3,3-bis(4-hydroxy-3-methylphenyl)-3H-2,1$l^{6}-benzoxathiole-1,1-dione

• ChemBase ID: 109636
• Molecular Formular: C21H18O5S
• Molecular Mass: 382.42962
• Monoisotopic Mass: 382.08749468
• SMILES: Cc1cc(ccc1O)C1(OS(=O)(=O)c2ccccc12)c1ccc(O)c(C)c1
• Canonical SMILES: Cc1cc(ccc1O)C1(OS(=O)(=O)c2c1cccc2)c1ccc(c(c1)C)O
• InChI: InChI=1S/C21H18O5S/c1-13-11-15(7-9-18(13)22)21(16-8-10-19(23)14(2)12-16)17-5-3-4-6-20(17)27(24,25)26-21/h3-12,22-23H,1-2H3
• InChIKey: OBRMNDMBJQTZHV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,3-bis(4-hydroxy-3-methylphenyl)-3H-2,1$l^{6}-benzoxathiole-1,1-dione; 3,3-bis(4-hydroxy-3-methylphenyl)-3H-2,1λ^6-benzoxathiole-1,1-dione
• IUPAC Traditional name: cresol red
• Synonyms: o-Cresolsulfonephthalein; o-CRESOL RED; Cresol Red; o-Cresolsulfonphthalein; Cresol red; 邻甲酚磺酰酞; 甲酚红

Database IDs

• CAS Number: 1733-12-6
• EC Number: 217-064-2
• MDL Number: MFCD00005878
• Beilstein Number: 343399
• Merck Index: 142578
• PubChem SID: 162096271; 24859594; 24847173
• PubChem CID: 73013
• Chemspider ID: 65818
• Wikipedia Title: Cresol_Red

CALCULATED PROPERTIES

• Acid pKa: 9.5177355
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.1354933
• LogD (pH = 7.4): 5.1322474
• Log P: 5.135535
• Molar Refractivity: 104.1992 cm^3
• Polarizability: 40.173042 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: > 300°C
• Absorption Wavelength: λmax 367 nm (2nd); λmax 570 nm

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥83%
• Grade: indicator; indicator grade; JIS special grade
• Compostion: Dye content, 95%
• Loss on Drying: ≤5% loss on drying
• pH Range: 7.2 - 8.8, yellow to red
• Visual Transition Interval: 0.5 - 2.5 (corresponds); 6.5 - 8.5 (corresponds)
• Useful pH Range: 1.8 - 2.0, orange to yellow (acid); 7.0 - 8.8, yellow to violet (alkaline)
• Empirical Formula (Hill Notation): C21H18O5S

DETAILS

MP Biomedicals - 05211963

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 32653

General description
Visit our Titration Center to learn more.

Sigma Aldrich - 114472

Packaging
5, 25 g in glass bottle
Application
Cresol Red is used as a tracking dye in DNA, RNA (agarose) and protein (polyacrylamide) electrophoresis. In agarose, Cresol Red runs with an apparent molecular size of approx. 125 bp DNA. Cresol Red does not inhibit Taq polymerase. Recently Cresol Red has been used as a pH sensitive indicator dye in nanoengineered optical urea biosensors films and hetero-core structured fiber optic pH sensor.

REFERENCES

• Acid-base indicator: pH 0.2 - 1.8; 7.0 - 8.8.