Cas no 2171171-33-6 ((1R)-1-(2-nitrophenyl)ethyl chloroformate)

(1R)-1-(2-Nitrophenyl)ethyl chloroformate is a chiral derivatizing agent widely used in the synthesis and resolution of enantiomerically pure compounds. Its key advantages include high reactivity as an acylating agent, enabling efficient protection of amines and alcohols under mild conditions. The presence of the 2-nitrophenyl group enhances stereoselectivity in asymmetric transformations, making it valuable for chiral auxiliary applications. This compound is particularly useful in peptide synthesis and pharmaceutical intermediates, where precise enantiomeric control is critical. Its stability and ease of handling further contribute to its utility in organic synthesis. Careful storage under anhydrous conditions is recommended to maintain reactivity.
(1R)-1-(2-nitrophenyl)ethyl chloroformate structure
2171171-33-6 structure
Product Name:(1R)-1-(2-nitrophenyl)ethyl chloroformate
CAS No:2171171-33-6
MF:C9H8ClNO4
MW:229.617121696472
CID:6326416
PubChem ID:165571190
Update Time:2025-05-20

(1R)-1-(2-nitrophenyl)ethyl chloroformate Chemical and Physical Properties

Names and Identifiers

    • (1R)-1-(2-nitrophenyl)ethyl chloroformate
    • 2171171-33-6
    • EN300-1612893
    • Inchi: 1S/C9H8ClNO4/c1-6(15-9(10)12)7-4-2-3-5-8(7)11(13)14/h2-6H,1H3/t6-/m1/s1
    • InChI Key: QRAXFOMREJXVAK-ZCFIWIBFSA-N
    • SMILES: ClC(=O)O[C@H](C)C1C=CC=CC=1[N+](=O)[O-]

Computed Properties

  • Exact Mass: 229.0141854g/mol
  • Monoisotopic Mass: 229.0141854g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 253
  • 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: 2.9
  • Topological Polar Surface Area: 72.1?2

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Additional information on (1R)-1-(2-nitrophenyl)ethyl chloroformate

Comprehensive Overview of (1R)-1-(2-nitrophenyl)ethyl chloroformate (CAS No. 2171171-33-6)

(1R)-1-(2-nitrophenyl)ethyl chloroformate (CAS No. 2171171-33-6) is a specialized chiral compound widely utilized in organic synthesis and pharmaceutical research. Its unique structure, featuring a nitrophenyl group and a chloroformate moiety, makes it a valuable intermediate for constructing complex molecules. The compound's enantiomeric purity (1R configuration) is particularly significant for applications requiring stereoselective reactions, such as asymmetric catalysis or drug development.

In recent years, the demand for chiral building blocks like (1R)-1-(2-nitrophenyl)ethyl chloroformate has surged due to advancements in green chemistry and sustainable synthesis. Researchers are increasingly focusing on atom-efficient reactions and catalytic processes, where this compound serves as a key reagent. Its role in forming carbamates and carbonates under mild conditions aligns with the industry's shift toward eco-friendly methodologies.

The compound's nitrophenyl group enhances its reactivity in nucleophilic substitution reactions, while the chloroformate moiety acts as an efficient leaving group. This dual functionality enables its use in peptide coupling, protecting group strategies, and polymer chemistry. Notably, its application in prodrug design has gained attention, as it facilitates controlled release mechanisms in therapeutic agents.

From an analytical perspective, CAS No. 2171171-33-6 is characterized by techniques such as HPLC, NMR spectroscopy, and mass spectrometry to ensure purity and structural integrity. Stability studies under varying pH and temperature conditions are critical for optimizing its storage and handling protocols. These insights are vital for industries prioritizing quality-by-design (QbD) principles.

Emerging trends in AI-driven drug discovery have also highlighted the importance of chiral intermediates like (1R)-1-(2-nitrophenyl)ethyl chloroformate. Computational models often predict its reactivity patterns, accelerating the development of novel bioactive compounds. Additionally, its compatibility with continuous flow chemistry systems makes it a candidate for scalable manufacturing processes.

In summary, (1R)-1-(2-nitrophenyl)ethyl chloroformate represents a versatile tool for modern synthetic chemists. Its alignment with sustainability goals, stereochemical precision, and broad applicability in pharmaceutical innovation ensures its continued relevance in scientific and industrial contexts.

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