82-18-8

Basic information

• Product Name: 1,5-DIBENZAMIDOANTHRAQUINONE
• Synonyms: n,n’-(9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis-benzamid;N,N’-(9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis-Benzamide;1,5-DIBENZAMIDOANTHRAQUINONE;N,N'-(9,10-dihydro-9,10-dioxoanthracene-1,5-diyl)bisbenzamide;N,N'-1,5-anthraquinonylenebisbenzamide;N,N′-(9,10-Dihydro-9,10-dioxoanthracen-1,5-diyl)bisbenzamid;Vat yellow 3 (C.I. 61725);1,5-Bis(benzoylamino)-9,10-anthraquinone
• CAS NO: 82-18-8
• Molecular Formula: C₂₈H₁₈N₂O₄
• Molecular Weight: 446.45
• EINECS: 201-401-5
• Mol File: 82-18-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 390 °C
• Boiling Point: 556.3 °C at 760 mmHg
• Flash Point: 159.5 °C
• Appearance: /
• Density: 1.409 g/cm³
• PKA: 12.04±0.20(Predicted)
• CAS DataBase Reference: 1,5-DIBENZAMIDOANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIBENZAMIDOANTHRAQUINONE(82-18-8)
• EPA Substance Registry System: 1,5-DIBENZAMIDOANTHRAQUINONE(82-18-8)

Safety Data

• Hazardous Substances Data: 82-18-8(Hazardous Substances Data)

Usage

Preparation

1,5-Diaminoanthraquinone and Benzoyl chloride (2 Moore) condensation.

Properties and Applications

yellow. Yellow powder. Soluble in four hydrogenated naphthalene and xylene. The strong sulfuric acid for dark olive brown, after diluted orange precipitation; In alkaline insurance powder is in stock for purplish red color; In the acidic insurance powder in the red ones, also for yellow. Can be used for the cotton fabric dyeing. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 5 5 6 4-5 5 5 5 AATCC 5 5 5 4 4

Standard

Ironing Fastness

Fading

Stain

ISO

5

AATCC

5

Synthetic route

1,5-diaminoanthraquinone (129-44-2) + benzamide (55-21-0) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
With hydrogenchloride; nitrobenzene

benzamide (55-21-0) + 1,5-Dichloroanthraquinone (82-46-2) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
With potassium carbonate; 1,2-dichloro-benzene; copper(I) bromide

1,5-diaminoanthraquinone (129-44-2) + benzoyl chloride (98-88-4) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
With 2,3-Dimethylaniline
With 1,2-dichloro-benzene at 140℃;
With nitrobenzene at 140℃;

1,5-diaminoanthraquinone (129-44-2) + benzoic acid anhydride (93-97-0) → 1,5-dibenzoylaminoanthraquinone (82-18-8) + 1-amino-5-benzamidoanthraquinone (117-06-6)

Conditions	Yield
With nitrobenzene at 175℃;

1.5-dinitroanthraquinone (82-35-9) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium sulfide 2: dimethylaniline View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4-hydroxy-anthraquinone (6370-96-3)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid
With sulfuric acid

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4,8-dichloro-anthraquinone (115605-23-7)

Conditions	Yield
With chlorine

sulfuric acid (7664-93-9) + 1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4-hydroxy-anthraquinone (6370-96-3)

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-diamino-4,8-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone (119393-92-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorine 3: H2SO4 View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4,8-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone (119504-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) → 6,12-dichloro-2,8-diphenyl-anthra[1,9-de;5,10-d'e']bis[1,3]oxazine (121474-48-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine 2: H2SO4 View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) + benzoyl chloride (98-88-4) → 1-Chloro-5-benzoylaminoanthraquinone (117-05-5)

Conditions	Yield
In nitrobenzene

Upstream product

• 129-44-2 1,5-diaminoanthraquinone 
• 98-88-4 benzoyl chloride 
• 82-35-9 1.5-dinitroanthraquinone 
• 93-97-0 benzoic acid anhydride 
• 55-21-0 benzamide 
• 82-46-2 1,5-Dichloroanthraquinone 

Downstream Products

• 117-05-5 1-Chloro-5-benzoylaminoanthraquinone 
• 121474-48-4 6,12-dichloro-2,8-diphenyl-anthra[1,9-de;5,10-d'e']bis[1,3]oxazine 
• 119504-37-9 1,5-bis-benzoylamino-4,8-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone 
• 6370-96-3 1,5-bis-benzoylamino-4-hydroxy-anthraquinone 
• 115605-23-7 1,5-bis-benzoylamino-4,8-dichloro-anthraquinone 

Relevant articles and documents

Process for the preparation of 1-acylamino-5(8)-chloroanthraquinones

The invention relates to a novel process for the preparation of 1-acylamino-5(8)-chloroanthraquinones, which are starting materials for the preparation of vat dyes. It is characterized in that 1,5(8)-dichloroanthraquinones is reacted with ammonia at temperatures of 190° to 240° C., the amino groups in the reaction mixture are completely acylated and the more sparingly soluble diacylaminoanthraquinone is separated off from the more readily soluble monoacylaminochloroanthraquinone. The new process yields reaction products which are purer and cheaper than those which are obtained by conventional methods. Moreover there are smaller waste water problems.