(2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]propanamide

• ChemBase ID: 69235
• Molecular Formular: C9H9FN4O5
• Molecular Mass: 272.1899632
• Monoisotopic Mass: 272.05569763
• SMILES: C(=O)([C@H](C)Nc1c(cc(c(c1)F)[N+](=O)[O-])[N+](=O)[O-])N
• Canonical SMILES: NC(=O)[C@@H](Nc1cc(F)c(cc1[N+](=O)[O-])[N+](=O)[O-])C
• InChI: InChI=1S/C9H9FN4O5/c1-4(9(11)15)12-6-2-5(10)7(13(16)17)3-8(6)14(18)19/h2-4,12H,1H3,(H2,11,15)/t4-/m0/s1
• InChIKey: NEPLBHLFDJOJGP-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]propanamide
• IUPAC Traditional name: (2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]propanamide
• Synonyms: Marfey’s reagent; (S)-2-((5-Fluoro-2,4-dinitrophenyl)-amino)propanamide; FDAA; Nα-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide; (S)-2-((5-Fluoro-2,4-dinitrophenyl)amino)propanamide; Marfey 试剂; Nα-(2,4-二硝基-5-氟苯基)-L-丙氨酰胺

Database IDs

• CAS Number: 95713-52-3
• MDL Number: MFCD00042049
• Beilstein Number: 6820069
• PubChem SID: 24886197; 162034963; 24894168
• PubChem CID: 5486955

CALCULATED PROPERTIES

• Acid pKa: 9.6447
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.3584696
• LogD (pH = 7.4): 1.3561574
• Log P: 1.3584992
• Molar Refractivity: 61.5099 cm^3
• Polarizability: 22.030888 Å^3
• Polar Surface Area: 141.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble10 mg/mL, clear, bright yellow
• Apperance: powder
• Optical Rotation: [α]20/D +56±2°, c = 1% in acetone

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0%; ≥99.0% (sum of enantiomers, TLC); 95+%
• Grade: for chiral derivatization
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C9H9FN4O5

DETAILS

Sigma Aldrich - D7906

Application
For derivatization and resolution of amino acids. Derivatized D- and L-amino acids can be resolved and quantitated by HPLC.

Sigma Aldrich - 42095

Other Notes
Chiral reagent used for the assay of enantiomeric purity of amino acids with HPLC1,2,3

Sigma Aldrich - 71478

Other Notes
Derivatization reagent for the assay of unusual chiral α-amino acid analogs1