Jacques Forrest
|Subscribers
About
How To Buy Dbol The King Of Bulking Steroids
Basic Information
Property Value
Common name 2‑butanone (also called methyl ethyl ketone, MEK, or simply "butanone")
Molecular formula C₄H₈O
Molar mass 72.11 g mol⁻¹
Boiling point 79.6 °C (173.7 °F)
Melting point –107 °C (–162 °F)
Density (20 °C) 0.791 g cm⁻³
Solubility in water 100 % at 25 °C (miscible)
---
1. What is Butanone?
Butanone, or butan-2-one, is the simplest α‑keto compound that has four carbon atoms and a methyl group on the second carbon. Its structure can be written as:
CH3–CO–CH2–CH3
The "α‑ketone" means the carbonyl (C=O) is directly adjacent to a methylene group (–CH₂–). This placement gives butanone its unique reactivity.
---
2. Chemical Properties
Property Detail
Molecular formula C₄H₈O
Boiling point ~56 °C
Density 0.81 g cm⁻³ (at 20 °C)
Solubility Miscible in water, ethanol, acetone; soluble in most organic solvents
Odor Sweet, fruity, slightly resinous
Stability Stable under normal conditions; decomposes at high temperatures (>250 °C).
Reactivity Acts as a mild carbonyl (aldehyde) compound. Reacts with nucleophiles forming addition products.
---
3. Applications of 4‑Methyl‑1,2‑oxazole
Field Typical Uses How 4‑Me‑Oxy is Incorporated
Organic Synthesis Synthetic building block – used to generate heterocycles, lactones, or to mask a reactive aldehyde. The oxazole ring can be opened (via nucleophilic attack) to give a substituted aldehyde or amide after reduction/oxidation.
Pharmaceuticals Lead compounds for anti‑inflammatory, antiviral, anticancer agents. Many drug candidates incorporate the oxazole core due to its metabolic stability and ability to form hydrogen bonds with protein targets.
Materials Science Conductive polymers or optical materials. Oxazoles can contribute to electron delocalization in polymer backbones, improving conductivity and optical properties.
---
3. Key Reactions Involving the Oxazole Ring
Below are some typical transformations that convert an oxazole into a functional group of interest. For each, a concise mechanism is provided.
Transformation Product Mechanism Overview
N‑Oxidation → N–oxide 1‑Hydroxy‑2‑(alkyl)oxazoline Oxidant (e.g., mCPBA, H₂O₂) forms a peracid or peroxide that attacks the nitrogen lone pair, creating an N‑oxide.
Ring‑Opening by Nucleophiles 1‑Hydroxy‑2‑(alkyl)oxazoline → β‑hydroxy alcohol + amine Protonation of the oxazole oxygen makes it a good leaving group; nucleophile attacks at C‑3, leading to cleavage.
Acidic Hydrolysis Oxazole → Carboxylic acid + amine Strong acids protonate the ring, facilitating water addition at C‑2 or C‑3 and subsequent rearrangement to open the ring.
Reduction (LiAlH₄) Oxazole → β‑hydroxy alcohol + secondary amine LiAlH₄ reduces both the heteroaromatic ring and the C=O bond, leading to cleavage of the C–N bond.
---
3. Detailed Mechanism for Hydrolysis of a Representative Oxazole
Substrate (example):
A simple 2‑(methyl)‑oxazole:
O
/ \
| |
| N
\ /
CH3
Step‑by‑Step
Step Transformation Electron Flow Key Intermediates/Factors
1. Protonation of the ring oxygen (acidic medium) Oxazole becomes an oxazolium ion H⁺ adds to O, pushing electrons onto N and C Increases electrophilicity at C‑2 (adjacent to protonated O)
2. Nucleophilic attack by water at C‑2 Water attacks electrophilic C‑2, opening the ring Lone pair of H₂O attacks C‑2; electrons shift from N=C bond to N, breaking N–C(=O) bond Forms tetrahedral intermediate with –OH on former C‑2
3. Proton transfer and collapse of intermediate Intermediate collapses, restoring aromaticity and generating a carboxylate group Loss of proton from N (or H₂O), re-aromatization; cleavage of N–C bond yields an amide or acid depending on conditions Produces a substituted benzoic acid derivative with –OH at position 2
Final product The ring is opened, yielding a phenolic carboxylic acid with substituents determined by the original alkyl groups The overall process is a reductive cleavage of the C–N bond in the aromatic system This transformation yields an open-chain benzoic acid derivative that can be further functionalized
The above steps outline the major transformations and key intermediates involved in this organic synthesis.