Cas no 477873-22-6 ((1S,2S)-Cyclopentane-1,2-diamine dihydrochloride)

(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride is a chiral diamine compound widely used as a ligand in asymmetric synthesis and catalysis. Its rigid cyclopentane backbone and well-defined stereochemistry enable high enantioselectivity in reactions such as hydrogenations, aldol additions, and Michael reactions. The dihydrochloride salt form enhances solubility in polar solvents, facilitating handling and reactivity. This compound is particularly valued for its ability to form stable metal complexes, improving catalytic efficiency in stereocontrolled transformations. Its consistent purity and stereochemical integrity make it a reliable choice for pharmaceutical intermediates and fine chemical synthesis. The product is typically supplied as a white crystalline solid, ensuring ease of storage and precise measurement.
(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride structure
477873-22-6 structure
Product Name:(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride
CAS No:477873-22-6
MF:C5H14Cl2N2
MW:173.084059238434
MDL:MFCD10000874
CID:931385
PubChem ID:329760374
Update Time:2025-06-11

(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride Chemical and Physical Properties

Names and Identifiers

    • (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride
    • (1S,2S)-trans-1,2-Cyclopentanediamine dihydrochloride
    • (1S,2S)-trans-1,2-Cyclopentanediamine dihydrochloride, 98.5-101.5% (AT)
    • SCHEMBL1459182
    • 477873-22-6
    • starbld0000394
    • (1S,2S)-Cyclopentane-1,2-diamine--hydrogen chloride (1/2)
    • DTXSID50647787
    • (1S,2S)-TRANS-1,2-CYCLOPENTANEDIAMINE DIHYDROCHLORIDE
    • (1S,2S)-cyclopentane-1,2-diamine;dihydrochloride
    • MDL: MFCD10000874
    • Inchi: 1S/C5H12N2.2ClH/c6-4-2-1-3-5(4)7;;/h4-5H,1-3,6-7H2;2*1H/t4-,5-;;/m0../s1
    • InChI Key: VZCLGIZICFQJBX-RSLHMRQOSA-N
    • SMILES: Cl.Cl.N[C@H]1CCC[C@@H]1N

Computed Properties

  • Exact Mass: 172.0534038g/mol
  • Monoisotopic Mass: 172.0534038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 55.1
  • Covalently-Bonded Unit Count: 3
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 52?2

Experimental Properties

  • Optical Activity: [α]/D +23.5±1.0°, c =?2 in 1 M HCl

(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: 26
  • Hazardous Material Identification: Xi
  • Storage Condition:storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)

(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride Pricemore >>

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Additional information on (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride

Introduction to (1S,2S)-Cyclopentane-1,2-diamine Dihydrochloride (CAS No. 477873-22-6)

(1S,2S)-Cyclopentane-1,2-diamine dihydrochloride, identified by its CAS number 477873-22-6, is a significant compound in the field of pharmaceutical chemistry and bioorganic synthesis. This chiral diamine derivative has garnered considerable attention due to its unique structural properties and potential applications in drug development, particularly in the design of peptidomimetics and enzyme inhibitors. The dihydrochloride salt form enhances its solubility and stability, making it a valuable reagent in both academic research and industrial settings.

The< strong> stereochemistry of (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride plays a crucial role in determining its biological activity. The specific arrangement of the amino groups at the 1 and 2 positions in the cyclopentane ring confers distinct interactions with biological targets, such as enzymes and receptors. This feature has been exploited in the development of novel therapeutic agents where precise stereoselectivity is essential for efficacy and safety.

In recent years, there has been a growing interest in the use of< strong>cyclopentane derivatives as pharmacophores due to their ability to mimic natural amino acid sequences while maintaining structural flexibility. (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride serves as a building block for constructing peptidomimetics that can bind to biological targets with high affinity and selectivity. Such mimetics have shown promise in treating various diseases, including cancer, inflammation, and infectious disorders.

One of the most compelling applications of this compound is in the development of< strong>enzyme inhibitors. Enzymes are critical biological catalysts that mediate numerous metabolic pathways. By designing inhibitors that target specific enzymatic activities, researchers can modulate these pathways to treat a wide range of conditions. The< strong> chiral environment provided by (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride allows for the creation of enantiomerically pure inhibitors that exhibit improved pharmacological profiles compared to racemic mixtures.

The< strong> synthesis of (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride involves sophisticated organic transformations that highlight the ingenuity of modern synthetic chemistry. Key steps include asymmetric hydrogenation or chiral resolution techniques to achieve the desired stereochemical configuration. The formation of the dihydrochloride salt is typically achieved through quaternization followed by salt formation with hydrochloric acid. These synthetic strategies underscore the compound's complexity and the expertise required to produce it in high purity.

Recent advancements in computational chemistry have further enhanced the understanding of how (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride interacts with biological targets. Molecular modeling studies have revealed insights into its binding mode and affinity for various enzymes and receptors. These computational approaches complement experimental work by providing rapid screening of potential drug candidates and optimizing their design for improved efficacy.

The< strong> pharmaceutical industry has taken note of the potential of (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride as a lead compound for drug discovery. Several companies are exploring its use in developing novel therapeutics targeting challenging diseases such as cancer and neurodegenerative disorders. Preclinical studies have demonstrated promising results in animal models, suggesting that derivatives of this compound may have significant clinical utility.

In addition to its therapeutic applications, (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride has found utility in research settings as a biochemical probe. Its ability to interact with specific biological targets makes it a valuable tool for studying enzyme mechanisms and developing new diagnostic assays. The compound's well-defined stereochemistry also allows researchers to investigate the influence of chirality on biological activity.

The< strong>solubility profile of (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride is another factor that contributes to its widespread use in pharmaceutical research. The dihydrochloride salt form exhibits good solubility in both aqueous and organic solvents, facilitating its incorporation into various reaction systems. This versatility makes it an attractive choice for synthetic chemists working on complex molecular architectures.

The< strong> future prospects for (1S,2S)-Cyclopentane-1,2-diamine dihydrochloride are bright given its diverse applications and potential for further development. As research continues to uncover new biological targets and therapeutic strategies, this compound is likely to play an increasingly important role in drug discovery and development. Its unique structural features and stereochemical properties make it a cornerstone in the design of innovative pharmacological agents.

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