Pyrogallol

Base Information

• Chemical Name: Pyrogallol
• CAS No.: 87-66-1
• Molecular Formula: C6H6O3
• Molecular Weight: 126.112
• Hs Code.: 2907 29 00
• European Community (EC) Number: 201-762-9
• ICSC Number: 0770
• NSC Number: 5035
• UN Number: 2811
• UNII: 01Y4A2QXY0
• DSSTox Substance ID: DTXSID6025983
• Nikkaji Number: J3.903I
• Wikipedia: Pyrogallol
• Wikidata: Q388692
• NCI Thesaurus Code: C80909
• Pharos Ligand ID: ZLU5MJ7FZPYA
• Metabolomics Workbench ID: 42469
• ChEMBL ID: CHEMBL307145
• Mol file: 87-66-1.mol

Synonyms:1,2,3-Trihydroxybenzene;acid, Pyrogallic;Pyrogallic acid;Pyrogallol

Chemical Property of Pyrogallol

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 10 mm Hg ( 167.7 °C)
• Melting Point: 43-47 °C(lit.)
• Refractive Index: n20/D 1.387
• Boiling Point: 309 °C at 760 mmHg
• PKA: pK1:9.03(0);pK2:11.63(+1) (25°C)
• Flash Point: 164.4 °C
• PSA: 60.69000
• Density: 1.488 g/cm³
• LogP: 0.80340
• Storage Temp.: Desiccate at RT
• Sensitive.: Light Sensitive
• Solubility.: water: soluble
• Water Solubility.: 400 g/L (25 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 126.031694049
• Heavy Atom Count: 9
• Complexity: 84.3
• Transport DOT Label: Poison

Purity/Quality:

99.8% min ^*data from raw suppliers

Pyrogallol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-52/53-68-40-36/38
• Safety Statements: 22-24/25-61-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=CC(=C(C(=C1)O)O)O
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. The substance is mildly irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: Pyrogallol is a natural oxidant that can generate superoxide (O2-) in alkaline solutions through autoxidation to a semiquinone radical. Importantly, the semiquinone radical can react with O2- in an acidic environment to produce a quinone and H2O2. Pyrogallol autoxidation is used in superoxide dismutase activity assays. It can also be used in assays to assess antioxidant capacity. Pyrogallol is used in some biological systems as an O2- scavenger. In other biological systems, it is used as an O2- generator. Pyrogallol effectively scavenges DPPH radical and ABTS+ in vitro. Pyrogallol is a product of tannin degradation to gallic acid by ruminant microbes and has hepatotoxic and nephrotoxic effects in vivo.
• Uses: Pyrogallol possesses importance as a spectrophotometric reagent in the determination of niobium and tantalum. The absorptions of niobium and tantalum complexes are usually measured at 340 and 335 nm, respectively. The niobium complex is formed in slightly acidic medium, and the tantalum complex in strongly acidic medium (4 N HC1). The absorption spectra are pH-dependen. Complexing agent; reducing agent; alkaline solution indicator for gaseous oxygen. Pyrogallol is used in the manufacture of various dyes; in dyeing furs, hairs, and feathers; for staining leather; in engraving;as a developer in photography; and as an analytical reagent..

Technology Process of Pyrogallol

There total 90 articles about Pyrogallol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

hydrogenchloride (7647-01-0,15364-23-5) + triphenylantimony o-hydroxy-o-phenylenediamine (187221-61-0) → triphenylantimony dichloride (594-31-0,34716-91-1,20265-29-6) + 2-hydroxyresorcinol (87-66-1)

Guidance literature:

heating (3 h, water bath); soln. pouring into Petri dish, solid extraction by benzene;

Reference yield: 50.0%

2,3-dimethoxyphenol (5150-42-5) → 3-methocycatechol (934-00-9) + 2-hydroxyresorcinol (87-66-1)

Guidance literature:

With aluminium(III) iodide; dimethyl sulfoxide; In acetonitrile; at 20 ℃; for 48h; Time;

DOI:10.1055/s-0037-1610996

Reference yield: 25.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → furfural (98-01-1) + 1,2,4-Trihydroxybenzene (533-73-3) + levulinic acid (123-76-2) + hydroquinone (123-31-9,8027-02-9) + 2-hydroxyresorcinol (87-66-1)

Guidance literature:

In water; at 330 ℃; for 0.075h; under 210017 Torr; other temperatures, other reaction times, other educt;

upstream raw materials:

1,2,3-trimethoxybenzene

aniline hydrochloride

pyridine hydrochloride

3,4,5-trihydroxybenzoic acid

Downstream raw materials:

4,6-bis-morpholin-4-ylmethyl-benzene-1,2,3-triol

4-methyldaphnetin

4-Chloro-1,2,3-trihydroxybenzene

1,2,3-trihydroxy-4,6-dichlorobenzene

Refernces

• 1、 Balawejder, Maciej,Barylyak, Adriana,Bobitski, Yaroslav,Kisa?a, Joanna,Tomaszewska, Anna. "Photocatalytic Degradation of 4,4′-Isopropylidenebis(2,6-dibromophenol) on Magnetite Catalysts vs. Ozonolysis Method: Process Efficiency and Toxicity Assessment of Disinfection By-Products". . . Retrieved 2022/03/31.
• 2、 -. "Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand". Paragraph 0106-0107; 0129. . Retrieved 2021/09/21.