(R)-5,7-Difluorochroman-4-OL
[CAS# 1270294-05-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: (R)-5,7-Difluorochroman-4-OL
• Molecular Formula: C₉H₈F₂O₂
• Molecular Weight: 186.16
• CAS Registry Number: 1270294-05-7
• EC Number: 859-874-4
• SMILES: C1COC2=C([C@@H]1O)C(=CC(=C2)F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.540, Calc.^*
• Boiling Point: 228.4±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 113.0±23.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary 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
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

(R)-5,7-Difluorochroman-4-OL is a significant chemical compound in the realm of organic chemistry, notable for its distinctive structure and diverse applications. This molecule is characterized by its chroman core with two fluorine atoms positioned at the 5 and 7 positions, and a hydroxyl group at the 4-position. The (R) configuration denotes a specific stereochemistry that plays a crucial role in its chemical behavior and applications.

The discovery of (R)-5,7-Difluorochroman-4-OL was part of research focusing on developing new fluorinated compounds with potential biological and industrial applications. Fluorination is a key modification in organic chemistry that can significantly alter the chemical and biological properties of a molecule. The presence of fluorine atoms in (R)-5,7-Difluorochroman-4-OL enhances its stability and influences its interactions with biological targets, making it a valuable compound for various applications.

The chroman structure, which consists of a benzene ring fused with a tetrahydro-pyran ring, is known for its presence in several biologically active compounds. The introduction of fluorine atoms at the 5 and 7 positions of the chroman ring increases the compound's lipophilicity and metabolic stability. This modification can improve the molecule's bioavailability and potency when used in pharmaceutical applications. The hydroxyl group at the 4-position adds further functionality, making the compound suitable for various chemical reactions and interactions.

One of the primary applications of (R)-5,7-Difluorochroman-4-OL is in drug discovery and development. The fluorine atoms in the molecule can enhance the binding affinity and selectivity of the compound towards specific biological targets. This feature is particularly useful in the development of pharmaceuticals, where precise interactions with biological macromolecules are crucial for efficacy and safety. The hydroxyl group can participate in hydrogen bonding interactions, further influencing the compound's biological activity and pharmacokinetics.

The compound also finds applications in medicinal chemistry as a starting material for synthesizing other biologically active molecules. Its structure allows for further chemical modifications that can lead to the development of new drugs with enhanced properties. The (R) configuration of the compound can be crucial for ensuring the desired biological activity, as chirality plays a significant role in drug-receptor interactions.

In addition to its pharmaceutical applications, (R)-5,7-Difluorochroman-4-OL is also used in materials science. The fluorinated chroman structure can be employed to create advanced materials with specific electronic or optical properties. For instance, it can be used to synthesize organic semiconductors or fluorescent dyes, leveraging its unique chemical features to achieve desired material characteristics.

The synthesis of (R)-5,7-Difluorochroman-4-OL involves several steps, including the introduction of fluorine atoms and the hydroxyl group. Typically, the fluorination is achieved through selective fluorination reactions, while the hydroxyl group can be introduced via reduction or substitution reactions. The stereochemistry of the compound is carefully controlled during synthesis to ensure the correct (R) configuration.

Overall, (R)-5,7-Difluorochroman-4-OL is a valuable compound in organic chemistry with diverse applications in drug discovery and materials science. Its unique structure and functional groups provide opportunities for developing new pharmaceuticals and advanced materials with specific properties. Ongoing research and exploration of this compound are expected to reveal further applications and benefits.