4-Bromo-1-naphthylamine
[CAS# 2298-07-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 4-Bromo-1-naphthylamine
• Synonyms: 1-Amino-4-bromonaphthalene
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08
• CAS Registry Number: 2298-07-9
• EC Number: 218-944-9
• SMILES: C1=CC=C2C(=C1)C(=CC=C2Br)N

Properties

• Melting point: 102-103 ºC

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Germ cell mutagenicity	Muta.	2	H341
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

4-Bromo-1-naphthylamine is a chemical compound with notable significance in both organic synthesis and materials science. It is characterized by a naphthalene ring system with a bromine substituent at the 4-position and an amine group attached to the 1-position of the ring. This structure makes it a versatile reagent in various chemical transformations.

The discovery of 4-bromo-1-naphthylamine can be traced back to the early 20th century, when researchers were exploring the properties of substituted naphthylamines. Its synthesis typically involves the bromination of 1-naphthylamine, a process that introduces the bromine atom into the 4-position of the naphthalene ring. This is achieved through electrophilic aromatic substitution reactions, often using bromine or brominating agents in the presence of a catalyst.

In organic synthesis, 4-bromo-1-naphthylamine serves as a valuable intermediate for the preparation of various other chemical compounds. Its bromine and amine groups are reactive sites that can participate in further chemical reactions, including nucleophilic substitutions and cross-coupling reactions. These reactions are utilized to create complex molecules for applications in pharmaceuticals, agrochemicals, and dyes.

One of the primary applications of 4-bromo-1-naphthylamine is in the synthesis of fluorescent dyes and pigments. The compound's unique structure allows it to form derivatives with distinctive optical properties, which are used in various applications such as fluorescence microscopy and material staining. These dyes are essential for research and industrial applications where precise colorimetric analysis is required.

Additionally, 4-bromo-1-naphthylamine is used in the development of organic electronic materials. Its ability to form stable and conjugated systems makes it suitable for creating organic semiconductors and light-emitting materials. These materials are used in electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where their electrical and optical properties are critical for device performance.

The compound's role extends to medicinal chemistry as well. It is used as a starting material for the synthesis of biologically active molecules and potential pharmaceutical agents. The bromine and amine groups can be modified to develop new compounds with specific biological activities, aiding in the discovery of novel therapeutic agents.

Overall, 4-bromo-1-naphthylamine is a significant compound in both synthetic organic chemistry and material science. Its applications span from dye and pigment development to organic electronics and medicinal chemistry, highlighting its versatility and importance in various fields of research and industry.