Product Name

  • Name

    DISPERSE RED 13

  • EINECS 221-668-1
  • CAS No. 3180-81-2
  • Density 1.31 g/cm3
  • Solubility 11.51ug/L(25 oC)
  • Melting Point 122-129 °C
  • Formula C16H17ClN4O3
  • Boiling Point 547.7 °C at 760 mmHg
  • Molecular Weight 348.789
  • Flash Point 285 °C
  • Transport Information
  • Appearance dark red powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3180-81-2 (DISPERSE RED 13)
  • Hazard Symbols IrritantXi
  • Synonyms C.I.Disperse Red 13 (7CI,8CI);Dispersol Fast Crimson B (6CI);Ethanol,2-[[4-[(2-chloro-4-nitrophenyl)azo]phenyl]ethylamino]- (9CI);4-Nitro-2-chloro-4'-[ethyl(2-hydroxyethyl)amino]azobenzene;Acetamine Rubine B;Acetate Fast Rubine B;Amacel Rubine B;C.I.11115;Celliton Discharging Rubine BL;Celliton Fast Rubine B;Celliton Ruby B;Cibacet Rubine BS;CibacetRubine R;Diacelliton Fast Blue Bordeaux B;Disperse Bordeaux S;Dispersol Rubine B;Fenacet Fast Rubine B;IntrasperseBordeaux BA;KCA Acetate Crimson B;Kayalon Fast Rubine B;Nyloquinone Bordeaux B;Perliton Rubine 4B;Serisol Fast Crimson BD 150;Setacyl Red 2B;Silotras Rubine TSB;Supracet Fast Crimson B;
  • PSA 94.01000
  • LogP 5.00540

Synthetic route

acryloyl chloride
814-68-6

acryloyl chloride

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

disperse red 13 acrylate

disperse red 13 acrylate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Cooling with ice;96%
succinic acid anhydride
108-30-5

succinic acid anhydride

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

4-[2-ethyl({4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)ethoxy]-4-oxobutanoic acid

4-[2-ethyl({4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)ethoxy]-4-oxobutanoic acid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;90%
With pyridine; dmap In dichloromethane at 0℃;63%
1,4-diisocyanatobenzene
104-49-4

1,4-diisocyanatobenzene

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C40H38Cl2N10O8

C40H38Cl2N10O8

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;84.7%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C40H36Cl2N8O8

C40H36Cl2N8O8

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;82.5%
With triethylamine In dichloromethane at 20℃; Cooling with ice;
p-Tolylisocyanate
622-58-2

p-Tolylisocyanate

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C24H24ClN5O4

C24H24ClN5O4

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;81%
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

5-bromopentyl 2-(N-ethyl-N-{4′-[(2″-chloro-4″-nitrophenyl)-phazo]phenyl}amino)ethyl ether
1174752-17-0

5-bromopentyl 2-(N-ethyl-N-{4′-[(2″-chloro-4″-nitrophenyl)-phazo]phenyl}amino)ethyl ether

Conditions
ConditionsYield
Stage #1: 2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol With potassium hydroxide; 18-crown-6 ether In tetrahydrofuran at 20℃; for 1h;
Stage #2: 1,5-dibromo-pentane In tetrahydrofuran at 20℃; for 20h;		78%
With 18-crown-6 ether; potassium hydroxide In tetrahydrofuran59%
6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
119613-87-5

6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester
930805-71-3

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 20h;70%
6-O-(3-carboxypropanoyl)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose
930805-63-3

6-O-(3-carboxypropanoyl)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2,2,5,5-tetramethyl-tetrahydro-1,3,4,6,8-pentaoxa-cyclopenta[a]inden-7-ylmethyl ester
930805-68-8

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2,2,5,5-tetramethyl-tetrahydro-1,3,4,6,8-pentaoxa-cyclopenta[a]inden-7-ylmethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 20h;70%
8,13-dioxatricyclo[12.4.0.02,7]octadeca-1(18),2(7),3,5,14,16-hexaen-10-yne-4-carboxylic acid

8,13-dioxatricyclo[12.4.0.02,7]octadeca-1(18),2(7),3,5,14,16-hexaen-10-yne-4-carboxylic acid

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C33H27ClN4O6

C33H27ClN4O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;61%
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

epichlorohydrin
106-89-8

epichlorohydrin

C19H21ClN4O4

C19H21ClN4O4

Conditions
ConditionsYield
With water; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In tetrahydrofuran at 20℃; for 16h;60%
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

di(4-isocyanatophenyl)methane
101-68-8

di(4-isocyanatophenyl)methane

C47H44Cl2N10O8

C47H44Cl2N10O8

Conditions
ConditionsYield
With stannous octoate In toluene at 85℃; for 4h;48.24%
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

Hexamethylene diisocyanate
822-06-0

Hexamethylene diisocyanate

C40H46Cl2N10O8

C40H46Cl2N10O8

Conditions
ConditionsYield
With stannous octoate In toluene at 85℃; for 4h;32.04%
nonadecanoyl chloride
59410-47-8

nonadecanoyl chloride

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

disperse red-13 stearate

disperse red-13 stearate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -4℃; for 24h; Acylation;
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C16H16N4O3ClSO2CH3

C16H16N4O3ClSO2CH3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12h;
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

N-ethyl-N-(2-azidoethyl)-4-(2-chloro-4-nitrophenylazo)phenylamine

N-ethyl-N-(2-azidoethyl)-4-(2-chloro-4-nitrophenylazo)phenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / CH2Cl2 / 12 h / 20 °C
2: 93 percent / sodium azide / dimethylsulfoxide / 16 h / 50 °C
View Scheme
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2-hydroxy-2-(3,4,5-trihydroxy-tetrahydro-furan-2-yl)-ethyl ester

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2-hydroxy-2-(3,4,5-trihydroxy-tetrahydro-furan-2-yl)-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / tetrahydrofuran / 20 h / 20 °C
2: aq. CF3COOH / 1.5 h / 20 °C
View Scheme
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / tetrahydrofuran / 20 h / 20 °C
2: aq. CF3COOH / 1.5 h / 20 °C
View Scheme
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester

succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / tetrahydrofuran / 20 h / 20 °C
2: aq. CF3COOH / 1.5 h / 20 °C
View Scheme
4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C23H20ClN5O7
404887-21-4

C23H20ClN5O7

Conditions
ConditionsYield
In pyridine at 70℃; for 0.666667h;
50/50 % (M/M) Styrene-Maleic anhydride copolymer

50/50 % (M/M) Styrene-Maleic anhydride copolymer

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

polymeric dye no. I

polymeric dye no. I

Conditions
ConditionsYield
Stage #1: 50/50 % (M/M) Styrene-Maleic anhydride copolymer; 2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol With dmap In 1,4-dioxane for 48h; Heating / reflux;
Stage #2: With sodium hydroxide In 1,4-dioxane; water for 0.5h;
Stage #3: With hydrogenchloride In water pH=8;
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C45H56Cl2N10O10

C45H56Cl2N10O10

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 20 °C / Cooling with ice
2: chloroform / 48 h / 50 - 60 °C / Cooling with ice
View Scheme
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

C41H51Cl2N9O10

C41H51Cl2N9O10

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / tetrahydrofuran / 16 h / 20 °C
2: N,N-dimethyl-formamide / 95 °C
View Scheme
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

1-[6-[[5-[2-[4-[(E)-(2-chloro-4-nitro-phenyl)azo]-N-ethyl-anilino]ethoxy]pentylamino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione

1-[6-[[5-[2-[4-[(E)-(2-chloro-4-nitro-phenyl)azo]-N-ethyl-anilino]ethoxy]pentylamino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide; 18-crown-6 ether / tetrahydrofuran
2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol
3180-81-2

2-[4-(2-chloro-4-nitrophenylazo)-N-ethylphenylamino]ethanol

1-[5-[[5-[2-[4-[(E)-(2-chloro-4-nitro-phenyl)azo]-N-ethyl-anilino]ethoxy]pentylamino]methyl]-3,4-dihydroxy-tetrahydrofuran-2-yl]pyrimidine-2,4-dione

1-[5-[[5-[2-[4-[(E)-(2-chloro-4-nitro-phenyl)azo]-N-ethyl-anilino]ethoxy]pentylamino]methyl]-3,4-dihydroxy-tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide; 18-crown-6 ether / tetrahydrofuran
2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C
3: trifluoroacetic acid / water / 0.17 h / 20 °C
View Scheme

Disperse Red 13 Consensus Reports

Reported in EPA TSCA Inventory.

Disperse Red 13 Specification

The IUPAC name of C.I. Disperse red 13 is 2-[4-[(2-chloro-4-nitrophenyl)diazenyl]-N-ethylanilino]ethanol. With the CAS registry number 3180-81-2 and EINECS 221-668-1, it is also named as Acetamine Rubine B. The product's categories are Dyes and Pigments; Organics. It is dark red powder which should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.22; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.22; (4)ACD/LogD (pH 7.4): 5.22; (5)#H bond acceptors: 7; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 8; (8)Polar Surface Area: 94.01 Å2; (9)Index of Refraction: 1.614; (10)Molar Refractivity: 92.17 cm3; (11)Molar Volume: 264.4 cm3; (12) Polarizability: 36.54×10-24 cm3; (13)Surface Tension: 51.5 dyne/cm; (14)Enthalpy of Vaporization: 87.04 kJ/mol; (15)Vapour Pressure: 7.88E-13 mmHg at 25°C; (16)Rotatable Bond Count: 6; (17)Exact Mass: 348.098918; (18)MonoIsotopic Mass: 348.098918; (19)Topological Polar Surface Area: 94; (20)Heavy Atom Count: 24; (21)Complexity: 424.

Preparation of C.I. Disperse red 13: First, diazotizing the 2-chloro-4-nitroaniline to get compound 1. And then, coupling the compound 1 and N-ethyl-N-hydroxyethyl aniline. After filtering, grinding and drying, we can get the product.

Uses of C.I. Disperse red 13: It is used for dyeing and printing of polyester and blended fabrics. It is also suitable for high temperature high pressure dyeing and carrier dyeing.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc2cc(ccc2N=Nc1ccc(cc1)N(CC)CCO)[N+]([O-])=O
2. InChI:InChI=1/C16H17ClN4O3/c1-2-20(9-10-22)13-5-3-12(4-6-13)18-19-16-8-7-14(21(23)24)11-15(16)17/h3-8,11,22H,2,9-10H2,1H3
3. InChIKey:FEJPWLNPOFOBSP-UHFFFAOYAQ

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