1,2-Naphthalenedione

Basic Information

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CAS Number

524-42-5

Molecular Formula

C10H6O2

Molecular Weight

158.16 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Fine Chemicals Dyes and Pigments Organic Dyes

Basic Physical Properties

Melting Point

139-142 °C (dec.)

Boiling Point

296.1±33.0 ºC (760 Torr),

Flash Point

117.4±11.0 ºC,

Refractive Index

1.5300 (estimate)

SMILES

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C1=CC=C2C(=C1)C=CC(=O)C2=O

InChI

InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H

InChIKey

KETQAJRQOHHATG-UHFFFAOYSA-N

LogP

1.4652

Topological Polar Surface Area

34.14 Å²

Hydrogen Bond Donor/Acceptor

0 / 2

Complexity

253

Safety Information

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GHS Hazard Pictograms

H302

H315

H319

H335

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Sensitiveness

sensitive to heat and air

Synonyms & References

English

1,2-Dione-Based Compound, 8
o-Naphthoquinone
1,2-NAPHTHOQUINONE
1,2-Dihydro-1,2-diketo-naphthalene
1,2-Naftochinon
BRN 0606546
MFCD00001698
SMR000059112
AI3-14930
UNII-804K62F61Q
cid_10667
AC-15181
CHEBI:34055
F30116
AM85414
4-07-00-02417 (Beilstein Handbook Reference)
DTXSID2060171
CHEMBL52347
FT-0606470
Naphthoquinone-(1,2)
PD147991
EINECS 208-360-2
1,2-Naftochinon [Czech]
EN300-31420
ortho-naphthoquinone
NSC 9831
1,2-Naphthalenedione
NS00032507
Z324553598
Q171721
MLS000069467

MDL Number

MFCD00001698

Customs Code

2914690090

FAQ

What are the physical and chemical properties of 1,2-Naphthalenedione (CAS: 524-42-5)?

1,2-Naphthalenedione (CAS: 524-42-5) is a crystalline compound with a molecular weight of 148.13 g/mol. It has a melting point of 174-175°C and low solubility in water but is more soluble in organic solvents like ethanol and acetone. The compound is relatively stable but can undergo hydrolysis under acidic conditions. It is a colorless to white crystalline solid and exhibits good thermal stability.

How is 1,2-Naphthalenedione (CAS: 524-42-5) typically synthesized?

1,2-Naphthalenedione (CAS: 524-42-5) is often synthesized via the oximation process, where naphthaldehyde is treated with an oxidizing agent such as potassium permanganate or potassium dichromate in an acidic medium. This process yields high purity compounds with good selectivity and yield. Additionally, it can be prepared by the condensation reaction of naphthylamine and formaldehyde in the presence of an acid catalyst.

What industries use 1,2-Naphthalenedione (CAS: 524-42-5)?

1,2-Naphthalenedione (CAS: 524-42-5) is used in various industries. It is a key intermediate in the synthesis of pharmaceuticals, where it contributes to the development of anti-inflammatory and analgesic drugs. It also finds applications in the production of dyes and pigments, as well as in the development of sensors and semiconductors due to its unique optical and electronic properties.

What precautions should be taken when handling 1,2-Naphthalenedione (CAS: 524-42-5)?

When handling 1,2-Naphthalenedione (CAS: 524-42-5), it is essential to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. It should be stored in a cool, dry place away from direct sunlight and heat sources. Fume hoods should be used during handling to minimize inhalation risks. In case of spill, clean up using appropriate absorbent materials and dispose of waste according to local regulations. Safety data sheets (SDS) should be consulted for detailed handling and safety information.