3'-Amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
[CAS# 376592-93-7]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 3'-Amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
• Synonyms: 3-(3-amino-2-hydroxyphenyl)benzoic acid
• Molecular Formula: C₁₃H₁₁NO₃
• Molecular Weight: 229.23
• CAS Registry Number: 376592-93-7
• EC Number: 814-404-7
• SMILES: C1=CC(=CC(=C1)C(=O)O)C2=C(C(=CC=C2)N)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.686, Calc.^*
• Boiling Point: 474.8±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 241.0±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

3'-Amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid is a chemical compound that belongs to the class of substituted biphenyl derivatives. This compound contains an amino group at the 3' position, a hydroxyl group at the 2' position, and a carboxyl group at the 3-position of the biphenyl structure, making it an important intermediate in organic chemistry.

The discovery of 3'-amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid can be traced back to its synthesis for various applications in chemical research and development. It is used primarily as a building block in the synthesis of more complex molecules. The combination of an amino group, a hydroxyl group, and a carboxyl group within the biphenyl structure imparts the compound with unique chemical properties that make it useful in different applications, particularly in the fields of pharmaceuticals and materials science.

In medicinal chemistry, 3'-amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid serves as a precursor for the synthesis of various biologically active compounds. The presence of the amino and hydroxyl groups on the biphenyl structure allows for further functionalization, which can improve the pharmacological properties of the resulting compounds. These modifications often aim to enhance the solubility, stability, and bioactivity of the molecules, making them suitable for drug development.

The compound is also used in the preparation of optically active materials. Due to its biphenyl backbone, it is explored for its potential in the design of liquid crystal materials, which have applications in display technologies, such as in liquid crystal displays (LCDs) and other electro-optic devices. The molecular structure of 3'-amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid provides versatility in tailoring the material properties, such as its alignment and response to external electric fields, making it a useful intermediate in the production of high-performance materials.

Furthermore, this compound has been studied for its potential use in the synthesis of coordination compounds. The amino and hydroxyl groups can serve as ligands in the formation of metal complexes, which are important in catalysis and materials science. The biphenyl structure can also provide stability and rigidity to these complexes, enhancing their performance in various catalytic processes.

In addition to its applications in organic synthesis and materials science, 3'-amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid is also useful in the study of molecular interactions. The functional groups on the biphenyl ring allow it to engage in hydrogen bonding and other non-covalent interactions, which are valuable in the design of molecular recognition systems and in the study of enzyme-substrate interactions.

In conclusion, 3'-amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid is a versatile compound with significant applications in organic synthesis, medicinal chemistry, materials science, and catalysis. Its functional groups enable the synthesis of a wide range of derivatives with enhanced properties, contributing to advances in drug development, optoelectronics, and catalysis.

References

2011. Eltrombopag. Pharmaceutical Substances.