Cas no 127199-16-0 (tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate)

Tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate is a chiral fluorinated cyclopropyl carbamate derivative, commonly employed as a key intermediate in organic synthesis and pharmaceutical research. Its stereospecific (1R,2S) configuration and fluorine substitution enhance its utility in the design of bioactive molecules, particularly in medicinal chemistry for probing steric and electronic effects. The tert-butyloxycarbonyl (Boc) protecting group offers stability under basic conditions while allowing selective deprotection under acidic conditions, facilitating controlled synthetic transformations. This compound’s well-defined stereochemistry and functional group compatibility make it valuable for constructing complex scaffolds, such as protease inhibitors or fluorinated analogs, with precise control over molecular geometry and reactivity.
tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate structure
127199-16-0 structure
Product Name:tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate
CAS No:127199-16-0
MF:C8H14FNO2
MW:175.200665950775
MDL:MFCD09955394
CID:63865
PubChem ID:10442211
Update Time:2025-08-05

tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate Chemical and Physical Properties

Names and Identifiers

    • (1R-cis)-(2-Fluorocyclopropyl)carbamic acid tert-butyl ester
    • CARBAMIC ACID, (2-FLUOROCYCLOPROPYL)-, 1,1-DIMETHYLETHYL ESTER, (1R-CIS)- (9CI)
    • tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate
    • (1R,2S)-1-(t-butoxycarbonylamino)-2-fluorocyclopropane
    • AB1004287
    • SureCN3178971
    • tert-butyl N-((1R,2S)-2-fluorocyclopropyl)carbamate
    • tert-butyl N-< (1R,2S)-2-fluorocyclopropyl> carbamate
    • tert-butyl ((1R,2S)-2-fluorocyclopropyl)carbamate(WX191572)
    • Carbamic acid,N-[(1R,2S)-2-fluorocyclopropyl]-, 1,1-dimethylethyl ester
    • 127199-16-0
    • rel-tert-Butyl ((1R,2S)-2-fluorocyclopropyl)carbamate
    • AC-8341
    • CS-0047458
    • tert-Butyl [(1R,2S)-2-fluorocyclopropyl]carbamate
    • SCHEMBL3178971
    • EN300-19650486
    • MFCD09955394
    • AKOS015950771
    • Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, cis- (9CI)
    • EN300-1654607
    • rac-tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate
    • t-Butyl ((1R,2S)-2-fluorocyclopropyl)carbamate
    • tert-Butyl ((1R,2S)-2-fluorocyclopropyl)carbamate
    • rel-tert-Butyl((1R,2S)-2-fluorocyclopropyl)carbamate
    • DTXSID80439910
    • W19684
    • 105919-35-5
    • (1R,2S)-1-(Boc-amino)-2-fluorocyclopropane
    • MDL: MFCD09955394
    • Inchi: 1S/C8H14FNO2/c1-8(2,3)12-7(11)10-6-4-5(6)9/h5-6H,4H2,1-3H3,(H,10,11)/t5-,6+/m0/s1
    • InChI Key: VWSDKMQGCVVQBV-NTSWFWBYSA-N
    • SMILES: F[C@H]1C[C@H]1NC(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 175.10100
  • Monoisotopic Mass: 175.10085685g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 188
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: 1.5
  • Topological Polar Surface Area: 38.3?2

Experimental Properties

  • Density: 1.09
  • Boiling Point: 238.4°C at 760 mmHg
  • Flash Point: 98°C
  • Refractive Index: 1.444
  • PSA: 38.33000
  • LogP: 2.01240

tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate Pricemore >>

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Additional information on tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate

Comprehensive Overview of tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate (CAS No. 127199-16-0)

The compound tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate (CAS No. 127199-16-0) is a fluorinated cyclopropyl derivative with significant applications in pharmaceutical and organic synthesis. Its unique stereochemistry and functional groups make it a valuable intermediate in the development of bioactive molecules. Researchers and industries are increasingly interested in this compound due to its potential in drug discovery, particularly in the design of protease inhibitors and other therapeutic agents.

One of the key features of tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate is its stereospecificity, which plays a crucial role in determining the biological activity of the final products. The presence of the fluorine atom enhances the metabolic stability and bioavailability of the molecules derived from this intermediate. This property aligns with the growing demand for fluorinated compounds in medicinal chemistry, as they often exhibit improved pharmacokinetic profiles.

In recent years, the search for novel synthetic routes and green chemistry approaches has gained traction among chemists. The synthesis of tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate has been optimized to reduce waste and improve yield, addressing the industry's focus on sustainability. Techniques such as flow chemistry and catalysis have been explored to enhance the efficiency of its production, making it a topic of interest in academic and industrial research.

The compound's CAS No. 127199-16-0 is frequently searched in databases like SciFinder and Reaxys, reflecting its relevance in chemical research. Users often inquire about its physical properties, such as melting point, solubility, and spectral data (NMR, IR), which are critical for its application in lab settings. Additionally, questions about its stability under various conditions and compatibility with other reagents are common, highlighting the need for detailed technical documentation.

Another area of interest is the role of tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate in the development of chiral drugs. As the pharmaceutical industry shifts toward enantiomerically pure therapeutics, this compound serves as a versatile building block. Its incorporation into drug candidates has been explored in treatments for central nervous system disorders and infectious diseases, aligning with global health priorities.

From a commercial perspective, the demand for high-purity intermediates like tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate is rising. Suppliers and manufacturers are investing in advanced analytical techniques, such as HPLC and GC-MS, to ensure product quality. This trend is driven by the need for reliable and consistent raw materials in drug development pipelines.

In conclusion, tert-butyl N-[(1R,2S)-2-fluorocyclopropyl]carbamate (CAS No. 127199-16-0) is a compound of significant scientific and industrial importance. Its applications in medicinal chemistry, coupled with advancements in sustainable synthesis, make it a focal point for ongoing research. As the field evolves, this intermediate is likely to remain a key player in the discovery of next-generation therapeutics.

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