Methyl 4-cyanobenzoate
[CAS# 1129-35-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanide/nitrile
• Name: Methyl 4-cyanobenzoate
• Synonyms: 4-Cyanobenzoic acid methyl ester
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• CAS Registry Number: 1129-35-7
• EC Number: 214-443-4
• SMILES: COC(=O)C1=CC=C(C=C1)C#N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 65-67 ºC (Expl.)
• Index of Refraction: 1.535, Calc.^*
• Boiling Point: 274.9±0.0 ºC (760 mmHg), Calc.^*, 142-144 ºC (12 mmHg) (Expl.)
• Flash Point: 131.2±9.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H302-H311-H312-H315-H319-H331-H332-H335
• Precautionary Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301

Discovory and Applicatios

Methyl 4-cyanobenzoate is an organic compound belonging to the family of benzoate esters, which consists of a methyl ester group (-COOCH3) attached to a 4-cyanobenzoic acid structure. The compound is characterized by the presence of both an ester group and a cyano group at the para-position of the benzene ring, making it a versatile intermediate in organic synthesis. It is used in various chemical reactions due to its ability to undergo nucleophilic substitution, esterification, and other transformations.

The discovery of methyl 4-cyanobenzoate dates back to the exploration of substituted benzoates and their potential reactivity. Early studies in the mid-20th century focused on developing efficient synthetic routes for obtaining substituted benzoate derivatives, which are important in both industrial and pharmaceutical applications. The introduction of the cyano group at the para-position was found to significantly affect the electronic properties of the aromatic ring, making it more reactive in certain reactions, especially in the formation of functionalized derivatives.

One of the primary applications of methyl 4-cyanobenzoate is in organic synthesis, where it serves as a valuable intermediate for the production of a variety of chemical compounds. Its cyano group, being an electron-withdrawing group, enhances the electrophilic nature of the aromatic ring, facilitating reactions such as nucleophilic aromatic substitution and electrophilic aromatic substitution. This makes methyl 4-cyanobenzoate a key building block in the synthesis of other esters, amides, and more complex aromatic compounds. These derivatives are widely used in the manufacture of specialty chemicals, including pharmaceuticals and agrochemicals.

Methyl 4-cyanobenzoate is also a crucial intermediate in the synthesis of various heterocyclic compounds. The presence of both the ester and cyano groups allows for the creation of diverse molecular structures through cyclization reactions. These heterocycles, which can be formed by nucleophilic addition to the cyano group or through other cyclization processes, are important in the design of biologically active compounds. In particular, the resulting derivatives can exhibit significant activity in medicinal chemistry, where they are tested as potential drug candidates.

In addition to its role in organic synthesis, methyl 4-cyanobenzoate is used in the development of functional materials. Its cyano group makes it a useful component in the synthesis of materials with specific electronic or optical properties. For example, methyl 4-cyanobenzoate is sometimes used in the creation of materials for organic electronics, including organic light-emitting diodes (OLEDs) and organic solar cells (OPVs), due to its ability to act as part of donor-acceptor systems. The presence of the cyano group in particular helps modulate the electronic properties of these materials, contributing to their performance in electronic devices.

Furthermore, methyl 4-cyanobenzoate finds use in the production of dyes and pigments. Its ability to undergo electrophilic substitution reactions at the aromatic ring makes it a useful precursor in the synthesis of colored compounds. These dyes are employed in various industries, including textiles, coatings, and printing, where their bright colors and stability are highly valued.

In conclusion, methyl 4-cyanobenzoate is a versatile compound with a wide range of applications in organic synthesis, materials science, and industrial chemistry. Its reactivity, particularly due to the electron-withdrawing effect of the cyano group, makes it a valuable intermediate for the production of complex organic compounds. Whether used in the synthesis of pharmaceuticals, agrochemicals, functional materials, or dyes, methyl 4-cyanobenzoate continues to play an important role in advancing chemical technologies.