2-Bromobenzo[b]naphtho[2,3-d]furan
[CAS# 1627917-16-1]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: 2-Bromobenzo[b]naphtho[2,3-d]furan
• Molecular Formula: C₁₆H₉BrO
• Molecular Weight: 297.15
• CAS Registry Number: 1627917-16-1
• EC Number: 841-744-3
• SMILES: C1=CC=C2C=C3C(=CC2=C1)C4=C(O3)C=CC(=C4)Br

Properties

• Solubility: Insoluble (5.3E^-6 g/L) (25 ºC), Calc.^*
• Density: 1.557±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.777, Calc.^*
• Boiling Point: 442.9±18.0 ºC (760 mmHg), Calc.^*
• Flash Point: 221.7±21.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H302-H315-H319-H335-H341
• Precautionary Statements: P203-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Germ cell mutagenicity	Muta.	2	H341

Discovory and Applicatios

2-Bromobenzo[b]naphtho[2,3-d]furan is an organic compound that features a fused polycyclic structure consisting of a benzene ring, a naphthalene ring, and a furan ring, with a bromine atom attached to the benzo group. This compound is a member of the class of polycyclic aromatic compounds, which are known for their stability and chemical reactivity due to their conjugated systems of π-electrons.

The compound is synthesized through methods that involve the bromination of a suitable precursor, typically using bromine or bromine-containing reagents in the presence of a catalyst. The specific position of the bromine atom on the aromatic ring is essential for the compound's reactivity and subsequent applications.

2-Bromobenzo[b]naphtho[2,3-d]furan is used primarily in the field of organic synthesis, where it serves as a versatile intermediate for the preparation of more complex organic molecules. The presence of the bromine atom makes the compound suitable for use in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are crucial for the formation of carbon-carbon bonds and are widely employed in the construction of larger, more complex organic structures, including materials for organic electronics and pharmaceuticals.

In particular, this compound has potential applications in the development of organic semiconductors and optoelectronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The fused aromatic system of 2-bromobenzo[b]naphtho[2,3-d]furan is conducive to charge transport and light emission, making it an interesting candidate for incorporation into materials designed for use in electronic and optical devices. The bromine atom serves to facilitate interactions with other organic materials, further enhancing its potential in these applications.

Moreover, 2-bromobenzo[b]naphtho[2,3-d]furan can be employed in the synthesis of novel bioactive compounds. Its structure, which includes both a furan ring and a bromine atom, is conducive to the design of molecules that could interact with biological targets. Research into the biological properties of polycyclic aromatic compounds has led to the discovery of some that exhibit anti-cancer, anti-inflammatory, or anti-viral activities, although specific studies on 2-bromobenzo[b]naphtho[2,3-d]furan in this context are limited.

In summary, 2-bromobenzo[b]naphtho[2,3-d]furan is a polycyclic aromatic compound that plays a significant role in organic synthesis, particularly in reactions that require the formation of carbon-carbon bonds. Its applications are prominent in the fields of organic electronics, such as OLEDs and OPVs, and potentially in the development of bioactive compounds. Its reactivity, due to the presence of the bromine atom, makes it a valuable intermediate in the design of advanced materials and complex organic molecules.