135-51-3

Basic information

• Product Name: Disodium 2-naphthol-3,6-disulfonate
• Synonyms: 2,7-Naphthalenedisulfonicacid,3-hydroxy-,disodiumsalt;2-naphthol-3,6-disulfonic;7-naphthalenedisulfonicacid,3-hydroxy-disodiumsalt;fericon;RGAcid;R SALT;SODIUM-2-NAPHTHOL-3,6-DISULFONATE;R ACID
• CAS NO: 135-51-3
• Molecular Formula: C₁₀H₆O₇S₂*2Na
• Molecular Weight: 348.26
• EINECS: 205-196-3
• Product Categories: Intermediates of Dyes and Pigments;Intermediates
• Mol File: 135-51-3.mol
• Article Data: 0

Chemical Properties

• Appearance: slightly grey solid
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Soluble in water
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3643184
• CAS DataBase Reference: Disodium 2-naphthol-3,6-disulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Disodium 2-naphthol-3,6-disulfonate(135-51-3)
• EPA Substance Registry System: Disodium 2-naphthol-3,6-disulfonate(135-51-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: QJ6477000
• Hazardous Substances Data: 135-51-3(Hazardous Substances Data)

Usage

Chemical Properties

slightly grey solid

Uses

3-Hydroxynaphthalene-2,7-disulfonic Acid Disodium Salt, is used in analytical studies for detecting organic explosives and propellants by fast liquid chromatography quadrupole time-of-flight mass spectrometry.

Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SO, and NazO. See also SULFONATES.

InChI:InChI=1/C10H8O7S2/c11-9-4-6-1-2-8(18(12,13)14)3-7(6)5-10(9)19(15,16)17/h1-5,11H,(H,12,13,14)(H,15,16,17)/p-2

Synthetic route

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + 3-{4-[(E)-2-(2,4-Dichloro-phenyl)-vinyl]-phenyl}-2-mercapto-4-oxo-3,4-dihydro-quinazoline-6-diazonium → C32H18Cl2N4O8S3(2-)*2Na(1+)

Conditions	Yield
With sodium carbonate; sodium chloride In water 1.) 0-5 deg C, 3 h; 2.) 60 deg C;	82%

1-adamantyl-(4-aminophenyl)methanone (1359877-34-1) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 4-(2-(4-(1-adamantylcarbonyl)phenyl)diazenyl)-3-hydroxynaphthalene-2,7-disulfonate disodium

Conditions	Yield
Stage #1: 1-adamantyl-(4-aminophenyl)methanone With hydrogenchloride; sodium nitrite In water for 0.25h; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt With sodium hydroxide In water for 0.25h;	76%

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + sodium 5-aminonaphthalene-1-sulfonate → C20H11N2O10S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: sodium 5-aminonaphthalene-1-sulfonate With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt In water at 0 - 5℃; pH=9 - 10;	71%

1-adamantyl-(3-aminophenyl)methanone (1359877-36-3) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 4-(2-(3-(1-adamantylcarbonyl)phenyl)diazenyl)-3-hydroxynaphthalene-2,7-disulfonate disodium

Conditions	Yield
Stage #1: 1-adamantyl-(3-aminophenyl)methanone With hydrogenchloride; sodium nitrite In water for 0.25h; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt With sodium hydroxide In water for 0.25h;	71%

4,4'-bipyridine (553-26-4) + cobalt(II) nitrate hexahydrate + water (7732-18-5) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → [{Co(4,4’-bipyridine)(H2O)4}.(3-hydroxy-2,7-naphthalenedisulfonate)·2H2O]n

Conditions	Yield
In methanol at 20℃; for 0.166667h;	70%

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + Sodium 2-aminonaphthalene-6-sulfonate → C20H11N2O10S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: Sodium 2-aminonaphthalene-6-sulfonate With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt In water at 0 - 5℃; pH=9 - 10;	63%

sodium 2-amino-5-naphthalenesulfonate (58306-87-9) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C20H11N2O10S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: sodium 2-amino-5-naphthalenesulfonate With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt In water at 0 - 5℃; pH=9 - 10;	62%

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + sodium 5-aminonaphthalene-2-sulfonate (28907-84-8) → C20H11N2O10S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: sodium 5-aminonaphthalene-2-sulfonate With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt In water at 0 - 5℃; pH=9 - 10;	57%

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3) → 1-(4-boronophenylazo)-2-hydroxy-3,6-naphthalenedisulfonic acid disodium salt

Conditions	Yield
Stage #1: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With hydrogenchloride; sodium nitrite for 0.25h; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt In water at 0 - 20℃; Further stages.;	33%
Stage #1: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt With sodium hydroxide In water for 0.75h; pH=6;	21.8%

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + 3,3'-dimethyl-biphenyl-4,4'-bisdiazonium; dichloride (13954-50-2) + β‐cyclodextrin (7585-39-9) → C42H70O35*C34H22N4O14S4(4-)*4Na(1+)

Conditions	Yield
With sodium carbonate	6%

4-Butylaniline (104-13-2) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C20H18N2O7S2(2-)*2Na(1+) (34293-75-9)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

4-isobutylaniline (30090-17-6) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C20H18N2O7S2(2-)*2Na(1+) (34895-10-8)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

4-hexylaniline (33228-45-4) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C22H22N2O7S2(2-)*2Na(1+) (34293-76-0)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

4-octylaniline (16245-79-7) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C24H26N2O7S2(2-)*2Na(1+) (33239-14-4)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

p-2-Aethylbutylanilin (34895-13-1) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C22H22N2O7S2(2-)*2Na(1+) (34293-77-1)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

p-2-Aethyl-4-methyl-pentylanilin (34895-14-2) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C24H26N2O7S2(2-)*2Na(1+) (33239-13-3)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + aniline (62-53-3) → disodium 3-hydroxy-4-(phenylazo)naphthalene-2,7-disulfonate (5859-00-7)

Conditions	Yield
(i) (diazotization), (ii) /BRN= 3643184/; Multistep reaction;

2-thiazolylamine (96-50-4) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 1-nitroso-2-naphthol-3,6-disulfonic acid (2007-19-4) + 3-hydroxy-4-thiazol-2-ylazo-naphthalene-2,7-disulfonic acid (2172-27-2)

Conditions	Yield
With sulfuric acid; sodium nitrite Rate constant; 1.) -10 deg C, 1 h; 2.) buffer solution; study at different pH;

1,3-thiazol-5-amine (17721-00-5) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 1-nitroso-2-naphthol-3,6-disulfonic acid (2007-19-4) + 3-Hydroxy-4-(thiazol-5-ylazo)-naphthalene-2,7-disulfonic acid

Conditions	Yield
With nitrosylsulfuric acid; sulfuric acid Rate constant; 1.) -10 deg C; 2.) buffer solution; study at different pH;

[1,3,4]Thiadiazol-2-ylamin (4005-51-0) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 1-nitroso-2-naphthol-3,6-disulfonic acid (2007-19-4) + 3-Hydroxy-4-([1,3,4]thiadiazol-2-ylazo)-naphthalene-2,7-disulfonic acid (104946-10-3)

Conditions	Yield
With nitrosylsulfuric acid; sulfuric acid Rate constant; 1.) -10 deg C; 2.) buffer solution; study at different pH;

1,3,4-thiadiazol-5-amine (7552-07-0) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 1-nitroso-2-naphthol-3,6-disulfonic acid (2007-19-4) + 3-Hydroxy-4-([1,2,4]thiadiazol-5-ylazo)-naphthalene-2,7-disulfonic acid

Conditions	Yield
With nitrosylsulfuric acid; sulfuric acid Rate constant; 1.) -10 deg C; 2.) buffer solution; study at different pH;

4-aminothiazole (17720-99-9) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 1-nitroso-2-naphthol-3,6-disulfonic acid (2007-19-4) + 3-Hydroxy-4-(thiazol-4-ylazo)-naphthalene-2,7-disulfonic acid

Conditions	Yield
With sulfuric acid; sodium nitrite Rate constant; 1.) -10 deg C, 1h; 2.) buffer solution; study at different pH;

3(5)-amino-1,2,4-triazole (61-82-5) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → 1-nitroso-2-naphthol-3,6-disulfonic acid (2007-19-4) + 3-Hydroxy-4-(4H-[1,2,4]triazol-3-ylazo)-naphthalene-2,7-disulfonic acid

Conditions	Yield
With nitrosylsulfuric acid; sulfuric acid Rate constant; Mechanism; 1.) -10 deg C; 2.) buffer solution; study at different pH;

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + 2-hydroxyphenyldiazonium chloride (19183-06-3) → C16H10N2O8S2(2-)*2Na(1+)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 1h;

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + C25H45N3(2+)*2Br(1-) (74403-07-9) → C35H50N3O7S2(1-)*Na(1+)

Conditions	Yield
With Tris buffer; potassium chloride at 15℃; Kinetics; Rate constant;
With Tris buffer; potassium chloride at 15℃;

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + C40H75N3(2+)*2Br(1-) → C50H80N3O7S2(1-)*Na(1+)

Conditions	Yield
With Tris buffer; potassium chloride at 15℃; Kinetics; Rate constant;
With Tris buffer; potassium chloride at 15℃;

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → sodium 2-hydroxy-1-nitrosonaphtalene-3,6-disulphonate (525-05-3)

Conditions	Yield
With hydrogenchloride; sodium nitrite In sodium hydroxide at 0℃;

3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + chloroacetic acid (79-11-8) → 3,6-disulphonaphthoxyacetic acid (54736-54-8)

Conditions	Yield
With sodium hydroxide for 1.25h; Heating;

4-[(E)-(4-aminophenyl)diazenyl]phenylamine (538-41-0, 98043-56-2, 137692-67-2) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) + 8',12',16',18',27',31',35',37'-octamethoxy-1,1,1'',1''-tetraethyldispiro(piperidinium-4,13'-[1,6,20,25]tetraoxa[6.1.6.1]paracyclophane-32',4''-piperidinium) dichloride → 2C58H84N2O12(2+)*C32H18N6O14S4(4-)

Conditions	Yield
Multistep reaction;

4-[(E)-(4-aminophenyl)diazenyl]phenylamine (538-41-0, 98043-56-2, 137692-67-2) + 3-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (135-51-3) → C36H60O30*C32H18N6O14S4(4-)*4Na(1+) + C32H18N6O14S4(4-)*4Na(1+)

Conditions	Yield
Multistep reaction. Yields of byproduct given;

Downstream Products

• 525-05-3 sodium 2-hydroxy-1-nitrosonaphtalene-3,6-disulphonate 
• 2007-19-4 1-nitroso-2-naphthol-3,6-disulfonic acid 
• 104946-10-3 3-Hydroxy-4-([1,3,4]thiadiazol-2-ylazo)-naphthalene-2,7-disulfonic acid 
• 2172-27-2 3-hydroxy-4-thiazol-2-ylazo-naphthalene-2,7-disulfonic acid 
• 5859-00-7 disodium 3-hydroxy-4-(phenylazo)naphthalene-2,7-disulfonate 
• 33239-13-3 C₂₄H₂₆N₂O₇S₂^(2-)*2Na⁽¹⁺⁾ 
• 34293-77-1 C₂₂H₂₂N₂O₇S₂^(2-)*2Na⁽¹⁺⁾ 
• 33239-14-4 C₂₄H₂₆N₂O₇S₂^(2-)*2Na⁽¹⁺⁾ 
• 34293-76-0 C₂₂H₂₂N₂O₇S₂^(2-)*2Na⁽¹⁺⁾ 
• 34895-10-8 C₂₀H₁₈N₂O₇S₂^(2-)*2Na⁽¹⁺⁾ 
• 34293-75-9 C₂₀H₁₈N₂O₇S₂^(2-)*2Na⁽¹⁺⁾