1-Bromo-3-hydroxynaphthalene

Basic Information

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CAS Number

5498-31-7

Molecular Formula

C10H7BrO

Molecular Weight

223.07 g/mol

Chemical Classification

Agricultural Chemicals Pesticides Herbicides

Basic Physical Properties

Melting Point

122-124 ºC

SMILES

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C1=CC=C2C(=C1)C=C(C=C2Br)O

InChI

InChI=1S/C10H7BrO/c11-10-6-8(12)5-7-3-1-2-4-9(7)10/h1-6,12H

InChIKey

PQNQMYMGUXGWTG-UHFFFAOYSA-N

LogP

3.307900000000002

Topological Polar Surface Area

20.23 Å²

Hydrogen Bond Donor/Acceptor

1 / 1

Complexity

160

Synonyms & References

English

2-Naphthalenol, 4-bromo-
1-Bromo-3-hydroxynaphthalene
4-bromonaphthalen-2-ol
2-Naphthalenol,4-bromo
4-Brom-[2]naphthol
4-Brom-2-hydroxy-naphthalin
4-Bromo-2-hydroxynaphthalene
4-Bromo-2-naphthol
4-bromonaphth-2-ol
4-bromo-naphthalen-2-ol
4-Bromo-2-naphthalenol
1-Bromo-3-naphthol
4-bromonapthalen-2-ol
1-bromo-naphtalen-3-ol
1-bromo-naphtalene-3-ol
4-Brom-2-oxy-naphthalin
PQNQMYMGUXGWTG-UHFFFAOYSA-N
FCH1333251
AK208611
SY029500
10.14272/PQNQMYMGUXGWTG-UHFFFAOYSA-N.1
AS-49862
DTXSID40477818
AKOS022506524
5498-31-7
PB43035
N11764
EN300-116055
DA-39801
AMY20074
doi:10.14272/PQNQMYMGUXGWTG-UHFFFAOYSA-N.1

MDL Number

MFCD01712260

Customs Code

2908199090

FAQ

What are the physical and chemical properties of 1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7)?

1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7) is a crystalline solid with a molecular weight of approximately 231.06 g/mol. It has a low solubility in water (less than 1 g/100 mL at 20°C) but is more soluble in organic solvents like ethanol, acetone, and dichloromethane. This compound is relatively stable under neutral conditions but can react with strong bases to form hydroxide salts. It is used as a precursor in organic synthesis and exhibits certain reactivity towards nucleophiles and reducing agents.

How is 1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7) typically synthesized?

1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7) is typically synthesized by the Brönsted oxidation of 3-hydroxynaphthalene using fuming sulfuric acid in the presence of acetic anhydride. The reaction is carried out under anhydrous conditions to prevent side reactions. The yield is usually around 70-80%, and the product is isolated by recrystallization from ethanol or acetone. This method provides a high degree of selectivity for the bromination of the hydroxyl group.

What industries use 1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7)?

1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7) is primarily used in the pharmaceutical industry as a precursor for the synthesis of various naphthylamines and other biologically active compounds. It is also used in the manufacturing of dyes and pigments, and in some cases, in the production of semiconductors and electronic materials due to its unique electronic properties.

What precautions should be taken when handling 1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7)?

When handling 1-Bromo-3-hydroxynaphthalene (CAS: 5498-31-7), it is important to wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. The compound should be used in a well-ventilated area or under a fume hood to minimize exposure to bromine vapor. Spills should be cleaned up with care using appropriate absorbents, and the area should be thoroughly rinsed with water. Always refer to the Safety Data Sheet (SDS) for specific handling and disposal instructions.