Marfey's reagent
Basic information
- CAS
95713-52-3- Standard SMILES
C[C@H](Nc1cc(F)c([N+](=O)[O-])cc1[N+](=O)[O-])C(N)=O- InChIKey
NEPLBHLFDJOJGP-BYPYZUCNSA-N- Molecular formula
- C9H9FN4O5
- Average molar mass
- 272.19 g/mol
- Monoisotopic mass
- 272.05569756
Overview
structure given in first source
Names & identifiers
- Preferred name
- Marfey's reagent
- IUPAC
- (2S)-2-(5-fluoro-2,4-dinitroanilino)propanamide
- English name
- (S)-2-(5-fluoro-2,4-dinitrophenylaMino)propanaMide
- Molecular formula
- C9H9FN4O5
- Molecular weight
- 272.19
Names & synonyms
95713-52-3Marfey's reagent1-FD-AA1-Fluoro-2,4-dinitrophenyl-5-alaninamide1-Fluoro-2,4-dinitrophenyl-5-L-ala-NH2N(2)-(5-Fluoro-2,4-dinitrophenyl)alaninamideDTXSID60241932RefChem:155790DTXCID90164423(S)-2-((5-Fluoro-2,4-dinitrophenyl)amino)propanamideFDAA(2S)-2-[(5-fluoro-2,4-dinitrophenyl)amino]propanamide
Show more names
Marfey1-FLUORO-2,4-DINITROPHENYL-5-L-ALANINE AMIDENALPHA-(5-FLUORO-2,4-DINITROPHENYL)-L-ALANINAMIDEaninamideS REAGENTTogni’FDNP-ALA-NH2Lawesson&rsquo
MFCD00042049(S)-2-((5-Fluoro-2,4-dinitrophenyl)-amino)propanamide(2S)-2-(5-fluoro-2,4-dinitroanilino)propanamiden-alpha-(2,4-dinitro-5-fluorophenyl)-l-alaninamideNalpha-(2,4-Dinitro-5-fluorophenyl)-L-alaninamideC9H9FN4O5Na-(2,4-Dinitro-5-fluorophenyl)-L-alaninamideN-(Alpha)-(2,4-Dinitro-5-fluorophenyl)-l-alaninamide
Database identifiers
- CAS
95713-52-3- PubChem CID
- 5486955
- DTXSID
DTXSID60241932- EC Number
- 635-549-0
- Nikkaji
- J353.471E
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 147 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 382
Physicochemical properties
- Melting point
- 229 °C · 229 °C
- Boiling point
- 544.5 · 544.5±50.0 °C(Predicted)
- Density
- 1.592 · 1.592±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL, · acetone: 10 mg/mL, clear, yellow
- form
- powder
- pka
- 15.61 · 15.61±0.50(Predicted)
- color
- yellow to orange
- optical activity
- 20 · [α]20/D +56±2°, c = 1% in acetone
- BRN
- 6820069 · 6820069
- 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
- SMILES
- C(N)(=O)[C@@H](NC1=CC(F)=C([N+]([O-])=O)C=C1[N+]([O-])=O)C
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 25 · NA.25
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29242990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesFDAA 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).
Uses(S)-2-(5-fluoro-2,4-dinitrophenylaMino)propanaMide can be used for chiral amino acid analysis.
UsesN-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. DerivatizedD- andL-amino acids can be resolved and quantitated by HPLC.
General DescriptionNα-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide (FDAA) is a chiral derivatizing agent (CDA), has high enantioselectivity but low sensitivity as compared to other CDAs. It is generally used to assign the stereochemistry of amino acids in trace amounts.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…