2,7-Dihydroxynaphthalene
[CAS# 582-17-2]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Naphthalenes
• Name: 2,7-Dihydroxynaphthalene
• Synonyms: 2,7-Naphthalenediol
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• CAS Registry Number: 582-17-2
• EC Number: 209-478-7
• SMILES: C1=CC(=CC2=C1C=CC(=C2)O)O

Properties

• Melting point: 184-189 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302-H315-H317-H318-H319-H335-H411
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Skin sensitization	Skin Sens.	1B	H317

Discovery and Applications

2,7-Dihydroxynaphthalene is a derivative of naphthalene and a polyhydroxy aromatic compound. It was first discovered in the early 20th century during the study of naphthalene derivatives and their chemical reactivity. The compound is characterized by two hydroxyl groups attached to the naphthalene ring at the 2 and 7 positions, unlike other hydroxynaphthalene isomers.

The molecular formula of 2,7-dihydroxynaphthalene is C10H8O2 and it is a crystalline solid. Its melting point is about 152°C. The presence of hydroxyl groups on the naphthalene ring increases its solubility in polar solvents compared to its parent compound naphthalene. This arrangement also affects its chemical reactivity and potential applications.

In chemical synthesis, 2,7-dihydroxynaphthalene is a valuable intermediate and it is used as a building block for the synthesis of various naphthyl compounds. The hydroxyl groups facilitate further chemical modifications, resulting in complex molecules with potential applications in pharmaceuticals and materials science.

2,7-Dihydroxynaphthalene is used in the synthesis of dyes and pigments. Its hydroxyl groups participate in complexation reactions with metal ions to form bright and stable colorants for textiles, inks and coatings.

In environmental chemistry, 2,7-dihydroxynaphthalene is used as a reference standard for the detection and quantification of naphthalene derivatives in environmental samples. Its presence can indicate pollution levels and help assess environmental health.

2,7-Dihydroxynaphthalene has been studied for its potential antioxidant properties. Studies have shown that it may exhibit protective effects against oxidative stress, making it a subject of study related to cellular health and disease prevention.

Handling 2,7-dihydroxynaphthalene requires standard laboratory safety practices, wearing appropriate protective gear such as gloves and goggles to prevent contact. Ensure that areas where this compound is used or stored are well ventilated. Store the compound in a cool, dry place away from direct sunlight and incompatible materials to maintain its stability and effectiveness.

If handled properly, 2,7-dihydroxynaphthalene generally has minimal impact on the environment. The compound is moderately biodegradable. Proper disposal methods should be followed to minimize environmental impact, especially with regard to waste management and chemical spill response.

References

2023. Novel synthetic methods toward the synthesis of Betti bases: an update. Chemical Papers, 77(10).
DOI: 10.1007/s11696-023-02825-0

2021. One-pot synthesis of phenazines from 2-naphthols with 1, 2-diamines and its biological importance and binding studies. Journal of Chemical Sciences, 133(1).
DOI: 10.1007/s12039-021-01907-4