4'-(Bromomethyl)acetophenone
[CAS# 51229-51-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 4'-(Bromomethyl)acetophenone
• Synonyms: p-(Bromomethyl)acetophenone; p-Acetylbenzyl bromide
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07
• CAS Registry Number: 51229-51-7
• EC Number: 827-425-1
• SMILES: CC(=O)C1=CC=C(C=C1)CBr

Properties

• Solubility: Very slightly soluble (0.66 g/L) (25 ºC), Calc.^*
• Density: 1.416±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 38.5-40.0 ºC^**
• Boiling point: 134-136 ºC (5 Torr)^***
• Flash point: 94.1±9.9 ºC, Calc.^*
• Index of refraction: 1.564 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Podgorsek, Ajda; Tetrahedron 2009, V65(22), P4429-4439.

^*** Hass, H. B.; Journal of the American Chemical Society 1949, V71, P1767-9.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H315-H318-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

4'-(Bromomethyl)acetophenone is an organic compound belonging to the class of acetophenones, which are derivatives of phenyl ketones. This specific compound consists of an acetophenone backbone with a bromomethyl group (-CH2Br) attached to the para position of the phenyl ring relative to the ketone group. The molecular structure of 4'-(Bromomethyl)acetophenone is characterized by its aromatic core, with a bromomethyl group at the 4-position, making it a valuable intermediate in organic synthesis.

The compound was first synthesized as part of efforts to develop new chemical reactions and explore the reactivity of bromomethyl groups. The bromomethyl group is a versatile functional group in organic chemistry, and its incorporation into molecules like acetophenone opens up numerous synthetic possibilities. The presence of the bromine atom in the molecule makes it electrophilic, meaning it is reactive in nucleophilic substitution reactions. This reactivity is often exploited to introduce other functional groups into the structure, allowing for the creation of more complex organic molecules.

4'-(Bromomethyl)acetophenone has found various applications in synthetic organic chemistry. Its main utility lies in its ability to serve as an intermediate for the synthesis of more complex compounds. The bromomethyl group can be easily replaced by other nucleophiles, such as alcohols, amines, or thiols, in substitution reactions. This makes 4'-(Bromomethyl)acetophenone a valuable building block in the preparation of diverse organic molecules.

One of the key applications of this compound is in the synthesis of pharmaceuticals and agrochemicals. The versatility of the bromomethyl group allows it to be incorporated into molecules that exhibit biological activity. For example, it can be used in the preparation of various bioactive compounds, including those with anti-inflammatory, antibacterial, or antifungal properties. Furthermore, the functionalization of 4'-(Bromomethyl)acetophenone can lead to the development of molecules with potential uses in drug discovery and medicinal chemistry.

In addition to its use in pharmaceutical chemistry, 4'-(Bromomethyl)acetophenone has applications in the synthesis of dyes, polymers, and other specialty chemicals. The ability to modify the bromomethyl group and introduce different functional groups onto the acetophenone backbone enhances the versatility of this compound in industrial applications. For example, it can be used in the production of polymeric materials with specific properties, such as improved solubility or reactivity, which are important for coatings, adhesives, and other materials.

The reactivity of 4'-(Bromomethyl)acetophenone, particularly its susceptibility to nucleophilic substitution reactions, also makes it a useful tool in the development of chemical reactions and methodologies. Researchers have studied its reactivity in various catalytic processes, such as palladium-catalyzed coupling reactions, which are essential in the synthesis of more complex organic structures.

Despite its versatility and usefulness in chemical synthesis, 4'-(Bromomethyl)acetophenone should be handled with care. Like many bromine-containing compounds, it can be hazardous if not properly managed. The bromine atom can be reactive and potentially harmful if inhaled, ingested, or exposed to skin in significant quantities. Safety protocols, such as the use of protective gloves, goggles, and a well-ventilated work environment, should always be followed when working with this compound.

In conclusion, 4'-(Bromomethyl)acetophenone is an important intermediate in organic chemistry with applications in the synthesis of pharmaceuticals, agrochemicals, dyes, polymers, and other specialty chemicals. Its versatility arises from the reactivity of the bromomethyl group, which can be replaced by various nucleophiles to introduce new functional groups into the molecule. This property makes it a valuable building block for developing a wide range of bioactive and industrial compounds.

References

1952. Die Synthese des p-Chlormethyl-acetophenons. Monatshefte f�r Chemie und verwandte Teile anderer Wissenschaften, 83(3).
DOI: 10.1007/bf00897817

2008. A Novel Method for the Synthesis of Thioacetates Using Benzyltriethylammonium Tetrathiomolybdate and Acetic Anhydride. Synlett, 2008(16).
DOI: 10.1055/s-0028-1083517

2021. Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light. Chemical Papers, 75(11).
DOI: 10.1007/s11696-021-01711-x