96233-02-2

Basic information

• Product Name: Acetamide, 2-chloro-2-fluoro-N-[(1S)-1-phenylethyl]-, (2R)-
• CAS NO: 96233-02-2
• Molecular Formula: C10H11ClFNO
• Molecular Weight: 215.655
• Mol File: 96233-02-2.mol

Chemical Properties

• CAS DataBase Reference: Acetamide, 2-chloro-2-fluoro-N-[(1S)-1-phenylethyl]-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, 2-chloro-2-fluoro-N-[(1S)-1-phenylethyl]-, (2R)-(96233-02-2)
• EPA Substance Registry System: Acetamide, 2-chloro-2-fluoro-N-[(1S)-1-phenylethyl]-, (2R)-(96233-02-2)

Safety Data

• Hazardous Substances Data: 96233-02-2(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 79-38-9 Chlorotrifluoroethylene 

Downstream Products

• 129172-16-3 (S)-N-[(S)-1-phenylethyl]-2-(1,3-dioxo-2-isoindolinyl)-2-fluoroethanamide 
• 126215-56-3 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-fluoro-N-((R)-1-phenyl-ethyl)-acetamide 
• 129172-17-4 (R)-N-[(S)-1-phenylethyl]-2-(1,3-dioxo-2-isoindolinyl)-2-fluoroethanamide 
• 126215-56-3 (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-fluoro-N-((R)-1-phenyl-ethyl)-acetamide 
• 129095-52-9 N-[(S)-1-phenylethyl]-2,2-bis(1,3-dioxo-2-isoindolinyl)ethanamide 
• 129095-53-0 (R)-N-[(S)-1-phenylethyl]-2-fluoro-2-iodoethanamide 
• 129117-19-7 (S)-N-[(S)-1-phenylethyl]-2-fluoro-2-iodoethanamide 

Relevant articles and documents

A Comparison of Laue and Monochromatic X-ray Analyses of a Small-Molecule Crystal

As part of the development of the Laue method for quantitative structure analysis we report on a detailed comparison of monochromatic (Mo Kα and Cu Kα) and synchrotron radiation Laue data from the same crystal of a small molecule, (S)-2-chloro-2-fluoro-N-

Synthesis and reactions of α-fluoro-α-amino amides

N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected α-fluoro-α-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The α-fluoro-α-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding α-fluorobetaine amide, and subsequent acidic hydrolysis led to α-fluorobetaine as the first example of an 'unprotected' α-fluoroamino acid.

Synthesis of α-heterosubstituted glycine derivatives from dihaloethanamides

A range of protected α-heterosubstituted analogues of glycine were synthesised from starting materials of the type CHFX-CONHR [X = Cl, Br, I; R = CH2Ph, (s)-CHMePh]; the final products included derivatives of glycine possessing N, O, F or S in the α-position, and the first example of a free α-fluoro-α-amino acid (α-fluorobetaine) whose structure was confirmed by X-ray crystal structure determination.

Asymmetric synthesis of protected α-fluoroglycines

Single crystal x-ray structure determination of a key fluoroiodoacetamide gives access to protected α-fluoroglycines of known absolute stereochemistry.