Benzene-1,4-dicarbonyl chloride

C8H4Cl2O2

benzene-1,4-dicarbonyl chloride

CAS100-20-9

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Identification

CAS Number
100-20-9
EC Number
202-829-5
UN Number
2923
PubChem CID
7488

Physical-chemical properties

Molecular Formula
C8H4Cl2O2
Molar Mass
203.02 g/mol
IUPAC Name
benzene-1,4-dicarbonyl chloride

Chemical Identifiers

InChI
InChI=1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H
InChI Key
LXEJRKJRKIFVNY-UHFFFAOYSA-N

Overview

Benzene-1,4-dicarbonyl chloride (CAS 100-20-9) is an aromatic acyl chloride compound featuring two reactive carbonyl chloride functional groups positioned para to each other on a benzene ring. This organic chemical compound, also known by its EC number 202-829-5, represents a crucial building block in synthetic organic chemistry with the molecular formula C8H4Cl2O2 and molecular weight of 203.02 g/mol. The symmetrical structure of benzene-1,4-dicarbonyl chloride makes it particularly valuable for creating polymeric materials and cross-linked chemical structures due to its bifunctional nature. As an acyl chloride derivative, this compound exhibits high reactivity toward nucleophiles, readily undergoing hydrolysis in the presence of moisture to form the corresponding dicarboxylic acid. The dual carbonyl chloride functionality allows for diverse chemical transformations, including amide formation, esterification reactions, and polymer synthesis. Similar to other acyl chlorides in this chemical family, such as 4-methoxybenzoyl chloride, benzene-1,4-dicarbonyl chloride requires careful handling due to its moisture sensitivity and corrosive properties. The compound finds extensive application in the pharmaceutical industry as an intermediate for drug synthesis, particularly in the preparation of anti-inflammatory and antimicrobial agents. In polymer chemistry, it serves as a key monomer for producing high-performance polyamides and polyesters with enhanced thermal and mechanical properties. Additionally, the chemical industry utilizes this compound in the synthesis of dyes, pigments, and specialty chemical intermediates. Transportation classification under ADR Class 8 indicates its corrosive nature, necessitating appropriate safety measures during handling and storage. OYSI maintains reliable supply chains for benzene-1,4-dicarbonyl chloride to support diverse industrial applications across European markets.

Safety & Classification

No Hazard Classification

This substance is not classified as hazardous according to CLP Regulation (EC) No 1272/2008.

Transport (ADR)

UN Number2923
ADR Class8
Packing GroupII
Tunnel CodeE
Proper Shipping NameBenzen-1,4-dicarbonyldichlorid
Marine PollutantNo

Frequently Asked Questions

What is benzene-1,4-dicarbonyl chloride?

Benzene-1,4-dicarbonyl chloride is an organic chemical compound with the molecular formula C8H4Cl2O2 and CAS number 100-20-9. This aromatic compound consists of a benzene ring with two carbonyl chloride (-COCl) groups attached at the 1,4-positions (para-positions). With a molecular weight of 203.02 g/mol, it serves as an important intermediate in organic synthesis and industrial chemical processes.

What are the physical and chemical properties of benzene-1,4-dicarbonyl chloride?

Benzene-1,4-dicarbonyl chloride is typically a white to pale yellow crystalline solid at room temperature. The compound is highly reactive due to its acid chloride functional groups, making it moisture-sensitive and prone to hydrolysis in the presence of water. It exhibits limited solubility in water but dissolves readily in organic solvents such as dichloromethane, chloroform, and aromatic hydrocarbons.

What is benzene-1,4-dicarbonyl chloride used for?

Benzene-1,4-dicarbonyl chloride is primarily used as a chemical intermediate in the synthesis of polymers, pharmaceuticals, and specialty chemicals. It serves as a key building block for producing polyamides, polyesters, and cross-linking agents. The compound is also utilized in the manufacture of dyes, pigments, and agrochemicals, where its dual reactive sites enable the formation of complex molecular structures.

How should benzene-1,4-dicarbonyl chloride be handled safely?

Benzene-1,4-dicarbonyl chloride requires careful handling with appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and protective clothing. Work should be conducted in a well-ventilated area or fume hood to avoid inhalation exposure. The compound is corrosive and can cause severe skin and eye irritation. Always handle in dry conditions to prevent hydrolysis reactions that can generate hydrochloric acid.

How should benzene-1,4-dicarbonyl chloride be stored correctly?

Benzene-1,4-dicarbonyl chloride must be stored in a cool, dry place away from moisture and humidity to prevent hydrolysis. Keep containers tightly sealed in a well-ventilated storage area away from incompatible materials such as alcohols, amines, and bases. Storage temperature should be controlled to prevent decomposition, and the storage area should be equipped with appropriate spill containment measures and ventilation systems.

What should be done in case of contact with benzene-1,4-dicarbonyl chloride?

Immediate action is required upon contact with benzene-1,4-dicarbonyl chloride. For skin contact, remove contaminated clothing and rinse the affected area with plenty of water for at least 15 minutes. In case of eye contact, flush immediately with water and seek medical attention. If inhaled, move the person to fresh air and provide respiratory support if needed. Always seek professional medical advice for any exposure incident.

How should benzene-1,4-dicarbonyl chloride be disposed of appropriately?

Benzene-1,4-dicarbonyl chloride disposal must comply with local and national hazardous waste regulations. The compound should not be disposed of through regular waste streams or sewage systems. Contact licensed hazardous waste disposal companies for proper treatment and disposal. Small quantities can be neutralized under controlled conditions by trained personnel, but this should only be done following established safety protocols and regulatory guidelines.

How should benzene-1,4-dicarbonyl chloride be transported?

Benzene-1,4-dicarbonyl chloride is classified under ADR Class 8 (corrosive substances), Packing Group II, indicating moderate danger during transport. Proper packaging must meet UN specification requirements for corrosive materials. Transport vehicles must display appropriate hazard placards and carry emergency response information. Shipments require proper documentation including safety data sheets and emergency contact information for specialized chemical transport companies.

Is benzene-1,4-dicarbonyl chloride subject to specific regulations?

Benzene-1,4-dicarbonyl chloride is subject to European REACH regulation requiring registration for commercial use and supply chain communication through safety data sheets. The compound must comply with CLP regulation for classification and labeling requirements. While not currently listed as a SVHC (Substance of Very High Concern), users must follow standard industrial chemical handling regulations and maintain appropriate exposure controls in workplace environments.

Where can benzene-1,4-dicarbonyl chloride be purchased in Europe?

Benzene-1,4-dicarbonyl chloride is available through OYSI, a specialized European distributor of technical chemicals and industrial raw materials. OYSI provides reliable supply chain solutions for businesses requiring this chemical intermediate. Professional buyers can contact OYSI directly for product specifications, availability, and technical support. As a technical chemical, purchase typically requires verification of intended industrial or research use applications.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.