What is Acetanilide? - Uses & Hazards

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

In this lesson we will be exploring the organic compound known as acetanilide. Topics that will be discussed include its structure and synthesis, its primary applications, and a health hazard associated with the compound.

An Important Lego Piece

Did you ever play with legos as a kid? Legos are a great way for kids to learn about building things and use their imaginations. Did you know that sometimes organic chemistry can be likened to playing with legos? You see, synthetic organic chemistry is very similar to building legos in the sense that you take small 'pieces' and put them together to build more complex structures.

As you can imagine, there are countless organic building blocks available for our use in organic chemistry, but the 'piece' we are going to be talking about today is known as acetanilide. Acetanilide is a derivative of aniline, where one of the hydrogens on the nitrogen atom has been replaced with an acetyl group. Acetanilide has a wide variety of uses and is a useful building block (or lego piece) in organic synthesis. We are going to be exploring acetanilide in terms of its structure and how it is synthesized, a few important applications it finds use in, and finally we will briefly mention a health concern associated with its use.

Structure and Synthesis of Acetanilide

Let's get started by looking at the structure of acetanilide so we'll know what we're looking at. Acetanilide has an amide functional group, meaning it has a nitrogen atom bonded directly to a carbonyl (carbon-oxygen double bond). Acetanilide can be described by two resonance structures, with the one that places a positive charge on the nitrogen atom helping to explain why it is non-basic.

Structure and resonance forms of acetanilide

In terms of how acetanilide is synthesized, it's most commonly made by reacting aniline with either acetyl chloride or acetic anhydride. Although both methods work equally well, the preparation from acetic anhydride tends to be preferred due to the corrosiveness and toxicity of acetyl chloride.

Synthesis of acetanilide from aniline and acetic anhydride

Applications and Uses of Acetanilide

As we mentioned previously, acetanilide finds a wide variety of uses in several applications. It has been used in the manufacture of colored dyes for fabrics and textiles, as a reagent in the production of rubber, and as a hydrogen peroxide decomposition inhibitor. Probably what it's best known for however is its role in the pharmaceutical field. In the late 1800s, acetanilide was found to possess painkilling properties, and was introduced as an analgesic under the name Antifebrin.

Acetanilide is also a building block in the synthesis of penicillin, an important antibiotic. Another vital way acetanilide is utilized is as an intermediate in the synthesis of sulfa drugs (drug compounds that contain a sulfonamide functional group). When acetanilide is reacted with chlorosulfonic acid (HSO3 Cl), it produces 4-acetamidobenzenesulfonyl chloride, which is then reacted with ammonia or organic primary amines to make sulfonamides.

Reaction of acetanilide with chlorosulfonic acid to produce 4-acetamidobenzenesulfonyl chloride

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