(2S,3R,4S,5R,6R)-2-[(6-bromonaphthalen-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 102326
• Molecular Formular: C16H17BrO6
• Molecular Mass: 385.20658
• Monoisotopic Mass: 384.02085026
• SMILES: Brc1ccc2cc(O[C@@H]3O[C@@H]([C@H](O)[C@H](O)[C@H]3O)CO)ccc2c1
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)ccc(c3)Br)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H17BrO6/c17-10-3-1-9-6-11(4-2-8(9)5-10)22-16-15(21)14(20)13(19)12(7-18)23-16/h1-6,12-16,18-21H,7H2/t12-,13+,14+,15-,16-/m1/s1
• InChIKey: NLRXQZJJCPRATR-LYYZXLFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-[(6-bromonaphthalen-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-2-[(6-bromonaphthalen-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 6-BROMO-2-NAPHTHYL-β-D-GALACTOPYRANOSIDE; 6-Bromo-2-naphthyl β-D-galactopyranoside

Database IDs

• CAS Number: 15572-30-2
• EC Number: 239-628-7
• MDL Number: MFCD00064182
• Beilstein Number: 92987
• PubChem SID: 162088397
• PubChem CID: 84995

CALCULATED PROPERTIES

• Acid pKa: 12.200141
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.1598417
• LogD (pH = 7.4): 1.1598349
• Log P: 1.1598418
• Molar Refractivity: 84.2563 cm^3
• Polarizability: 34.84967 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 213-216 °C
• Optical Rotation: [α]20/D -45±2°, c = 1% in pyridine

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Impurities: ≤0.1% free bromonaphthol
• Empirical Formula (Hill Notation): C16H17BrO6

DETAILS

MP Biomedicals - 02101147

Crystalline
Histochemical substrate for
β-galactosidase.

Sigma Aldrich - 17664

Other Notes
Substrate for β-galactosidase1,2,3