1655-29-4

Basic information

• Product Name: Disodium 1,5-naphthalenedisulfonate
• Synonyms: Sodium1,5-naphthalenedisulfonate;DISODIUM 1,5-NAPHTHALENEDISULFONATE HYDRATE;DISODIUM 1,5-NAPHTHALENEDISULFONATE;DISODIUM NAPHTHALENE-1,5-DISULPHONATE;1,5-NAPHTHALENEDISULFONIC ACID DISODIUM SALT HYDRATE;1,5-NAPHTHALENEDISULFONIC ACID DISODIUM SALT;1,5-NAPHTHALENEDISULFONIC ACID, NA SALT;1,5-NAPHTHALENE DISULFONIC ACID DISUDIUM SALT
• CAS NO: 1655-29-4
• Molecular Formula: C₁₀H₆O₆S₂*2Na
• Molecular Weight: 332.26
• EINECS: 216-732-0
• Product Categories: Intermediates of Dyes and Pigments;ntermediates of Dyes and Pigments
• Mol File: 1655-29-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 300℃[at 101 325 Pa]
• Appearance: grey powder
• Density: 1.704 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Store at RT.
• Solubility: almost transparency in Water
• Water Solubility: 113.4g/L at 20℃
• BRN: 3642373
• CAS DataBase Reference: Disodium 1,5-naphthalenedisulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Disodium 1,5-naphthalenedisulfonate(1655-29-4)
• EPA Substance Registry System: Disodium 1,5-naphthalenedisulfonate(1655-29-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 1
• Hazardous Substances Data: 1655-29-4(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Sodium 1,5-Naphthalenedisulfonate is a petroleum disulfonates in crude oil; It is used in the synthesis of Levobunolol Hydrochloride; Also, it is capable of recycling wastewater.

Flammability and Explosibility

Notclassified

Purification Methods

Recrystallise it from pKEst aqueous acetone [Okahata et al. J Am Chem Soc 108 2863 1986]. [Beilstein 11 IV 561.]

InChI:InChI=1/C10H6O4S2.2Na/c11-15(12)9-5-1-3-7-8(9)4-2-6-10(7)16(13)14;;/h1-6H;;/rC10H6Na2O4S2/c11-17(13,14)9-5-1-3-7-8(9)4-2-6-10(7)18(12,15)16/h1-6H

Synthetic route

naphthalene-1,5-disulfonate (81-04-9) → disodium 1,5-naphthalenedisulfonate (1655-29-4)

Conditions	Yield
With sodium hydroxide at 20℃; Sonication;
Stage #1: naphthalene-1,5-disulfonate With 4-nitro-2,6-dichloroaniline; sulfuric acid; cis-nitrous acid In 1,2-dimethoxyethane at 0 - 5℃; for 0.166667h; Stage #2: With sodium carbonate; m-acetylamino-N,N-diethylanilne In 1,2-dimethoxyethane at 0 - 40℃; for 0.5h; pH=6 - 8;

[2-((R)-cyclohexyl-hydroxy-phenyl-methyl)-oxazol-5-ylmethyl]-dimethyl-(3-phenoxy-propyl)-ammonium bromide + disodium 1,5-naphthalenedisulfonate (1655-29-4) → [2-((R)-cyclohexyl-hydroxy-phenyl-methyl)-oxazol-5-ylmethyl]-dimethyl-(3-phenoxy-propyl)-ammonium hemi-naphthalene-1,5-disulfonate

Conditions	Yield
In dichloromethane; water at 20℃;	94%
In dichloromethane; water at 20℃;	94%

disodium 1,5-naphthalenedisulfonate (1655-29-4) + (S)-(+)-clopidogrel bisulfate (120202-66-6) → clopidogrel 1,5-naphthalenedisulfonate

Conditions	Yield
In water; isopropyl alcohol at 5 - 70℃; for 17h; Product distribution / selectivity;	94%
In methanol; water at 5 - 70℃; for 17h; Product distribution / selectivity;	94%
In diethyl ether; water at 5 - 20℃; for 17h; Product distribution / selectivity;	85%
In water; toluene at 5 - 20℃; for 17h; Product distribution / selectivity;	84%
In water at 5 - 20℃; for 17h; Product distribution / selectivity;	84%

clopidogrel besylate + disodium 1,5-naphthalenedisulfonate (1655-29-4) → clopidogrel 1,5-naphthalenedisulfonate

Conditions	Yield
In methanol; water at 5 - 60℃; for 17h; Product distribution / selectivity;	94%
In water; isopropyl alcohol at 5 - 70℃; for 17h; Product distribution / selectivity;	86%

(+)-clopidogrel camphorsulfonic acid + disodium 1,5-naphthalenedisulfonate (1655-29-4) → clopidogrel 1,5-naphthalenedisulfonate

Conditions	Yield
In water; isopropyl alcohol at 5 - 70℃; for 17h; Product distribution / selectivity;	92%

bis(1,1,1-tris(aminoethyl)ethane)cobalt(III) chloride (60909-16-2) + disodium 1,5-naphthalenedisulfonate (1655-29-4) → Co(1,1,1-tris(aminomethyl)ethane)2(1,5-naphthalenedisulfonate)Cl(H2O)3

Conditions	Yield
In water ligand added to soln. of Co-complex in H2O, allowed to stand at 0°C for 12 h; ppt. filtered, washed with EtOH, Et2O; elem. anal. for dihydrate;	91%

clopidogrel hydrobromide + disodium 1,5-naphthalenedisulfonate (1655-29-4) → clopidogrel 1,5-naphthalenedisulfonate

Conditions	Yield
In water; isopropyl alcohol at 5 - 70℃; for 17h; Product distribution / selectivity;	91%

(+)-(S)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester hydrochloride salt + disodium 1,5-naphthalenedisulfonate (1655-29-4) → clopidogrel 1,5-naphthalenedisulfonate

Conditions	Yield
In water; isopropyl alcohol at 5 - 70℃; for 17h; Product distribution / selectivity;	88%
In methanol; water at 5 - 20℃; for 17h; Product distribution / selectivity;	85%

clopidogrel (1R)-(-)-camphor-10-sulfonate + disodium 1,5-naphthalenedisulfonate (1655-29-4) → clopidogrel 1,5-naphthalenedisulfonate

Conditions	Yield
In water; isopropyl alcohol at 5 - 70℃; for 17h; Product distribution / selectivity;	88%

disodium 1,5-naphthalenedisulfonate (1655-29-4) + cadmium(II) acetate dihydrate (5743-04-4) + N,N`-dimethylethylenediamine (110-70-3) → [Cd(N,N'-dimethylethylenediamine)2](1,5-naphthalenedisulfonate)

Conditions	Yield
In water 2 equiv. of N,N'-dimethylethylenediamine added with stirring to aq. soln. of Cd compd.; treated with 1 equiv. of sodium 1,5-naphthalenedisulfonate; crystd. over 4 d; elem. anal.;	80%

1H-imidazole (288-32-4) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + cadmium(II) acetate dihydrate (5743-04-4) → [Cd(imidazole)4(2,6-naphthalenedisulfonate)]n

Conditions	Yield
In water disodium 1,5-naphthalenedisulfonate, imidazole added to aq. Cd(OAc)2; stirred for 4 h at 70°C; filtered; crystd. after 5 d; elem. anal.;	80%

[2-(4-chloro-benzyloxy)-ethyl]-[2-((R)-cyclohexylhydroxyphenylmethyl)-oxazol-5-ylmethyl]dimethylammonium bromide (1045862-70-1) + disodium 1,5-naphthalenedisulfonate (1655-29-4) → [2-(4-chloro-benzyloxy)-ethyl]-[2-((R)-cyclohexylhydroxyphenylmethyl)-oxazol-5-ylmethyl]dimethylammonium heminaphthalene-1,5-disulfonate

Conditions	Yield
In dichloromethane; water at 20℃; for 1.16667h; Product distribution / selectivity;	77%

disodium 1,5-naphthalenedisulfonate (1655-29-4) → barium 1,5-naphthalenedisulfonate monohydrate

Conditions	Yield
With barium(II) chloride dihydrate; water In ethanol; N,N-dimethyl-formamide at 100℃; for 72h; High pressure;	76%

1,4-bis(imidazol-l-yl-methyl)benzene (56643-83-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + cadmium(II) acetate (543-90-8) → [Cd(naphthalene-1,5-disulfonate)(1,4-bis(imidazol-1-ylmethyl)benzene)]n

Conditions	Yield
With nitric acid; sodium hydroxide In water at 160℃; for 72h; pH=4.5; Autoclave; High pressure;	75%

1,10-Phenanthroline (66-71-7) + nickel(II) nitrate hexahydrate + disodium 1,5-naphthalenedisulfonate (1655-29-4) → [Ni(1,10-phenanthroline)2(H2O)(1,5-naphthalenedisulfonate)]

Conditions	Yield
In water High Pressure; at 170°C under autogenous pressure for 66 h; cooled to ambient temp. in open air, decanted, washed (H2O), air-dried; elem. anal.;	73%

copper(II) choride dihydrate + disodium 1,5-naphthalenedisulfonate (1655-29-4) + N,N`-dimethylethylenediamine (110-70-3) → diaquabis(N,N'-dimethylethylenediamine)copper(II) 1,5-naphthalenedisulfonate monohydrate (347380-99-8)

Conditions	Yield
In water 2 equiv. of N,N'-dimethylethylenediamine added with stirring to aq. soln. of Cu salt; treated with 1 equiv. of Na2(C10H6(SO3)2); crystd. over 1 d; elem. anal.;	72%

2,4,5-tris(4-pyridinyl)imidazole (23974-93-8) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + cadmium(II) acetate dihydrate (5743-04-4) → [Cd(2,4,5-tris(pyridin-4-yl)imidazole)(naphthalene-1,5-disulfonate)]n

Conditions	Yield
In water at 180℃; for 72h;	70%
In water at 180℃; for 72h; Sealed tube;	70%

2-(2-(pyridin-4-yl)vinyl)-1H-imidazo[4,5-c]pyridine + water (7732-18-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + nickel(II) nitrate → 2C13H10N4*4H2O*C10H6O6S2(2-)*Ni(2+)

Conditions	Yield
In methanol at 95℃; for 48h; Activation energy; Sealed tube;	70%

disodium 1,5-naphthalenedisulfonate (1655-29-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [Mg(H2O)5(DMF)]1,5-naphthalenedisulfonate

Conditions	Yield
Stage #1: disodium 1,5-naphthalenedisulfonate With magnesium(II) chloride hexahydrate In ethanol; water at 20℃; for 2h; Stage #2: N,N-dimethyl-formamide	67%

zinc(II) nitrate (10196-18-6) + 2-(2-(pyridin-4-yl)vinyl)-1H-imidazo[4,5-c]pyridine + water (7732-18-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) → 2C13H10N4*Zn(2+)*4H2O*C10H6O6S2(2-)

Conditions	Yield
In methanol at 95℃; for 48h; Activation energy; Sealed tube;	65%

water (7732-18-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + silver nitrate + 2,5-di(3-pyridylmethylidene)cyclopentanone (47084-31-1) → {[Ag2(2,5-bispyridine-3-ylmethylenecyclopentanone)2(naphthalene disulfonate)]*3H2O}n

Conditions	Yield
Stage #1: water; disodium 1,5-naphthalenedisulfonate; silver nitrate; 2,5-di(3-pyridylmethylidene)cyclopentanone In methanol; N,N-dimethyl-formamide Stage #2: With ammonium hydroxide In methanol; N,N-dimethyl-formamide for 48h;	64.23%

water (7732-18-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + silver nitrate + 2,2'-bis(4-pyridylmethylidene)cyclopentanone (108977-83-9) → {[Ag2(2,5-bispyridine-4-ylmethylenecyclopentanone)2(naphthalene disulfonate)]*4H2O}n

Conditions	Yield
Stage #1: water; disodium 1,5-naphthalenedisulfonate; silver nitrate; 2,2'-bis(4-pyridylmethylidene)cyclopentanone In methanol; N,N-dimethyl-formamide Stage #2: With ammonium hydroxide In methanol; N,N-dimethyl-formamide for 48h;	62.12%

1,10-Phenanthroline (66-71-7) + cobalt(II) nitrate hexahydrate + disodium 1,5-naphthalenedisulfonate (1655-29-4) → [Co(1,10-phenanthroline)2(1,5-naphthalenedisulfonate)]

Conditions	Yield
In water High Pressure; at 170°C under autogenous pressure for 72 h; cooled to ambient temp. in open air, decanted, washed (H2O), air-dried; elem. anal.;	56%

water (7732-18-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + silver nitrate + 2,6-di(3-pyridylmethylidene)cyclohexanone (132727-07-2) → {[Ag2(2,5-bispyridine-3-ylmethylenecyclohexanone)2(naphthalene disulfonate)]*2H2O}n

Conditions	Yield
Stage #1: water; disodium 1,5-naphthalenedisulfonate; silver nitrate; 2,6-di(3-pyridylmethylidene)cyclohexanone In methanol; N,N-dimethyl-formamide for 48h; Stage #2: With ammonium hydroxide In methanol; N,N-dimethyl-formamide	55.65%

disodium 1,5-naphthalenedisulfonate (1655-29-4) → naphthalene-1,5-disulphonyl chloride (1928-01-4)

Conditions	Yield
With phosphorus pentachloride	54%
With pyridine; hydrogenchloride; phosphorus pentachloride 2.) 80 deg C, 5,5h; Yield given. Multistep reaction;

copper(II) choride dihydrate + disodium 1,5-naphthalenedisulfonate (1655-29-4) + ethylenediamine (107-15-3) → bis(ethylenediamine)copper(II) 1,5-naphthalenedisulfonatedihydrate

Conditions	Yield
In water 2 equiv. of ethylenediamine added to aq. soln. of Cu salt; treated with 1 equiv. of Na2(C10H6(SO3)2); crystd. over 6 d; elem. anal.;	52%

copper(II) choride dihydrate + disodium 1,5-naphthalenedisulfonate (1655-29-4) + 1,2-diaminopropan (78-90-0, 10424-38-1) → diaquabis(2,3-diaminopropane)copper(II) 1,5-naphthalenedisulfonate

Conditions	Yield
In water 2 equiv. of 2,3-diaminopropane added with stirring to aq. soln. of Cu salt; treated with 1 equiv. of Na2(C10H6(SO3)2); crystd. over 1 d; elem. anal.;	52%

1,3,5-tris(1-imidazolyl)benzene + zinc(II) nitrate hexahydrate + water (7732-18-5) + disodium 1,5-naphthalenedisulfonate (1655-29-4) → {[Zn(1,3,5-tris(1-imidazolyl)benzene)(H2O)]•(1,5-nds)}n

Conditions	Yield
at 120℃; for 72h; High pressure;	43.1%

lead(II) nitrate + 5-methyl-1,10-phenanthroline (3002-78-6) + disodium 1,5-naphthalenedisulfonate (1655-29-4) → Pb(1,5-naphthalenedisulfonate)(5-methyl-1,10-phenanthroline)(H2O)

Conditions	Yield
With uranyl nirate hexahydrate In 1-methyl-pyrrolidin-2-one; water at 140℃; for 168h; High pressure;	40%

1,4,8,11-Tetraazacyclotetradecane (295-37-4) + copper(II) choride dihydrate + disodium 1,5-naphthalenedisulfonate (1655-29-4) → (1,4,8,11-tetraazacyclotetradecane)copper(II) 1,5-naphthalenedisulfonate (347142-23-8)

Conditions	Yield
In methanol; water aq. soln. of Cu salt treated slowly with 1 equiv. of cyclam in MeOH withstirring; 1 equiv. of Na2(C10H6(SO3)2) dissolved in distd. water; cryst d. by slow diffusion of two solns. into U-tube contg. agar gel for 5 d; elem. anal.;	10%

2,2',2''-triaminotriethylamine (4097-89-6) + disodium 1,5-naphthalenedisulfonate (1655-29-4) + copper dichloride → di-μ-chloro-bis[[2-[N,N-bis(2-aminoethyl)amino-κ3N]ethylaminium]copper(II)] bis(naphthalene-1,5-disulfonate) pentahydrate

Conditions	Yield
In water aq. soln. disodium naphthalene-1,5-disulfonate and CuCl2 (1:1 mol) was treated with tris(2-aminoethyl)amine (1 mol); room temp., 10 d;	10%

Upstream product

• 81-04-9 naphthalene-1,5-disulfonate 

Downstream Products

• 1928-01-4 naphthalene-1,5-disulphonyl chloride 
• 5325-88-2 1,5-naphthalenedithiol 
• 81-04-9 naphthalene-1,5-disulfonate 
• 83-56-7 1,5-dihydroxynaphthalene 
• 6654-67-7 naphthalene-1,3,5,7-tetrasulphonic acid 

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