(2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]-3-methylbutanamide

• ChemBase ID: 137338
• Molecular Formular: C11H13FN4O5
• Molecular Mass: 300.2431232
• Monoisotopic Mass: 300.08699776
• SMILES: CC(C)[C@@H](C(=O)N)Nc1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])F
• Canonical SMILES: CC([C@@H](C(=O)N)Nc1cc(F)c(cc1[N+](=O)[O-])[N+](=O)[O-])C
• InChI: InChI=1S/C11H13FN4O5/c1-5(2)10(11(13)17)14-7-3-6(12)8(15(18)19)4-9(7)16(20)21/h3-5,10,14H,1-2H3,(H2,13,17)/t10-/m0/s1
• InChIKey: ZTFFRKNPAXXEBL-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]-3-methylbutanamide
• IUPAC Traditional name: (2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]-3-methylbutanamide
• Synonyms: Nα-(2,4-Dinitro-5-fluorophenyl)-L-valinamide; Nα-(2,4-二硝基-5-氟苯基)-L-缬氨酰胺

Database IDs

• CAS Number: 132679-61-9
• MDL Number: MFCD00155636
• PubChem SID: 24867344; 162231601; 24866371
• PubChem CID: 14718555

CALCULATED PROPERTIES

• Acid pKa: 9.774612
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.2459724
• LogD (pH = 7.4): 2.2442567
• Log P: 2.2459943
• Molar Refractivity: 72.5139 cm^3
• Polarizability: 25.6241 Å^3
• Polar Surface Area: 146.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173-177 °C; 173-177 °C(lit.)
• Optical Rotation: [α]20/D +14.0±1.5°, c = 2% in acetone; [α]20/D +14.0°, c = 2 in acetone

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: ≥98%; ≥98.0%; ≥98.0% (sum of enantiomers, HPLC)
• Grade: Flukabrand™ ChiraSelect reagent; for chiral derivatization
• Optical Purity: ee: ≥99; enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Linear Formula: FC6H2(NO2)2NH[CHCH(CH3)2]CONH2

DETAILS

Sigma Aldrich - 437069

Application
Useful for the analysis of chiral amino acids by HPLC.1 Valine analog of Marfey′s reagent that provides improved resolution in the separation of D- and L-amino acids as well as analogs of phenylalanine and proline.2 It has also aided in understanding the separation mechanism of these reagents.3
Legal Information
Flukabrand is a trademark of Sigma-Aldrich GmbH

Sigma Aldrich - 42102

Other Notes
Chiral derivatizing agent (chiral Sanger′s Reagent) for determining the enantiomeric purity of amino acids with HPLC1; This analogue of Marfey′s reagent can also be used with amines2,3
Packaging
100 mg in glass bottle