• Name

  Mordant Orange 1

• EINECS 218-818-3
• CAS No. 2243-76-7
• Article Data13
• CAS DataBase
• Density 1.49 g/cm³
• Solubility Soluble in water
• Melting Point 250 °C
• Formula C₁₃H₉N₃O₅
• Boiling Point 571.4 °C at 760 mmHg
• Molecular Weight 287.232
• Flash Point 299.4 °C
• Transport Information
• Appearance brown powder
• Safety 24/25-26
• Risk Codes 22-36
• Molecular Structure
• Hazard Symbols Xn
• Synonyms Benzoicacid, 2-hydroxy-5-[(4-nitrophenyl)azo]- (9CI);C.I. Mordant Orange 1 (7CI,8CI);Salicylic acid, 5-(p-nitrophenylazo)- (6CI);2-Hydroxy-5-(4-nitrophenylazo)benzoic acid;4-Nitrobenzene-1-azo-5-salicylicacid;5-(4-Nitrophenylazo)salicylic acid;5-(p-Nitrophenylazo)salicylic acid;Acid Alizarine Yellow R;Alizarin orange;Alizarine ChromeOrange G;Alizarine Orange 2GN;Alizarine Orange R;Alizarine Yellow R-CF;Alizarol OrangeR;Alphacroic Orange R;Anthranol Chrome Yellow R;Azochromol Orange R;Brasilan Chrome Orange R;C.I. 14030;Calcochrome Orange R;Chromacid Orange S;ChromeOrange R;Chrome Orange RLE;Chrome Yellow 3RN;Eniacromo Orange R;Eriochrome OrangeAOR;Hispacrom Orange R;Java ChromeYellow 3R;Java Unichrome Yellow 3R;Lighthouse Chrome Orange;Magracrom orange;Mitsui ChromeOrange A;Mitsui Chrome Orange AN;Monochrome Orange R;Orthochrome Orange R;PNBAS;Peerachrome Yellow R;Pontachrome Yellow 3RN;SynchromateOrange AOR;Terra Cotta RRN;Terracotta 2RN;p-Nitrobenzeneazosalicylic acid;
• PSA 128.07000
• LogP 3.93720

Synthetic route

100-01-6

4-nitro-aniline

69-72-7

salicylic acid

2243-76-7

alizarin yellow R

Conditions

Conditions	Yield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at -0.16℃; for 0.166667h; Stage #2: salicylic acid With sodium hydroxide In water	80%
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; Flow reactor; Stage #2: salicylic acid With glycine; sodium hydroxide In water; N,N-dimethyl-formamide at 25℃; pH=8.55 - 9; Flow reactor;

54-21-7

sodium salicylate

100-01-6

4-nitro-aniline

2243-76-7

alizarin yellow R

Conditions

Conditions	Yield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.75h; Stage #2: sodium salicylate In water at 0 - 5℃; for 2h; Alkaline conditions;	60%

456-27-9

4-nitrobenzenediazonium tetrafluoroborate

69-72-7

salicylic acid

2243-76-7

alizarin yellow R

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; Inert atmosphere; Darkness;	18%

14368-49-1

p-nitrobenzenediazonium

69-72-7

salicylic acid

2243-76-7

alizarin yellow R

Conditions

Conditions	Yield
With alkali hydroxide

100-05-0

4-nitrobenzenediazonium chloride

3147-53-3

2-hydroxy-5-phenylazo-benzoic acid

2243-76-7

alizarin yellow R

100-05-0

4-nitrobenzenediazonium chloride

3147-53-3

2-hydroxy-5-phenylazo-benzoic acid

A

93656-74-7

2,4-Bis-(4-nitro-phenylazo)-phenol

B

2243-76-7

alizarin yellow R

...Expand

3147-53-3

2-hydroxy-5-phenylazo-benzoic acid

2243-76-7

alizarin yellow R

Conditions

Conditions	Yield
With sodium nitrate; sulfuric acid

7664-93-9

sulfuric acid

7697-37-2

nitric acid

3147-53-3

2-hydroxy-5-phenylazo-benzoic acid

2243-76-7

alizarin yellow R

...Expand

56-35-9

bis(tri-n-butyltin)oxide

2243-76-7

alizarin yellow R

Bu3Sn(5-[(E)-2-(4-nitrophenyl)-1-diazenyl]-2-hydroxybenzoate)

Conditions

Conditions	Yield
In toluene ligand was mixed with Sn-compound in toluene, refluxed for 3 h; solvent was distilled and removed by rotary evaporator, dissolved in petroleum ether under cold conditions, recrystd. from petroleum ether for several ds; elem. anal.;	83%

60984-63-6

mono-6-deoxy-6-(2-aminoethylamino)-β-cyclodextrin

2243-76-7

alizarin yellow R

C57H83N5O38

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1) 0 deg C, 3 h; 2) rt, 10 h;	37%

67-56-1

methanol

2243-76-7

alizarin yellow R

21460-91-3

2-hydroxy-5-(4-nitro-phenylazo)-benzoic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid

64-17-5

ethanol

2243-76-7

alizarin yellow R

2-hydroxy-5-(4-nitro-phenylazo)-benzoic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid

2243-76-7

alizarin yellow R

16616-47-0

2,4,5-trichloro-3,6-dioxo-cyclohexa-1,4-dienecarboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hypochlorite

10016-20-3

alpha cyclodextrin

2243-76-7

alizarin yellow R

C36H60O30*C13H8N3O5(1-)

Conditions

Conditions	Yield
In water Rate constant; Equilibrium constant; in neutral region;

10016-20-3

alpha cyclodextrin

2243-76-7

alizarin yellow R

C36H60O30*C13H7N3O5(2-)

Conditions

Conditions	Yield
In water Rate constant; Equilibrium constant; in basic region;

2243-76-7

alizarin yellow R

7664-41-7

ammonia

Conditions

Conditions	Yield
beim Aufbewahren;

sodium hydrogensulfite

2243-76-7

alizarin yellow R

A

100-01-6

4-nitro-aniline

B

5-amino-x-sulfo-salicylic acid

5-amino-x-sulfo-salicylic acid

...Expand

2243-76-7

alizarin yellow R

Na2SO3

Na2SO3

A

101-51-9

5-(4-amino-phenylazo)-2-hydroxy-benzoic acid

B

100-01-6

4-nitro-aniline

C

5-amino-x-sulfo-salicylic acid

5-amino-x-sulfo-salicylic acid

...Expand

2243-76-7

alizarin yellow R

Na2S2O4

Na2S2O4

A

89-57-6

5-Aminosalicylic Acid

B

106-50-3

1,4-phenylenediamine

Conditions

Conditions	Yield
in alkal.Loesung;

...Expand

7647-01-0

hydrogenchloride

2243-76-7

alizarin yellow R

sodium hypochlorite

sodium hypochlorite

A

4-nitro-benzenediazonium-chloride-(1)

4-nitro-benzenediazonium-chloride-(1)

B

trichlorobenzoquinone-carboxylic acid

trichlorobenzoquinone-carboxylic acid

...Expand

2243-76-7

alizarin yellow R

106-50-3

1,4-phenylenediamine

Conditions

Conditions	Yield
With sodium hydroxide; sodium dithionite In water at 100℃; for 1h; Product distribution; Further Variations:; Temperatures; Solvents; pH-values; reflux condenser;

2243-76-7

alizarin yellow R

2-acetoxy-5-(4-nitro-phenylazo)-benzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: durch Acetylierung View Scheme

copper(II) choride dihydrate

nickel(II) chloride hexahydrate

493-52-7

methyl red

2243-76-7

alizarin yellow R

Cu(2+)*2Ni(2+)*C6H4(N(CH3)2)NNC6H4COO(1-)*C6H4NO2NNC6H3(COO)O(2-)*NH3*3OH(1-)*6H2O=CuNi2C28H21N6O7(NH3)(OH)3(H2O)4*2H2O

Conditions

Conditions	Yield
In ethanol; ammonia aq. ammonia=NH3; a soln. of CuCl2*2H2O in water-ammonia is added to a soln. of NiCl2*6H2O, Methyl Red and Alizarin Yellow R in EtOH/aq. NH3; the solvents are evapd., the ppt. is filtered, washed, dried, elem. anal.;

...Expand

nickel(II) chloride hexahydrate

493-52-7

methyl red

2243-76-7

alizarin yellow R

2Ni(2+)*C6H4(N(CH3)2)NNC6H4(COO)(1-)*C6H4(NO2)NNC6H3(COO)(O)(2-)*3NH3*OH(1-)=Ni2(C15H14N3O2)(C13H7N3O5)(NH3)3(OH)

Conditions

Conditions	Yield
In ethanol; ammonia aq. ammonia=NH3; a soln. of Methyl Red in hot ethanol is mixed with a soln. of Alizarin Yellow R in hot water-ethanol, to this soln. is added the metal salt in water-ammonia; the solvents are partially evapd., the ppt. is filtered., washed, dried, elem. anal.;

...Expand

copper(II) choride dihydrate

493-52-7

methyl red

2243-76-7

alizarin yellow R

2Cu(2+)*C6H4(N(CH3)2)NNC6H4(COO)(1-)*C6H4(NO2)NNC6H3(COO)(O)(2-)*3NH3*OH(1-)*4H2O=Cu2C28H21N6O7(NH3)3(OH)*4H2O

Conditions

Conditions	Yield
In ethanol; ammonia aq. ammonia=NH3; a soln. of Methyl Red in hot ethanol is mixed with a soln. of Alizarin Yellow R in hot water-ethanol, to this soln. is added the metal salt in water-ammonia; the solvents are partially evapd., the ppt. is filtered, washed, dried,elem. anal.;

...Expand

copper(II) choride dihydrate

493-52-7

methyl red

2243-76-7

alizarin yellow R

3Cu(2+)*C6H4(N(CH3)2)NNC6H4(COO)(1-)*C6H4(NO2)NNC6H3(COO)(O)(2-)*4(NH3)*3OH(1-)*5H2O=Cu3C28H21N6O7(NH3)4(H2O)4(OH)3*H2O

Conditions

Conditions	Yield
In ethanol; ammonia aq. ammonia=NH3; a soln. of CuCl2*2H2O in water-ammonia is added to a soln. of CuCl2*2H2O, Methyl Red and Alizarin Yellow R in EtOH/aq. NH3; the solvents are evapd., the ppt. is filtered, washed, dried, elem. anal.;

...Expand

copper(II) choride dihydrate

cobalt(II) chloride hexahydrate

493-52-7

methyl red

2243-76-7

alizarin yellow R

Cu(2+)*2Co(2+)*C6H4(N(CH3)2)NNC6H4COO(1-)*C6H4NO2NNC6H3(COO)O(2-)*NH3*6H2O*3OH(1-)=CuCo2C28H21N6O7(H2O)4(NH3)(OH)3*2H2O

Conditions

Conditions	Yield
In ethanol; ammonia aq. ammonia=NH3; a soln. of CuCl2*2H2O in water-ammonia is added to a soln. of CoCl2*6H2O, Methyl Red and Alizarin Yellow R in EtOH/aq. NH3; the solvents are evapd., the ppt. is filtered, washed, dried, elem. anal.;

...Expand

7705-08-0

iron(III) chloride

493-52-7

methyl red

2243-76-7

alizarin yellow R

Fe(3+)*C6H4(N(CH3)2)NNC6H4(COO)(1-)*2C6H4(NO2)NNC6H3(COO)(OH)(1-)=Fe(C15H14N3O2)(C13H8N3O5)2

Conditions

Conditions	Yield
In ethanol; ammonia aq. ammonia=NH3; a soln. of Methyl Red in hot ethanol is mixed with a soln. of Alizarin Yellow R in hot water-ethanol, to this soln. is added the metal salt in water-ammonia; the solvents are partially evapd., the ppt. is filtered, washed, dried,elem. anal.;

...Expand

Mordant Orange 1 Chemical Properties

The Molecular formula of  p-NITROBENZENEAZOSALICYLIC ACID(2243-76-7):C₁₃H₉N₃O₅
The Molecular Weight of  p-NITROBENZENEAZOSALICYLIC ACID(2243-76-7):287.23  
The Molecular Structure of  p-NITROBENZENEAZOSALICYLIC ACID(2243-76-7) is:
Density:1.49 g/cm³ 
Melting point:250 ^°CBoiling point:500.2 ^°C at 760 mmHg 
Flash point:256.3 ^°C     
Solubility in water:SOLUBLE
Colour Index:14030
Merck:255 
Index of Refraction:1.671 
Molar Refractivity:71.68 cm³  
Molar Volume:191.5 cm³
Polarizability:28.41 10^-24cm³
Surface Tension:67.3 dyne/cm 
Enthalpy of Vaporization:80.96 kJ/mol   
Vapour Pressure:7.94E-11 mmHg at 25^°C 
Appearance:brown powder
IUPAC Name:(3E)-3-[(4-nitrophenyl)hydrazinylidene]-6-oxocyclohexa-1,4-diene-1-carboxylic acid
Synonyms:CI NO 14030;P-NITROBENZENEAZOSALICYLIC ACID SODIUM SALT;CI 14030;CHROME ORANGE;ALIZARIN YELLOW R;ALIZARIN ORANGE;5-(P-NITROPHENYLAZO)SALICYLIC ACID SODIUM SALT;MORDANT ORANGE 1

Mordant Orange 1 Uses

Mordant Orange 1 Toxicity Data With Reference

Mordant Orange 1 Consensus Reports

Mordant Orange 1 Safety Profile

Mordant Orange 1 Specification