

4-cyanobenzyl bromide

Downstream raw materials:

DT₁₀₅₈-138-7

DT₁₀₅₈-143-3

Refernces