134-47-4

Basic information

• Product Name: 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)
• Synonyms: 4,4'-dihydroxy-7,7'-ureylenedi(naphthalene-2-sulphonic acid);7,7'-(Carbonyldiimino)bis[4-hydroxy-2-naphthalenesulfonic acid];6,6'-ureylene-bis(1-naphthol-3-sulfonic acid);phosgenated;N,N'-bis(4-hydroxy-2-sulfonaphthalene-7-yl)urea;7,7'-Ureylenebis(4-hydroxy-2-naphthalenesulfonic acid);N,N'-Bis[6-(1-naphthol-3-sulfonic acid)]urea;2-Naphthalenesulfonic acid, 7,7-(carbonyldiimino)bis4-hydroxy-
• CAS NO: 134-47-4
• Molecular Formula: C₂₁H₁₆N₂O₉S₂
• Molecular Weight: 504.49
• EINECS: 205-142-9
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 134-47-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.798 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.17±0.40(Predicted)
• CAS DataBase Reference: 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)(134-47-4)
• EPA Substance Registry System: 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)(134-47-4)

Safety Data

• Hazardous Substances Data: 134-47-4(Hazardous Substances Data)

Usage

Uses

7,7''-(Carbonylbis(azanediyl))bis(4-hydroxynaphthalene-2-sulfonic acid) (cas# 134-47-4) is a pharmacologically active compound capable of selective nonbisphosphonate inhibition of human geranylgeranyl diphosphate synthase, and inhibition of shikimate dehydrogenase and shikimate kinase in shikimate pathway of Helicobacter pylori.

Synthetic route

bis(trichloromethyl) carbonate (32315-10-9) + 1-hydroxy-6-amino-3-naphthalenesulfonic acid (87-02-5) → AMI-1 (134-47-4)

Conditions	Yield
With sodium hydroxide at 60℃; for 6h; pH=7 - 8;	90%

phosgene (75-44-5) + 1-hydroxy-6-amino-3-naphthalenesulfonic acid (87-02-5) → AMI-1 (134-47-4)

Conditions	Yield
With sodium carbonate

phosgene (75-44-5) + 1-hydroxy-6-amino-3-naphthalenesulfonic acid (87-02-5) + alkali → AMI-1 (134-47-4)

AMI-1 (134-47-4) + N,N-Bis-(3-formamidopropyl)methylamine + 4-methoxy-3-nitrobenzyl chloride (6378-19-4) → C51H68N12O11S2(2+)*2Cl(1-)

Conditions	Yield
Multistep reaction;

AMI-1 (134-47-4) + diazotized 4-nitro-2-amino-phenol → 4,4'-dihydroxy-3,3'-bis-(2-hydroxy-5-nitro-phenylazo)-7,7'-ureylene-bis-naphthalene-2-sulfonic acid

3-aminobenzoic acid ethyl ester (582-33-2) + AMI-1 (134-47-4) → C39H32N6O13S2

Conditions	Yield
Stage #1: 3-aminobenzoic acid ethyl ester With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 4-amino-2,3,5,6-tetrafluorobenzoic acid (944-43-4) → C35H16F8N6O13S2

Conditions	Yield
Stage #1: 4-amino-2,3,5,6-tetrafluorobenzoic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 2,4-dibromo-aniline (615-57-6) → C33H20Br4N6O9S2

Conditions	Yield
Stage #1: 2,4-dibromo-aniline With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 3-(4-aminophenyl)propionic acid (2393-17-1) → 3-{4-[6-(3-{6-[4-(2-carboxy-ethyl)-phenylazo]-5-hydroxy-7-sulfo-naphthalen-2-yl}-ureido)-1-hydroxy-3-sulfo-naphthalen-2-ylazo]-phenyl}-propionic acid

Conditions	Yield
Stage #1: 3-(4-aminophenyl)propionic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 4-amino 3-methylbenzoic acid (2486-70-6) → C37H28N6O13S2

Conditions	Yield
Stage #1: 4-amino 3-methylbenzoic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + trans-p-aminocinnamic acid (17570-30-8) → (E)-3-{4-[6-(3-{6-[4-((E)-2-Carboxy-vinyl)-phenylazo]-5-hydroxy-7-sulfo-naphthalen-2-yl}-ureido)-1-hydroxy-3-sulfo-naphthalen-2-ylazo]-phenyl}-acrylic acid

Conditions	Yield
Stage #1: trans-p-aminocinnamic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 3-methoxy-4-aminobenzoic acid (2486-69-3) → C37H28N6O15S2

Conditions	Yield
Stage #1: 3-methoxy-4-aminobenzoic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 2-(4-aminophenyl)-succinic acid (22511-21-3) → 2-{4-[6-(3-{6-[4-(1,2-dicarboxy-ethyl)-phenylazo]-5-hydroxy-7-sulfo-naphthalen-2-yl}-ureido)-1-hydroxy-3-sulfo-naphthalen-2-ylazo]-phenyl}-succinic acid

Conditions	Yield
Stage #1: 2-(4-aminophenyl)-succinic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 3-amino-2,5,6-trifluoro benzoic acid (133622-65-8) → C35H18F6N6O13S2

Conditions	Yield
Stage #1: 3-amino-2,5,6-trifluoro benzoic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + meta-aminobenzoic acid (99-05-8) → C35H24N6O13S2

Conditions	Yield
Stage #1: meta-aminobenzoic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + 4-amino-benzoic acid (150-13-0) → calcomine orange

Conditions	Yield
Stage #1: 4-amino-benzoic acid With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

AMI-1 (134-47-4) + p-aminoethylbenzoate (94-09-7) → C39H32N6O13S2

Conditions	Yield
Stage #1: p-aminoethylbenzoate With sulfuric acid; sodium nitrite Diazotization; Stage #2: AMI-1 With sodium carbonate at 20℃; pH=9; azo coupling;

Upstream product

• 75-44-5 phosgene 
• 87-02-5 7-amino-4-hydroxy-2-naphthalenesulfonic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 47893-59-4 calcomine orange 

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