1-(2-Nitrophenyl)-1,2-ethanediol: Properties & Lab Uses

1-(2-Nitrophenyl)-1,2-ethanediol is an aromatic vicinal diol bearing an ortho-nitro substituent on the phenyl ring, widely used as a synthetic intermediate and reference standard in organic and medicinal chemistry research.

Chemical Name

1-(2-Nitrophenyl)-1,2-ethanediol

SKU

N472484

Molecular Formula

C8H9NO4

Functional Groups

Vicinal diol (1,2-diol) and aromatic nitro group

Ring Substitution Pattern

ortho-nitro substitution on phenyl ring

Primary Use

Organic synthesis intermediate and analytical reference standard

Chemical Identity and Structure

1-(2-Nitrophenyl)-1,2-ethanediol (SKU N472484) is an aromatic vicinal diol with the molecular formula C₈H₉NO₄. Its structure consists of a phenyl ring bearing a nitro group at the ortho (2-) position, connected to a two-carbon chain containing two hydroxyl groups at C1 and C2. The ortho-nitro group confers significant electron-withdrawing character to the aromatic ring, influencing the reactivity of the adjacent diol moiety.

The compound possesses a chiral center at C1, meaning it can exist as two enantiomers: the (R)- and (S)-configurations. This stereochemical feature makes it relevant as a chiral building block or as a substrate for studying stereoselective transformations. The compound is also catalogued under Sigma-Aldrich reference number 274526, facilitating cross-referencing in published literature and procurement workflows.

Physicochemical Properties

As an aromatic diol, 1-(2-Nitrophenyl)-1,2-ethanediol exhibits characteristic properties arising from the interplay of its hydroxyl groups and the electron-deficient aromatic ring. The two hydroxyl groups enable hydrogen-bond donation and acceptance, contributing to moderate water solubility relative to purely aromatic compounds. The compound is expected to be a solid at room temperature, consistent with other structurally related nitrophenyl diols.

The nitro group at the ortho position introduces steric and electronic effects that differentiate this compound from its meta- and para-nitrophenyl analogues. These effects can influence reaction rates in esterification, oxidation, and cyclization reactions, making careful selection of reaction conditions essential when using this reagent.

Note: Specific numerical values for melting point, boiling point, density, and solubility are not confirmed in the current source material and should be verified against the certificate of analysis (CoA) supplied with SKU N472484.

Laboratory Applications and Synthetic Utility

1-(2-Nitrophenyl)-1,2-ethanediol serves as a versatile intermediate in synthetic organic chemistry. Its vicinal diol functionality can be exploited in several transformations:

• Oxidative cleavage: Periodate-mediated cleavage of the 1,2-diol yields the corresponding ortho-nitrobenzaldehyde and formaldehyde, offering a route to reactive aldehyde intermediates.
• Cyclic acetal formation: Reaction with ketones or aldehydes under acid catalysis affords 1,3-dioxolane derivatives, which are useful protecting groups in multi-step synthesis.
• Chiral resolution and asymmetric synthesis: As a compound with a chiral center, enantiomerically enriched forms are valuable in asymmetric synthesis and as chiral reference standards.
• Reduction to aminophenyl diol: The nitro group can be selectively reduced to an amine, generating an aminophenyl diol useful in pharmaceutical and heterocyclic chemistry.

These applications make the compound of interest in pharmaceutical intermediate synthesis, agrochemical research, and material science contexts.

Handling, Storage, and Safety Considerations

As with all nitroaromatic compounds, appropriate precautions should be observed when handling 1-(2-Nitrophenyl)-1,2-ethanediol. General guidelines for this compound class include:

• Use appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat.
• Work in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.
• Store the compound in a cool, dry, well-ventilated area away from strong oxidizers, reducing agents, and incompatible materials.
• Dispose of waste according to local institutional and regulatory guidelines for organic nitro compounds.

Note: A full Safety Data Sheet (SDS) specific to SKU N472484 should be consulted before use. Specific hazard classifications, GHS pictograms, and exposure limits are not confirmed in the current source material and require verification from the SDS.

Frequently asked questions

What is the cross-reference number for 1-(2-Nitrophenyl)-1,2-ethanediol at other suppliers?

1-(2-Nitrophenyl)-1,2-ethanediol is listed under Sigma-Aldrich catalog number 274526, as noted in the product source material for Aladdin SKU N472484. This cross-reference facilitates literature searches and procurement verification.

Does 1-(2-Nitrophenyl)-1,2-ethanediol have a chiral center?

Yes, the compound possesses one chiral center at the C1 carbon bearing the hydroxyl group adjacent to the aromatic ring, giving rise to (R)- and (S)-enantiomers. Researchers requiring a specific enantiomer should confirm the stereochemical specification when ordering.

What typical reactions can be performed with the 1,2-diol functionality of this compound?

The vicinal diol group can undergo periodate-mediated oxidative cleavage to yield aldehyde fragments, acid-catalyzed acetal formation with carbonyl compounds to give 1,3-dioxolane protecting groups, and selective oxidation to the corresponding alpha-hydroxy ketone. These reactions are standard in synthetic organic chemistry workflows.

How should 1-(2-Nitrophenyl)-1,2-ethanediol be stored to maintain stability?

General best practice for nitroaromatic diols is to store the compound in a tightly sealed container in a cool, dry, and well-ventilated location, protected from light and heat. Researchers should consult the product-specific SDS and certificate of analysis for confirmed storage temperature and shelf-life data.

References

1. Sigma-Aldrich product listing for 1-(2-Nitrophenyl)-1,2-ethanediol, catalog number 274526.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for vicinal diol reactions including periodate cleavage and acetal formation.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.