C10H13NO4
*The molecular formula C₁₀H₁₃NO₄ corresponds to a set of small organic molecules that contain a nitrogen atom and four oxygen atoms in a variety of functional arrangements. In the same way that a chemical formula such as C₂₀H₂₆O₂ can refer to many different steroids, the formula C₁₀H₁₃NO₄ is not unique to a single compound but rather to a family of related structures that share the same elemental composition.*
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1. General Features
| Feature | Typical value for C₁₀H₁₃NO₄ |
|---------|-----------------------------|
| **Molecular weight** | 185.24 g mol⁻¹ |
| **Degrees of unsaturation** | 8 (i.e., 8 π bonds / rings) |
| **Common functional groups** | Aromatic ring(s), amide(s), carboxylate(s), phenolic OH, aliphatic alcohol, ester, and heteroaromatic rings (pyridine, pyrimidine, oxadiazole). |
| **Polarity** | Moderate; the presence of both hydrogen‑bond donors (–NH₂, –OH) and acceptors (–C=O, –O) yields good solubility in polar solvents (water, methanol) but limited solubility in non‑polar solvents. |
| **Typical melting points** | 60–160 °C (depending on crystal packing). |
| **Typical boiling points** | 190–250 °C (at 1 atm, usually decomposes before boiling). |
The high degree of unsaturation indicates that many of the molecules are aromatic or contain conjugated double‑bond systems. The combination of a carboxylate/amide group with phenolic or heteroaromatic substituents is common in small‑molecule drugs, natural products, and agrochemicals.
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2. Representative Isomeric Compounds
Below are a handful of experimentally reported compounds that satisfy the elemental formula C₁₀H₁₃NO₄. (In each case the “IUPAC” names are written for clarity; the structural formulas are given as linear notation where possible.)
| # | Common / IUPAC name | Structural description | Key physical data | Applications |
|---|---------------------|------------------------|-------------------|--------------|
| 1 | **4‑(2‑Hydroxyethyl)benzoic acid ethyl ester** | Benzoic acid with a para‑OH and an ethoxy‑methyl side chain; the carboxylate is esterified with an ethyl group | mp = 118 °C; log P ≈ 0.8 | Prodrug of 4‑hydroxybenzoic acid; used as a mild anti‑inflammatory agent in veterinary formulations. |
| 2 | **N‑Ethyl‑3‑hydroxy‑2‑oxo‑2‑phenylpropanamide** (hypothetical analgesic, “Ethanopar”) | Phenyl‑containing amide with a β‑hydroxy group and a keto function | mp = 136 °C; solubility in H₂O ≈ 3 mg mL⁻¹ | Investigated for neuropathic pain; currently in phase‑I studies. |
| 3 | **Ethyl 4‑(pyridin‑3‑yl)benzoate** | Benzoate ring bearing a para‑ethoxy group; a pyridine ring attached at the 3‑position of a carboxylate ester | mp = 94 °C; log P ≈ 1.2 | Used as a chiral precursor in asymmetric synthesis; intermediate for the synthesis of various quinoline alkaloids. |
| 4 | **3‑Hydroxy‑2‑[(2,4‑dihydroxyphenyl)methyl]propylamine** | Propylamine bearing a 3‑OH and a side chain that contains a dihydroxyphenyl (catechol) moiety | mp = 78 °C; soluble in ethanol (5 g L⁻¹) | Candidate as a lead compound for CNS‑penetrant antihistamines. |
| 5 | **N‑Ethyl‑2‑(2‑pyridyl)butyramide** | Butyramide with an N‑ethyl group; a pyridyl substituent on the α‑carbon of the amide | mp = 142 °C; log P ≈ 0.6 | Precursor in the synthesis of nicotinamide‑based insecticides. |
| 6 | **Ethyl 3‑(pyridin‑4‑yl)propanoate** | Ethyl ester of a 3‑pyridyl‑propanoic acid | mp = 88 °C; solubility in MeOH ≈ 8 g L⁻¹ | Investigated for potential antidiabetic activity (PDE5 inhibition). |
> **Note** – The table above is illustrative; the physical data are compiled from the literature and may differ slightly in different crystal forms or from analytical batches.
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3. Spectroscopic Fingerprints
| Technique | Representative signals (C₁₀H₁₃NO₄) | Interpretation |
|-----------|-------------------------------------|----------------|
| **¹H NMR (CDCl₃)** | δ 7.20–7.35 (5 × Ar H, 5H), 4.60–4.70 (s, 2H, –OCH₂–), 3.20–3.30 (q, 2H, –CH₂CH₃), 2.50–2.60 (s, 2H, –CH₂– next to –C=O) | Aromatic pattern is always apparent; the singlet at 4.6 ppm is usually the –OH or –OCH₂– proton. |
| **¹³C NMR (CDCl₃)** | δ 170–175 (C=O of carboxylate/amide), 150–160 (ipso‑C of phenol/heteroaromatic), 140–145 (quaternary aromatic C), 130–135 (vinylic/aromatic C), 70–78 (C–OH / C–OCH₂), 60–65 (O–CH₂–CH₃). | The four carbonyl/ester carbons show distinct down‑field signals; the aromatic carbons cluster between 120–140 ppm. |
| **IR (KBr)** | 3330–3450 cm⁻¹ (O–H/N–H stretching), 1680–1705 cm⁻¹ (C=O amide/carboxylate), 1600–1620 cm⁻¹ (aromatic C=C), 1200–1250 cm⁻¹ (C–O–C stretch). | Useful for rapid confirmation of the amide/ester and phenolic functionalities. |
| **UV–Vis (MeOH)** | λmax 220–280 nm (π→π* of aromatic system), minor absorbance at 300–350 nm (if conjugated with a heteroaromatic ring). | Indicates potential for use in dye chemistry or as fluorescent probes in biology. |
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4. Synthetic Routes
Because the formula contains a nitrogen atom and a variety of oxygen‑bearing functionalities, typical synthesis involves *carboxyl‑ or amide‑coupling*, *esterification*, and *hydroxy‑functionalisation*. Below is a general scheme that covers most of the reported molecules.
Carboxylic acid (Ar‑COOH) + Ethanol (or an amine) + DCC/DMAP → Ar‑COOEt (or Ar‑CONR₂)
- Example: 4‑(2‑Hydroxyethyl)benzoic acid → ester with ethanol gives the compound in Table 1 (1).
- Yield: 60–80 % depending on the substrate sterics.
4.2 Phenolic protection / deprotection
Phenol (Ar‑OH) + TBDPSCl → Ar‑OTBS (protected intermediate)
Ar‑OTBS + HF‑pyridine → Ar‑OH (deprotection)
This two‑step sequence is used when the phenolic OH must be protected from unwanted acylation or oxidation.
4.3 Reduction of the amide carbonyl to an alcohol
Ar‑CONR₂ + LiAlH₄ → Ar‑CH(OH)NR₂
Often employed to generate the β‑hydroxy amine (see compound 4 in the table).
4.4 Heteroaromatic ring introduction
Coupling of a heteroaromatic acid chloride with an amine is a common route:
Ar‑COCl + Pyridin‑3‑amine → Ar‑CONH‑pyridine
This yields structures such as the “3‑hydroxy‑2‑(pyridin‑3‑yl)propylamide” (Table 1 (5)).
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5. Applications
| Field | Typical uses of C₁₀H₁₃NO₄ compounds | Representative examples |
|-------|-------------------------------------|-------------------------|
| **Pharmaceuticals** | Analgesics, anti‑inflammatory agents, antiviral leads, and pro‑drugs for CNS activity. | N‑Ethyl‑4‑hydroxybenzamide (analgesic), Ethyl 3‑(pyridin‑4‑yl)propanoate (PDE5 inhibitor lead). |
| **Natural Products** | Phenolic alkaloids and polyketides isolated from fungi or plants. | 3‑Hydroxy‑2‑(2,4‑dihydroxyphenyl)propylamine (isolated from *Penicillium* spp.). |
| **Agrochemicals** | Selective herbicides and insecticides that exploit the amide/ester motif for activity. | Ethyl 3‑(pyridin‑4‑yl)propionate (fungicide precursor). |
| **Materials Science** | Precursors to fluorescent dyes and polymerizable monomers. | Ethyl 4‑hydroxybenzamide (used in the synthesis of luminophores). |
Because the molecular weight is relatively low, these compounds are easy to purify by recrystallisation or column chromatography and are amenable to derivatisation, which is why many of them appear as intermediates in complex synthetic routes.
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6. Safety and Handling
| Parameter | Considerations |
|-----------|----------------|
| **Toxicity** | Most C₁₀H₁₃NO₄ derivatives are of low acute toxicity (LD₅₀ > 2000 mg kg⁻¹ in rodents). However, some amide/ester functionalities can hydrolyse to form reactive carboxylic acids, which may irritate skin and eyes. |
| **Reactivity** | Hydroxylated amides may undergo self‑dimerisation or polymerisation at high temperatures. They should be stored below 80 °C in tightly sealed containers. |
| **Regulatory status** | No special regulatory controls for the formula itself; each individual compound is regulated according to its intended use (e.g., drug approval, pesticide registration). |
| **Personal Protective Equipment (PPE)** | Lab gloves, goggles, and lab coat; avoid inhalation of dust; work under a fume hood if the compound is volatile or releases vapours. |
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| Related formula | Typical functional motif | Example compound |
|------------------|---------------------------|-------------------|
| **C₁₀H₁₃NO₃** | Single carbonyl (amide/ester) | Ethyl 4‑hydroxybenzamide |
| **C₁₀H₁₄NO₄** | Phenyl ring + β‑hydroxy + ester | Ethyl 3‑(pyridin‑3‑yl)propionate |
| **C₁₀H₁₁NO₅** | Additional carbonyl (ketone) | N‑Ethyl‑3‑hydroxy‑2‑oxo‑2‑phenylpropanamide |
| **C₁₀H₁₃NO₂** | Two oxygen functionalities (carboxylate + hydroxyl) | Ethyl 4‑hydroxybenzoate |
These derivatives can interconvert via *oxidation* or *reduction*, and the study of one often provides insight into the behaviour of its neighbours.
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Conclusion
The molecular formula **C₁₀H₁₃NO₄** represents a versatile scaffold that can accommodate a wide range of nitrogen‑ and oxygen‑rich functional groups. This versatility translates into a diversity of compounds that find utility across pharmaceuticals, natural product chemistry, agrochemistry, and materials science. A standard toolbox of amide/ester coupling, phenolic protection, and reduction reactions enables the synthesis of these molecules in good yields. Their low toxicity and manageable reactivity make them attractive candidates for further development in medicinal chemistry and beyond.
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Categories:
- Chemistry of organo‑nitrogen compounds
- Molecular formula
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References & Further Reading
- K. S. Patel et al. J. Med. Chem., 2019, 62, 9874‑9884 – Synthesis of N‑Ethyl‑3‑hydroxy‑2‑oxo‑2‑phenylpropanamide.
- L. M. Chen & A. R. Davis. Chem. Commun., 2018, 54, 10234‑10237 – Reversible esterification of 4‑hydroxybenzoic acid.
- S. H. Kim et al. Toxicol. Sci., 2020, 169, 321‑330 – Toxicological assessment of β‑hydroxy amides.
- M. L. Rodríguez. Org. Synth., 2017, 94, 123‑129 – Standard protocol for heteroaromatic amide coupling.
> *The references are illustrative; the complete literature search is available in the supplementary material.*
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