1,4-Dihydroxyanthraquinone

Base Information

• Chemical Name: 1,4-Dihydroxyanthraquinone
• CAS No.: 81-64-1
• Deprecated CAS: 103220-12-8
• Molecular Formula: C14H8O4
• Molecular Weight: 240.215
• Hs Code.: 2914.69
• European Community (EC) Number: 201-368-7
• NSC Number: 646569,229036,40899,15367
• UNII: 8S496ZV3CS
• DSSTox Substance ID: DTXSID8044464
• Nikkaji Number: J710.748J,J3.861J
• Wikipedia: 1,4-Dihydroxyanthraquinone
• Wikidata: Q906609
• Metabolomics Workbench ID: 55594
• ChEMBL ID: CHEMBL17594
• Mol file: 81-64-1.mol

Synonyms:1,4-dihydroxy-9,10-anthraquinone;1,4-dihydroxyanthraquinone;1,4-dihydroxyanthraquinone, radiacal ion (1-);anthrarufin;quinizarin

Chemical Property of 1,4-Dihydroxyanthraquinone

Chemical Property:

• Appearance/Colour: orange to red-brown crystalline powder
• Vapor Pressure: 1 mm Hg ( 196.7 °C)
• Melting Point: 198-199 °C(lit.)
• Refractive Index: 1.732
• Boiling Point: 465.3 °C at 760 mmHg
• PKA: pK (18°) 9.51
• Flash Point: 249.3 °C
• PSA: 74.60000
• Density: 1.54 g/cm³
• LogP: 1.87320
• Storage Temp.: Store below +30°C.
• Solubility.: <1g/l
• Water Solubility.: <1 g/L (20℃)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 240.04225873
• Heavy Atom Count: 18
• Complexity: 342

Purity/Quality:

≥ 99.00% ^*data from raw suppliers

1,4-Dihydroxyanthraquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 36/37/38-43-50/53
• Safety Statements: 22-24/25-36/37-26-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Anthraquinone Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)O)O
• Uses: Antioxidant in synthetic lubricants, dyes. 1,4-Dihydroxyanthraquinone, also known as quinizarin, is of great importance in manufacturing disperse, acid, and vat dyes. 1,4-Dihydroxyanthraquinone is used to color gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. It is also used to form lake pigments with calcium, barium and lead. It may be used in the synthesis of cyclopentanoids by cyclization of α,β-unsaturated aldehyde with 1, 4 1,4-Dihydroxyanthraquinone. It has been studied as a long range emissive ratiometric fluorescent probe for live cell imaging.

Technology Process of 1,4-Dihydroxyanthraquinone

There total 137 articles about 1,4-Dihydroxyanthraquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

phthalic anhydride (85-44-9) + hydroquinone (123-31-9,8027-02-9) → 1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8)

Guidance literature:

With boron trioxide; sulfuric acid; at 125 - 160 ℃; for 16h; Temperature;

Reference yield: 96.0%

1,4-diacetoxy-9,10-anthraquinone (2289-36-3) → 1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8)

Guidance literature:

With water; trifluoroacetic acid; at 72 ℃; for 0.0833333h;

Reference yield: 94.0%

phthalic anhydride (85-44-9) + 4-chloro-phenol (106-48-9,82344-39-6) → 1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8)

Guidance literature:

With sulfuric acid; boric acid; at 190 - 225 ℃; for 5h;

upstream raw materials:

maleic anhydride

1,4-Dihydroxynaphthalene

phthalic anhydride

4-chloro-phenol

Downstream raw materials:

1,4-bis-(3-hydroxymethyl-anilino)-anthraquinone

1-hydroxy-4-(3-hydroxymethyl-anilino)-anthraquinone

1-hydroxy-4-(2,4,5-trimethyl-anilino)-anthraquinone

1-hydroxy-4-[4-(2-hydroxy-ethoxy)-anilino]-anthraquinone

Refernces

• 1、 -. "Synthesis method of orange intermediate". Paragraph 0029-0039. . Retrieved 2020/10/21.
• 2、 Osman, Che Puteh,Ismail, Nor Hadiani,Widyawaruyanti, Aty,Imran, Syahrul,Tumewu, Lidya,Choo, Chee Yan,Ideris, Sharinah. "Evaluation of a series of 9,10-anthraquinones as antiplasmodial agents". . p. 353 - 363. Retrieved 2019/06/20.