P-XYLENOLPHTHALEIN Chemical Properties

Melting point:

276°C

Boiling point:

569.6±50.0 °C(Predicted)

Density 

1.270±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Solubility Insoluble in water; soluble in ethanol, acetone

pka

9.7(at 25℃)

form 

powder

color 

Pale yellow or cream-colored

PH Range

Colorless (9.0) to indigo-blue (10.5)

BRN 

346799

Major Application

Inks, detergent, photoresist, toothpaste and mouthwash, disinfectant, cosmetics, paints

InChI

InChI=1S/C24H22O4/c1-13-11-21(25)15(3)9-19(13)24(20-10-16(4)22(26)12-14(20)2)18-8-6-5-7-17(18)23(27)28-24/h5-12,25-26H,1-4H3

InChIKey

PXCIPOXPHMTCIL-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(C2=CC(C)=C(O)C=C2C)(C2=CC(C)=C(O)C=C2C)O1

Safety Information

WGK Germany 

3

HS Code 

2932.99.7000

MSDS

• Language:English Provider:SigmaAldrich

P-XYLENOLPHTHALEIN Usage And Synthesis

Uses

p-Xylenolphthalein is related to phenolphthalein which is used as a pH change indicator.

Synthesis

General procedure for the synthesis of 3,3-bis-(4-hydroxy-3,6-dimethylphenyl)-1-(3H)-isobenzofuranone from 2,5-dimethylphenol and phthalic anhydride: a mixture of 2,5-dimethylphenol (0.133 mol), phthalic anhydride (0.074 mol), reaction medium (0.416 mol) and Lewis acid (0.029 mol ) were placed in a reaction flask, stirred and heated at 90 °C for 5 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and subsequently slowly poured into an ice-water mixture to induce precipitation of the product. The precipitate was collected by filtration and washed with plenty of water to remove impurities. The crude product was dried and recrystallized from methanol to afford pure 3,3-bis-(4-hydroxy-3,6-dimethylphenyl)-1-(3H)-isobenzofuranone as light yellow crystals in 85% yield. The product was analyzed by IR (KBr) showing that the characteristic absorption peaks were located at 3393 cm^-1 (O-H stretching vibration), 1729 cm^-1 (C=O stretching vibration), and 1611 cm^-1 (C=C stretching vibration of the aromatic ring).The 1H-NMR (DMSO-d6) spectrum showed the following: δ 9.40 (s, 2H, 2×OH), 1.95 (s, 12H, 4 × CH3), 6.59-6.63 (m, 4H, aromatic protons), 7.46-7.91 (m, 4H, aromatic protons) ppm. mass spectrometry analysis showed the molecular ion peak m/z 374 (M+).

References

[1] Patent: US2006/222601, 2006, A1. Location in patent: Page/Page column 25
[2] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6261 - 6263
[3] Zeitschrift fuer Anorganische und Allgemeine Chemie, 1929, vol. 178, p. 54,56
[4] Roczniki Chemii, 1931, vol. 11, p. 103,109; dtsch. Ref. S. 111
[5] Chem. Zentralbl., 1931, vol. 102, # I, p. 2473

P-XYLENOLPHTHALEIN(50984-88-8)Related Product Information

• Thymolphthalein
• o-Cresolphthalein Complexone
• Methyl Orange
• o-Cresolphthalein
• alpha-Naphtholphthalein
• Phenolphthalein
• Thymolphthalein monophosphate magnesium salt
• THYMOL VIOLET
• THYMOLPHTHALEIN MONOPHOSPHATE DISODIUM SALT
• Thymolphthalein monophosphate 2-amino-2-methyl-1,3-propanediol salt
• Thymolphthalein Complexone
• Thymolphthalein complexone disodium salt
• P-XYLENOLPHTHALEIN
• Thymolphthalein phosphoric acid diammonium salt
• Thymolphthalein monophosphoric acid disodium salt trihydrate
• THYMOLPHTHALEIN MONOPHOSPHATE MAGNESIUM SALT
• THYMOLPHTHALEIN MONOPHOSPHORIC ACID, DI-2-AMINO-2-METHYL-1,3-PROPANEDIOL SALT
• PHENOLPHTHALEIN-THYMOLPHTHALEIN