2-Hydroxy-1,2-diphenylethanone (CAS 92-91-1) | Acyloin Condensation Product for Laboratory Synthesis

1. Product Overview

2-Hydroxy-1,2-diphenylethanone (CAS 92-91-1) is an α-hydroxy aryl ketone with the molecular formula C₁₄H₁₂O₂ and a molecular weight of 212.25 g/mol. This compound is the prototypical acyloin formed via the benzoin condensation of benzaldehyde. It serves as a key precursor to benzil and benzilic acid, and is widely employed as a scaffold in the synthesis of oxazole and imidazole derivatives.

2. Key Features and Benefits

• Acyloin Core Structure: Contains a benzylic hydroxyl adjacent to a ketone, enabling diverse redox and cyclization chemistry.

• Versatile Intermediate: Readily converted to 1,2-diketones (benzil) via oxidation or to α-hydroxy carboxylic acids via rearrangement.

• Stable Solid Form: Crystalline powder stable at room temperature under recommended storage conditions.

• Synthetic Utility: Used in the preparation of photoactive molecules and coordination ligands.

3. Major Applications

• Organic Synthesis: Substrate for oxidation to benzil and subsequent benzilic acid rearrangement studies.

• Heterocycle Construction: Cyclization with nitrogen nucleophiles to form substituted oxazoles and imidazoles.

• Mechanistic Studies: Model compound for investigating nucleophilic catalysis (e.g., NHC catalysis).

• Material Science: Precursor to functionalized ligands for transition metal complexes.

4. Technical Specifications

Item Description
Product Name 2-Hydroxy-1,2-diphenylethanone
Synonyms α-Hydroxybenzyl phenyl ketone; (±)-2-Hydroxy-1,2-diphenylethanone
CAS Number 92-91-1
Molecular Formula C₁₄H₁₂O₂
Molecular Weight 212.25 g/mol
Assay (Purity) ≥98% (HPLC)
Appearance White to off-white crystalline powder
Melting Point 133–137 °C
Boiling Point ~344 °C (Decomposes)
Density ~1.31 g/cm³ (Predicted)
Calculated LogP ~2.3–2.8
Polar Surface Area (PSA) 37.3 Ų
Hydrogen Bond Donors 1 (OH)
Hydrogen Bond Acceptors 2 (C=O, OH)
Solubility Soluble in hot ethanol, methanol, ethyl acetate, and dichloromethane; practically insoluble in water.
SMILES OC(C(=O)c1ccccc1)c2ccccc2
InChI Key GPYLWHDSKFGRHY-UHFFFAOYSA-N
Storage Room temperature or 2–8 °C, sealed, protect from light
HS Code 2914.40.00

5. Storage and Handling

Store in a tightly sealed container at room temperature or 2–8 °C, protected from light. The compound is stable as a solid for extended periods but may darken slightly upon prolonged exposure to air. Handle in a well-ventilated area. Standard personal protective equipment (lab coat, nitrile gloves, safety goggles) is recommended. Avoid inhalation of dust and contact with skin or eyes.

6. Safety Summary

• GHS Classification: GHS07 – Warning

• Signal Word: Warning

• Hazard Statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

• Precautionary Statements: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501

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