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

Description

Disperse Orange 76 is an orange azo dye that is commonly used in the dyeing and printing of polyester and blended fabrics. It is characterized by its dark red light orange color and dark orange shade, and is available in the form of an orange powder that is insoluble in water. The dye exhibits good lifting force in polyester and is suitable for dyeing polyester/cotton and polyester/stick blends in a one-bath process.

Uses

Used in Textile Industry:
Disperse Orange 76 is used as a dye for polyester and blended fabrics, providing a dark red light orange color and dark orange shade. It is particularly useful for dyeing polyester/cotton and polyester/stick blends in a one-bath process.
Used in Environmental Testing:
Disperse Orange 76 is also used in environmental testing, specifically for the detection and analysis of dyes and their metabolites in various samples.
Standard:
Disperse Orange 76 meets certain standards for ironing fastness, light fastness, perspiration fastness, and washing fastness, as indicated by the following ratings:
Ironing Fastness: 3-4 (AATCC)
Light Fastness: 6-7 (AATCC)
Perspiration Fastness: 5 (AATCC)
Washing Fastness: 5 (AATCC)
These ratings indicate that Disperse Orange 76 has good resistance to fading and staining under various conditions, making it a reliable choice for dyeing applications.

Preparation

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

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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