2,4-Difluoro-L-Phenylalanine
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2,4-Difluoro-L-Phenylalanine

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Category
Fluorinated amino acids
Catalog number
BAT-014113
CAS number
31105-93-8
Molecular Formula
C9H9F2NO2
Molecular Weight
201.17
2,4-Difluoro-L-Phenylalanine
IUPAC Name
(2S)-2-amino-3-(2,4-difluorophenyl)propanoic acid
Synonyms
L-Phe(2,4-DiF)-OH; (S)-2-Amino-3-(2,4-difluorophenyl)propionic acid; L-2,4-Difluorophe
Purity
≥ 98% by Chiral HPLC
Density
1.379±0.06 g/cm3(Predicted)
Boiling Point
306.1±42.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H9F2NO2/c10-6-2-1-5(7(11)4-6)3-8(12)9(13)14/h1-2,4,8H,3,12H2,(H,13,14)/t8-/m0/s1
InChI Key
UEFLPVKMPDEMFW-QMMMGPOBSA-N
Canonical SMILES
C1=CC(=C(C=C1F)F)CC(C(=O)O)N
1. 2-(3,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide
Aneeka Mahan, Ray J Butcher, Prakash S Nayak, B Narayana, H S Yathirajan Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 1;69(Pt 3):o402-3. doi: 10.1107/S1600536813002341. Epub 2013 Feb 20.
In the title compound, C19H17Cl2N3O2, there are three mol-ecules (A, B and C) in the asymmetric unit and each differs in the conformation adopted. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 44.5 (2) and 56.2 (2)°, respectively in A, 51.1 (2) and 54.1 (2)° in B, and 53.8 (2) and 54.6 (2)° in C. The dihedral angles between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings are 54.8 (2), 76.2 (2) and 77.5 (2)° in mol-ecules A, B and C, respectively, while the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings make dihedral angles of 45.3 (2), 51.2 (2) and 42.8 (2)°, respectively. In the crystal, two of the mol-ecules are linked through N-H⋯O hydrogen bonding to an adjoining mol-ecule, forming dimers of the R2(2)(10) type, while the third mol-ecule forms such dimers with itself. C-H⋯O inter-actions link the dimers.
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