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77-09-8

Basic Information
CAS No.: 77-09-8
Name: 1(3H)-Isobenzofuranone,3,3-bis(4-hydroxyphenyl)-
Article Data: 45
Cas Database
Molecular Structure:
Molecular Structure of 77-09-8 (1(3H)-Isobenzofuranone,3,3-bis(4-hydroxyphenyl)-)
Formula: C20H14O4
Molecular Weight: 318.329
Synonyms: Phenolphthalein(8Cl);3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranone;3,3-Bis(4-hydroxyphenyl)phthalide;3,3-Bis(p-hydroxyphenyl)phthalide;Euchessina;Koprol;Laxogen;Lilo;NSC 10464;NSC 215214;Phthalimetten;Phthalin;Purga;Purgen;Purgophen;Spulmako-lax;
EINECS: 201-004-7
Density: 1.385 g/cm3
Melting Point: 258-263 °C
Boiling Point: 557.8 °C at 760 mmHg
Flash Point: 206.5 °C
Solubility: Water: <0.1 g/100 mL
Appearance: White to light yellow crystal powder
Hazard Symbols: HarmfulXn,ToxicT,FlammableF,IrritantXi
Risk Codes: 40-22-10-36/38-23/25-11-36/37/38
Safety: 45-36/37-33-24-16-7-36-26
Transport Information: UN 1993
PSA: 66.76000
LogP: 3.56010
Synthetic route
85-44-9

phthalic anhydride

108-95-2

phenol

77-09-8

phenolphthalein

Conditions
ConditionsYield
With methanesulfonic acid at 90℃; for 5h;94%
With Noccaea caerulescens extract at 80℃; for 0.25h;90%
With mixed metal catalyst derived from Thlaspi at 80℃; for 0.0833333h; Friedel-Crafts Acylation;90%
85-44-9

phthalic anhydride

108-95-2

phenol

A

77-09-8

phenolphthalein

B

596-24-7

spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one

Conditions
ConditionsYield
With sulfuric acid at 115 - 120℃;
509-77-3

3,3-bis(4-aminophenyl)isobenzofuran-1-(3H)-one

77-09-8

phenolphthalein

Conditions
ConditionsYield
With potassium nitrite saure Loesung;
88-99-3

benzene-1,2-dicarboxylic acid

108-95-2

phenol

77-09-8

phenolphthalein

Conditions
ConditionsYield
With tin(IV) chloride
With sulfuric acid
85-57-4

2-(4-hydroxy-benzoyl)-benzoic acid

108-95-2

phenol

77-09-8

phenolphthalein

Conditions
ConditionsYield
at 180℃;
84755-69-1

phenolphthaleine glucuronide

77-09-8

phenolphthalein

Conditions
ConditionsYield
With water at 37℃; for 0.75h; β-glucuronidase; addition of Mn2+, V5+, Ni2+, Co2+, Cu+, Ca2+, Cd2+, or Zn2+; influence of regucalcin; effect of dithiothreitol or dipicolinate;

1-(1-cyclohexenyl)-methyl-2-aminomethyl-pyrrolidine

5-methylsulphamoyl-2-methyl-2,3-dihydrobenzofuran-7-carbonyl chloride

77-09-8

phenolphthalein

Conditions
ConditionsYield
With ammonia In chloroform
62625-15-4

phenolphthalein dibutyrate

77-09-8

phenolphthalein

Conditions
ConditionsYield
With recombinant Arthrobacter globiformis carboxylesterase; water at 45℃; Enzymatic reaction;
83-44-3

Deoxycholic acid

β-cyclodextrin phenolphthalein complex (1:1)

A

37777-96-1

C24H40O4*C42H70O35

B

77-09-8

phenolphthalein

Conditions
ConditionsYield
at 25℃; pH=10.5; carbonate buffer;
128-13-2

ursodeoxycholic acid

β-cyclodextrin phenolphthalein complex (1:1)

A

137078-96-7

C24H40O4*C42H70O35

B

77-09-8

phenolphthalein

Conditions
ConditionsYield
at 25℃; pH=10.5; carbonate buffer;
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Consensus Reports

NTP 10th Report on Carcinogens. Reported in EPA TSCA Inventory.

Specification

The Phenolphthalein with CAS registry number of 77-09-8 is also known as 3,3-Bis(p-hydroxyphenyl)phthalide. The IUPAC name is 3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1-one. It belongs to product categories of Furan&Benzofuran; Analytical Chemistry; Indicator (pH); pH Indicators; Chemistry; Indicator Solutions; Indicators; Titration; Indicator SolutionsStains and Dyes; P; Stains&Dyes, A to. Its EINECS registry number is 201-004-7. In addition, the formula is C20H14O4 and the molecular weight is 318.32. This chemical is a white to light yellow crystal powder and should be stored in sealed containers.

Physical properties about Phenolphthalein are: (1)ACD/LogP: 2.63; (2)ACD/LogD (pH 5.5): 2.63; (3)ACD/LogD (pH 7.4): 2.62; (4)ACD/BCF (pH 5.5): 58.76; (5)ACD/BCF (pH 7.4): 57.9; (6)ACD/KOC (pH 5.5): 642.52; (7)ACD/KOC (pH 7.4): 633.18; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.693; (12)Molar Refractivity: 88.1 cm3; (13)Molar Volume: 229.7 cm3; (14)Surface Tension: 65 dyne/cm; (15)Density: 1.385 g/cm3; (16)Flash Point: 206.5 °C; (17)Enthalpy of Vaporization: 87.1 kJ/mol; (18)Boiling Point: 557.8 °C at 760 mmHg; (19)Vapour Pressure: 4.76E-13 mmHg at 25 °C.

Preparation of Phenolphthalein: it is prepared by condensation of phthalic anhydride with two equivalents of phenol under acidic conditions.

Phenolphthalein is prepared by condensation of phthalic anhydride with two equivalents of phenol under acidic conditions.

Uses of Phenolphthalein: it is used to produce 2-(4,4'-dihydroxy-benzhydryl)-benzoic acid. The reaction occurs with reagent zinc, sodium hydroxide and solvent H2O with other condition of heating for 96 hours. The yield is about 99%. Besides, it is used to perform a presumptive blood test known as the Kastle-Meyer test. It also is used as an acid or base indicator and used in toys.

Phenolphthalein is used to produce 2-(4,4'-dihydroxy-benzhydryl)-benzoic acid.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It is toxic by inhalation and if swallowed. However, there is limited evidence of a carcinogenic effect. What's more, it is highly flammable. During using it, wear suitable protective clothing and gloves. Avoid contact with skin. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately and take precautionary measures against static discharges. After using it, keep container tightly closed away from sources of ignition.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C2C(=C1)C(=O)OC2(C3=CC=C(C=C3)O)C4=CC=C(C=C4)O
2. InChI: InChI=1S/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H
3. InChIKey: KJFMBFZCATUALV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 29mg/kg (29mg/kg) GASTROINTESTINAL: GASTRITIS

GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Postgraduate Medical Journal. Vol. 60, Pg. 491, 1984.
rat LD oral > 1gm/kg (1000mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 25, 1953.
rat LDLo intraperitoneal 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 30, 1953.