2475-33-4

Basic information

• Product Name: Vat Brown 1
• Synonyms: VAT BROWN 1;16,23-dihydronaphth[2',3':6,7]indolo[2,3-c]dinaphtho[2,3-a:2'3'-i]carbazole-5,10,15,17,22,24-hexone;Vat Brown BR Powder;Naphth2,3:6,7indolo2,3-cdinaphtho2,3-a:2,3-icarbazole-5,10,15,17,22,24-hexone, 16,23-dihydro-;C.I.VATBROWN1;Vat brown 1 (C.I. 70800);Brown BR;Anthramar Brown BR
• CAS NO: 2475-33-4
• Molecular Formula: C₄₂H₁₈N₂O₆
• Molecular Weight: 646.60212
• EINECS: 219-599-7
• Product Categories: Organics
• Mol File: 2475-33-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 675.58°C (rough estimate)
• Appearance: Fine, dark brown to black crystalline powder with a slight odor
• Density: 1.2856 (rough estimate)
• Refractive Index: 1.4670 (estimate)
• PKA: 11.33±0.20(Predicted)
• CAS DataBase Reference: Vat Brown 1(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Brown 1(2475-33-4)
• EPA Substance Registry System: Vat Brown 1(2475-33-4)

Safety Data

• Hazardous Substances Data: 2475-33-4(Hazardous Substances Data)

Usage

Preparation

1,4-Diaminoanthraquinone and 1-Bromoanthracene-9,10-dione or 1-Bromoanthracene-9,10-dione (2 Moore) condensation, its product in Pyridine with Aluminium chloride heating.

General Description

Fine, dark brown to black crystalline powder with a slight odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Oxidizing agents and reducing agents may destroy Vat Brown 1's color. .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Vat Brown 1 may emit toxic fumes of carbon oxides and nitrogen oxides.

Fire Hazard

Flash point data for Vat Brown 1 are not available; however, Vat Brown 1 is probably combustible. Dust clouds may form explosive mixtures with air.

Properties and Applications

red light brown. Dark brown powder. Slightly soluble in hot 1, 2, 3, 4 – Tetrahydronaphthalene and thermal Xylene, insoluble in cold Xylene. In concentrated sulfuric acid to Copenhagen green, dilution after brown precipitation. Alkaline reduction leuco for yellow brown; Acid reduction leuco for dark olive. Mainly used for cotton, hemp, silk and viscose dyeing and printing, cotton yarn dyeing common varieties. Used for polyester/cotton blended fabric two bath dyeing of polyester with little color. The leuco used for dyeing cotton knitwear. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 5 4-5 7 4-5 4-5 5 5 AATCC 5 5 8 4-5 4-5

Standard

Ironing Fastness

Fading

Stain

ISO

5

AATCC

5

InChI:InChI=1/C42H18N2O6/c45-20-11-9-17-15-26-18(13-19(17)14-20)10-12-25-29-32-31-28(46)16-27-30(40(48)22-6-2-1-5-21(22)39(27)47)37(31)44-38(32)34-33(36(29)43-35(25)26)41(49)23-7-3-4-8-24(23)42(34)50/h1-15,44H,16H2

Synthetic route

1,4-bis-(1-anthraquinonylamino)anthraquinone (116-76-7) → 16,23-dihydro-naphtho[2',3':6,7]indolo[2,3-c]dinaphtho[2,3-a;2',3'-i]carbazole-5,10,15,17,22,24-hexaone (2475-33-4)

Conditions	Yield
With pyridine; aluminium trichloride at 125 - 130℃; Reinigung durch Behandeln des Reaktionsprodukts mit alkal. Natriumhypochlorit-Loesung;
With titanium tetrachloride
With aluminium trichloride

6-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-16H-dinaphtho[2,3-a;2',3'-i]carbazole-5,10,15,17-tetraone → 16,23-dihydro-naphtho[2',3':6,7]indolo[2,3-c]dinaphtho[2,3-a;2',3'-i]carbazole-5,10,15,17,22,24-hexaone (2475-33-4)

Conditions	Yield
With titanium tetrachloride
With aluminium trichloride
With aluminium trichloride
With titanium tetrachloride

C42H22N2O6 → 16,23-dihydro-naphtho[2',3':6,7]indolo[2,3-c]dinaphtho[2,3-a;2',3'-i]carbazole-5,10,15,17,22,24-hexaone (2475-33-4)

Conditions	Yield
With pyridine; aluminum (III) chloride Heating; Large scale;

Upstream product

• 116-76-7 1,4-bis-(1-anthraquinonylamino)anthraquinone 

Relevant articles and documents

Method for synthesizing vat brown BR

The invention relates to the technical field of dyes, specifically to a method for synthesizing vat brown BR. The method comprises the following steps: condensing 1,4-dihydroxy anthraquinone and 1-amino anthraquinone under the catalysis of a phase transfer catalyst and copper powder so as to obtain a vat brown BR imine intermediate, wherein boric acid is added as a hydroxyl protective agent in thereaction; and allowing the vat brown BR imine intermediate to react with aluminum trichloride for ring closure so as to obtain the vat brown BR. The method for synthesizing the vat brown BR providedby the invention has the following advantages: the reaction is more thorough; the conversion rate of the method is improved from 78-80% in the prior art to 95% or above; the quality of an obtained product is higher; only materials and water are contained in the product; a large amount of sodium carbonate and sodium acetate which are added as acid-binding agents in a conventional production processare removed, so emission of pollutants is reduced; the use of a raw material, namely 1-chloroanthraquinone which can be produced only by producing a large amount of waste acid and heavy metal mercuryis avoided, so the discharge of a large amount of pollutants is indirectly reduced; and the obtained intermediate imine product has higher quality, so the step of oxidation in the production processof a finished product is reduced, and the production operation process is simplified.