(4S)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2λ5-dioxaphosphinan-2-one

• ChemBase ID: 44817
• Molecular Formular: C12H17O5P
• Molecular Mass: 272.234141
• Monoisotopic Mass: 272.08136027
• SMILES: P1(=O)(O[C@H](c2c(OC)cccc2)C(CO1)(C)C)O
• Canonical SMILES: COc1ccccc1[C@H]1OP(=O)(O)OCC1(C)C
• InChI: InChI=1S/C12H17O5P/c1-12(2)8-16-18(13,14)17-11(12)9-6-4-5-7-10(9)15-3/h4-7,11H,8H2,1-3H3,(H,13,14)/t11-/m1/s1
• InChIKey: HNFXKRNIAWHFJN-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2λ^5-dioxaphosphinan-2-one; (4S)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2$l^{5}-dioxaphosphinan-2-one
• IUPAC Traditional name: (4S)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2λ^5-dioxaphosphinan-2-one; (4S)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2$l^{5}-dioxaphosphinan-2-one
• Synonyms: (S)-(-)-2-Hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide; (S)-(-)-Anicyphos; (s)-(-)-Anicyphos; (4S)-(-)-5,5-Dimethyl-4-(2-methoxyphenyl)-1,3,2-dioxaphosphinan-2-ol 2-oxide; (4S)-(-)-5,5-Dimethyl-2-hydroxy-4-(2-methoxyphenyl)-1,3,2-dioxaphosphinane 2-oxide; (S)-(-)-2-羟基-4-(2-甲氧苯基)-5,5-二甲基-1,3,2-二噁磷己环 2-氧化物

Database IDs

• CAS Number: 98674-83-0; 98674-82-9
• MDL Number: MFCD00190173
• PubChem SID: 24870173; 162049580
• PubChem CID: 16213083

CALCULATED PROPERTIES

• Polarizability: 26.510054 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 1.8512338
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.13140187
• LogD (pH = 7.4): -0.15361162
• Log P: 2.2224965
• Molar Refractivity: 66.0182 cm^3

PROPERTIES

Physical Property

• Melting Point: 194-196 °C(lit.)
• Optical Rotation: [α]22/D -59°, c = 1 in methanol

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: >99%; 97%
• Empirical Formula (Hill Notation): C12H17O5P

DETAILS

Sigma Aldrich - 464384

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Chiral phosphoric acid used for the resolution of amines, amino acids, and amino alcohols.1,2,3