2,2'-Dibromobiphenyl
[CAS# 13029-09-9]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 2,2'-Dibromobiphenyl
• Synonyms: 2,2'-Dibromo-1,1'-biphenyl; 2,2'-Dibromodiphenyl; NSC 91566; PBB 4; o,o'-Dibromobiphenyl
• Molecular Formula: C₁₂H₈Br₂
• Molecular Weight: 312.00
• CAS Registry Number: 13029-09-9
• EC Number: 625-732-3
• SMILES: C1=CC=C(C(=C1)C2=CC=CC=C2Br)Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting Point: 78-82 ºC (Expl.)
• Index of Refraction: 1.626, Calc.^*
• Boiling Point: 332.9±17.0 ºC (760 mmHg), Calc.^*
• Flash Point: 180.0±20.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302-H315-H319-H335-H400-H410
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovory and Applicatios

2,2'-Dibromobiphenyl is a chemical compound belonging to the biphenyl family, where two benzene rings are connected by a single bond. In this compound, two bromine atoms are attached to the benzene rings at the 2-position, making it a halogenated biphenyl derivative. This substance is of interest in various chemical and industrial applications, including its role as a precursor in the synthesis of other organic compounds and as a key intermediate in the production of certain pharmaceuticals and materials. Its unique chemical properties and reactivity make it valuable in different fields, ranging from material science to environmental research.

The discovery of 2,2'-dibromobiphenyl can be traced back to the early 20th century when halogenated biphenyls became the subject of increasing interest due to their diverse applications in the chemical industry. The introduction of bromine atoms into the biphenyl structure alters the compound's physical and chemical properties, such as its solubility, melting point, and reactivity. These changes are significant because they enhance the substance's utility as an intermediate in organic synthesis. Like other halogenated biphenyls, 2,2'-dibromobiphenyl was explored for its potential to undergo substitution reactions, which made it useful for creating a variety of chemical derivatives.

2,2'-Dibromobiphenyl has several applications, particularly in the synthesis of organic compounds. One major use of this compound is as a building block in the synthesis of more complex chemicals, such as pharmaceuticals, agrochemicals, and liquid crystals. The presence of the bromine atoms in the molecule provides specific sites for chemical reactions, allowing for controlled modifications of the compound. This reactivity is particularly useful in the formation of new carbon-carbon bonds, which is essential in the synthesis of various organic molecules.

The compound is also used in the preparation of materials with specialized electronic properties. As a precursor for liquid crystals, 2,2'-dibromobiphenyl is significant in the electronics industry, particularly in the development of displays and other optoelectronic devices. The liquid crystals derived from halogenated biphenyls, including 2,2'-dibromobiphenyl, exhibit unique alignment properties when subjected to an electric field, making them ideal for use in devices such as televisions, computer screens, and monitors. The ability to control the optical properties of these materials by modifying their chemical structure has made halogenated biphenyls crucial in the advancement of modern display technologies.

In addition to its applications in electronics, 2,2'-dibromobiphenyl has been explored for its potential in other fields, such as catalysis and the production of specialty polymers. The bromine atoms in the compound are useful in facilitating specific reactions that require the activation of certain bonds, making it a valuable intermediate in various catalytic processes. The compound has also been tested as a precursor for the development of high-performance polymers, which are used in a range of industries, from aerospace to medical devices.

However, despite its industrial uses, 2,2'-dibromobiphenyl is not without its environmental and health concerns. Like other halogenated compounds, it can be toxic and persistent in the environment, posing risks to both human health and ecosystems. The substance is classified as a persistent organic pollutant (POP) due to its ability to bioaccumulate in living organisms and persist in the environment for extended periods. As such, its production and use are subject to regulatory oversight, and efforts are being made to develop safer alternatives for certain applications.

In conclusion, 2,2'-dibromobiphenyl is an important chemical compound with various applications in organic synthesis, material science, and electronics. Its discovery and development have contributed to advancements in several industries, though concerns regarding its environmental impact highlight the need for careful management and ongoing research into more sustainable alternatives.