o-Cresolphthalein

Base Information

• Chemical Name: o-Cresolphthalein
• CAS No.: 596-27-0
• Deprecated CAS: 80045-63-2
• Molecular Formula: C22H18O4
• Molecular Weight: 346.383
• Hs Code.: 2932209090
• European Community (EC) Number: 209-881-8
• UNII: XOU2D9049G
• DSSTox Substance ID: DTXSID9060491
• Nikkaji Number: J6.782B
• Wikipedia: O-Cresolphthalein
• Wikidata: Q15634165
• ChEMBL ID: CHEMBL1443546
• Mol file: 596-27-0.mol

Synonyms:3,3'-dimethylphenolphthalein;cresolphthalein

Chemical Property of o-Cresolphthalein

Chemical Property:

• Appearance/Colour: white to pink or beige to tan powder
• Vapor Pressure: 6.29E-13mmHg at 25°C
• Melting Point: 223-225 °C
• Refractive Index: 1.668
• Boiling Point: 555 °C at 760 mmHg
• PKA: 9.40(at 25℃)
• Flash Point: 198.8 °C
• PSA: 66.76000
• Density: 1.32 g/cm³
• LogP: 4.17690
• Solubility.: Solubility Slightly soluble in water; soluble in ethanol
• Water Solubility.: slightly soluble
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 346.12050905
• Heavy Atom Count: 26
• Complexity: 506

Purity/Quality:

99% ^*data from raw suppliers

o-Cresolphthalein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-36/37/38-20/21/22
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Indicator Dyes
• Canonical SMILES: CC1=C(C=CC(=C1)C2(C3=CC=CC=C3C(=O)O2)C4=CC(=C(C=C4)O)C)O
• Uses: As indicator: pH range, 8.2 colorless, 9.8 red. Analytical reagent. O-Cresolphthalein has been used as a component in calcifying media for calcification assay.

Technology Process of o-Cresolphthalein

There total 3 articles about o-Cresolphthalein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

phthalic anhydride (85-44-9) + ortho-cresol (95-48-7,77504-84-8) → o-cresolphthalein (596-27-0)

Guidance literature:

With methanesulfonic acid; at 90 ℃; for 5h;

DOI:10.1016/j.tetlet.2009.09.007

Reference yield:

phthalic anhydride (85-44-9) + ortho-cresol (95-48-7,77504-84-8) + phenol (108-95-2,27073-41-2) → phenolphthalein (77-09-8) + [3-(3'-methyl-4'-hydroxyphenyl)-3-(4''-hydroxyphenyl)phthalide] (854-76-2) + o-cresolphthalein (596-27-0)

Guidance literature:

ortho-cresol; phenol; With zinc(II) chloride; In nitrobenzene; at 50 - 60 ℃;

phthalic anhydride; With zinc(II) chloride; In nitrobenzene; at 120 - 130 ℃; for 4h; Overall yield = 34 %; Overall yield = 5.9 g;

DOI:10.1134/S1070427215040278

Reference yield:

→ o-cresolphthalein (596-27-0)

Guidance literature:

Aus o-Kresol, Phthalsaeureanhydrid m. AlCl3 in Tetrachloraethan b. 100-130grad, in geringerer Menge neben 2-<4-Hydroxy-3-methyl-benzoyl>-benzoesaeure u. 2-<2-Hydroxy-3-methyl-benzoyl>-benzoesaeure;

upstream raw materials:

phthalic anhydride

ortho-cresol

phenol

Downstream raw materials:

ortho-cresolphthalein

4,4'-dihydroxy-3,3'-dimethyl-benzophenone

2-phenyl-3,3-bis(4-cyanato-3-methylphenyl)phthalimidine

2-phenyl-3,3-bis(4-hydroxy-3-methylphenyl)phthalimidine

Refernces

• 1、 Sabnis, Ram W.. "A facile synthesis of phthalein indicator dyes". experimental part. p. 6261 - 6263. Retrieved 2010/01/11.