D(-)-Phenylglycinamide
[CAS# 6485-67-2]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glycine derivatives
• Name: D(-)-Phenylglycinamide
• Synonyms: (2R)-2-amino-2-phenylacetamide
• Protein Sequence: X
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.18
• CAS Registry Number: 6485-67-2
• EC Number: 420-370-0
• SMILES: C1=CC=C(C=C1)[C@H](C(=O)N)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 125-129 ºC
• alpha: -48.5 º (c=0.55, EtOH)
• Index of Refraction: 1.588, Calc.^*
• Boiling Point: 322.8±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 149.0±25.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H317-H319
• Precautionary Statements: P261-P264+P265-P272-P273-P280-P302+P352-P305+P351+P338-P321-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

D(-)-Phenylglycinamide, an amide derivative of phenylglycine, is an organic compound characterized by the molecular formula C8H10N2O. This compound is notable for its chirality, with the D(-) designation indicating its specific optical isomer. D(-)-Phenylglycinamide has garnered interest in various fields due to its potential applications in pharmaceuticals and biochemistry.

The discovery of D(-)-phenylglycinamide is rooted in the study of amino acids and their derivatives, which became prominent in the late 19th and early 20th centuries. Phenylglycine itself was first synthesized by the German chemist Hermann Emil Fischer in the 1880s during his investigations into amino acids and proteins. The transformation of phenylglycine into its amide form, D(-)-phenylglycinamide, involves a straightforward chemical reaction where phenylglycine is reacted with an amine or ammonia. This synthesis paved the way for further exploration of the compound's properties and its potential applications.

D(-)-Phenylglycinamide has been studied for its role in drug synthesis and development. It serves as a valuable intermediate in the production of various pharmaceuticals, particularly those targeting neurological disorders. Research has indicated that compounds derived from D(-)-phenylglycinamide may influence neurotransmitter systems, suggesting potential therapeutic benefits in treating conditions such as depression and anxiety. The ability to modify the compound's structure opens avenues for designing new medications with improved efficacy and specificity.

The chiral nature of D(-)-phenylglycinamide is particularly important in the pharmaceutical industry, where the activity of drug molecules can be highly dependent on their stereochemistry. The compound is often used as a chiral building block in the synthesis of enantiomerically pure drugs. This aspect of D(-)-phenylglycinamide is critical for developing pharmaceuticals that interact selectively with biological targets, thereby enhancing therapeutic effects and reducing side effects.

In addition to its applications in drug development, D(-)-phenylglycinamide is used in various chemical reactions and syntheses in organic chemistry. Its structural features enable it to participate in a range of chemical transformations, making it a versatile intermediate in the synthesis of more complex organic molecules. Researchers utilize D(-)-phenylglycinamide in laboratory settings to explore new synthetic pathways and to develop novel compounds with desired biological activities.

D(-)-Phenylglycinamide has also been explored for its potential use in biochemical research. Its ability to mimic certain biological substrates allows it to serve as a tool for studying enzyme mechanisms and metabolic pathways. By incorporating D(-)-phenylglycinamide into experimental designs, researchers can gain insights into the roles of amino acids and their derivatives in biological systems.

Despite its promising applications, safety precautions are essential when handling D(-)-phenylglycinamide. Like many organic compounds, it should be used with care in laboratory settings, with appropriate safety measures to minimize exposure risks. Following standard laboratory practices, including the use of personal protective equipment and proper waste disposal, is crucial.

In summary, D(-)-phenylglycinamide is a significant compound with a rich history of discovery and diverse applications in pharmaceuticals, organic synthesis, and biochemical research. Its unique properties and potential therapeutic benefits continue to inspire research, highlighting its relevance in modern science and medicine.