(1S,2R)-(-)-cis-1-Amino-2-indanol
[CAS# 126456-43-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: (1S,2R)-(-)-cis-1-Amino-2-indanol
• Synonyms: (1S,2R)-(-)-cis-1-Amino-2-hydroxyindane
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• CAS Registry Number: 126456-43-7
• EC Number: 603-144-8
• SMILES: C1[C@H]([C@H](C2=CC=CC=C21)N)O

Properties

• Melting point: 117-121 °C
• alpha: -62 ° (c=0.5, CHCl3)
• Water solubility: slightly soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(1S,2R)-(-)-cis-1-amino-2-indanol is an important chemical compound with unique properties and wide applications in organic chemistry and pharmaceuticals. Its unique stereochemistry and functional groups make it an essential substance in various chemical transformations and drug development processes.

The discovery of (1S,2R)-(-)-cis-1-amino-2-indanol stems from the study of chiral amines and their applications in asymmetric synthesis. The compound is a chiral secondary amine with a cis configuration characterized by (1S,2R) stereochemistry. The specific arrangement of its atoms gives it unique chemical properties that make it valuable in a variety of applications.

One of the main applications of (1S,2R)-(-)-cis-1-amino-2-indanol is in asymmetric synthesis. Its chiral center enables it to act as an efficient chiral auxiliary or ligand in catalytic processes. This property is particularly useful in the synthesis of enantiomerically pure compounds, which is essential for the pharmaceutical industry to develop highly effective drugs with minimal side effects.

In the pharmaceutical industry, (1S,2R)-(-)-cis-1-amino-2-indanol is useful as an intermediate in the synthesis of a variety of bioactive molecules. Its chirality allows it to influence the stereochemistry of the final product, which is important for the activity and selectivity of the agent. The compound is involved in drug development for a range of diseases, including neurological and cardiovascular diseases.

In addition, (1S,2R)-(-)-cis-1-amino-2-indanol can be used in the development of chiral materials. Its ability to influence the stereochemistry of polymerizable compounds makes it valuable for creating specialty polymers with specific optical and electronic properties. This application is relevant to the fields of materials science and nanotechnology.

Overall, (1S,2R)-(-)-cis-1-amino-2-indanol is a versatile compound with important applications in asymmetric synthesis, pharmaceuticals, and materials science. Its unique stereochemical properties make it a valuable tool for creating enantiomerically pure compounds and developing new materials with tailored properties. As research continues, the applications of (1S,2R)-(-)-cis-1-amino-2-indanol are expected to expand, highlighting its importance in modern chemical and industrial processes.

References

1992. Chiral Inhibitors of HIV-1 Protease Using 1-Amino-2-indanol. Journal of Medicinal Chemistry, 35(22).
DOI: 10.1021/jm00101a011

2017. Chiral 1-Amino-2-indanol as a Ligand in Organometallic Catalysis. Organometallics, 36(14).
DOI: 10.1021/acs.organomet.7b00345

2015. Lipase-Catalyzed Kinetic Resolution of 1-Amino-2-indanol. Journal of Molecular Catalysis B: Enzymatic, 122.
DOI: 10.1016/j.molcatb.2015.09.004