Fumaric acid Polarity

Is C₄H₄O₄ (Fumaric acid) Polar or Nonpolar? Molecular Polarity & Structure Analysis

Figure 1: 2D Lewis Structure (C ₄H ₄O ₄; bent oxygen centre)

Polarity Parameters of C₄H₄O₄

CAS Registry Number	110-17-8
Molecular Formula	C4H4O4
Molecular Weight	116.07 g/mol
Valence Electrons	44
Lewis Structure Guide	View C4H4O4 Lewis Structure Guide
Dipole Moment (μ)	The lowest-energy conformer is centrosymmetric and has μ = 0 D exactly, but other conformers inside the thermally accessible window generated by the conformer search (within about 6 kcal mol⁻¹ of the minimum) carry up to ≈3.26 D; the Boltzmann-weighted ensemble dipole is ≈2.08 D, and the measured gas-phase value is a population average near it
Dielectric Constant (εr)	Not quoted — the Debye estimate would inherit a dipole that this method does not deliver reliably for this class of compound
Snyder Polarity Index (P′)	Not conventionally assigned
XlogP3-AA	-0.29 (Crippen calculated, RDKit) (computed descriptor)

Note: Snyder P′ is a chromatographic solvent scale developed for conventional liquid solvents; no dipole magnitude is quoted: the lowest-energy conformer is centrosymmetric, so the gas-phase value is a conformer population average, so the polarity verdict rests on symmetry and structure alone; no relative permittivity is quoted, because the Debye estimate would inherit an unreliable dipole; XlogP is a calculated partition descriptor, not a direct measure of solvent polarity.

1. Molecular Polarity Analysis of Fumaric acid: Geometry & Dipole Vector

To determine whether Fumaric acid (C₄H₄O₄) is polar or nonpolar, the decisive question is whether the bond dipoles of the molecule cancel once its three-dimensional shape is taken into account. Fumaric acid is a carboxylic acid, built from 2 × carboxylic acid (–COOH). As set out in the C₄H₄O₄ Lewis Structure Guide, C₄H₄O₄ has 8 heavy atoms and 2 rotatable bonds. For fumaric acid (USEPA/OPP Pesticide Code: 051201) there are 0 labels match..

The bond polarities follow from electronegativity. The largest differences in the structure are C–O (ΔEN ≈ 0.89), so electron density is pulled toward oxygen. In three dimensions, the oxygen centre is bent; the 2 non-bonding pairs on oxygen compress the X–O–X angle below the tetrahedral value. As a result, the lowest-energy conformer is centrosymmetric and has μ = 0 D exactly, but polar conformers inside the thermally accessible window give a Boltzmann-weighted ensemble dipole of ≈2.08 D at 298 K, and the measured gas-phase value is a population average near it rather than the value of any single geometry. The dipole is conformation-dependent: across the low-energy conformers the calculation spans ≈0.00–3.26 D, and the value quoted above is the one for the lowest-energy conformer. For a flexible molecule the measured gas-phase dipole is the Boltzmann average over that population, so it lies between the two, not at either end.

For formulation and process work, the useful consequences are these: the calculated topological polar surface area is 74.6 Ų, 2 hydrogen-bond donors and 2 hydrogen-bond acceptors, the Crippen calculated partition coefficient is logP ≈ -0.29 and the calculated molar refractivity is 24.41 cm³ mol⁻¹. A negative logP indicates a net preference for the aqueous phase over octanol, which is what one expects when polar and ionisable groups dominate a small molecule. PubChem’s curated experimental record adds: Fumaric acid is less than 1 mg/mL at 72 °F (NTP, 1992).

2. Fumaric acid application: For fumaric acid (USEPA/OPP Pesticide Code: 051201) there are 0…

PubChem’s use and manufacturing record describes Fumaric acid as follows: For fumaric acid (USEPA/OPP Pesticide Code: 051201) there are 0 labels match. These applications are what make the polarity question practical — solvent choice, extraction recovery, cleaning and formulation all turn on how strongly the molecule interacts with polar phases.

The measured physical behaviour recorded for this substance is consistent with that picture. Solubility: less than 1 mg/mL at 72 °F (NTP, 1992). Physical Description: Fumaric acid appears as a colorless crystalline solid.. Density: 1.635 at 68 °F (USCG, 1999) - Denser than water;. Melting Point: 572 to 576 °F (NTP, 1992). These are database values and should be read with the conditions (temperature, purity, pressure) that the source states.

No dilute-gas permittivity is reported here: the Debye estimate would have to inherit a dipole moment that this method does not deliver reliably for this class of compound (the lowest-energy conformer is centrosymmetric, so the gas-phase value is a conformer population average), and for an ionic substance the equation does not apply at all.

Structurally the reactivity sits in 2 × carboxylic acid (–COOH). That functional inventory, together with the substantial dipole, is what predicts the solubility and adsorption behaviour: polar groups give the molecule a handle on polar solvents and on polar surfaces, while the hydrocarbon portion resists them.

PubChem’s GHS record for this substance lists H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation] and H319 (99.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]. Those classifications, not the polarity of the molecule, normally determine packaging, labelling, ventilation and transport requirements.

Recommended Analytical Quality-Control Strategy

• Identity confirmation: FTIR or Raman against a reference spectrum, supported by GC–MS or LC–MS where the compound is amenable; this is the fastest way to catch a mis-labelled lot.
• Assay / purity: GC-FID or GC-MS for volatile material, HPLC with a validated detector for non-volatile or thermally labile material; state the basis (area %, assay on dried substance, or titrimetric) on the certificate of analysis.
• Water content: Karl Fischer titration is the default for a substance whose polarity and hydrogen-bonding capacity make it hygroscopic; moisture is the single most common cause of out-of-specification lots.
• Related substances: a gradient HPLC or GC method capable of resolving the synthesis by-products and the isomeric impurities typical of this structure.
• Acid–base / ionisable content: a validated acid–base titration or potentiometric determination, since the ionisable group controls both the assay and the behaviour in use.

In short, specify Fumaric acid by assay, water content, impurity profile, packaging and transport class, and state the intended application on the enquiry. The polarity analysis above explains behaviour in use; it does not replace a specification.

3. Polarity Comparison: C₄H₄O₄ and Related Industrial Fluids

The comparison below places C₄H₄O₄ next to structurally related substances from the same catalogue. Dipole moments come from one consistent protocol (GFN2-xTB//MMFF94, gas phase, single conformer) and are quoted only where that protocol has been validated; where it has not, the cell says so instead of giving a number. Permittivities are dilute-gas estimates from the Debye equation, logP values are Crippen calculations, and the solubility column is a qualitative inference from the calculated descriptors rather than a measurement.

The spread across this table is the point: composition alone does not set the polarity verdict. C₄H₄O₄ sits where it does because of the balance between its polar functional groups and the asymmetry of its shape, and any of the neighbouring entries can be the better choice once the temperature, the phase and the required polarity window are fixed.

4. Expert R&D Commentary

5. Regulatory, Safety & Sustainability Trends

Regulatory status is specific to the substance and to the jurisdiction, and it changes. For CAS 110-17-8 the authoritative public sources are the ECHA registered-substance database for the EU, and the OSHA and NIOSH tables for occupational exposure in the United States.

PubChem’s GHS record for this substance lists H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation] and H319 (99.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]. These statements are the ones that must appear on the label and in section 2 of the safety data sheet; they, rather than the polarity of the molecule, drive classification, packaging group and transport documentation.

No occupational exposure limit for this substance is quoted in this article, because none was present in the database record used here. Publishing a limit that is not on the record would be worse than publishing none: obtain the applicable value from the OSHA Z-table, the NIOSH pocket guide or the equivalent national instrument before designing the ventilation or monitoring programme.

From a compliance and sustainability standpoint, the polarity of C₄H₄O₄ is a means rather than an end. It determines which solvent can replace another, how completely the substance can be recovered from a stream, and how much energy the separation will cost — so it belongs in the process justification, while the hazard classification and the exposure limits belong in the safety case.

6. Guidechem's Procurement Tips: What to Specify for Fumaric acid

A purchase enquiry for Fumaric acid (CAS 110-17-8) should state the grade, assay basis, permitted impurity limits, water content, packaging, and the transport and regulatory status required for the destination market. Where the substance is used as a reagent or intermediate, the impurity profile usually matters more than the nominal percentage.

Because polarity governs phase behaviour, it also governs recovery: a substantial molecule is easier to strip from a non-polar stream and harder to dry than a non-polar one, and vice versa. Confirm the Guidechem supply listing for current availability and compare lots on the certificate of analysis rather than on the label alone.

Frequently Asked Questions (FAQs)

References & Academic Databases

1. PubChem Compound Summary: Fumaric acid, CAS RN 110-17-8, CID 444972. National Center for Biotechnology Information. pubchem.ncbi.nlm.nih.gov
2. ECHA Substance Information: Fumaric acid, CAS 110-17-8 — REACH registration status, harmonised classification and regulatory context. European Chemicals Agency.
3. NIST Chemistry WebBook / CCCBDB: experimental geometry, vibrational data and dipole-moment compilations for Fumaric acid. National Institute of Standards and Technology.
4. CRC Handbook of Chemistry and Physics, 92nd ed. (Haynes, W. M., ed.), CRC Press, 2011 — electronegativity, dielectric constant and dipole-moment tables.
5. Nelson, R. D.; Lide, D. R.; Maryott, A. A.: Selected Values of Electric Dipole Moments for Molecules in the Gas Phase, NSRDS-NBS 10, National Bureau of Standards, 1967.
6. Snyder, L. R.: solvent-polarity classification and the P′ scale for liquid chromatographic solvents. The P′ scale is defined only for conventional liquid solvents and is not assigned to substances outside that scope.
7. Bannwarth, C.; Ehlert, S.; Grimme, S.: GFN2-xTB — an accurate and broadly parametrised self-consistent tight-binding quantum chemical method with multipole electrostatics and density-dependent dispersion contributions. J. Chem. Theory Comput. 2019, 15 (3), 1652–1671.
8. RDKit / Halgren, T. A.: MMFF94 force field for geometry generation (J. Comput. Chem. 1996, 17, 490–519) and the RDKit cheminformatics toolkit used for the Crippen logP, TPSA and hydrogen-bond descriptors quoted here.