2,4-Dichloro-L-β-homophenylglycine
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2,4-Dichloro-L-β-homophenylglycine

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Category
β−Amino acids
Catalog number
BAT-006717
CAS number
778571-53-2
Molecular Formula
C9H9Cl2NO2
Molecular Weight
234.08
2,4-Dichloro-L-β-homophenylglycine
IUPAC Name
(3R)-3-amino-3-(2,4-dichlorophenyl)propanoic acid
Synonyms
H-Phg(2,4-Cl2)-(C#CH2)OH; H-β-Phe(2,4-Cl2)-OH; (R)-3-Amino-3-(2,4-dichlorophenyl)propanoic acid
Appearance
White powder
Purity
≥ 99% (HPLC, Chiral purity)
Density
1.447g/cm3
Melting Point
239-243 °C(dec.)
Boiling Point
371.1°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H9Cl2NO2/c10-5-1-2-6(7(11)3-5)8(12)4-9(13)14/h1-3,8H,4,12H2,(H,13,14)/t8-/m1/s1
InChI Key
QGHQDRDWQIHGKZ-MRVPVSSYSA-N
Canonical SMILES
C1=CC(=C(C=C1Cl)Cl)C(CC(=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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