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125-20-2

Basic Information
CAS No.: 125-20-2
Name: Thymolphthalein
Article Data: 4
Cas Database
Molecular Structure:
Molecular Structure of 125-20-2 (Thymolphthalein)
Formula: C28H30O4
Molecular Weight: 430.544
Synonyms: 1(3H)-Isobenzofuranone, 3,3-bis(4-hydroxy-2-methyl-5-(1-methylethyl)phenyl)-;Phenolphthalein, 5,5-diisopropyl-2,2-dimethyl- (8CI);3,3-Bis(4-hydroxy-5-isopropyl-o-tolyl)phthalide;Phenolphthalein, 5,5-diisopropyl-2,2-dimethyl-;3,3-bis(4-hydroxy-2-methyl-5-propan-2-yl-phenyl)isobenzofuran-1-one;1(3H)-Isobenzofuranone,3,3-bis[4-hydroxy-2- methyl-5-(1-methylethyl)phenyl]-;Thymol Phthalein;
EINECS: 204-729-7
Density: 1.187 g/cm3
Melting Point: 251-253 °C(lit.)
Boiling Point: 571.6 °C at 760 mmHg
Flash Point: 187.5 °C
Solubility: Insoluble in water
Appearance: white fine crystalline powder
Hazard Symbols: FlammableF,HarmfulXn
Risk Codes: 11-40
Safety: 7-16-36/37-24/25-22
Transport Information: UN 1170 3/PG 3
PSA: 66.76000
LogP: 6.42370
Synthetic route
85-44-9

phthalic anhydride

89-83-8

thymol

125-20-2

thymolphthalein

Conditions
ConditionsYield
With methanesulfonic acid at 90℃; for 5h;90%
With niobium pentachloride In methanesulfonic acid at 90℃; for 1.33333h; Friedel-Crafts Acylation;70%
With tin(IV) chloride at 110℃;
3068-34-6, 38874-23-6, 41355-44-6, 51236-40-9, 74081-14-4, 79897-03-3, 100759-09-9, 109581-83-1

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride

125-20-2

thymolphthalein

thymolphthalein-N-acetyl-3,4,6-O-triacetyl-β-D-glucopyranoside

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water at 10 - 20℃; for 3h;61.2%
125-20-2

thymolphthalein

21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

thymolphtaleine-α-acetyl-D-glucuronic acid methyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water at 10 - 20℃; for 3h;46.7%
125-20-2

thymolphthalein

21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

thymolphthalein β-D-glucuronide

Conditions
ConditionsYield
Stage #1: thymolphthalein; 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester With silver(l) oxide In methanol at 20℃; for 8h;
Stage #2: With methanol; sodium hydroxide at 20℃; for 4h; Reagent/catalyst; Solvent;
35%
125-20-2

thymolphthalein

108-24-7

acetic anhydride

3,3-bis-(4-acetoxy-5-isopropyl-2-methyl-phenyl)-phthalide

Conditions
ConditionsYield
With sulfuric acid; acetic acid
125-20-2

thymolphthalein

74-88-4

methyl iodide

3,3-bis-(5-isopropyl-4-methoxy-2-methyl-phenyl)-phthalide

Conditions
ConditionsYield
With potassium carbonate; acetone
125-20-2

thymolphthalein

zinc dust

zinc dust

KOH-solution

KOH-solution

thymolphthalyne

thymolphthalyne

Raw Materials
89-83-8
85-44-9
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Standards and Recommendations

DYE CONTENT: 95.0% min
LOSS ON DRYING: 3.0% max
CLARITY OF SOLUTION: pass
TRANSITION INTERVAL: pH 8.8 to colourless, pH 10.5 to blue
ABSORPTION: 592 - 596 nm 

Specification

The IUPAC name of Thymolphthalein is 3,3-bis(4-hydroxy-2-methyl-5-propan-2-ylphenyl)-2-benzofuran-1-one. With the CAS registry number 125-20-2, it is also named as Phenolphthalein, 5',5''-diisopropyl-2',2''-dimethyl-. The product's categories are miscellaneous biochemicals; analytical chemistry; indicator (pH); pH indicators. It is white fine crystalline powder which is insol in water, soluble in alcohol, acetone and also soluble in dilute alkalies with a blue color, in H2SO4 with a carmine-red color. In addition, Thymolphthalein should be sealed in a container which must be kept in a cool, well-ventilated area.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.23; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.23; (4)ACD/LogD (pH 7.4): 6.23; (5)ACD/BCF (pH 5.5): 31874.84; (6)ACD/BCF (pH 7.4): 31777.03; (7)ACD/KOC (pH 7.4): 58051.44; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.612; (12)Molar Refractivity: 126.12 cm3; (13)Molar Volume: 362.4 cm3; (14)Polarizability: 50×10-24 cm3; (15)Surface Tension: 49.5 dyne/cm; (16)Enthalpy of Vaporization: 88.89 kJ/mol; (17)Vapour Pressure: 1.15E-13 mmHg at 25°C; (18)Rotatable Bond Count: 4; (19)Tautomer Count: 45; (20)Exact Mass: 430.214409; (21)MonoIsotopic Mass: 430.214409; (22)Topological Polar Surface Area: 66.8; (23)Heavy Atom Count: 32.

Preparation of Thymolphthalein: Heating the mixture of thymol, phthalic anhydride and anhydrous zinc chloride. Adding ether and benzene, refluxing in a water bath and pouring out the upper solvent. Adding methanol to the solid, heating, and extracting the reagents. Extracted remaining solids with methanol, dropping water until seeing the precipitation, then cooling to get the product.

Uses of Thymolphthalein: It acts as pH indicator, changing from colorless to blue between the pH 9.3 to 10.5. And it is also used as reagent for blood after decolorizing the alkaline soln by boiling with zinc dust.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, So it should be kept away from sources of ignition. And it has limited evidence of a carcinogenic effect. Furthermore, people must not breathe dust and avoid contact with skin and eyes. If you want to contact this product, you must wear suitable protective clothing and gloves. 

People can use the following data to convert to the molecule structure.
1. SMILES: O=C1OC(c2ccccc12)(c3cc(c(O)cc3C)C(C)C)c4cc(c(O)cc4C)C(C)C;
2. InChI: InChI=1/C28H30O4/c1-15(2)20-13-23(17(5)11-25(20)29)28(22-10-8-7-9-19(22)27(31)32-28)24-14-21(16(3)4)26(30)12-18(24)6/h7-16,29-30H,1-6H3.