143-74-8

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H315 (99.51%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (42.16%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (94.12%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes:

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories:

Skin Irrit. 2 (99.51%)
Eye Irrit. 2 (42.16%)
STOT SE 3 (94.12%)

Hazards Summary:

Dust may be irritating if inhaled; [CHEMINFO]

Usage

Chemical Properties

dark red powder

Uses

Different sources of media describe the Uses of 143-74-8 differently. You can refer to the following data:
1. As indicator in 0.02-0.05% alcohol solution. pH 6.8 yellow, 8.4 red.
2. Phenol red is used as a non absorbed marker in gravimetric method. It is a pH indicator used in cell biology laboratories and in home swimming pool test kits. It is used to check the kidney function based on the excreted phenol red by colorimetric method.

Definition

ChEBI: 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.

Biochem/physiol Actions

Phenol Red is a pH indicator which changes color from yellow to red.

Safety Profile

Moderately toxic by ingestion and intravenous routes. Mutation data reported. When heated to decomposition it emits toxicvapors of SOx.

Enzyme inhibitor

This pH-indicating dye (FW = 354.38 g/mol; CAS 143-74-8; pKa = 7.9; yellow < pH 6.8; red > pH 8.4), also known as phenolsulfonphthalein and sulfophthalein, is a diagnostic aid for evaluating renal function. A typical stock indicator solution is 0.1 g phenol red in 28.2 mL 10 mM NaOH and 221.8 mL water. Target(s): aldehyde reductase; glutaminase; gglutamyl transpeptidase; glutathione S-transferase; 4- methyleneglutaminase; phosphate uptake; thromboxane A2/prostaglandin H2 receptor; and thyroglobulin iodination.

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

Synthetic route

2-sulfobenzoic acid cyclic anhydride (81-08-3) + phenol (108-95-2) → phenol red (143-74-8)

Conditions	Yield
for 0.00416667h; Microwave irradiation;	81.6%
at 130 - 135℃;

saccharin (81-07-2) + phenol (108-95-2) → phenol red (143-74-8)

Conditions	Yield
With sulfuric acid at 140℃; for 3.5h; Neat (no solvent);	26%
With sulfuric acid at 120℃;

2-(4-hydroxy-benzoyl)-benzenesulfonic acid (861784-67-0) → phenol red (143-74-8)

Conditions	Yield
at 135℃;
With phenol at 135℃;

phenol (108-95-2) + benzoic acid o-sulfonic acid-dichloride → phenol red (143-74-8)

Conditions	Yield
With zinc(II) chloride at 140℃;

phenol (108-95-2) + benzoic acid sulfonic acid-(2)-dichloride → phenol red (143-74-8)

Conditions	Yield
at 135 - 140℃;

phenol (108-95-2) + 1-halo-dodecane → phenol red (143-74-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 135 - 140 °C 2: phenol / 135 °C View Scheme

phenol red (143-74-8) → bromophenol blue (115-39-9)

Conditions	Yield
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;

phenol red (143-74-8) + 5-(4-(4-bromobutoxyl)phenyl)10,15,20-triphenyl porphyrin → C67H50N4O6S

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 150℃; for 24h;	15%

2,4,5-trimethylaniline (137-17-7) + phenol red (143-74-8) → 3,3-bis-[4-(2,4,5-trimethyl-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 180℃;

phenol red (143-74-8) + 4-methoxy-aniline (104-94-9) → 3,3-bis-(4-p-anisidino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 180℃;

phenol red (143-74-8) + ethylamine (75-04-7) → 3,3-bis-(4-ethylamino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 140℃;

phenol red (143-74-8) + 4-Ethoxyaniline (156-43-4) → 3,3-bis-(4-p-phenetidino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 180℃;

phenol red (143-74-8) + 2,4-Xylidine (95-68-1) → 3,3-bis-[4-(2,4-dimethyl-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 180℃;

phenol red (143-74-8) + methylamine (74-89-5) → 3,3-bis-(4-methylamino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 140℃;

phenol red (143-74-8) + o-toluidine (95-53-4) → 3,3-bis-(4-o-toluidino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
at 180℃;

phenol red (143-74-8) → 3,3-bis-(4-amino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide (4538-11-8)

Conditions	Yield
With ammonium hydroxide at 150℃;

phenol red (143-74-8) → 3,3-bis-(4-propylamino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit Propylamin und Aethanol;

phenol red (143-74-8) → 3,3-bis-(4-isobutylamino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsgemisches mit Isobutylamin und Aethanol;

phenol red (143-74-8) → 3,3-bis-[4-(2-hydroxy-ethylamino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit 2-Amino-aethanol und Aethanol;

phenol red (143-74-8) → 3,3-bis-(4-benzylamino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit Benzylamin und Aethanol;

phenol red (143-74-8) → 3,3-bis-[4-(4-hydroxy-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit 4-Amino-phenol und Aethanol;

phenol red (143-74-8) → 3,3-bis-[4-(4-amino-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit p-Phenylendiamin und Aethanol;

phenol red (143-74-8) → 3,3-bis-[4-(3-hydroxy-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit 3-Amino-phenol und Aethanol;

phenol red (143-74-8) → 3,3-bis-[4-(2-bromo-anilino)-phenyl]-3H-benz[c][1,2]oxathiol-1,1-dioxide

Conditions	Yield
With phosphorus pentachloride; acetyl chloride Erwaermen des Reaktionsprodukts mit 2-Brom-anilin und Aethanol;

phenol red (143-74-8) → 4,4'-Dihydroxybenzophenone (611-99-4) + phenol (108-95-2)

Conditions	Yield
bei der Kalischmelze;

phenol red (143-74-8) → bromocresol red (2800-80-8) + bromophenol blue (115-39-9)

Conditions	Yield
With dihydrogen peroxide; sodium bromide In phosphate buffer at 30℃; for 5.83333h; pH=0.5 - 4.5; Bromination;

phenol red (143-74-8) + water (7732-18-5) + zinc dust → 2-(4,4'-dihydroxy-benzhydryl)-benzenesulfonic acid (172464-36-7)

phenol red (143-74-8) + aniline (62-53-3) → diphenylamine-sulfonphthalein

Conditions	Yield
at 140 - 150℃;

Upstream product

• 108-95-2 phenol 
• 81-07-2 saccharin 
• 861784-67-0 2-(4-hydroxy-benzoyl)-benzenesulfonic acid 
• 81-08-3 2-sulfobenzoic acid cyclic anhydride 

Downstream Products

• 4538-11-8 3,3-bis-(4-amino-phenyl)-3H-benz[c][1,2]oxathiol-1,1-dioxide 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 108-95-2 phenol 
• 2800-80-8 bromocresol red 
• 115-39-9 bromophenol blue 
• 172464-36-7 2-(4,4'-dihydroxy-benzhydryl)-benzenesulfonic acid 

Related news

Effect of Phenol Red (cas 143-74-8) dye on monocrystal growth, crystalline perfection, and optical and dielectric properties of zinc (tris) thiourea sulfate09/30/2019

In this work, the growth of large size (∼25 × 29 × 5 mm and ∼25 × 24 × 6 mm) colorful single crystals of zinc (tris) thiourea sulfate (ZTS) in the presence of 0.05–2 wt% phenol red (PR) dye was achieved using a simple and low‐cost technique. Powder X‐ray diffraction patterns confirm the...detailed

Photodegradation of Phenol Red (cas 143-74-8) in the presence of oxyhydroxide of Fe(III) (Goethite) under artificial and a natural light09/29/2019

The (α‐FeOOH) Goethite composite is a stable and an efficient catalyst in aqueous suspension under irradiation at 365 nm and by solar light. The photocatalytic activities of this composite were evaluated using Phenol Red (PR) dye (phenolsulfonphthalein class). In the dark, controlling factors,...detailed

Highly efficient adsorption of Naphthol Green B and Phenol Red (cas 143-74-8) dye by Combination of Ultrasound wave and Copper‐Doped Zinc Sulfide Nanoparticles Loaded on Pistachio‐Nut Shell09/28/2019

The simultaneous and competitive ultrasound‐assisted removal of naphthol green B (NG‐B) and phenol red (PH‐R) dye from aqueous solutions were rapidly performed onto copper‐doped zinc sulfide nanoparticles loaded on pistachio‐nut shell activated carbon (Zn‐S: Cu‐NPs‐PAC). Novel adsorbent ...detailed

Relevant academic research and scientific papers

Solvent-free one-pot synthesis of sulfonephthaleins from saccharin and phenols

Sulfonephthaleins can be synthesized in a single pot from saccharin and phenol via the in situ formation of 2-sulfobenzoic anhydride, followed by its reaction with phenol using H2SO4 as the condensing agent, in the absence of any solvent. This solvent-free synthesis is more economical and environmentally benign. Copyright Taylor & Francis Group, LLC.

Solvent-free synthesis of sulfonephthaleins, sulfonefluoresceins and fluoresceins under microwave irradiation

An efficient solvent-free synthesis of sulfonephthaleins, sulfonefluoresceins and fluoresceins under microwave irradiation is reported.

Method for preparing high molecular weight meningococcal Group C vaccine

A vaccine against Group C meningococcal meningitis consisting of a polysaccharide of which at least 80% by weight has a molecular weight in excess of 1,000,000 daltons is prepared. The polysaccharide was isolated from Group C hexadecyl trimethylammonium bromide cell paste with 1.0M CaCl2 extraction and purified by phenol extraction, ultracentrifugation at 100,000 g. and ethanol fractionation (30%-45% v/v in ethanol).