1,3-Dichlorobenzene
[CAS# 541-73-1]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 1,3-Dichlorobenzene
• Synonyms: m-Dichlorobenzene
• Molecular Formula: C₆H₄Cl₂
• Molecular Weight: 147.00
• CAS Registry Number: 541-73-1
• EC Number: 208-792-1
• SMILES: C1=CC(=CC(=C1)Cl)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.288 g/mL (Expl.)
• Melting point: -25--22 ºC (Expl.)
• Index of Refraction: 1.549, Calc.^*
• Boiling Point: 180.4 ºC (760 mmHg), Calc.^*, 172-173 ºC (Expl.)
• Flash Point: 63.3 ºC, Calc.^*, 67 ºC (Expl.)
• Water solubility: 0.0123 g/100 mL (25 ºC)

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302-H315-H317-H336-H411
• Precautionary Statements: P261,

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - single exposure	STOT SE	3	H336
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	3	H331
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	1	H370
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317

• Transport Information: UN 9255

Discovory and Applicatios

1,3-Dichlorobenzene is a chemical compound that belongs to the class of chlorinated aromatic hydrocarbons. It is one of the three isomers of dichlorobenzene, with the chlorines positioned at the 1 and 3 positions on the benzene ring. This compound is used in a variety of industrial applications due to its solvent properties and its ability to serve as an intermediate in the synthesis of other chemicals.

The discovery of 1,3-dichlorobenzene can be traced back to the early studies on the chlorination of benzene, which is a process that introduces chlorine atoms into the aromatic ring structure. Dichlorobenzene is produced by chlorinating benzene in the presence of a catalyst such as iron chloride, which facilitates the substitution of hydrogen atoms with chlorine atoms on the benzene ring. The different positional isomers, including 1,3-dichlorobenzene, are formed depending on the specific positions of the chlorine atoms on the ring.

1,3-Dichlorobenzene is primarily used as a solvent in various applications, particularly in the chemical and pharmaceutical industries. It is employed as a solvent in the manufacture of resins, paints, coatings, and adhesives due to its ability to dissolve a wide range of materials. In addition to its solvent properties, 1,3-dichlorobenzene is also used as an intermediate in the production of various chemicals, including pharmaceuticals, pesticides, and dyes. It is an important building block in the synthesis of other organic compounds, which contributes to its widespread industrial use.

In the field of chemical manufacturing, 1,3-dichlorobenzene is utilized as a precursor in the synthesis of other valuable chemicals. For example, it can be used in the production of 1,3-dichloro-2-methylbenzene (also known as o-xylene), a compound that is important in the production of plastics, synthetic fibers, and solvents. Additionally, 1,3-dichlorobenzene is used in the synthesis of certain herbicides and insecticides, which further demonstrates its role as a key intermediate in the chemical industry.

1,3-Dichlorobenzene has also been studied for its potential role in environmental contamination, as it is a persistent pollutant in the environment. It is released into the atmosphere and water during industrial processes, particularly in areas where chlorinated compounds are produced. It is considered a hazardous substance due to its toxicity and potential environmental impact. 1,3-Dichlorobenzene has been detected in various environmental media, including air, water, and soil, and its presence in these environments is associated with industrial pollution.

In terms of human exposure, 1,3-dichlorobenzene can be inhaled, ingested, or absorbed through the skin, especially in occupational settings where workers may come into contact with the substance. Prolonged exposure to high levels of 1,3-dichlorobenzene has been associated with adverse health effects, including liver and kidney damage, as well as potential carcinogenicity. As a result, safety measures and regulations have been put in place to limit exposure to this compound in industrial and environmental settings.

In environmental monitoring, the detection and quantification of 1,3-dichlorobenzene are commonly performed using gas chromatography, which allows for the sensitive analysis of this compound in air and water samples. The presence of 1,3-dichlorobenzene in the environment is an indicator of industrial contamination, and efforts to reduce emissions of chlorinated compounds have been a focus of environmental protection agencies.

In conclusion, 1,3-dichlorobenzene is an important chemical compound used primarily as a solvent and intermediate in the production of various chemicals. Its industrial applications include use in the manufacturing of resins, paints, coatings, and the synthesis of other valuable chemicals. However, its potential environmental and health risks have led to regulations aimed at minimizing exposure to this compound. As a persistent pollutant, 1,3-dichlorobenzene is carefully monitored in environmental studies to assess contamination levels and to ensure public and occupational safety.

References

1962. Für die gaschromatographische Trennung von isomeren Dichlorbenzolen. Fresenius' Zeitschrift für Analytische Chemie, 188(1).
DOI: 10.1007/bf00522063

2023. Excretion kinetics of 1,3-dichlorobenzene and its urinary metabolites after controlled airborne exposure in human volunteers. Archives of Toxicology, 97(4).
DOI: 10.1007/s00204-023-03447-x

2023. Effect of weak electrical stimulation on m-dichlorobenzene biodegradation in biotrickling filters: Insights from performance and microbial community analysis. Bioresource Technology, 390.
DOI: 10.1016/j.biortech.2023.129881