13301-61-6

Basic information

• Product Name: Disperse Orange 76
• Synonyms: 3-[[4-[(2,6-dichloro-4-nitrophenyl)azo]phenyl]ethylamino]-propanenitril;3-[ethyl[4-[(2,6-dichloro-4-nitrophenyl)azo]phenyl]amino]-Propanonitrile;3-[p-[(2,6-Dichloro-4-nitrophenyl)azo]-N-ethylanilino]propionitrile;Propanenitrile,3-[[4-[(2,6-dichloro-4-nitrophenyl)azo]phenyl]ethylamino]-;3-[[4-[(2,6-dichloro-4-nitrophenyl)azo]phenyl]ethylamino]propiononitrile;C.I. Disperse Orange 76 press cake;3-[4-(2,6-Dichloro-4-nitrophenylazo)-N-ethylanilino]propionitrile;disperse orange 37/76
• CAS NO: 13301-61-6
• Molecular Formula: C₁₇H₁₅Cl₂N₅O₂
• Molecular Weight: 392.2393
• EINECS: 236-325-1
• Product Categories: Dyes and Pigments;Organics
• Mol File: 13301-61-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 144-146 °C
• Boiling Point: 603.1 °C at 760 mmHg
• Flash Point: 318.6 °C
• Appearance: /
• Density: 1.35
• PKA: 2.12±0.50(Predicted)
• BRN: 6348868
• CAS DataBase Reference: Disperse Orange 76(CAS DataBase Reference)
• NIST Chemistry Reference: Disperse Orange 76(13301-61-6)
• EPA Substance Registry System: Disperse Orange 76(13301-61-6)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 13301-61-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13301-61-6 differently. You can refer to the following data:
1. Disperse Orange 76 is an orange azo dye used in plastics.
2. Disperse Orange 37 is an orange azo dye used in plastics. Dyes and metabolites, Environmental Testing.

Preparation

2,6-Dichioro-4-nitroaniline diazo, and N-ethyl-N-cyanoethylaniline?coupling.

Properties and Applications

Dark red light orange, dark orange. Orange powder, insoluble in water. Used for polyester and blended fabric, vinegar fiber of dyeing and printing. In the dark tonal for polyester orange, in the vinegar on dark red light for fiber award in color. Have good in polyester lifting force. Suitable for polyester/cotton, polyester/stick a bath dyeing of blended. And C.I. Disperse orange 76 chemical structure is the same. Standard Ironing Fastness Light Fastness Persperation Fastness Washing Fastness Fading Stain Fading Stain Fading Stain AATCC 3-4 6-7 5 5 5

Standard

Ironing Fastness

Fading

Stain

InChI:InChI=1/C17H15Cl2N5O2/c1-2-23(9-3-8-20)13-6-4-12(5-7-13)21-22-17-15(18)10-14(24(25)26)11-16(17)19/h4-7,10-11H,2-3,9H2,1H3/b22-21+

Synthetic route

4-nitro-2,6-dichloroaniline (99-30-9) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2',6'-dichloro-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene (13301-61-6)

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;
Stage #1: 4-nitro-2,6-dichloroaniline With naphthalene-1,5-disulfonate In ethyl acetate at 50℃; for 0.166667h; Stage #2: With tert.-butylnitrite In ethyl acetate at 25℃; for 0.333333h; Stage #3: N-ethyl-N-(2-cyanoethyl)aniline With hydrogenchloride In water at 0 - 5℃; for 0.166667h;

Upstream product

• 99-30-9 4-nitro-2,6-dichloroaniline 
• 148-87-8 N-ethyl-N-(2-cyanoethyl)aniline 

Relevant articles and documents

Stable diazonium salts of weakly basic amines—Convenient reagents for synthesis of disperse azo dyes

A new synthetic strategy for industrially important deep-shade disperse azo dyes was presented in this study. The key procedure is to prepare stable solid diazonium salts of weakly basic amines in the absence of concentrated sulfuric acid. Diazotization by tert-butyl nitrite in ethyl acetate was allowed to proceed in the presence of equivalent 1,5-naphthalenedisulfonic acid as stabilizer of diazonium salts and donor of hydrogen ion for the reaction. The separated solid diazonium salts exhibited good thermal stability. The corresponding disperse azo dyes were subsequently synthesized through the azo-coupling of the prepared solid diazonium salts with a range of aromatic tertiary amines. The azo dyes were produced in short reaction time, excellent yields, mild reaction conditions, simple experimental procedure and low energy consumption.

Synthesis of some New Disperse Dyes

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