Marfey's reagent

Base Information

• Chemical Name: Marfey's reagent
• CAS No.: 95713-52-3
• Molecular Formula: C₉H₉FN₄O₅
• Molecular Weight: 272.193
• Hs Code.: 29242990
• European Community (EC) Number: 635-549-0
• DSSTox Substance ID: DTXSID60241932
• Nikkaji Number: J353.471E
• Wikidata: Q72472517
• Mol file: 95713-52-3.mol

Synonyms:1-FD-AA;1-fluoro-2,4-dinitrophenyl-5-alaninamide;1-fluoro-2,4-dinitrophenyl-5-L-Ala-NH2;Marfey's reagent;N(2)-(5-fluoro-2,4-dinitrophenyl)alaninamide

Chemical Property of Marfey's reagent

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 6.47E-12mmHg at 25°C
• Melting Point: 229 °C
• Refractive Index: 1.641
• Boiling Point: 544.5 ºC at 760 mmHg
• PKA: 15.61±0.50(Predicted)
• Flash Point: 283.1 ºC
• PSA: 146.76000
• Density: 1.592 g/cm³
• LogP: 2.74750
• Storage Temp.: 2-8°C
• Solubility.: acetone: 10 mg/mL, clear, yellow
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 272.05569756
• Heavy Atom Count: 19
• Complexity: 382

Purity/Quality:

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

Nα-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(=O)N)NC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])F
• Isomeric SMILES: C[C@@H](C(=O)N)NC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])F
• Uses: FDAA was used as derivatizing reagent, in a study performed to understand unusual amino acids using reversed phase high performance liquid chromatography-electrospray ionization mass spectrometry (RPHPLC-ESI-MS). (S)-2-(5-fluoro-2,4-dinitrophenylaMino)propanaMide can be used for chiral amino acid analysis. N-α-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide is suitable for use for the derivatization of amino acids. glutamate and analine present in cell wall. Derivatized?D- and?L-amino acids can be resolved and quantitated by HPLC.

Technology Process of Marfey's reagent

There total 4 articles about Marfey's reagent 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%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + (S)-2-aminopropane carboxamide hydrochloride → N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (95713-52-3)

Guidance literature:

(S)-2-aminopropane carboxamide hydrochloride; With magnesium sulfate; sodium hydroxide; In water; at 20 ℃; for 4h; Inert atmosphere;

1,5-difluoro-2,4-dinitrobenzene; In acetone; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.202002599

Reference yield: 93.0%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + (S)-alaninamide hydrochloride (33208-99-0) → N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (95713-52-3)

Guidance literature:

(S)-alaninamide hydrochloride; With magnesium sulfate; sodium hydroxide; In water; acetone; at 20 ℃; for 4h;

1,5-difluoro-2,4-dinitrobenzene; In water; acetone; at 1 ℃; for 20h;

DOI:10.1021/acs.jmedchem.0c01536

Reference yield: 67.0%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + D-alaninamide (35320-22-0) → Nα-(2,4-dinitro-5-fluorophenyl)-D-alaninamide (95713-52-3)

Guidance literature:

D-alaninamide; With magnesium sulfate; sodium hydroxide; In acetone; at 20 ℃; for 3h;

1,5-difluoro-2,4-dinitrobenzene; In acetone; for 0.5h;

DOI:10.1039/c5ob01801c

upstream raw materials:

1,5-difluoro-2,4-dinitrobenzene

(S)-alaninamide hydrochloride

L-alanine amide

D-alaninamide

Downstream raw materials:

L-FDAA-L-Leu

L-FDAA-L-Pro

L-Phe-L-FDAA

L-FDAA-L-asparagine

Refernces

• 1、 van Lier, Roos C. W.,de Bruijn, A. Dowine,Roelfes, Gerard. "A Water-Soluble Iridium Photocatalyst for Chemical Modification of Dehydroalanines in Peptides and Proteins". supporting information. p. 1430 - 1437. Retrieved 2020/12/11.
• 2、 Lanigan, Rachel M.,Karaluka, Valerija,Sabatini, Marco T.,Starkov, Pavel,Badland, Matthew,Boulton, Lee,Sheppard, Tom D.. "Direct amidation of unprotected amino acids using B(OCH2CF3)3". supporting information. p. 8846 - 8849. Retrieved 2016/07/22.