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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) |
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1. What is Butanone?
Butanone, http://picscrazy.in/member.php?action=viewpro&member=Maximo16C 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.
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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. |
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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. |
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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. |
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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.