Fmoc-L-phenylalanyl chloride

Base Information

• Chemical Name: Fmoc-L-phenylalanyl chloride
• CAS No.: 103321-57-9
• Molecular Formula: C24H20ClNO3
• Molecular Weight: 405.881
• DSSTox Substance ID: DTXSID20449033
• Nikkaji Number: J362.279G
• Wikidata: Q72478713
• Mol file: 103321-57-9.mol

Synonyms:FMOC-L-PHENYLALANYL CHLORIDE;103321-57-9;(S)-(9H-Fluoren-9-yl)methyl (1-chloro-1-oxo-3-phenylpropan-2-yl)carbamate;9H-FLUOREN-9-YLMETHYL N-[(2S)-1-CHLORO-1-OXO-3-PHENYLPROPAN-2-YL]CARBAMATE;Fmoc-L-Phe-Cl;Fmoc-L-Phe-Chloride;N-Fmoc-L-Phenylalanyl Chloride;SCHEMBL4947537;DTXSID20449033;LRAXUKFFZHLNMX-QFIPXVFZSA-N;MFCD00235827;AKOS015837319;J-000934;(S)-(9H-fluoren-9-yl)methyl 1-chloro-1-oxo-3-phenylpropan-2-ylcarbamate;Carbamicacid,N-[(1S)-2-chloro-2-oxo-1-(phenylmethyl)ethyl]-,9H-fluoren-9-ylmethylester

Chemical Property of Fmoc-L-phenylalanyl chloride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 116-118℃
• Refractive Index: 1.622
• Boiling Point: 596.205 °C at 760 mmHg
• Flash Point: 314.374 °C
• PSA: 55.40000
• Density: 1.279 g/cm³
• LogP: 5.29270
• Storage Temp.: Store at 0°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 405.1131712
• Heavy Atom Count: 29
• Complexity: 555

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-l-phenylalanylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)Cl)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)Cl)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-L-phenylalanyl chloride

There total 4 articles about Fmoc-L-phenylalanyl chloride 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: 95.8%

N-Fmoc L-Phe (35661-40-6) → 2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride (103321-57-9)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00369a042

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride (103321-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / acetone

2: thionyl chloride / dichloromethane

With thionyl chloride; sodium carbonate; In dichloromethane; acetone;

DOI:10.1039/c3ra41898g

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → 2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride (103321-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / acetone

2: thionyl chloride / dichloromethane

With thionyl chloride; sodium carbonate; In dichloromethane; acetone;

DOI:10.1039/c3ra41898g

upstream raw materials:

N-Fmoc L-Phe

L-phenylalanine

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

Downstream raw materials:

N-α-Fmoc-L-phenylalanine pentafluorophenyl ester

(S)-2-{N'-tert-Butoxycarbonyl-N-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-hydrazino}-3-phenyl-propionic acid methyl ester

(S)-Ethyl 2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanamido)-3-phenylpropanoate

Fmoc-Phe-Pro-Gly-OBzl

Refernces

• 1、 Chen, Laizhong,Li, Jing,Liu, Zhenzhen,Ma, Zhao,Zhang, Wei,Du, Lupei,Xu, Wenfang,Fang, Hao,Li, Minyong. "A novel pH "off-on" fluorescent probe for lysosome imaging". . p. 13412 - 13416. Retrieved 2013.
• 2、 Kantharaju, Kamanna,Khatavi, Santosh Y.. "Eco-friendly synthesis of peptides using fmoc-amino acid chlorides as coupling agent under biphasic condition". . p. 699 - 707. Retrieved 2021/08/23.