256269

(S,S)-(−)-Hydrobenzoin

99%, optical purity ee: 99% (GLC)

• Synonym(s): (S,S)-(−)-1,2-Diphenyl-1,2-ethanediol, (S,S)-1,2-Diphenylethylene glycol
• Linear Formula: C₆H₅CH(OH)CH(OH)C₆H₅
• CAS Number: 2325-10-2
• Molecular Weight: 214.26
• Beilstein: 2330888
• MDL number: MFCD00064255
• UNSPSC Code: 12352002
• PubChem Substance ID: 24855513
• NACRES: NA.22

Properties

• Assay: 99%
• optical activity: [α]24/D −94°, c = 2.5 in ethanol
• optical purity: ee: 99% (GLC)
• mp: 148-150 °C (lit.)
• functional group: hydroxyl; phenyl
• SMILES string: O[C@H]([C@@H](O)c1ccccc1)c2ccccc2
• InChI: 1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m0/s1
• InChI key: IHPDTPWNFBQHEB-KBPBESRZSA-N

Description

General description

Chiral reagent.

Application

(S,S)-(-)-Hydrobenzoin may also be used to prepare (1S,2S,1′S)- and (1S,2S,1′R)-2-(cyclohex-2′-enyloxy)-1,2-diphenylethanol, which are intermediates to prepare enantiopure cyclohexitols. The (S,S)-(-)-hydrobenzoin/Ca complex may be used to catalyze the direct asymmetric aldol reaction of acetophenone and pivalaldehyde to form (R)-3-hydroxy-4,4-dimethyl-1-phenylpentan-1-one.

C₂ symmetric chiral diol with versatile applications as a chiral auxiliary, building block, and chiral ligand.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves