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3180-81-2

Basic Information
CAS No.: 3180-81-2
Name: DISPERSE RED 13
Molecular Structure:
Molecular Structure of 3180-81-2 (DISPERSE RED 13)
Formula: C16H17ClN4O3
Molecular Weight: 348.789
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;
EINECS: 221-668-1
Density: 1.31 g/cm3
Melting Point: 122-129 °C
Boiling Point: 547.7 °C at 760 mmHg
Flash Point: 285 °C
Solubility: 11.51ug/L(25 oC)
Appearance: dark red powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 94.01000
LogP: 5.00540
Synthetic route
814-68-6

acryloyl chloride

3180-81-2

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

disperse red 13 acrylate

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

succinic acid anhydride

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

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

1,4-diisocyanatobenzene

3180-81-2

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

C40H38Cl2N10O8

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

terephthaloyl chloride

3180-81-2

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

C40H36Cl2N8O8

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

p-Tolylisocyanate

3180-81-2

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

C24H24ClN5O4

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;81%
111-24-0

1,5-dibromo-pentane

3180-81-2

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

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%
119613-87-5

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

3180-81-2

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

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%
930805-63-3

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

3180-81-2

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

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

3180-81-2

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

C33H27ClN4O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;61%
3180-81-2

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

106-89-8

epichlorohydrin

C19H21ClN4O4

Conditions
ConditionsYield
With water; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In tetrahydrofuran at 20℃; for 16h;60%
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    DISPERSE RED 13

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  • 3180-81-2  CAS NO.3180-81-2

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    3180-81-2 CAS NO.3180-81-2

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  • 4,4'-BIS(BROMOMETHYL)-DIPHENYL ETHER

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Consensus Reports

Reported in EPA TSCA Inventory.

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