Cas no 4187-53-5 ((1S)-1-(4-nitrophenyl)ethan-1-amine)

(1S)-1-(4-Nitrophenyl)ethan-1-amine is a chiral amine compound featuring a nitrophenyl substituent, commonly utilized as a key intermediate in asymmetric synthesis and pharmaceutical applications. Its stereospecific (S)-configuration makes it valuable for producing enantiomerically pure compounds, particularly in the development of active pharmaceutical ingredients (APIs) and fine chemicals. The presence of the nitro group enhances reactivity in reduction and substitution reactions, facilitating further functionalization. This compound exhibits high chemical stability and compatibility with a range of reaction conditions, making it suitable for use in multi-step synthetic routes. Its well-defined chirality ensures precise control over stereochemical outcomes in catalytic and stoichiometric transformations.
(1S)-1-(4-nitrophenyl)ethan-1-amine structure
4187-53-5 structure
Product Name:(1S)-1-(4-nitrophenyl)ethan-1-amine
CAS No:4187-53-5
MF:C8H10N2O2
MW:166.177201747894
MDL:MFCD00137390
CID:44822
PubChem ID:1268055
Update Time:2025-11-02

(1S)-1-(4-nitrophenyl)ethan-1-amine Chemical and Physical Properties

Names and Identifiers

    • (S)-1-(4-Nitrophenyl)ethanamine
    • (S)-4-NITRO-ALPHA-METHYLBENZYLAMINE
    • (S)-1-(4-NITROPHENYL)-ETHYLAMINE
    • S-O-NITRO-A-METHYLBENZYLAMINE
    • (S)-A-METHYL-4-NITROBENZYLAMINE
    • (S)-p-Nitro-alpha-methylbenzylamine
    • Nitrosolve
    • Benzenemethanamine, α-methyl-4-nitro-, (αS)-
    • (S)-1-(4-Nitrophenyl)ethylamine
    • (S)-1-(p-nitrophenyl)ethylamine
    • (S)-N-[1-(4-nitrophenyl)ethyl] acetamide
    • 1-(S)-4-Nitrophenyl ethylamine
    • AC1LOQVF
    • AC1Q29I0
    • AG-F-48801
    • PubChem23250
    • SureCN352795
    • AC-26775
    • DTXSID70361438
    • (S)-(+)-Alpha-methyl-4-nitrobenzylamine
    • (S)-1-(4-nitrophenyl)ethan-1-amine
    • F53523
    • Benzenemethanamine,a-methyl-4-nitro-,(aS)-
    • A6876
    • EN300-89295
    • (S)-alpha-methyl-4-nitrobenzylamine
    • 4187-53-5
    • (1S)-1-(4-nitrophenyl)ethan-1-amine
    • Benzenemethanamine, -methyl-4-nitro-, (S)-
    • (1S)-1-(4-nitrophenyl)ethanamine
    • SCHEMBL352795
    • 1-(4-Nitrophenyl)ethanamine #
    • AMY32685
    • AKOS015833478
    • DB-005563
    • EN300-224775
    • BDBM626109
    • MDL: MFCD00137390
    • Inchi: 1S/C8H10N2O2/c1-6(9)7-2-4-8(5-3-7)10(11)12/h2-6H,9H2,1H3/t6-/m0/s1
    • InChI Key: RAEVOBPXEHVUFY-LURJTMIESA-N
    • SMILES: [O-][N+](C1C=CC(=CC=1)[C@H](C)N)=O

Computed Properties

  • Exact Mass: 166.0743
  • Monoisotopic Mass: 166.074
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 159
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.3
  • Topological Polar Surface Area: 71.8A^2

Experimental Properties

  • Density: 1.199
  • Boiling Point: 288.8oC at 760 mmHg
  • Flash Point: 128.4 oC
  • Refractive Index: 1.576
  • PSA: 69.16
  • LogP: 2.83800

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Additional information on (1S)-1-(4-nitrophenyl)ethan-1-amine

Comprehensive Guide to (1S)-1-(4-nitrophenyl)ethan-1-amine (CAS No. 4187-53-5): Properties, Applications, and Market Insights

(1S)-1-(4-nitrophenyl)ethan-1-amine (CAS No. 4187-53-5) is a chiral amine compound with significant importance in pharmaceutical and chemical research. This optically active molecule features a 4-nitrophenyl group attached to an ethanamine backbone, making it a valuable intermediate in asymmetric synthesis. The compound's chiral purity and nitro aromatic functionality have drawn considerable attention from researchers exploring novel drug candidates and specialty chemicals.

The growing demand for chiral building blocks in drug development has positioned (1S)-1-(4-nitrophenyl)ethan-1-amine as a compound of interest. Its molecular structure (C8H10N2O2) with a molecular weight of 166.18 g/mol offers unique reactivity patterns that synthetic chemists frequently utilize. Recent literature indicates increasing applications in the development of enzyme inhibitors and pharmaceutical intermediates, particularly in neurological and cardiovascular research areas.

From a chemical properties perspective, (1S)-1-(4-nitrophenyl)ethan-1-amine typically appears as a yellow to orange crystalline powder with moderate solubility in organic solvents. The compound's optical rotation and stereochemical purity are critical quality parameters that researchers carefully monitor. Advanced analytical techniques like HPLC and chiral chromatography are commonly employed to characterize this substance, ensuring it meets the stringent requirements of pharmaceutical applications.

The synthesis of CAS 4187-53-5 typically involves asymmetric reduction methods or resolution techniques to obtain the desired (S)-enantiomer. Modern synthetic approaches emphasize green chemistry principles, with researchers developing more efficient catalytic systems to improve yield and enantiomeric excess. These advancements align with current industry trends toward sustainable chemical production and atom economy.

In pharmaceutical applications, (1S)-1-(4-nitrophenyl)ethan-1-amine serves as a key intermediate for various bioactive molecules. Its structural features make it particularly valuable in designing dopamine receptor modulators and serotonergic compounds. Recent patent literature reveals its incorporation in potential treatments for neurological disorders, capitalizing on the compound's ability to interact with specific neurotransmitter systems.

The global market for chiral amine derivatives like 4187-53-5 has shown steady growth, driven by increasing demand from the pharmaceutical sector. Market analysts project continued expansion as drug developers seek more sophisticated asymmetric synthesis building blocks. Quality specifications for this compound have become more rigorous, with pharmaceutical-grade material commanding premium pricing in specialty chemical markets.

Storage and handling of (1S)-1-(4-nitrophenyl)ethan-1-amine require standard laboratory precautions for nitroaromatic compounds. While not classified as highly hazardous, proper chemical safety protocols should be followed, including protection from light and moisture. The compound's stability under various conditions has been well-documented, with recommended storage in amber containers at controlled temperatures.

Analytical characterization of CAS 4187-53-5 typically includes NMR spectroscopy, mass spectrometry, and polarimetry to confirm identity and purity. Recent advancements in analytical technology have enabled more precise determination of enantiomeric purity, a critical parameter for pharmaceutical applications. These developments support the compound's growing use in quality-by-design approaches to drug development.

Regulatory status of (1S)-1-(4-nitrophenyl)ethan-1-amine varies by jurisdiction, but it generally falls under standard chemical regulations rather than controlled substance categories. Manufacturers and researchers should consult local regulations regarding chemical registration and safety data sheet requirements. The compound's increasing use in pharmaceutical research may lead to more specific regulatory attention in the future.

Future research directions for 4187-53-5 include exploration of its potential in catalysis and material science applications. Some studies suggest possible utility in designing novel ligand systems for asymmetric catalysis or as building blocks for advanced materials. The compound's versatility continues to attract interest from diverse scientific disciplines beyond its traditional pharmaceutical applications.

For researchers sourcing (1S)-1-(4-nitrophenyl)ethan-1-amine, quality verification through certificate of analysis review is essential. Reputable suppliers provide comprehensive characterization data, including chromatographic purity and optical rotation specifications. The market has seen increasing availability of custom synthesis services for this compound, accommodating specific research needs with various purity grades and packaging options.

Environmental considerations for CAS 4187-53-5 follow standard protocols for nitroaromatic compounds. While not classified as a persistent environmental pollutant, proper waste disposal methods should be employed according to local regulations. The pharmaceutical industry's focus on green chemistry has prompted investigations into more environmentally benign synthetic routes for this and related compounds.

In conclusion, (1S)-1-(4-nitrophenyl)ethan-1-amine represents an important chiral building block with growing significance in pharmaceutical research and development. Its unique structural features and synthetic versatility position it as a valuable tool for medicinal chemists exploring new therapeutic agents. As asymmetric synthesis techniques advance and demand for enantiomerically pure intermediates increases, this compound will likely see expanded applications across multiple scientific disciplines.

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