90-40-4

Basic information

• Product Name: 8-Hydroxy-2-naphthylamine-3,6-disulfonic acid
• Synonyms: 8-Hydroxy-2-naphthylamine-3,6-disulfonic acid;3-amino-5-hydroxynaphthalene-2,7-disulphonic acid;3-Amino-5-hydroxy-2,7-naphthalenedisulfonic acid;3-amino-5-hydroxynaphthalene-2,7-disulfonic acid;3-azanyl-5-hydroxy-naphthalene-2,7-disulfonic acid;2,7-Naphthalenedisulfonicacid, 3-aMino-5-hydroxy-;2-Amino-8-naphthol-6-disulfonic acid;VNWVMZDJPMCAKD-UHFFFAOYSA-N
• CAS NO: 90-40-4
• Molecular Formula: C₁₀H₉NO₇S₂
• Molecular Weight: 319.31096
• EINECS: 201-989-3
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 90-40-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 603.18℃[at 101 325 Pa]
• Appearance: /
• Density: 1.88 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Water Solubility: 35.36g/L at 25℃
• CAS DataBase Reference: 8-Hydroxy-2-naphthylamine-3,6-disulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Hydroxy-2-naphthylamine-3,6-disulfonic acid(90-40-4)
• EPA Substance Registry System: 8-Hydroxy-2-naphthylamine-3,6-disulfonic acid(90-40-4)

Safety Data

• Hazardous Substances Data: 90-40-4(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H9NO7S2/c11-8-4-7-5(2-10(8)20(16,17)18)1-6(3-9(7)12)19(13,14)15/h1-4,12H,11H2,(H,13,14,15)(H,16,17,18)

Synthetic route

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4)

Conditions	Yield
With alkali at 220 - 260℃;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) + alkali → 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4)

Conditions	Yield
at 220 - 260℃;

tetrasodium-salt of/the/ 2-amino-naphthalene-1.3.6.8-tetrasulfonic acid → 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4)

Conditions	Yield
With sodium hydroxide at 200℃;

phosgene (75-44-5) + 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 5,5'-dihydroxy-3,3'-ureylene-bis-naphthalene-2,7-disulfonic acid ; sodium salt

Conditions	Yield
With sodium carbonate

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + 6-nitro-1-naphthoic acid chloride (175697-96-8) → 5,5'-dihydroxy-3,3'-(5,5'-ureylene-bis-[1]naphthoylamino)-bis-naphthalene-2,7-disulfonic acid

Conditions	Yield
Reduktion und Behandlung des Reaktionsprodukts mit Phosgen bei Gegenwart von Natriumacetat in waessr. Loesung;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + 4-nitrobenzenediazonium chloride (100-05-0) → 3-amino-4-(4-amino-phenylazo)-5-hydroxy-naphthalene-2,7-disulfonic acid

Conditions	Yield
und Reduktion mit Natriumsulfid;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + 4-nitrobenzenediazonium chloride (100-05-0) → 3-amino-5-hydroxy-4-(4-nitro-phenylazo)-naphthalene-2,7-disulfonic acid

Conditions	Yield
With acetic acid

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + benzene diazonium chloride (100-34-5) → 6-amino-4-hydroxy-3-phenylazo-naphthalene-2,7-disulfonic acid

Conditions	Yield
With alkali

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With sulfuric acid at 200℃;
With hydrogenchloride at 200℃;
With phosphoric acid at 200℃;
With formic acid at 200℃;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 6-amino-2,3,5,7-tetrabromo-[1,4]naphthoquinone (858020-15-2)

Conditions	Yield
With bromine; acetic acid

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 5,5'-dihydroxy-3,3'-imino-bis-naphthalene-2,7-disulfonic acid

Conditions	Yield
With sodium hydrogensulfite

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 8-hydroxy-3,6-disulfo-naphthalene-2-diazonium-betaine (34043-07-7)

Conditions	Yield
Diazotization;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + aniline hydrochloride (142-04-1) + aniline (62-53-3) → 3-anilino-5-hydroxy-naphthalene-2,7-disulfonic acid (73525-19-6)

Conditions	Yield
at 160℃;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + aniline (62-53-3) → 3-anilino-5-hydroxy-naphthalene-2,7-disulfonic acid (73525-19-6)

Conditions	Yield
With aniline hydrochloride at 160℃;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + m-nitrobenzoic acid chloride (121-90-4) → 5-hydroxy-3-(3-nitro-benzoylamino)-naphthalene-2,7-disulfonic acid ; disodium-salt hydrate

Conditions	Yield
With sodium acetate

sulfuric acid (7664-93-9) + 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
at 200℃;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + bromine (7726-95-6) + water containing acetic acid → 6-amino-2,3,5,7-tetrabromo-[1,4]naphthoquinone (858020-15-2)

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + diazotized 4-chloro-5-amino-2-oxalamino-anisole → 6-(2,4-diamino-5-sulfo-phenylazo)-3-[4-(2,4-diamino-5-sulfo-phenylazo)-2-chloro-5-methoxy-phenylazo]-4-hydroxy-naphthalene-2,7-disulfonic acid

Conditions	Yield
With sodium carbonate ueber mehrere Stufen;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) + alkali → 7-amino-1.3-or 1.6-dioxy-naphthalene-sulfonic acid-(6 or 3)

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 6-acetylamino-2,3,5,7-tetrabromo-[1,4]naphthoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: sulfuric acid View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 2,3,5,7-tetrabromo-6-diacetylamino-[1,4]naphthoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: sulfuric acid View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-diacetoxynaphthalene (51850-49-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C 2: pyridine / 100 °C View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-di-trans-cinnamoyloxy-naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C 2: benzene; pyridine View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-bis-benzoyloxy-naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C 2: potassium carbonate; benzene View Scheme
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C 2: pyridine View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-bis-allophanoyloxy-naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C 2: benzene View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-bis-phenylcarbamoyloxy-naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-bis-(4-nitro-benzoyloxy)-naphthalene

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid / 200 °C 2: benzene View Scheme

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → C30H25N7O11S3 (742661-00-3)

Conditions	Yield
Stage #1: C20H19N5O4S Stage #2: 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid

Upstream product

• 118-03-6 7-aminonaphthalene-1,3,6-trisulfonic acid 

Downstream Products

• 575-38-2 1,7-Dihydroxynaphthalene 
• 73525-19-6 3-anilino-5-hydroxy-naphthalene-2,7-disulfonic acid 
• 51850-49-8 1,7-diacetoxynaphthalene 
• 742661-00-3 C₃₀H₂₅N₇O₁₁S₃ 
• 847687-80-3 C₁₉H₁₃Cl₂N₇O₁₀S₃ 
• 1056963-27-9 C₁₆H₁₂N₄O₁₂S₃ 

Relevant articles and documents

Monoazo compounds having vinylsulfone type fiber reactive group and method for dyeing or printing fiber materials using the same

A monoazo compound of the following formula, STR1 wherein D is phenylene or naphthylene; X is halogeno, pyridinio or STR2 B is --OR3, --SR4, STR3 in which R3, R4, R5 and R6 are each hydrogen, alkyl, phenyl, naphthyl or benzyl, r is 0 or 1, and E is O, SO, SO2, CH2 or NR8, in which R8 is hydrogen or C1 -C4 alkyl; R, R1, R2 and R7 are each hydrogen or alkyl; A1, A2 and A3 are each phenylene, naphthylene or alkylene; Z1, Z2 and Z3 are each --SO2 CH=CH2 or --SO2 CH2 CH2 Y, in which Y is a splittable group; and p is 0 or 1; which compound is useful for dyeing or printing fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.

Copper complexes of sulpho groups containing disazo dyestuffs

The new disazo dyestuffs of the formula (I) STR1 in which the substituents and indices have the meaning given in the description, and salts thereof are outstandingly suitable for dyeing cellulose-containing materials and leather in blue shades having good wet- and light-fastnesses.

New reactive dyes

A reactive dye which in the free acid form has the formula: wherein:, A is the residue of a diazo component;, the -NRY group is attached to the naphthalene nucleus in the 6- or 7-position relative to the -OH group;, n is 0 or 1, the SO3H group, when n is 1, being attached to the 5-position or to whichever is free of the 6- and 7-positions;, R is optionally substituted alkyl or alkenyl containing up to 10 carbon atoms;, Q is H or optionally substituted alkyl or alkenyl containing up to 10 carbon atoms;, Z is an optionally substituted aryl group;, D is H, chloro, C1 4-alkoxy, SO3H or C1 4-alkyl;, B is OH or NR1R2; and, R1 and R1 are independently selected from H and optionally substituted alkyl or alkenyl containing up to 10 carbon atoms.