2-hydroxy-1,2-diphenylethan-1-one

• ChemBase ID: 89839
• Molecular Formular: C14H12O2
• Molecular Mass: 212.24388
• Monoisotopic Mass: 212.08372962
• SMILES: O=C(c1ccccc1)C(c1ccccc1)O
• Canonical SMILES: OC(C(=O)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
• InChIKey: ISAOCJYIOMOJEB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-1,2-diphenylethan-1-one
• IUPAC Traditional name: (+-)-benzoin
• Synonyms: α-Hydroxy-α-phenylacetophenone; α-Hydroxybenzyl phenyl ketone; Benzoin; 2-hydroxy-1,2-diphenylethanone; desyl alcohoe; bitter almond oil camphor; 2-Hydroxy-1,2-diphenylethanone; α-Hydroxy-α-phenylacetophenone; α-Hydroxybenzyl phenyl ketone; 2-Hydroxy-2-phenylacetophenone; Benzoin; α-羟基-α-苯基苯乙酮; 2-羟基-2-苯基苯乙酮; 苯偶姻; 安息香

Database IDs

• CAS Number: 119-53-9
• EC Number: 204-331-3
• MDL Number: MFCD00004496
• Beilstein Number: 391839
• Merck Index: 141093
• PubChem SID: 24864811; 24900870; 24892088; 162076694
• PubChem CID: 8400
• CHEBI ID: 17682
• CHEMBL: 190677
• Chemspider ID: 8093
• FEMA ID: 2132
• KEGG ID: C01408
• Unique Ingredient Identifier: L7J6A1NE81
• Wikipedia Title: Benzoin
• Council of Europe Number: 162
• Flavis Number: 7.028

CALCULATED PROPERTIES

• Acid pKa: 12.617625
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.6500747
• LogD (pH = 7.4): 2.650072
• Log P: 2.6500747
• Molar Refractivity: 62.5209 cm^3
• Polarizability: 24.280083 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly Soluble in ethanol; Slightly Soluble in water
• Apperance: off-white crystals
• Melting Point: 131-136°C; 132–137 °C; 133-135 °C; 133-137°C; 134-136°C; 134-138 °C(lit.)
• Boiling Point: 194 °C/12 mmHg(lit.); 194°C; 334-344°C; 334-344°C; 344 °C
• Flash Point: 170 °C; 181°C; 181°C(357°F); 338 °F
• Density: 1.31; 1.31 g/cm^3; 1.310; 1.310 g/ml @ 20°C
• Vapor Pressure: 1 mm Hg at 135.6 °C
• Organoleptic: medicinal; vanilla

Safety Information

• Storage Condition: 2-8°C
• RTECS: DI1590000
• German water hazard class: 2
• TSCA Listed: 是
• NFPA704:
  

  1

  2

  0
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C
• Regulation Compliance: FDA 21 CFR (172.515); FDA 21 CFR (73.1)

Pharmacology Properties

• Gene Information: human ... ACHE(43), BCHE(590), CES1(1066)

Product Information

• Purity: ≥98%; ≥99.0% (GC); ≥99.5%; 98%; 99%; 99.5%
• Grade: Kosher; purum; zone-refined
• Purified By: sublimation
• Linear Formula: C6H5CH(OH)COC6H5

DETAILS

MP Biomedicals - 02150438

Crystalline

MP Biomedicals - 05209548

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B8681

Packaging
100, 500 g in poly bottle
2 kg in poly bottle
5 g in glass bottle

Sigma Aldrich - 399396

Packaging
5 g in glass bottle

Sigma Aldrich - 399418

Packaging
1 g in glass bottle

REFERENCES

• Exclusive C-alkylation occurs with an alkyl bromide and NaOH in DMSO: Liebigs Ann. Chem., 735, 56 (1970). Borohydride reduction and periodate cleavage of the product lead to a useful synthesis of aryl ketones, with benzoin functioning as a benzoyl anion equivalent: Synthesis, 268 (1975):
  
• This has been extended to include alkylation with other electrophiles including primary and secondary alkyl iodides and Michael acceptors, and the route shortened by direct cleavage of the alkylated benzoin with hydrogen peroxide: Synthesis, 36 (1980).