149-45-1

Basic information

• Product Name: Tiron
• Synonyms: TIRON (1,2-DIHYDROXYBENZENE-3,5-DISULFONIC ACID DISODIUM SALT);DISODIUM PYROCATECHOL-3,5-DISULFONATE;Tiron, Powder;4,5-dihydroxy-1,3-benzenedisulfonic acid. 2Na;4,5-Dihydroxy-1,3-benzenedisulfonic acid disodium salt, Pyrocatechol-3,5-disulfonic acid disodium salt;4,5-Dihydroxy-1,3-benzenedisulfonic acid disodium;Disodium catechol-3,5-disulfonate;4,5-Dihydroxy-1,3-ben
• CAS NO: 149-45-1
• Molecular Formula: C₆H₄Na₂O₈S₂
• Molecular Weight: 332.22
• EINECS: 205-741-5
• Product Categories: Aromatic Phenols
• Mol File: 149-45-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 300 °C
• Appearance: Off-white/Powder
• Density: 2.064g/cm3 at 20℃
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: 1350g/l
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9465
• BRN: 4629740
• CAS DataBase Reference: Tiron(CAS DataBase Reference)
• NIST Chemistry Reference: Tiron(149-45-1)
• EPA Substance Registry System: Tiron(149-45-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CZ9263000
• F: 3-9
• Hazardous Substances Data: 149-45-1(Hazardous Substances Data)

Usage

Chemical Properties

light tan powder

Uses

Different sources of media describe the Uses of 149-45-1 differently. You can refer to the following data:
1. In determination of trace metals.
2. Tiron is a superoxide scavenger used in the study and examination of oxide electronics. Maintains the ability to remove or destroy magnetic moments which may occur on the surface of such materials.

Purification Methods

Recrystallise it from water [Hamaguchi et al. Anal Chim Acta 9 563 1962]. Itisan indicator colour reagent for Fe, Mn, Ti and Mo ions and complexes with Al, Cd, Co, Co, Fe (III), Mn, Pd, UO22+, VO2+ and Zn. [Beilstein 11 IV 630.]

InChI:InChI=1/C6H6O8S2.2Na/c7-4-1-3(15(9,10)11)2-5(6(4)8)16(12,13)14;;/h1-2,7-8H,(H,9,10,11)(H,12,13,14);;/q;2*+1/p-2/rC6H4Na2O8S2/c7-15-17(11,12)3-1-4(9)6(10)5(2-3)18(13,14)16-8/h1-2,9-10H

Synthetic route

benzene-1,2-diol (120-80-9) → tiron (149-45-1)

Conditions	Yield
Stage #1: benzene-1,2-diol With sulfuric acid at 95℃; for 5h; Stage #2: With sodium hydroxide In water at 50℃; Product distribution / selectivity;	73%
Stage #1: benzene-1,2-diol With sulfuric acid at 20 - 90℃; Stage #2: With sodium hydrogen sulfate monohydrate In water at 50℃; Product distribution / selectivity;

1,10-Phenanthroline (66-71-7) + holmium(III) nitrate hexahydrate + tiron (149-45-1) → C42H28Ho2N4O24S6

Conditions	Yield
In ethanol; water at 20 - 150℃; for 49h;	97.5%

1,10-Phenanthroline (66-71-7) + lutetium(III) nitrate hexahydrate + tiron (149-45-1) → C42H28Lu2N4O24S6

Conditions	Yield
In ethanol; water at 20 - 150℃; for 49h;	94.5%

1,10-Phenanthroline (66-71-7) + iron(III) chloride hexahydrate + tiron (149-45-1) → Fe(1,10-phenanthroline)3·4,5-dihydroxy-1,3-benzenedisulfonate

Conditions	Yield
In water for 1h; Reflux;	85%

terbium(III) chloride + tiron (149-45-1) + acetylacetone (123-54-6) → Na2Tb(2,4-pentanedione)3(4,5-dihydroxy-1,3-benzenedisulfonic acid(-2H))

Conditions	Yield
In ethanol; water at 60℃; for 1h;	82.94%

[2,2]bipyridinyl (366-18-7) + iron(III) chloride hexahydrate + tiron (149-45-1) → Fe(2,2'-bipyridine)3·4,5-dihydroxy-1,3-benzenedisulfonate·5H2O

Conditions	Yield
In water for 1h; Reflux;	80%

1,10-Phenanthroline (66-71-7) + tiron (149-45-1) → C48H38N6O21S4Sr3(2-)*1.5C12H8N2*2H(1+)*8H2O

Conditions	Yield
Stage #1: 1,10-Phenanthroline; tiron With water; sodium hydroxide; strontium chloride for 3h; pH=5; Stage #2: at 120℃; for 48h; Autoclave; High pressure;	75%

tiron (149-45-1) + epichlorohydrin (106-89-8) → 2-hydroxymethyl-1,4-benzodioxanedisulfonic acid disodium salt

Conditions	Yield
Stage #1: tiron With sodium carbonate In water at 20℃; for 0.166667h; Stage #2: epichlorohydrin In water at 20 - 70℃; for 15h;	73%

tiron (149-45-1) → [NaSr(HTiron)(H2O)5]·H2O

Conditions	Yield
Stage #1: tiron With strontium (III) chloride hexahydrate In water for 1h; High pressure; Stage #2: In water at 130℃; for 72h; Sealed tube; High pressure;	72%

oxirane (75-21-8) + tiron (149-45-1) → disodium 4,5-bis(2-hydroxyethoxy)-1,3-benzenedisulfonate

Conditions	Yield
With calcium chloride at 50℃; for 24h;	70%

1,10-Phenanthroline (66-71-7) + tiron (149-45-1) → C36H26N4O19S4Sr2(4-)*2C12H8N2*2H2O*4H(1+)

Conditions	Yield
Stage #1: 1,10-Phenanthroline; tiron With water; sodium hydroxide; strontium chloride for 3h; pH=5; Stage #2: at 120℃; for 48h; Autoclave; High pressure;	70%

lanthanum(III) chloride + water (7732-18-5) + tiron (149-45-1) → C6H3O8S2(3-)*La(3+)*2H2O

Conditions	Yield
at 150℃; for 48h; High pressure;	67%

dihydrate + 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) + 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (96042-30-7) + tiron (149-45-1) + 4-methylmorpholine N-oxide (7529-22-8) → methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (106146-94-5)

Conditions	Yield
In water; ethyl acetate; tert-butyl alcohol	62%

water (7732-18-5) + tiron (149-45-1) + barium(II) chloride → barium 4,5-dihydroxybenzene-1,3-disulfonate dihydrate

Conditions	Yield
at 140℃; for 72h; High pressure;	62%

4,4'-bipyridine (553-26-4) + cobalt(II) nitrate hexahydrate + tiron (149-45-1) → [Co3(tiron-(4,4'-bipyridyl))2(4,4'-bipyridyl)(H2O)8]*(H2O)2

Conditions	Yield
Stage #1: 4,4'-bipyridine; cobalt(II) nitrate hexahydrate; tiron In water at 20℃; for 1h; Stage #2: at 140℃; for 72h; Autoclave;	60%

1,10-Phenanthroline (66-71-7) + tiron (149-45-1) + ferric nitrate (7782-61-8) → Fe(1,10-phenanthroline)3·4,5-dihydroxy-1,3-benzenedisulfonate

Conditions	Yield
In water at 20℃; for 1h;	60%

[2,2]bipyridinyl (366-18-7) + water (7732-18-5) + tiron (149-45-1) + ferric nitrate (7782-61-8) → Fe(2,2'-bipyridine)3·4,5-dihydroxy-1,3-benzenedisulfonate·5H2O

Conditions	Yield
at 20℃; for 1h;	60%

1,10-Phenanthroline (66-71-7) + terbium(III) nitrate hexahydrate + tiron (149-45-1) → Tb2(4,5-dihydroxy-1,3-benzenedisulfonic acid)3(1,10-phenanthroline)2

Conditions	Yield
In water at 120℃; for 36h; Autoclave;	55%

4,4'-bipyridine (553-26-4) + cadmium(II) nitrate tetrhydrate + tiron (149-45-1) → [Cd(tiron)(4,4'-bipyridyl)2(H2O)2]*0.5H2O

Conditions	Yield
Stage #1: 4,4'-bipyridine; cadmium(II) nitrate tetrhydrate; tiron In water at 20℃; for 1h; Stage #2: at 140℃; for 72h; Autoclave;	30%

oxirane (75-21-8) + tiron (149-45-1) → 4-hydroxy-5-(2-hydroxyethoxy)benzene-1,3-disulfonic acid

Conditions	Yield
With calcium chloride at 50℃; for 24h;

tiron (149-45-1) + methyloxirane (75-56-9, 16033-71-9) → disodium 4,5-bis(2-hydroxypropoxy)-1,3-benzenedisulfonate

Conditions	Yield
With calcium chloride

pyrrole (109-97-7) + tiron (149-45-1) → polypyrrole doped with 1,2-dihydroxybenzene-3,5-disulfonic acid disodium salt

Conditions	Yield
In water Electrochemical reaction;

tiron (149-45-1) + 4-(bromomethyl)benzophenone (32752-54-8) → 4,5-bis(4-benzoylphenylmethyleneoxy)benzene-1,3-disulfonic acid disodium salt

Conditions	Yield
Stage #1: tiron; 4-(bromomethyl)benzophenone In tetrahydrofuran; methanol; chloroform; water Heating / reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water for 3h; Heating / reflux; Stage #3: 4-(bromomethyl)benzophenone With sodium hydroxide In tetrahydrofuran; water for 12h; Heating / reflux;

N-methyl morpholine N-oxide + 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) + tiron (149-45-1) → 3R,2S-Methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate + methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (106146-94-5)

Conditions	Yield
In water; ethyl acetate; tert-butyl alcohol

2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethyl-3H-indolium bromide + tiron (149-45-1) → 2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethyl-3H-indolium, 4,5-dihydroxy-1,3-benzendisulfonic acid salt

Conditions	Yield
In ethanol; water at 20℃; for 2.16667h; in the dark;

2-[2-[3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-2-(phenylthio)-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethyl-3H-indolium chloride (269401-43-6) + tiron (149-45-1) → 2-[2-[3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-2-phenylthio-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethyl-3H-indolium, 4,5-dihydroxy-1,3-benzenedisulfonic acid salt

Conditions	Yield
In methanol; water at 20℃; for 2h; in the dark;

tiron (149-45-1) + ferric nitrate (7782-61-8) → [Fe(tironato)3](9-)

Conditions	Yield
In water (Ar); using Schlenk techniques; addn. of 13.0 equiv. of NaOH to soln. ofFe(NO3)3 (0.1 mM) and tiron (0.3 mM) in water; not isolated, monitoring by UV-vis;

gallium(III) + tiron (149-45-1) → gallium(III) tiron 1:1 complex

Conditions	Yield
In not given Kinetics; monitored by visible spectra; not isolated;

europium(III) chloride (10025-76-0) + tiron (149-45-1) → Eu(1,2-dihydroxy(3,5-disulfo)benzene(4-))(1-) + Eu(1,2-dihydroxy(3,5-disulfo)benzene(3-))

Conditions	Yield
In water under Ar, photospectrometric and potentiometric titration, pH = 8, 25.0°C, 0.1 M KNO3, equilibrium;

Upstream product

• 120-80-9 benzene-1,2-diol 

Downstream Products

• 149-46-2 tiron 

Related news

Tiron (cas 149-45-1) protects against UVB‐induced senescence‐like characteristics in human dermal fibroblasts by the inhibition of superoxide anion production and glutathione depletion09/29/2019

Background/Objectives:  Free radicals and reactive oxygen species (ROS), which are generated by UV irradiation, may induce an irreversible growth arrest similar to senescence. Tiron, 4,5‐dihydroxy‐1,3‐benzene disulfonic acid, is a widely used antioxidant to rescue ROS‐evoked cell death. The ...detailed

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