2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one
Indigo
CAS: 482-89-3
Molecular Formula: C16H10N2O2
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one - Names and Identifiers
| Name | Indigo |
| Synonyms | Indigo C.I. 73000 d+cblueno6 Vat Blue 1 Indigo blue D+C Blue No. 6 PIGMENT BLUE 66 C.I. Vat Blue 1 (2,2'-Biindoline)-3,3'-dione (2,2'-biindoline)-3,3'-dione 2,2'-biindole-3,3'(1H,1'H)-dione (delta(2,2')-biindoline)-3,3'-dione 2,2'-Bis(2,3-dihydro-3-oxoindolylidene) (delta(2,2'(3h,3'h))-biindole)-3,3'-dione 2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one |
| CAS | 482-89-3 |
| EINECS | 207-586-9 |
| InChI | InChI=1/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18H |
| InChIKey | COHYTHOBJLSHDF-BUHFOSPRSA-N |
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one - Physico-chemical Properties
| Molecular Formula | C16H10N2O2 |
| Molar Mass | 262.26 |
| Density | 1.01g/mLat 20°C |
| Melting Point | >300°C(lit.) |
| Boling Point | 405.51°C (rough estimate) |
| Flash Point | >220℃ |
| Water Solubility | <0.1 g/100 mL |
| Solubility | DMSO (Slightly, Heated, Sonicated), DMF (Slightly) |
| Vapor Presure | 0Pa at 100℃ |
| Appearance | Blue powder |
| Color | Dark blue to violet |
| Merck | 14,4943 |
| BRN | 88275 |
| pKa | -3.83±0.20(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5800 (estimate) |
| MDL | MFCD00005722 |
| Physical and Chemical Properties | Melting point 390-392°C (dec.) water-soluble <0.1g/100 mL hue or shade: Blue |
| Use | Mainly used for cotton, cotton, wool or silk dyeing The pigment is an important vat dye indigo pigment processing products, with excellent light resistance, the color fastness to climate and heat stability give a blue tone, and can be used to prepare a liquid dispersion dosage form, mainly used in viscose fiber pulp coloring and printing and dyeing. |
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one - Risk and Safety
| Risk Codes | R36/38 - Irritating to eyes and skin. R36/37/38 - Irritating to eyes, respiratory system and skin. R48/20/21/22 - |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| UN IDs | UN 3264 8/PG 3 |
| WGK Germany | 1 |
| RTECS | DU2988400 |
| HS Code | 32041510 |
| Toxicity | LD50 oral in mouse: > 32gm/kg |
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one - Upstream Downstream Industry
| Raw Materials | Aniline Chloroacetic acid Potassium hydroxide Sodium hydroxide Ammonia Chloroacetic acid Sodium |
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one - Reference
| Reference Show more | 1. Cheng Pei, Xia Ye, Fang Yu et al. Determination of indigo and indirubin in horse Blue from different habitats and different medicinal parts [J]. Medical leads 2015(10):1363. 2. Xiao Yinghua Xia Ye Cheng Pei et al. Simultaneous determination of indigo and indirubin in folium isatidis by RP-HPLC [J]. Medical leads 2015 34(11):1506-1508. 3. Chang Baoqin, Li Meimei, Hui Huaji, etc. Extraction and analysis of alkaloid indigo and indirubin from Radix isatidis [J]. Agricultural science and technology and information, 2019, 000(022):40-43. 4. Kongshujia, Yanwen Li. Determination of indigo in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetics [J]. China Pharmacy, 2017, 28(007):912-915. 5. Li Haiyi, Li Yanguang, Liang Qingyun, et al. Comparison of extraction and content of indigo and indirubin in leaves and roots of Isatis indigotica [J]. Guangdong Chemical Industry, 2016, 43(02):27-28. 6. Liang Zhenbao, Li Haiyi, Li Yanguang, etc. Studies on the effective components in the root, stem and leaf of Isatis indigotica [J]. Guangzhou Chemical Industry, 2016(11):156-157. 7. Li Xiao-Chen, Wei Wei, Zhang Jian-Yu, Li Li, cow bud. Study on correlation between starch content and active component content in radix isatidis [J]. Chemical Engineer, 2020,34(07):24-26 16. 8. Zhang Yiming, Wan Hui Hua, Su Yong, Lu Meng, Yang Wei, Zhi Junwen. Effects of frostbite bluish on the contents of four indolyl derivatives in broad-sense postrinus plants [J]. Journal of Northwest Botany, 2020,40(11):1951-1958. 9. [IF=4.411] Zhiqin Xu et al."Optimization of Extraction of Bioactive Compounds from Baphicacanthus cusia Leaves by Hydrophobic Deep Eutectic Solvents."Molecules. 2021 Jan;26(6):1729 10. [IF=4.162] Jiuling Deng et al."A Network Pharmacology-Based Investigation to the Pharmacodynamic Material Basis and Mechanisms of the Anti-Inflammatory and Anti-Viral Effect of Isatis indigotica."Drug Des Dev Ther. 2021; 15: 3193-3206 11. [IF=2.984] Yi-Ming Zhang et al."Integration of the metabolome and transcriptome reveals indigo biosynthesis in Phaius flavus flowers under freezing treatment."Peerj. 2022 Mar;10:e13106 |
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one - Reference Information
| color index | 73000 |
| LogP | 2.7 at 23℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | indigo is a vat dye with a history of more than 3,000 years. During the Warring States Period, Xun Kuang's famous sentence "Green is better than blue from blue" originated from the blue dyeing technology at that time. "Green" here refers to cyan, and "blue" refers to the bluegrass that makes indigo. Before the Qin and Han dynasties, the application of indigo was quite common. |
| traits | dark blue powder, insoluble in water. |
| uses | all kinds of fabrics are dyed with blue colorant, indigo color is rich and has very good fastness. they have been loved by people for thousands of years. edible synthetic pigments are suitable for use with other pigments. as a food colorant, China stipulates that it can be used in red and green silk with a maximum usage of 0.02 g/kg; In fruit juice (flavor) drinks, carbonated drinks, prepared wine, candy, colored cakes, dyed cherry cans (for decoration) and green plum, the maximum usage is 0.10 g/kg; The maximum usage in dipped side dishes is 0.01 g/kg. mainly used for dyeing cotton yarn, cotton cloth, wool or silk reduced indigo is mainly used for dyeing cotton yarn and cotton cloth, and is the main dye for dyeing blue denim. It is also used for dyeing wool and silk and as food coloring and organic pigments. Eat blue pigment. Mainly used for dyeing cotton yarn, cotton cloth, wool or silk. Pure products are used to make food dyes or process them into organic pigments. Used for biochemical agents and indicators. |
| production method | an edible natural blue pigment made from the leaves of polygonum (Polygonum tinctorium). Accumulate the indigo leaves and water them frequently to ferment for 2 to 3 months to become black soil. After pounding with mortar, it is called ball indigo, containing 2% ~ 10% indigo pigment. Add wood ash, lime and bran into the ball indigo, add water to mix, heat to 30~40 ℃, expose to the air, and become blue insoluble indigo. Using phenylglycine as raw material, indoxol is obtained by alkali fusion, and then oxidized with air to obtain the product. There are many methods for the synthesis of phenylglycine. my country basically adopts the condensation method of aniline and chloroacetic acid. For the convenience of refining phenylglycine, the insoluble iron salt is first prepared to remove impurities, and then converted into soluble sodium salt, Enter the alkali melting process.. (1) preparation of indigo. Edible indigo is actually disodium indigo disulfonic acid, sulfonated from indigo with concentrated sulfuric acid, diluted with water after sulfonation, neutralized with soda ash, and finally added sodium chloride salted out, filtered, washed, and dried to obtain the finished product. (2) Preparation of indigo aluminum lake. Aluminum hydroxide is prepared from aluminum salts such as aluminum chloride, aluminum sulfate and bases such as sodium carbonate, and then added to the lime indigo aqueous solution to precipitate the product. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral administration-mouse LD50: >32000 mg/kg; Abdominal cavity-mouse LD50: 2200 mg/kg |
| flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxide smoke |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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Raw Materials for 2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one