14233-37-5

Basic information

• Product Name: Solvent Blue 36
• Synonyms: SOLVENT BLUE 36;WAXOLINE BLUE;UNISOL BLUE AS;DUPONT OIL BLUE A;DISPERSE BLUE 134;c.i. disperse blue 134;CI 61551;1,4-BIS(ISOPROPYLAMINO)ANTHRAQUINONE
• CAS NO: 14233-37-5
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.4
• EINECS: 238-101-9
• Product Categories: Solvent Dyestuff;Solvent Dye
• Mol File: 14233-37-5.mol

Chemical Properties

• Melting Point: 176-178 °C
• Boiling Point: 540.6 °C at 760 mmHg
• Flash Point: 189.3 °C
• Appearance: Dark blue powder
• Density: 1.217 g/cm³
• Vapor Pressure: 9.4E-12mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: 2-8°C
• PKA: 6.13±0.20(Predicted)
• CAS DataBase Reference: Solvent Blue 36(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Blue 36(14233-37-5)
• EPA Substance Registry System: Solvent Blue 36(14233-37-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14233-37-5(Hazardous Substances Data)

Usage

Preparation

1,4-Dihydroxyanthracene-9,10-dione and ?Propan-2-amine?(2 Moore) condensation.

Properties and Applications

blue. And C.I. Solvent Blue 36 the same chemical structure. Standard(polypropylene fiber) Ironing Fastness Light Fastness Persperation Fastness Washing Fastness Fading Stain Fading Stain Fading Stain ISO 4 4 5

Standard(polypropylene fiber)

Ironing Fastness

Fading

Stain

InChI:InChI=1/C20H22N2O2/c1-11(2)21-15-9-10-16(22-12(3)4)18-17(15)19(23)13-7-5-6-8-14(13)20(18)24/h5-12,21-22H,1-4H3

Synthetic route

1,4-diamino-9,10-anthraquinone (128-95-0) + isopropyl bromide (75-26-3) → 1,4-Bis[(1-methylethyl)amino]-9,10-anthracenedione (14233-37-5)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In 1,2-dichloro-ethane at 50℃; for 10h;	30%

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + isopropylamine (75-31-0) → 1,4-Bis[(1-methylethyl)amino]-9,10-anthracenedione (14233-37-5) + 1-isopropylamino-4-hydroxy-anthraquinone

Conditions	Yield
In acetonitrile Heating;	A 25% B 15%

isopropylamine (75-31-0) + 1-isopropylamino-4-hydroxy-anthraquinone → 1,4-Bis[(1-methylethyl)amino]-9,10-anthracenedione (14233-37-5)

Conditions	Yield
In acetonitrile Heating;

1,4-dihydroxy-9,10-anthracenedione (81-64-1) → 1,4-Bis[(1-methylethyl)amino]-9,10-anthracenedione (14233-37-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 15 percent / acetonitrile / Heating 2: acetonitrile / Heating View Scheme

Upstream product

• 128-95-0 1,4-diamino-9,10-anthraquinone 
• 75-26-3 isopropyl bromide 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 75-31-0 isopropylamine 

Relevant articles and documents

Concerning the Question of Covalent Bonding in Hypericin-Chromoproteins: Schiff Base Formation?

Depending on the reaction conditions, peri-hydroxy substituted anthraquinones like 1,8-dihydroxyanthraquinone and 1,4-dihydroxyanthraquinone could be derivatized with ammonia, propylamine, isopropylamine, and a lysine derivative to yield a variety of imino and amino substitution and addition products.However, hypericin resisted such derivatization under a variety of reaction conditions.Therefore, the hypothesis that hypericin is bound to its apoprotein in photopigments via a Schiff base to the ε-amino group of a lysine residue or a terminal amino group seems to be rather unlikely. - Keywords.Hypericin; Stentor; Schiff base; Anthraquinone imines; Aminoanthraquinones.

Phase transfer catalysed N-monoalkylation of amino anthraquinones

1-Alkylaminoanthraquinones (2a-f) and 1,4-bisalkylaminoanthraquinones (4a-c) were prepared from aminoanthraquinones (1,3) by alkylation with alkyl sulphate/alkyl halide in presence of powdered sodium hydroxide, potassium carbonate and phase transfer catalyst.