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Home > Encyclopedia > 4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol

4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol

4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol structure

4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol 

structure
  • CAS No:

    19800-42-1

  • Formula:

    C19H15N5O4

  • Chemical Name:

    4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol

  • Synonyms:

    Phenol,4-[2-[2-methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]-;Phenol,p-[[2-methoxy-4-[(p-nitrophenyl)azo]phenyl]azo]-;Phenol,4-[[2-methoxy-4-[(4-nitrophenyl)azo]phenyl]azo]-;4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol;C.I. Disperse Orange 29;Disperse Orange 29;Resolin Yellow Brown 3GL;Palanil Orange GL;Samaron Yellow Brown HRSL;Synten Orange P-GRL;Sumikaron Orange SE-RBL;Intrasil Orange L 2R;Intrasil Orange L 2R200;Hisperse Orange C-GS;4-[[2-Methoxy-4-[(4-nitrophenyl)azo]phenyl]azo]phenol;Foron Yellow Brown SE-RL;Dianix Yellow Brown SE-R;125936-66-5;61902-11-2

  • Categories:

    Dyes and Pigments  >  Dye

Description

DryPowder


DryPowder

4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol Basic Attributes

377.35

377.35

243-325-5

DTXSID5066532

2927000090

Characteristics

121

6.66300

1.34

616.2±55.0 °C(Predicted)

315ºC

1.652

Safety Information

P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501

H302

|Warning|H302 (43.75%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 39 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

4-[2-[2-Methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol Use and Manufacturing

Methods of Manufacturing

Taking p-nitroaniline, o-methoxyaniline, and phenol as raw materials, firstly, p-nitroaniline is diazotized and coupled with o-methoxyaniline, and then the coupling product is diazotized and coupled with phenol to obtain the product. After filtering and drying, the finished product is obtained. . In the first coupling reaction in this synthesis method, the pH value is controlled below 0.89, and the yield is only about 50%, so it is difficult to realize industrial production. A new coupling process has been developed internally, that is, o-aniline and sodium hydroxymethanesulfonate are first formed into a salt, and then coupled with p-nitroazobenzene, the yield can reach 88%. The reaction process is as follows: Finally, it is further diazotized and coupled to obtain the product. Add 80mL water, 3g formaldehyde (pure), 13.5g sodium bisulfite into the reactor, stir at 25-30℃ for 1h, then add 12.5g o-methoxyaniline, heat up to 70-75℃, react for 2h, To room temperature, add 200 mL of water to obtain o-aniline omega salt solution for later use. Add 90 mL of water, 27.4 mL of hydrochloric acid, and 14.2 g of p-nitroaniline to the reactor, stir and make slurry for 3 hours, and add 150 mL of water. Cool down to -1°C, add 7.18g sodium nitrite in one go, keep it at 0-5°C for 1h, destroy excess sodium nitrite, filter to obtain diazonium liquid. Add the above-mentioned o-anisidine omega salt solution to the coupling, cool to 5-10℃, add 2g of diffusing agent MF, slowly drip diazonium liquid within 60-90min, continue the reaction for 1h to the end after adding Adjust the pH value of sodium hydroxide solution to 13, heat up to 80-85°C, keep for 3 hours, cool, filter, and dry to obtain about 24g of monoazo compound. Add 190mL of water, 54mL of hydrochloric acid, and 27.5g of monoazo compound to the reactor, beating for 3h, cooling to 10-15℃, adding 7.18g of sodium nitrite (100%), adding within 1-1.5h, continue the reaction 2h, after destroying excess sodium nitrite, filter to obtain diazonium solution for use. Add 600mL water, 2g diffusing agent, 20g sodium acetate, 9.4g phenol into the coupling, cool to 5℃, slowly add the above diazonium liquid dropwise within 60-90min, and add sodium hydroxide solution dropwise to maintain the reaction liquid pH=5.6, temperature 5-10℃. After adding the diazonium solution, continue stirring for 1 hour. Then the temperature is increased to 85-90°C for 3 hours, filtered and dried to obtain about 30g of dye.

Uses

Disperse Orange SE-5RL is mainly used for dyeing and printing of polyester and its blended fabrics, and can also be used for printing and dyeing of cellulose acetate.


Dyes


Fabric, textile, and leather products not covered elsewhere

Production

100,000 - 500,000 lb

Textiles, apparel, and leather manufacturing|Phenol, 4-[2-[2-methoxy-4-[2-(4-nitrophenyl)diazenyl]phenyl]diazenyl]-: ACTIVE

Computed Properties

Molecular Weight:377.4
XLogP3:4.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:377.11240398
Monoisotopic Mass:377.11240398
Topological Polar Surface Area:125
Heavy Atom Count:28
Complexity:551
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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