14379-00-1

Basic information

• Product Name: CROCONIC ACID, DISODIUM SALT
• Synonyms: CROCONIC ACID, DISODIUM SALT;4,5-DIHYDROXY-4-CYCLOPENTENE-1,2,3-TRIONE, DISODIUM SALT;4,5-Dihydroxy-cyclopent-4-ene-1,2,3-trione disodiumsalt;Croconic acid disodium salt 97%;disodium:3,4,5-trioxocyclopentene-1,2-diolate
• CAS NO: 14379-00-1
• Molecular Formula: C₅O₅*2Na
• Molecular Weight: 186.03
• Mol File: 14379-00-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: CROCONIC ACID, DISODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: CROCONIC ACID, DISODIUM SALT(14379-00-1)
• EPA Substance Registry System: CROCONIC ACID, DISODIUM SALT(14379-00-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 14379-00-1(Hazardous Substances Data)

Usage

General Description

Croconic Acid, Disodium Salt is a chemical compound also known as disodium 2,5-cyclohexadiene-1,4-dione-2,5-bis(olate). It has a molecular formula of C5H2Na2O5. This chemical belongs to the class of organic compounds known as croconic acids and derivatives. These are organic compounds containing a croconic acid moiety, which consists of a five-membered unsaturated cyclic dione. Croconic Acid, Disodium Salt is usually utilized in chemical reactions as an intermediate. Its exact applications can vastly differ depending on the industry – from use in the synthesis of other compounds to chemical research and analysis.

InChI:InChI=1/C5H2O5.2Na/c6-1-2(7)4(9)5(10)3(1)8;;/h6-7H;;/q;2*+1/p-2

Synthetic route

rhodizonic acid (118-76-3) → croconic acid disodium salt (14379-00-1)

Conditions	Yield
With sodium hydroxide

croconic acid (488-86-8) + sodium hydroxide (1310-73-2) → croconic acid disodium salt (14379-00-1)

Conditions	Yield
In water for 12h;

croconic acid (488-86-8) → croconic acid disodium salt (14379-00-1)

Conditions	Yield
With sodium hydroxide In water

1,8-bis(trans-Pt(PEt3)2NO3)anthracene (313674-46-3) + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → cyclobis[(1,8-bis[trans-Pt(PEt3)2]anthracene)(μ-1,2-C5O5)]*2H2O

Conditions	Yield
In water; acetone to an acetone soln. of Pt-complex an aq. soln. of disodium salt of acid was added drop by drop with continuous stirring (15 min); ppt. was filtered, washed with acetone and water; elem. anal.;	97.8%

3,6-bis[trans-Pt(PEt3)2(NO3)2]phenanthrene (531500-32-0) + croconic acid disodium salt (14379-00-1) + acetone (67-64-1) → cyclobis[(2,9-bis[trans-Pt(PEt3)2]phenanthrene)(μ-1,3-C5O5)]*4CH3COCH3

Conditions	Yield
In water; acetone an aq. soln. of disodium salt of acid was added to an acetone-soln. of complex (1:1 stoichiometric ratio) at room temp.; elem. anal.;	90.1%

copper(II) perchlorate hexahydrate + croconic acid disodium salt (14379-00-1) + water (7732-18-5) + bis[(2-pyridyl)methyl]amine (1539-42-0) → [dicopper(II)(bis(2-pyridylmethyl)amine)2(μ1,1,2,3-croconate)(H2O)]2(perchlorate)4*2H2O

Conditions	Yield
In water Na2C5O5 added to hot soln. of Cu salt and C12H12N3 (in equimolar amts.) in H2O, heated for 15 min on a steam-bath; filtered (celite), crystd. at room temp. for 1 wk, filtered off, washed (propan-2-ol, ether), dried in air; elem. anal.;	89%

copper(II) perchlorate hexahydrate + croconic acid disodium salt (14379-00-1) + tris[2-(1-pyrazolyl)ethyl]amine (80049-12-3) → [dicopper(II)(tris[2-ethyl(1-pyrazolyl)]amine)2(μ-4,5-dihydroxycyclopent-4-ene-1,2,3-trionate(-2H))](perchlorate)2

Conditions	Yield
In methanol; water Na2(C5O5) (0.25 mmol) aq. soln. added dropwise to soln. of CuClO4*6H2O (0.50 mmol) and tepza (0.50 mmol) (H2O/MeOH 1:1), heated on steam-bath for 10 min; filtered, crystd. at room temp. over 1 d, ppt. filtered off, washed with2-propanol and ether, air dried; elem. anal.;	88%

tetrakis(thiourea)platinum(II) dichloride + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → tetrakis(thiourea)platinum(II) crotonate - water (1/2.5)

Conditions	Yield
In water Pt complex in H2O mixed with Na2C5O5 in H2O; crystd. at room temp. for 4 d, elem. anal.;	78.2%

4,4'-bipyridine (553-26-4) + cadmium(II) nitrate tetrhydrate + croconic acid disodium salt (14379-00-1) → ([Cd2(croconate)2(4,4'-bipyridine)(H2O)]*(H2O)).infin.

Conditions	Yield
In water High Pressure; react. Cd(NO3)2*4H2O, Na2C5O5, 4,4'-bpy, and water (2:2:2:1:3333) at 180°C for 3 days;	78%
In water High Pressure; react. Cd(NO3)2*4H2O, Na2C5O5, 4,4'-bpy, and water (2:2:1:3333) at 180°C for 3 days;	75%
In water High Pressure; react. Cd(NO3)2*4H2O, Na2C5O5, 4,4'-bpy, and water (1:1:1:3333) at 180°C for 3 days; elem. anal.;	36.29%

copper(II) perchlorate hexahydrate + 3,3'-Diamino-N-methyldipropylamine (105-83-9) + croconic acid disodium salt (14379-00-1) → [Cu2(Medpt)2(C5O5)](ClO4)2*H2O

Conditions	Yield
With water Heating;	77%

cobalt(II) nitrate hexahydrate + bis(4-pyridyl) disulfide (2645-22-9) + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → ([Co2(4,4'-bipyridyl disulfide)2(croconate)2(H2O)4]*(H2O)3)n

Conditions	Yield
In methanol; water CH3OH soln. of Co(NO3)2*6H2O added to CH3OH soln. 4,4'-bipyridyl disulfide dropwise with constant stirring; aq. soln. of Na2-croconate added; stirred for 30 min; filtered; filtrate kept in CaCl2 desiccator after a few days; elem. anal.;	75%

croconic acid disodium salt (14379-00-1) + silver nitrate → [AgNa(croconate)(H2O)2](n)

Conditions	Yield
In water Na2C5O5 dissolved in H2O added dropwise to aq. soln. of AgNO3 at room temp.; mixt. stirred for 30 min; filtered; filtrate allowed to crystallize slowly in CaCl2 dessicator; elem. anal.;	72%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + croconic acid disodium salt (14379-00-1) + iron(II) bromide → [Fe(μ3-croconate)0.5(μ4-croconate)0.5(anti-1,2-bis(4-pyridyl)ethane)0.5(gauche-1,2-bis(4-pyridyl)ethane)0.5] (681180-54-1)

Conditions	Yield
In water aq. soln. sodium croconate was added to aq. soln. FeBr2 and 1,2-bis(4-pyridyl)ethane (1:1:1) at room temp.; elem. anal.;	70%
In water FeCl2:Na2C5O5:(CH2(C5H4N))2 molar ratio = 1:1:1; slowly evapd. (several d);

4,4'-bipyridine (553-26-4) + cobalt(II) nitrate hexahydrate + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → ([Co(4,4'-bipyridyl)(H2O)4]*croconate*(H2O)2)n

Conditions	Yield
In methanol; water slow diffusion of CH3OH soln. of 4,4'-bipyridyl and aq. Na2-croconate over aq. Co(NO3)2*6H2O; elem. anal.;	70%

4,4'-bipyridine (553-26-4) + Ammonium iron sulfate + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → ([Fe(4,4'-bipyridyl)(H2O)4]*croconate*(H2O)2)n

Conditions	Yield
In methanol; water CH3OH soln. of 4,4'-bipyridyl gently poured into aq. soln. of Na2-croconate; Fe-compound in water added to soln. dropwise with constant stirring; complex sepd. out; elem. anal.;	70%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + manganese(II) chloride tetrahydrate + croconic acid disodium salt (14379-00-1) → [Mn(μ3-croconate)0.5(μ4-croconate)0.5(anti-1,2-bis(4-pyridyl)ethane)0.5(gauche-1,2-bis(4-pyridyl)ethane)0.5] (681180-53-0)

Conditions	Yield
In water aq. soln. sodium croconate was added to aq. soln. MnCl2*4H2O and 1,2-bis(4-pyridyl)ethane (1:1:1) at room temp.; elem. anal.;	68%
In water MnCl2*4H2O:Na2C5O5:(CH2(C5H4N))2 molar ratio = 1:1:1; slowly evapd. (several d);

copper(II) choride dihydrate + croconic acid disodium salt (14379-00-1) + bis[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]amine (85650-01-7) → [Cu(bis(2-(3,5-dimethylpyrazol-1-yl)ethyl)amine)(μ2-C5O5)]*4H2O

Conditions	Yield
With water In methanol for 0.25h; Heating;	67%

copper(II) perchlorate hexahydrate + N-(2-Aminoethyl)-1,3-propanediamine (13531-52-7) + croconic acid disodium salt (14379-00-1) → [Cu3(N-(2-aminoethyl)-1,3-propanediamine)3(μ2-C5O5)(μ3-C5O5)(H2O)](ClO4)2*1.6H2O

Conditions	Yield
With water for 0.25h; Heating;	65%

tetrakis(thiourea)platinum(II) dichloride + croconic acid disodium salt (14379-00-1) + dimethyl sulfoxide (67-68-5) → tetrakis(thiourea)platinum(II) crotonate - dimethylsulfoxide (1/4)

Conditions	Yield
In water; dimethyl sulfoxide Pt complex in DMSO mixed with Na2C5O5 in H2O; crystd.(slow diffusion of CH3CN), elem. anal.;	63.3%

N-propanamide-N,N-bis-(2-pyridylmethyl)amine (195606-52-1) + copper(II) perchlorate hexahydrate + croconic acid disodium salt (14379-00-1) → [Cu2(N-propionamide-N,N-bis(2-pyridylmethyl)amine)2(μ2-C5O5)](ClO4)2*2H2O

Conditions	Yield
With water Heating;	62%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + croconic acid disodium salt (14379-00-1) + cobalt(II) chloride (7646-79-9) → [Co(crotonate)(1,2-bis(4-pyridyl)ethane)] (959698-29-4)

Conditions	Yield
In water soln. of Na2C5O5 (0.1 mmol) added to soln. of CoCl2 (0.1 mmol) and (CH2(C5H4N))2 (0.1 mmol) (room temp., pH 7.97); kept (several d); elem. anal.;	43%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + cadmium(II) nitrate tetrhydrate + croconic acid disodium salt (14379-00-1) → [Cd(μ3-croconate)0.5(μ4-croconate)0.5(anti-1,2-bis(4-pyridyl)ethane)0.5(gauche-1,2-bis(4-pyridyl)ethane)0.5] (681180-55-2)

Conditions	Yield
In water High Pressure; aq. soln. sodium croconate was added to aq. soln. Cd(NO3)2*4H2O and 1,2-bis(4-pyridyl)ethane (1:1:1) and heated at 180°C for 3 days; react. mixt. was cooled, crystals were washed with water; elem. anal.;	36%
In water High Pressure; Cd(NO3)2*4H2O:Na2C5O5:(CH2(C5H4N))2 molar ratio = 1:1:1; hydrothermal treatment (180°C, 3 d); slowly evapd. (several d);

samarium(III) nitrate hexahydrate + [Cu(II)(ethylenediamine)2]Cl2 + croconic acid disodium salt (14379-00-1) → [Cu(ethylenediamine)2][Sm2(oxalate)3(croconate)(H2O)2]·8H2O

Conditions	Yield
With water	17%

copper(II) choride dihydrate + croconic acid disodium salt (14379-00-1) → Na2[Cu(II)(croconate)2(H2O)2]*4H2O + copper(II) croconate trihydrate

Conditions	Yield
In water mixing at room temp.; slow evapn. of soln. for two weeks; elem. anal.;	A 12.62% B n/a

croconic acid disodium salt (14379-00-1) + water (7732-18-5) + nickel dichloride → Na2[Ni(II)(croconate)2(H2O)2]*4H2O

Conditions	Yield
In water mixing at room temp.; slow evapn. of soln. for two weeks; elem. anal.;	2.94%

croconic acid disodium salt (14379-00-1) → disodium squarate (107817-28-7, 132898-15-8, 57013-14-6)

Conditions	Yield
With oxygen In sodium hydroxide Irradiation;	100 % Spectr.
With oxygen In sodium hydroxide Kinetics; Quantum yield; Rate constant; Irradiation; influence of pH, electron acceptors and radical traps; mechanism;	100 % Spectr.

croconic acid disodium salt (14379-00-1) + malononitrile (109-77-3) → C11N4O3(2-)*2Na(1+)

Conditions	Yield
In water at 70℃; for 2h;

cadmium(II) nitrate tetrhydrate + croconic acid disodium salt (14379-00-1) → cadmium croconate dihydrate

Conditions	Yield
In water Na2C5O5 dissolved in H2O added to aq. soln. of Cd(NO3)2*4H2O with continuos stirring; solid filtered off; washed (H2O);

croconic acid disodium salt (14379-00-1) → [Cd(croconate)(NH3)2](n) (524919-12-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: water 2: water View Scheme

gadolinium nitrate hydrate + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → [GdNa(croconate)2(H2O)7]n

Conditions	Yield
In water for 4 - 5h;

neodymium(III) chloride hydrate + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → [GdNa(croconate)2(H2O)7]n

Conditions	Yield
In water for 4 - 5h;

dysprosium(III) chloride hydrate + croconic acid disodium salt (14379-00-1) + water (7732-18-5) → [GdNa(croconate)2(H2O)7]n

Conditions	Yield
In water for 4 - 5h;

Upstream product

• 930-60-9 maleic anhydride 
• 488-86-8 croconic acid 
• 1310-73-2 sodium hydroxide 
• 118-76-3 rhodizonic acid 

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