Alizarin
Alizarin
CAS: 72-48-0
Molecular Formula: C14H8O4
Alizarin - Names and Identifiers
| Name | Alizarin |
| Synonyms | Alizarin Alizarine alizarinb alizarine C.I. 58000 Alizarine B C.I. 58000C Alizarine 3B Mordant Red 11 Alizarine L Paste C.I. Pigment Red 83 C.I. Mordant Red 11 Alizarine Indicator C.I. Pigment Red 83C C.I. Mordant Red 11C Alizarine Lake Red 2P Alizarine Lake Red 3P 1,2-Dihydroxyanthraquinone 1,2-Dihydroxy-9,10-Anthracenedione 1,2-dihydroxyanthracene-9,10-dione |
| CAS | 72-48-0 |
| EINECS | 200-782-5 |
| InChI | InChI=1/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H |
| InChIKey | RGCKGOZRHPZPFP-UHFFFAOYSA-N |
Alizarin - Physico-chemical Properties
| Molecular Formula | C14H8O4 |
| Molar Mass | 240.21 |
| Density | 1.06g/mLat 20°C |
| Melting Point | 287 °C |
| Boling Point | 430 °C |
| Flash Point | 430°C subl. |
| Water Solubility | Soluble in hexane and chloroform. Slightly soluble in water. |
| Solubility | Soluble in hot methanol and ether at 25°C. Soluble in benzene, glacial acetic acid, pyridine, carbon disulfide, slightly soluble in water. |
| Vapor Presure | 5.34E-08mmHg at 25°C |
| Appearance | Orange red crystal or brown yellow powder |
| Color | Orange to orange-brown |
| Maximum wavelength(λmax) | ['567nm, 609nm'] |
| Merck | 14,251 |
| BRN | 1914037 |
| pKa | 6.77(at 25℃) |
| PH | 5.5～7.2 |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| Refractive Index | 1.5190 (estimate) |
| MDL | MFCD00001201 |
| Physical and Chemical Properties | density 430 melting point 287-289°C boiling point 430°C |
| Use | Medium for the synthesis of acid dyes such as red S-80 |
Alizarin - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/38 - Irritating to eyes and skin. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | YO8300000 |
| TSCA | Yes |
| HS Code | 29146990 |
Alizarin - Reference
| Reference Show more | 1. [IF=9.811] Manjie Gao et al."High-Crystallinity Covalent Organic Framework Synthesized in Deep Eutectic Solvent: Potentially Effective Adsorbents Alternative to Macroporous Resin for Flavonoids."Chem Mater. 2021;33(20):8036–8051 |
Alizarin - Reference Information
| Color index | 58000 |
| pH range of acid-base indicator color change | Yellow (5.5) to red (6.8);Red (10.1) to purple (12.1) |
| Main application | Plasma displays, Antireflective coatings, chemical-mechanical testing, photoreceptors, glass coatings, thermoplastics, wood coloring, textiles, pH sensor device, detent, hair dyes, darkening skin, cosmetics, parasitide, antifungal agent |
| Biological applications | Detecting microorganizations; treating dermatological conditions |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Source | in 1868, German chemists, Carl graeb, and Karl Liebermann alizarin was synthesized from anthracene extracted from coal tar. It is industrially prepared by heating anthraquinone-β-sulfonic acid, caustic soda and potassium chlorate or potassium nitrate together. It can also be obtained from the roots of the plant cordifolia. |
| Overview | alizarin, also known as "1, 2-dihydroxyanthraquinone", yields orange or red prismatic needle-like crystals from ethanol. Soluble in ethanol, ether, acetone, benzene, water-soluble, insoluble in chloroform, but also soluble in NaOH and carbonate. Its alkaline aqueous solution is blue and brown in concentrated hydrochloric acid. It reacts with nitric acid to generate phthalic acid, reacts with sulfuric acid and manganese dioxide to generate 1,2, 4-trihydroxyanthraquinone, which can be reduced by zinc powder to anthracene, and reacts with Zn/NH3 to generate 3, 4-dihydroxyanthranone. It is present in the root of the root of the root of the root of the root of the root of the root of the root. for cotton dyeing and printing, bright red is obtained with aluminum mordant, red light brown is obtained with chromium mordant, purple is obtained with iron mordant, yellow-red color was obtained when using tin mordant. It is also used for dyeing wool and silk and for making alizarin lakes. They have recently been substituted for ice dyes. In addition, it can be used as acid-base indicator [pH5.5 (yellow) ~ 6.1 (red)], and as a drop test indicator of aluminum, indium, Mercury, etc. |
| solubility | easy sublimation, almost insoluble in water, 100g of water can be dissolved in 0.034 * C. Soluble in ethanol and ether, acetone, benzene, CS2, hot methanol. Insoluble in chloroform. And pyridine can be dissolved indefinitely. |
| preparation | with anthraquinone -2-sulfonic acid as raw material, it was heated to 50% ~ 180 ℃ with 200 sodium hydroxide solution and sodium nitrate, and reacted at a pressure of 1.0MPa for 20H. The reactants were diluted with water, adjusted to pH = 1.2~2 with sulfuric acid, and filtered, the filter residue was washed with water until neutral and dried to obtain crude alizarin. Refined alizarin can be obtained by sublimation or recrystallization in ethanol. |
| Use | dye intermediate, acid-base indicator for the synthesis of acid dye media red S-80 and so on acid-base indicator (0.5% solution),pH color change range 5.5 (yellow)-6.8 (red). As a drop reagent for aluminum, indium, mercury, zinc and zirconium. Neural tissue and protozoan living stain. |
| production method | in nature alizarin is present in the root of cordifolia. Melt anthraquinone -2-sulfonic acid with caustic soda and potassium chlorate or potassium nitrate, then pour the melt into hot water, and then precipitate alizarin with hydrochloric acid, 30g of sodium anthraquinone -2-sulfonate and 110g of sodium hydroxide were co-dissolved in 170 of water and reacted with 25g at ° C. In an autoclave. After cooling, the reaction was extracted several times with 150ml of water each time. The aqueous extract was filtered and the filtrate was acidified with hydrochloric acid. After cooling, the precipitated precipitate was suction-filtered, washed and dried to obtain about 20g of alizarin. |
Last Update：2024-04-09 21:01:54
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