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Phenol Red

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Name

Phenol Red

EINECS 205-609-7
CAS No. 143-74-8 Density 1.477 g/cm3
PSA 92.21000 LogP 4.18940
Solubility 0.77 g/L in water Melting Point 300 °C
Formula C19H14O5S Boiling Point 562.8 °C at 760 mmHg
Molecular Weight 354.383 Flash Point 294.2 °C
Transport Information N/A Appearance dark red powder
Safety 37/39-26-45-36/37/39-27 Risk Codes 36/37/38-34
Molecular Structure Molecular Structure of 143-74-8 (Phenol Red) Hazard Symbols IrritantXi,CorrosiveC
Synonyms

Phenol,4,4'-(3H-2,1-benzoxathiol-3-ylidene)di-, S,S-dioxide (8CI);3H-2,1-Benzoxathiole, 3,3-bis(4-hydroxyphenyl)-, 1,1-dioxide;Fenolipuna;NSC10459;PSP;Phenolsulfonephthalein;Sulfonphthal;TF-R 2;a-Hydroxy-a,a-bis(p-hydroxyphenyl)-o-toluenesulfonicacid g-sultone;

Article Data 10

Phenol Red Synthetic route

81-08-3

2-sulfobenzoic acid cyclic anhydride

108-95-2

phenol

143-74-8

phenol red

Conditions
ConditionsYield
for 0.00416667h; Microwave irradiation;81.6%
at 130 - 135℃;
81-07-2

saccharin

108-95-2

phenol

143-74-8

phenol red

Conditions
ConditionsYield
With sulfuric acid at 140℃; for 3.5h; Neat (no solvent);26%
With sulfuric acid at 120℃;
861784-67-0

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

143-74-8

phenol red

Conditions
ConditionsYield
at 135℃;
With phenol at 135℃;
108-95-2

phenol

benzoic acid o-sulfonic acid-dichloride

benzoic acid o-sulfonic acid-dichloride

143-74-8

phenol red

Conditions
ConditionsYield
With zinc(II) chloride at 140℃;
108-95-2

phenol

benzoic acid sulfonic acid-(2)-dichloride

benzoic acid sulfonic acid-(2)-dichloride

143-74-8

phenol red

Conditions
ConditionsYield
at 135 - 140℃;
108-95-2

phenol

1-halo-dodecane

1-halo-dodecane

143-74-8

phenol red

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 135 - 140 °C
2: phenol / 135 °C
View Scheme
143-74-8

phenol red

115-39-9

bromophenol blue

Conditions
ConditionsYield
With perchloric acid; dihydrogen peroxide; C14H9BrN2O4V(1-); potassium bromide In water at 0 - 24℃; for 0.666667h; Catalytic behavior; Reagent/catalyst; Temperature;89%
With C12H8N2*C13H11N3O3(2-)*OV(2+); dihydrogen peroxide; potassium bromide In water Kinetics; Concentration; aq. phosphate buffer;
With [V(1,3-benzenedicarboxyliate)(2,6-pyridinedicarboxylate)(H2O)2]; potassium bromide In water; N,N-dimethyl-formamide at 30℃; pH=5.8; Kinetics; Reagent/catalyst;
143-74-8

phenol red

5-(4-(4-bromobutoxyl)phenyl)10,15,20-triphenyl porphyrin

C67H50N4O6S

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 150℃; for 24h;15%
137-17-7

2,4,5-trimethylaniline

143-74-8

phenol red

3,3-bis-[4-(2,4,5-trimethyl-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions
ConditionsYield
at 180℃;
143-74-8

phenol red

104-94-9

4-methoxy-aniline

3,3-bis-(4-p-anisidino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions
ConditionsYield
at 180℃;

Phenol Red Consensus Reports

Reported in EPA TSCA Inventory.

Phenol Red Specification

The IUPAC name of Phenolsulfonphthalein is 4-[3-(4-hydroxyphenyl)-1,1-dioxo-2,1λ6-benzoxathiol-3-yl]phenol. With the CAS registry number 143-74-8, it is also named as 4,4'-(3H-2,1-Benzoxathiol-3-ylidene)diphenol S,S-dioxide. The product's categories are analytical chemistry; indicator (pH); stains and dyes; general stains / dyes for stem cell biologystains and dyes; cell culture; cell viability and proliferation; stains, dyes and indicators; stem cell characterization. It is dark red powder that the solubility is 0.77 grams per liter (g/L) in water, 2.9 g/L in ethanol, and almost insoluble in ether and chloroform. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.02; (4)ACD/LogD (pH 7.4): 3.01; (5)ACD/BCF (pH 5.5): 116.16; (6)ACD/BCF (pH 7.4): 113.4; (7)ACD/KOC (pH 5.5): 1046.52; (8)ACD/KOC (pH 7.4): 1021.65; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.697; (13)Molar Refractivity: 92.38 cm3; (14)Molar Volume: 239.7 cm3; (15)Polarizability: 36.62×10-24 cm3; (16)Surface Tension: 69.2 dyne/cm; (17)Enthalpy of Vaporization: 87.75 kJ/mol; (18)Vapour Pressure: 2.84E-13 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 3; (21)Exact Mass: 354.056194; (22)MonoIsotopic Mass: 354.056194; (23)Topological Polar Surface Area: 92.2; (24)Heavy Atom Count: 25.

Preparation of Phenolsulfonphthalein: Heating and melting the o-sulfonic acid anhydride and phenol, then adding anhydrous zinc chloride at 135-140 °C to react 7h, and then put the condensate into the hot water, filtering, washing the solid with water, and further purified by acid-base precipitation to get the product.

Uses of Phenolsulfonphthalein: It acts as a pH indicator that is frequently used in cell biology laboratories, changing from yellow to red between the pH 6.8-8.4. And it is also used in the phenolsulfonphthalein test which is used to estimate the overall blood flow through the kidney and is now obsolete. Sometimes labelled with a different name, it is used as a pH indicator in home swimming pool test kits.

When you are using this chemical, please be cautious about it as the following:
It can cause burns. And it is also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. 

People can use the following data to convert to the molecule structure. 
1. SMILES: O=S2(=O)OC(c1ccccc12)(c3ccc(O)cc3)c4ccc(O)cc4;
2. InChI: InChI=1/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 1368mg/kg (1368mg/kg)   Drugs in Japan Vol. -, Pg. 930, 1990.
rat LD50 intravenous 752mg/kg (752mg/kg)   Drugs in Japan Vol. -, Pg. 930, 1990.
rat LD50 subcutaneous > 600mg/kg (600mg/kg)   Clinical Toxicology. Vol. 4(2), Pg. 185, 1971.

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