Cas no 135859-36-8 ((R)-4,4,4-Trifluorobutane-1,3-diol)

(R)-4,4,4-Trifluorobutane-1,3-diol is a chiral fluorinated diol with significant utility in synthetic organic chemistry and pharmaceutical applications. Its trifluoromethyl group enhances metabolic stability and lipophilicity, making it valuable in the design of bioactive molecules. The (R)-enantiomer offers stereochemical precision for asymmetric synthesis, particularly in constructing fluorinated intermediates. The compound’s dual hydroxyl groups provide versatile reactivity for derivatization, enabling the formation of heterocycles, esters, or ethers. Its high purity and well-defined configuration ensure reproducibility in research and industrial processes. This diol is particularly useful in medicinal chemistry for developing fluorinated analogs with improved pharmacokinetic properties.
(R)-4,4,4-Trifluorobutane-1,3-diol structure
135859-36-8 structure
Product Name:(R)-4,4,4-Trifluorobutane-1,3-diol
CAS No:135859-36-8
MF:C4H7F3O2
MW:144.092392206192
MDL:MFCD03093014
CID:105601
PubChem ID:2779068
Update Time:2025-05-21

(R)-4,4,4-Trifluorobutane-1,3-diol Chemical and Physical Properties

Names and Identifiers

    • (R)-4,4,4-Trifluorobutane-1,3-diol
    • (3R)-4,4,4-TRIFLUOROBUTANE-1,3-DIOL
    • 1,3-Butanediol,4,4,4-trifluoro-, (3R)-
    • (R)-4,4,4-trifluoro-1,3-butanediol
    • (R)-4,4,4-trifluoro-butane-1,3-diol
    • AC1L2Y14
    • AC1Q6BKI
    • CHEBI:53168
    • CPD-8668
    • Picrocrocin
    • saffron-bitter
    • UNII-ON5B022511
    • MFCD03093015
    • AKOS005063785
    • 135859-36-8
    • DTXSID701292570
    • A18170
    • SCHEMBL2988228
    • (R)-4,4,4-Trifluorobutane-1,3-diol, technical grade
    • 1,3-Butanediol,4,4,4-trifluoro-,(3R)-
    • CS-0527397
    • A18167
    • (3R)-4,4,4-Trifluoro-1,3-butanediol
    • MDL: MFCD03093014
    • Inchi: 1S/C4H7F3O2/c5-4(6,7)3(9)1-2-8/h3,8-9H,1-2H2/t3-/m1/s1
    • InChI Key: SCLIIHMYYAHRGK-GSVOUGTGSA-N
    • SMILES: FC([C@@H](CCO)O)(F)F

Computed Properties

  • Exact Mass: 144.03981
  • Monoisotopic Mass: 144.04
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 2
  • Complexity: 80.4
  • 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
  • Topological Polar Surface Area: 40.5A^2
  • XLogP3: 0.4

Experimental Properties

  • Density: 1.354
  • Boiling Point: 94-95/4.5mm
  • Flash Point: 67.6°C
  • PSA: 40.46
  • LogP: 0.29200

(R)-4,4,4-Trifluorobutane-1,3-diol Security Information

  • Hazard Statement: Irritant
  • Hazardous Material Identification: Xi

(R)-4,4,4-Trifluorobutane-1,3-diol Pricemore >>

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Additional information on (R)-4,4,4-Trifluorobutane-1,3-diol

Chemical Profile of (R)-4,4,4-Trifluorobutane-1,3-diol (CAS No. 135859-36-8)

(R)-4,4,4-Trifluorobutane-1,3-diol is a fluorinated diol compound with significant applications in the field of pharmaceuticals and specialty chemicals. Its unique structural features, characterized by the presence of three fluorine atoms and two hydroxyl groups, make it a versatile intermediate in organic synthesis. The compound is identified by the Chemical Abstracts Service Number (CAS No.) 135859-36-8, which distinguishes it in the scientific literature and industrial databases.

The stereochemistry of this compound is crucial, with the (R) configuration indicating a specific spatial arrangement of atoms that influences its reactivity and biological activity. This aspect is particularly important in pharmaceutical research, where enantiomeric purity can significantly impact the efficacy and safety of drug candidates.

In recent years, there has been growing interest in fluorinated compounds due to their enhanced metabolic stability and improved binding affinity to biological targets. The introduction of fluorine atoms into molecular structures often leads to increased lipophilicity and resistance to enzymatic degradation, making such compounds valuable in drug design. (R)-4,4,4-Trifluorobutane-1,3-diol exemplifies this trend, as its fluorinated backbone provides a scaffold for developing novel therapeutic agents.

One of the most compelling applications of (R)-4,4,4-Trifluorobutane-1,3-diol lies in its role as a chiral building block in asymmetric synthesis. Chiral compounds are essential in medicinal chemistry because they often exist as enantiomers with distinct pharmacological properties. The (R)-enantiomer, in particular, has been explored in the development of beta-blockers, antiviral agents, and other therapeutic molecules where stereochemical specificity is critical.

Recent studies have highlighted the utility of this compound in the synthesis of fluorinated analogs of known drugs. By leveraging its reactive hydroxyl groups and fluorinated side chain, researchers have been able to create derivatives with improved pharmacokinetic profiles. For instance, modifications to the trifluorobutyl moiety have led to compounds with enhanced solubility and bioavailability, which are key factors in drug formulation.

The pharmaceutical industry has also shown interest in (R)-4,4,4-Trifluorobutane-1,3-diol for its potential as a precursor in the synthesis of protease inhibitors. Proteases are enzymes that play a crucial role in various physiological processes and are often targeted by antiviral and anticancer drugs. The fluorine atoms in this compound can enhance binding interactions with protease active sites, leading to more effective inhibition.

Beyond pharmaceuticals, this compound finds applications in materials science and agrochemicals. Its unique properties make it a valuable intermediate for synthesizing polymers with enhanced thermal stability and chemical resistance. Additionally, fluorinated diols have been explored as intermediates in the production of herbicides and pesticides due to their ability to interact selectively with biological targets.

The synthesis of (R)-4,4,4-Trifluorobutane-1,3-diol typically involves multi-step organic reactions that require careful optimization to achieve high enantiomeric purity. Advances in catalytic methods and chiral resolution techniques have made it more feasible to produce this compound on an industrial scale. These advancements are particularly important for pharmaceutical applications where impurities can compromise the efficacy and safety of final products.

In conclusion, (R)-4,4,4-Trifluorobutane-1,3-diol (CAS No. 135859-36-8) is a multifaceted compound with broad applications across multiple industries. Its structural features and stereochemical properties make it a valuable tool in pharmaceutical research and industrial chemistry. As scientific understanding continues to evolve,this compound is likely to play an even greater role in the development of innovative therapies and materials.

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