Product Name

  • Name

    6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)

  • EINECS 205-142-9
  • CAS No. 134-47-4
  • Article Data4
  • CAS DataBase
  • Density 1.798 g/cm3
  • Solubility
  • Melting Point 86-88°C
  • Formula C21H16N2O9S2
  • Boiling Point
  • Molecular Weight 504.498
  • Flash Point
  • Transport Information
  • Appearance dry grey-white powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 134-47-4 (6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid))
  • Hazard Symbols
  • Synonyms 1-Naphthol-3-sulfonicacid, 6,6'-ureylenebis- (6CI);2-Naphthalenesulfonic acid, 7,7'-ureylenebis[4-hydroxy-(8CI);6,6'-Ureylenebis(1-naphthol-3-sulfonic acid);Carbonyl J;I AcidUrea;J acid urea;N,N'-Bis(5-hydroxy-7-sulfo-2-naphthyl)urea;NSC 1699;NSC 45174;UreaJ Acid;Scarlet Acid;
  • PSA 207.09000
  • LogP 5.84920

Synthetic route

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-hydroxy-6-amino-3-naphthalenesulfonic acid
87-02-5

1-hydroxy-6-amino-3-naphthalenesulfonic acid

AMI-1
134-47-4

AMI-1

Conditions
ConditionsYield
With sodium hydroxide at 60℃; for 6h; pH=7 - 8;90%
phosgene
75-44-5

phosgene

1-hydroxy-6-amino-3-naphthalenesulfonic acid
87-02-5

1-hydroxy-6-amino-3-naphthalenesulfonic acid

AMI-1
134-47-4

AMI-1

Conditions
ConditionsYield
With sodium carbonate
phosgene
75-44-5

phosgene

1-hydroxy-6-amino-3-naphthalenesulfonic acid
87-02-5

1-hydroxy-6-amino-3-naphthalenesulfonic acid

alkali

alkali

AMI-1
134-47-4

AMI-1

...Expand
AMI-1
134-47-4

AMI-1

N,N-Bis-(3-formamidopropyl)methylamine

N,N-Bis-(3-formamidopropyl)methylamine

4-methoxy-3-nitrobenzyl chloride
6378-19-4

4-methoxy-3-nitrobenzyl chloride

C51H68N12O11S2(2+)*2Cl(1-)

C51H68N12O11S2(2+)*2Cl(1-)

Conditions
ConditionsYield
Multistep reaction;
...Expand
AMI-1
134-47-4

AMI-1

diazotized 4-nitro-2-amino-phenol

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

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

3-aminobenzoic acid ethyl ester

AMI-1
134-47-4

AMI-1

C39H32N6O13S2

C39H32N6O13S2

Conditions
ConditionsYield
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

AMI-1

4-amino-2,3,5,6-tetrafluorobenzoic acid
944-43-4

4-amino-2,3,5,6-tetrafluorobenzoic acid

C35H16F8N6O13S2

C35H16F8N6O13S2

Conditions
ConditionsYield
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

AMI-1

2,4-dibromo-aniline
615-57-6

2,4-dibromo-aniline

C33H20Br4N6O9S2

C33H20Br4N6O9S2

Conditions
ConditionsYield
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

AMI-1

3-(4-aminophenyl)propionic acid
2393-17-1

3-(4-aminophenyl)propionic acid

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

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
ConditionsYield
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

AMI-1

4-amino 3-methylbenzoic acid
2486-70-6

4-amino 3-methylbenzoic acid

C37H28N6O13S2

C37H28N6O13S2

Conditions
ConditionsYield
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

AMI-1

trans-p-aminocinnamic acid
17570-30-8

trans-p-aminocinnamic acid

(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

(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
ConditionsYield
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

AMI-1

3-methoxy-4-aminobenzoic acid
2486-69-3

3-methoxy-4-aminobenzoic acid

C37H28N6O15S2

C37H28N6O15S2

Conditions
ConditionsYield
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

AMI-1

2-(4-aminophenyl)-succinic acid
22511-21-3

2-(4-aminophenyl)-succinic acid

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

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
ConditionsYield
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

AMI-1

3-amino-2,5,6-trifluoro benzoic acid
133622-65-8

3-amino-2,5,6-trifluoro benzoic acid

C35H18F6N6O13S2

C35H18F6N6O13S2

Conditions
ConditionsYield
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

AMI-1

meta-aminobenzoic acid
99-05-8

meta-aminobenzoic acid

C35H24N6O13S2

C35H24N6O13S2

Conditions
ConditionsYield
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

AMI-1

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

calcomine orange

calcomine orange

Conditions
ConditionsYield
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

AMI-1

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

C39H32N6O13S2

C39H32N6O13S2

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

6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid) Specification

The IUPAC name of 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid) is 4-hydroxy-7-[(5-hydroxy-7-sulfonaphthalen-2-yl)carbamoylamino]naphthalene-2-sulfonic acid. With the CAS registry number 134-47-4 and EINECS 205-142-9, it is also named as 7,7'-(Carbonyldiimino)bis(4-hydroxy-2-naphthalenesulfonic acid). The product's category is Intermediates of Dyes and Pigments.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.94; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -6.44; (4)ACD/LogD (pH 7.4): -6.47; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 11; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 145.51 Å2; (13)Index of Refraction: 1.822; (14)Molar Refractivity: 122.38 cm3; (15)Molar Volume: 280.5 cm3; (16)Polarizability: 48.51×10-24 cm3; (17)Surface Tension: 110.3 dyne/cm; (18)Rotatable Bond Count: 4; (19)Tautomer Count: 43; (20)Exact Mass: 504.029722; (21)MonoIsotopic Mass: 504.029722; (22)Topological Polar Surface Area: 207; (23)Heavy Atom Count: 34; (24)Complexity: 886.

Uses of 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid): It is used as intermediate of azo dyes. And it is also used to produce Direct Orange S, Direct Fast Scarlet 4BS.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=S(=O)(O)c2cc1cc(ccc1c(O)c2)NC(=O)Nc3ccc4c(c3)cc(cc4O)S(=O)(=O)O
2. InChI:InChI=1/C21H16N2O9S2/c24-19-9-15(33(27,28)29)7-11-5-13(1-3-17(11)19)22-21(26)23-14-2-4-18-12(6-14)8-16(10-20(18)25)34(30,31)32/h1-10,24-25H,(H2,22,23,26)(H,27,28,29)(H,30,31,32) 
3. InChIKey:PCGISRHGYLRXSR-UHFFFAOYAI
4. Std. InChI:InChI=1S/C21H16N2O9S2/c24-19-9-15(33(27,28)29)7-11-5-13(1-3-17(11)19)22-21(26)23-14-2-4-18-12(6-14)8-16(10-20(18)25)34(30,31)32/h1-10,24-25H,(H2,22,23,26)(H,27,28,29)(H,30,31,32)
5. Std. InChIKey:PCGISRHGYLRXSR-UHFFFAOYSA-N

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