(s)-1-(2-Nitrophenyl)ethanamine CAS No. 198756-82-0

Product Description

(S)-1-(2-Nitrophenyl)ethanamine is the S-enantiomer of a chiral, ortho-substituted nitroaryl ethylamine. The molecule contains a benzene ring bearing an electron-withdrawing nitro group at the 2-position and, on the adjacent benzylic carbon, an (S)-configured primary amine and a methyl substituent. This stereocenter is generated either by classical resolution of the racemate with a chiral acid or, more elegantly, by asymmetric reductive amination of 2-nitroacetophenone with chiral Ru–BINAP catalysis. The resulting yellow crystalline solid (usually handled as its hygroscopic hydrochloride salt, mp ≈ 200 °C with decomposition) is soluble in methanol and must be stored dry and light-protected. While the free base is corrosive and harmful if swallowed (GHS 07), the hydrochloride salt, though milder, still irritates skin, eyes and respiratory tract. Its dual functionality—an ortho-nitro aromatic ring and a readily derivatizable chiral amine—makes (S)-1-(2-nitrophenyl)ethanamine a valued pharmaceutical intermediate and a potential chiral ligand for asymmetric catalysis.

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Product Use & Characteristics

1. Identity

   IUPAC name: (1S)-1-(2-nitrophenyl)ethanamine

   Molecular formula: C₈H₁₀N₂O₂

   Molecular weight: 166.18 g mol⁻¹

2. Structural / stereochemical features

   Single chiral center at the benzylic carbon – S-configuration

   Functional groups: 2-nitrophenyl (ortho-NO₂), primary amine (–NH₂)

3. Physical properties

   Appearance: light-yellow solid or oil (free base); yellow hydrochloride salt crystals

   Solubility: freely soluble in MeOH, EtOH, CH₂Cl₂, CHCl₃, EtOAc; low in water

   Hygroscopic hydrochloride salt; mp (HCl) 184–188 °C (dec.)

4. Stability / storage

   Light-sensitive; store dark, dry, sealed; RT or 2–8 °C for long term

5. Chemical reactivity

   Amine: basic, forms salts, amides, ureas; readily alkylated/acylated

   Nitro: electron-withdrawing; can undergo reduction to aniline; promotes electrophilic substitution

6. Synthesis methods

   Chiral resolution of racemate with chiral acid

   Asymmetric reductive amination of 2-nitroacetophenone (Ru–BINAP, enzymes)

   Published lab route: protection–nitration–deprotection (overall ~35 %)

7. Uses

   Pharmaceutical intermediate (CNS-active drug synthesis, BBB permeable)

   Chiral ligand / organocatalyst for asymmetric synthesis

   Peptoid monomer (Ns2ne) to modulate secondary structure (helix vs threaded loop)

   Precursor for nitrogen-containing heterocycles (quinolines, benzimidazoles)

8. Safety / handling

   GHS pictogram GHS07

   H-phrases: H302, H314/315, H319, H335

   Use gloves, goggles, fume hood; incompatible with acids, acid anhydrides

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