Fmoc-3-bromo-L-phenylalanine

Base Information

• Chemical Name: Fmoc-3-bromo-L-phenylalanine
• CAS No.: 220497-48-3
• Molecular Formula: C24H20BrNO4
• Molecular Weight: 466.331
• Hs Code.: 29223900
• DSSTox Substance ID: DTXSID00370316
• Wikidata: Q72478152
• Mol file: 220497-48-3.mol

Synonyms:220497-48-3;Fmoc-3-bromo-L-phenylalanine;FMOC-PHE(3-BR)-OH;(s)-n-fmoc-3-bromophenylalanine;(2S)-3-(3-bromophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic Acid;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-bromophenyl)propanoic acid;FMOC-3-BROMO-L-PHE-OH;FMOC-L-PHE(3-BR)-OH;SCHEMBL18301540;DTXSID00370316;fmoc-phe(3-br)-oh, AldrichCPR;(S)-Fmoc-3-bromo-L-phenylalanine;MFCD01311744;AKOS015837233;AKOS015895729;AC-9635;AM82713;AS-15746;CS-0101112;A50191;EN300-3412113;N-Fluorenemethoxycarbonyl-D-3-Bromo Phenylalanine;J-300374;3-Bromo-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine;(2S)-3-(3-bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(3-BROMOPHENYL)PROPANOIC ACID

Chemical Property of Fmoc-3-bromo-L-phenylalanine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.31E-18mmHg at 25°C
• Melting Point: 144.2 °C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 660.8 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 353.4 °C
• PSA: 75.63000
• Density: 1.459 g/cm³
• LogP: 5.37440
• Storage Temp.: Store at 0°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 465.05757
• Heavy Atom Count: 30
• Complexity: 592

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-3-bromo-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=CC=C4)Br)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)Br)C(=O)O

Technology Process of Fmoc-3-bromo-L-phenylalanine

There total 1 articles about Fmoc-3-bromo-L-phenylalanine 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:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0) → (9H-fluoren-9-yl)methyl (S)-(3-bromo)phenylalanine (220497-48-3,220497-81-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 25 ℃; for 22h;

DOI:10.1016/j.bmc.2018.03.023

Reference yield: 94.0%

(9H-fluoren-9-yl)methyl (S)-(3-bromo)phenylalanine (220497-48-3,220497-81-4) + methylamine hydrochloride (593-51-1) → (9H-fluoren-9-yl)methyl (S)-(3-(3-bromophenyl)-1-(methylamino)-1-oxopropan-2-yl)carbamate

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 12.5h;

DOI:10.1016/j.bmc.2018.03.023

Reference yield: 47.6%

Fmoc-Leu-Wang resin + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + (9H-fluoren-9-yl)methyl (S)-(3-bromo)phenylalanine (220497-48-3,220497-81-4) + Boc-Tyr(t-Bu)-OH (47375-34-8) → H2N-Tyr-Gly-Gly-(meta-Br)Phe-Leu-OH

Guidance literature:

Fmoc-Leu-Wang resin; In dichloromethane; N,N-dimethyl-formamide; for 0.25h; Wang resin

With piperidine; In dichloromethane; N,N-dimethyl-formamide; at 70 ℃; for 0.0833333h; Wang resin Inert atmosphere;

N-(fluoren-9-ylmethoxycarbonyl)glycine; (9H-fluoren-9-yl)methyl (S)-(3-bromo)phenylalanine; Boc-Tyr(t-Bu)-OH; Further stages;

DOI:10.3390/molecules24244542

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(S)-2-amino-3-(3-bromophenyl)propanoic acid

Refernces