4-methoxybenzoyl chloride

C8H7ClO2

CAS100-07-2

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Identification

CAS Number
100-07-2
EC Number
202-816-4
UN Number
1729
PubChem CID
7477

Physical-chemical properties

Molecular Formula
C8H7ClO2
Molar Mass
170.59 g/mol
IUPAC Name
4-methoxybenzoyl chloride

Chemical Identifiers

InChI
InChI=1S/C8H7ClO2/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3
InChI Key
MXMOTZIXVICDSD-UHFFFAOYSA-N

Overview

4-methoxybenzoyl chloride (CAS 100-07-2) is an aromatic acyl chloride compound featuring a methoxy substituent and reactive carbonyl chloride functionality. This organic compound belongs to the family of substituted benzoyl chlorides, characterized by its white to pale yellow crystalline appearance and distinctive chemical reactivity. The presence of both an electron-donating methoxy group at the para position and a highly electrophilic acyl chloride group makes 4-methoxybenzoyl chloride a valuable synthetic intermediate in organic chemistry. Its molecular structure, with the formula C8H7ClO2 and molecular weight of 170.59 g/mol, provides an ideal balance between reactivity and selectivity for various chemical transformations. As an acyl chloride, this compound exhibits typical properties of this functional group class, including high reactivity toward nucleophiles and sensitivity to moisture. It readily undergoes acylation reactions, making it particularly useful for introducing the 4-methoxybenzoyl protecting group or for synthesizing more complex aromatic compounds. The methoxy substituent influences both the electronic properties and reactivity patterns compared to unsubstituted benzoyl chloride or other halogenated derivatives like benzene-1,4-dicarbonyl chloride. Key industrial applications include pharmaceutical intermediate synthesis, where it serves as a building block for various active pharmaceutical ingredients, agrochemical production for developing crop protection agents, and specialty chemical manufacturing for producing dyes and pigments. The compound's versatility in forming amides, esters, and other derivatives through nucleophilic acyl substitution reactions makes it indispensable in fine chemical synthesis. OYSI provides reliable access to high-quality 4-methoxybenzoyl chloride for European customers requiring this essential synthetic building block for their chemical manufacturing processes.

Safety & Classification

No Hazard Classification

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

Transport (ADR)

UN Number1729
ADR Class8
Packing GroupII
Tunnel CodeE
Proper Shipping Namep-Anisoylchlorid, flüssig*
Marine PollutantNo

Frequently Asked Questions

What is 4-methoxybenzoyl chloride?

4-Methoxybenzoyl chloride is an organic compound with the molecular formula C8H7ClO2 and CAS number 100-07-2. It belongs to the family of acyl chlorides, specifically being a benzoyl chloride derivative with a methoxy group in the para position. This white to pale yellow crystalline solid has a molecular weight of 170.59 g/mol and is highly reactive due to its acyl chloride functional group, making it valuable as an intermediate in organic synthesis.

What are the physicochemical properties of 4-methoxybenzoyl chloride?

4-Methoxybenzoyl chloride appears as a white to pale yellow crystalline solid at room temperature. It has a characteristic pungent, irritating odor typical of acyl chlorides. The compound is highly reactive with water, undergoing hydrolysis to form the corresponding carboxylic acid. It is soluble in organic solvents such as dichloromethane, chloroform, and ether, but reacts violently with protic solvents like water and alcohols, releasing hydrogen chloride gas.

What is 4-methoxybenzoyl chloride used for?

4-Methoxybenzoyl chloride serves as an important intermediate in pharmaceutical and fine chemical synthesis. It is primarily used for acylation reactions to introduce the 4-methoxybenzoyl protecting group in organic synthesis. The compound finds applications in the manufacture of pharmaceuticals, agrochemicals, and specialty chemicals. It is particularly valuable in peptide synthesis and the production of various benzoate esters used in cosmetics and pharmaceutical formulations.

How to handle 4-methoxybenzoyl chloride safely?

4-Methoxybenzoyl chloride requires careful handling due to its corrosive nature and reactivity with moisture. Essential personal protective equipment includes chemical-resistant gloves, safety goggles, and a lab coat. Work should be conducted in a well-ventilated area or under a fume hood to avoid inhalation of vapors or hydrogen chloride gas released upon contact with moisture. Avoid contact with skin, eyes, and clothing, and ensure all equipment is dry before use.

How to store 4-methoxybenzoyl chloride correctly?

4-Methoxybenzoyl chloride must be stored in a cool, dry place away from moisture and humidity to prevent hydrolysis. Keep containers tightly sealed in an inert atmosphere when possible. Store away from incompatible materials such as water, alcohols, amines, and strong bases. The storage area should be well-ventilated and equipped with appropriate spill containment measures. Temperature should be controlled to prevent decomposition and maintain product stability.

What to do in case of contact with 4-methoxybenzoyl chloride?

In case of skin contact with 4-methoxybenzoyl chloride, immediately remove contaminated clothing and flush the affected area with plenty of water for at least 15 minutes. For eye contact, rinse immediately with water for at least 15 minutes while holding eyelids open. If inhaled, move the person to fresh air immediately. Seek medical attention promptly in all cases of exposure. Do not induce vomiting if ingested and provide supportive care while awaiting medical assistance.

How to dispose of 4-methoxybenzoyl chloride properly?

4-Methoxybenzoyl chloride must be disposed of according to local, national, and international regulations as hazardous chemical waste. The compound should be carefully hydrolyzed under controlled conditions to convert it to less hazardous 4-methoxybenzoic acid before disposal. Never pour down drains or into the environment. Contact licensed waste disposal companies for proper handling and disposal. Maintain documentation of disposal activities as required by regulations.

How to transport 4-methoxybenzoyl chloride?

4-Methoxybenzoyl chloride is classified under ADR Class 8 (Corrosive substances), Packing Group II, indicating it poses significant transport hazards. It requires proper packaging in UN-approved containers with appropriate labeling and documentation. Transport vehicles must comply with ADR regulations including proper placarding and emergency equipment. Only trained personnel should handle transportation, and emergency response information must be readily available during transit.

Is 4-methoxybenzoyl chloride subject to specific regulations?

4-Methoxybenzoyl chloride is subject to various chemical regulations including REACH registration requirements in the European Union. It is not classified as a Substance of Very High Concern (SVHC) under REACH. However, users must comply with CLP regulation requirements for classification, labeling, and packaging. Industrial users should maintain safety data sheets and implement appropriate risk management measures. Export/import regulations may also apply depending on the destination country.

Where to buy 4-methoxybenzoyl chloride in Europe?

4-Methoxybenzoyl chloride is available through OYSI, a specialized European distributor of technical chemicals and intermediates. OYSI provides reliable supply chains for pharmaceutical and chemical industry customers across Europe. When sourcing this compound, ensure the supplier provides proper documentation including certificates of analysis, safety data sheets, and regulatory compliance information. Consider factors such as purity specifications, packaging options, and technical support when selecting a supplier.

Data Sources

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