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3180-81-2

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    1. Product Name: DISPERSE RED 13
    2. Synonyms: CI 11115;CELLITON RUBINE B;DISPERSE RED 13;ACETAMINE RUBINE B;2-[4-(2-CHLORO-4-NITROPHENYLAZO)-N-ETHYLPHENYLAMINO]ETHANOL;SETACYL RED 2B;2-((4-((2-chloro-4-nitrophenyl)azo)phenyl)ethylamino-ethano;2-[[4-[(2-chloro-4-nitrophenyl)azo]phenyl]ethylamino]-ethano
    3. CAS NO:3180-81-2
    4. Molecular Formula: C16H17ClN4O3
    5. Molecular Weight: 348.78
    6. EINECS: 221-668-1
    7. Product Categories: Dyes and Pigments;Organics
    8. Mol File: 3180-81-2.mol
    9. Article Data: 0

  • Chemical Properties

    1. Melting Point: 122-129 °C(lit.)
    2. Boiling Point: 547.7 °C at 760 mmHg
    3. Flash Point: 285 °C
    4. Appearance: dark red powder
    5. Density: 1.4131 (rough estimate)
    6. Vapor Pressure: 7.88E-13mmHg at 25°C
    7. Refractive Index: 1.6470 (estimate)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.53±0.10(Predicted)
    11. Water Solubility: 11.51ug/L(25 oC)
    12. CAS DataBase Reference: DISPERSE RED 13(CAS DataBase Reference)
    13. NIST Chemistry Reference: DISPERSE RED 13(3180-81-2)
    14. EPA Substance Registry System: DISPERSE RED 13(3180-81-2)

  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS: KK1990000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 3180-81-2(Hazardous Substances Data)

3180-81-2 Usage

Description

Disperse Red 13 (DR13) is an azo dye that can be used as a non-linear optical (NLO) material. It is an azobenzene functionalized molecule with reversible cis-trans photoisomerization, which can be used for optical memory and switching devices.

Uses

Used in Environmental Testing:
Disperse Red 13 is used as an organic dye for environmental testing, particularly for the detection and monitoring of dyes and their metabolites in various environmental samples.
Used in Non-linear Optical Materials:
Disperse Red 13 is used as a non-linear optical (NLO) material for the development of optical memory and switching devices, due to its reversible cis-trans photoisomerization properties.
Used in Textile Industry:
Disperse Red 13 is used as a dye for polyester, acetate fiber, triacetate fiber, and acrylic and blended fabrics in dyeing and printing processes. It is also used for wool and plastic coloring.
Standard:
Disperse Red 13 has the following standards for various fastness properties:
Ironing Fastness: ISO 4-5
Light Fastness: ISO 3-4
Perspiration Fastness: ISO 4-5
Washing Fastness: ISO 4-5
Fading and Staining Resistance:
Fading: ISO 4-5
Stain: ISO 4-5
Properties and Applications:
Disperse Red 13 is a dark red powder that is soluble in ethanol, acetone, benzene, and pottery, especially solvent. It exhibits different color shades in various acidic solutions, such as orange to brown in strong sulfuric acid, orange in nitric acid, and blu-ray red in strong hydrochloric acid. The color and lustre remain unchanged in sodium hydroxide solution.

Preparation

2-chloro-4-nitrobenzenamine diazo. And N-ethyl-N-hydroxyethylaniline?coupling

Standard

Ironing Fastness

Fading

Stain

ISO

4-5

Check Digit Verification of cas no

The CAS Registry Mumber 3180-81-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,8 and 0 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3180-81:
(6*3)+(5*1)+(4*8)+(3*0)+(2*8)+(1*1)=72
72 % 10 = 2
So 3180-81-2 is a valid CAS Registry Number.
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/b19-18+

3180-81-2 Well-known Company Product Price

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  • (Code)Product description
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  • Aldrich

  • (364827)  DisperseRed13  Dye content 95 %

  • 3180-81-2

  • 364827-5G

  • 796.77CNY

  • Detail

  • Aldrich

  • (364827)  DisperseRed13  Dye content 95 %

  • 3180-81-2

  • 364827-25G

  • 2,990.52CNY

  • Detail

3180-81-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[4-[(2-chloro-4-nitrophenyl)diazenyl]-N-ethylanilino]ethanol

1.2 Other means of identification

Product number -
Other names Cibacet Rubine R

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3180-81-2 SDS

3180-81-2Synthetic 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

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