1-(Chloromethyl)-4-ethynylbenzene
[CAS# 10601-98-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkyne
• Name: 1-(Chloromethyl)-4-ethynylbenzene
• Molecular Formula: C₉H₇Cl
• Molecular Weight: 150.6
• CAS Registry Number: 10601-98-6
• SMILES: C#CC1=CC=C(C=C1)CCl

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 221.0±23.0 ºC 760 mmHg (Calc.)^*
• Flash point: 82.8±18.0 ºC (Calc.)^*
• Index of refraction: 1.553 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P280-P305+P351+P338-P310

Discovory and Applicatios

1-(Chloromethyl)-4-ethynylbenzene is an aromatic compound featuring a benzene ring substituted with two functional groups: a chloromethyl group (-CH2Cl) at position 1 and an ethynyl group (-C≡CH) at position 4. This structure is a derivative of benzene, where the positions 1 and 4 on the ring are substituted with highly reactive groups that impart distinct chemical reactivity.

The chloromethyl group is a common electrophilic group used in organic synthesis for nucleophilic substitution reactions. It can easily undergo substitution reactions with nucleophiles, such as amines, alcohols, or thiols, making this compound useful for the synthesis of a variety of other organic molecules. The presence of the -CH2Cl group also makes this compound a potential precursor for further functionalization, especially in the context of creating bi-functionalized molecules or intermediates for pharmaceutical and material sciences.

The ethynyl group, or acetylene group, at position 4 is a powerful functionality known for its reactivity in a variety of reactions. It can undergo coupling reactions, such as Sonogashira coupling, to form carbon-carbon bonds with other carbon-based units, making it useful for building more complex molecules. Additionally, the triple bond in the ethynyl group provides opportunities for reactions such as cycloaddition, which is a common method in the synthesis of heterocyclic compounds or other complex structures. The ethynyl group is also important in the formation of conjugated systems, enhancing the electronic properties of the molecule, which could be useful in material science applications such as the development of organic electronics or light-emitting devices.

The combination of the chloromethyl group and the ethynyl group in this molecule provides versatility in synthetic applications. For instance, the chloromethyl group may first react with nucleophiles to install other functional groups, while the ethynyl group can participate in cross-coupling reactions, enabling the construction of larger, more complex structures. This type of reactivity makes 1-(chloromethyl)-4-ethynylbenzene a valuable building block in the synthesis of various organic compounds, including potential drugs, polymers, and materials.

In conclusion, 1-(Chloromethyl)-4-ethynylbenzene is a structurally simple yet highly reactive compound that can be utilized in the synthesis of more complex organic molecules. Its combination of a chloromethyl group and an ethynyl group gives it significant potential in both traditional organic synthesis and specialized applications such as material science and drug development.