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 diacid chloride featuring two highly reactive carbonyl chloride functional groups in para position. This organic compound, also known as terephthaloyl chloride, represents a crucial intermediate in polymer chemistry and industrial synthesis. With the molecular formula C8H4Cl2O2 and a molecular weight of 203.02 g/mol, this crystalline solid exhibits exceptional reactivity due to its dual acid chloride functionality. The para-substituted benzene ring provides structural rigidity while the carbonyl chloride groups serve as highly electrophilic reaction centers, making this compound invaluable for condensation polymerization reactions. Benzene-1,4-dicarbonyl chloride demonstrates typical acid chloride properties, including moisture sensitivity and the ability to release hydrogen chloride gas upon contact with water or alcohols. The compound requires careful handling under anhydrous conditions and appropriate ventilation due to its corrosive nature, classified under ADR Class 8. Unlike simpler acylating agents such as 4-methoxybenzoyl chloride, this bifunctional molecule enables the formation of extended polymer chains and cross-linked networks. The compound finds primary application in the production of high-performance polymers, particularly aramid fibers and polyesters. It serves as a key monomer in the synthesis of para-aramids like Kevlar, where it reacts with diamines to form strong, heat-resistant materials. Additionally, it functions as an intermediate in pharmaceutical synthesis and specialty chemical manufacturing, where precise molecular architecture is essential. OYSI offers benzene-1,4-dicarbonyl chloride as part of our comprehensive portfolio of specialty organic intermediates, supporting European chemical manufacturers with reliable supply and technical expertise.

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 compound with the molecular formula C8H4Cl2O2 and CAS number 100-20-9. This aromatic acid chloride features a benzene ring with two carbonyl chloride groups positioned at the 1,4 (para) positions. With a molecular weight of 203.02 g/mol, it serves as an important intermediate in organic synthesis and polymer chemistry.

What are the physicochemical properties of benzene-1,4-dicarbonyl chloride?

Benzene-1,4-dicarbonyl chloride is typically a white to off-white crystalline solid at room temperature. It exhibits high reactivity due to its acid chloride functional groups, making it moisture-sensitive and prone to hydrolysis in humid conditions. The compound has 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 key intermediate in polymer synthesis, particularly for producing high-performance polyamides, polyesters, and polyimides. It serves as a crucial building block in the manufacture of aramid fibers, engineering plastics, and specialty chemicals. Additionally, it finds applications in pharmaceutical synthesis and as a cross-linking agent in various industrial formulations.

How to handle benzene-1,4-dicarbonyl chloride safely?

Benzene-1,4-dicarbonyl chloride requires careful handling due to its corrosive nature and reactivity with moisture. Essential protective equipment includes chemical-resistant gloves, safety goggles, and appropriate respiratory protection. Work should be conducted in a well-ventilated area or under a fume hood. Avoid contact with skin, eyes, and clothing, and prevent exposure to moisture which can cause violent hydrolysis reactions.

How to store benzene-1,4-dicarbonyl chloride correctly?

Benzene-1,4-dicarbonyl chloride must be stored in a cool, dry environment away from moisture and humidity. Keep containers tightly sealed in their original packaging and store in a well-ventilated area away from heat sources and incompatible materials such as alcohols, amines, and water. The storage area should be equipped with appropriate containment measures and maintained at stable temperatures.

What to do in case of contact with benzene-1,4-dicarbonyl chloride?

In case of skin contact with benzene-1,4-dicarbonyl chloride, immediately remove contaminated clothing and flush the affected area with plenty of water for at least 15 minutes. For eye contact, rinse thoroughly with water and seek immediate medical attention. If inhaled, move to fresh air and consult a physician. For ingestion, do not induce vomiting and seek emergency medical care immediately.

How to dispose of benzene-1,4-dicarbonyl chloride appropriately?

Benzene-1,4-dicarbonyl chloride disposal must comply with local and national hazardous waste regulations. The compound should never be discharged into drains or the environment. Waste material must be collected in appropriate containers and disposed of through licensed hazardous waste management companies. Small quantities can be carefully hydrolyzed under controlled conditions before neutralization and proper disposal.

How to transport benzene-1,4-dicarbonyl chloride?

Benzene-1,4-dicarbonyl chloride is classified under ADR Class 8 (Corrosive substances), Packing Group II, indicating its corrosive nature during transport. Proper packaging must meet UN specification requirements with appropriate labeling and documentation. Transportation should be conducted by qualified carriers familiar with hazardous materials regulations, ensuring compliance with international shipping standards and emergency response procedures.

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

Benzene-1,4-dicarbonyl chloride is subject to standard chemical regulations including REACH registration requirements in Europe and CLP classification for hazard communication. While not currently listed as an SVHC (Substance of Very High Concern), it must comply with workplace safety regulations and environmental protection standards. Users should maintain safety data sheets and follow applicable occupational exposure guidelines.

Where to buy benzene-1,4-dicarbonyl chloride in Europe?

Benzene-1,4-dicarbonyl chloride is available through OYSI, a specialized European distributor of technical chemicals serving industrial customers across the continent. OYSI provides reliable supply chains for chemical intermediates and specialty compounds, ensuring proper packaging, documentation, and regulatory compliance for professional users in polymer manufacturing, pharmaceutical synthesis, and other industrial applications.

Data Sources

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