Indigo

Base Information

• Chemical Name: Indigo
• CAS No.: 482-89-3
• Deprecated CAS: 11129-41-2,12000-74-7,12626-73-2,93660-98-1,136797-30-3,210488-46-3,908005-94-7,1131642-59-5,2089217-02-5,2089217-38-7,1131642-59-5,12000-74-7,12626-73-2,136797-30-3,2089217-02-5,2089217-38-7,210488-46-3,908005-94-7,93660-98-1
• Molecular Formula: C16H10N2O2
• Molecular Weight: 262.268
• Hs Code.: 32041510
• European Community (EC) Number: 207-586-9
• NSC Number: 8645
• UNII: 1G5BK41P4F
• DSSTox Substance ID: DTXSID3026279
• Nikkaji Number: J1.210.939C,J2.292.935F,J5.983H
• Wikipedia: Indigo_dye
• Wikidata: Q422662,Q104967020,Q104389767
• NCI Thesaurus Code: C71644
• ChEMBL ID: CHEMBL599552,CHEMBL35479
• Mol file: 482-89-3.mol

Synonyms:(delta-2,2'-biindole)-3,3'-dione;2-(1,3-Dihydro-3-oxo-5-sulpho-2H-indol-2-ylidene)-3- oxoindoline-5-sulphonic acid;Carmine, Indigo;D and C Blue NO. 6;FD and C Blue No. 2;indigo;Indigo Blue;Indigo Blue, Soluble;Indigo Carmine;Indigo Disulfonate;indigotin;Indigotindisulfonate;Indigotindisulfonate Sodium;Indigotindisulfonic Acid;Soluble Indigo Blue

Chemical Property of Indigo

Chemical Property:

• Appearance/Colour: dark violet powder
• Vapor Pressure: 1.27E-06mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.709
• Boiling Point: 400.4 °C at 760 mmHg
• PKA: -3.83±0.20(Predicted)
• Flash Point: 158.2 °C
• PSA: 58.20000
• Density: 1.417 g/cm³
• LogP: 3.09080
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly, Heated, Sonicated), DMF (Slightly)
• Water Solubility.: <0.1 g/100 mL
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 262.074227566
• Heavy Atom Count: 20
• Complexity: 448

Purity/Quality:

94% indigo, ^*data from raw suppliers

Indigo ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-48/20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Other Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)C3=NC4=CC=CC=C4C3=O)O
• Recent ClinicalTrials: Indigo Naturalis in Treating Atopic Dermatitis Topically
• Uses: 1.? It can be used as food coloring agent with the provisions of China being able to be used in red and green silk and the maximum usage amount of 0.02g/kg; it can be used in the juice (flavor) beverages, carbonated beverages, wine, candy, pastry coloring, dyeing cherry can decorative) and green plum with the maximum usage amount of 0.10g/kg; the maximal usage amount in the dipping pickles of 0.01g/kg. 2.? It is mainly used for the dyeing of cotton yarn, cotton, wool or silk. 3.? Reduced indigo is mainly used for dyeing cotton yarn and cotton cloth, being the major dye for blue dye denim. It is also used for wool, silk dyeing and as food coloring and organic pigments. 4.? Edible blue pigment; 5.? It is mainly used for dyeing cotton yarn, cotton cloth, wool or silk. Pure product can be used for the manufacturing of food dyes, or processed into organic pigments. In recent years researchers have used genetic engineering using Escherichia coli to convert tryptophan into indigo. The desire for natural organic products has also revived traditional production methods of indigo on a small scale. Indigo's dominant use is as a textile dye, but indigo-related compounds have limited use as indicators and in food coloring.the Food and Drug Administration's FD&C Blue #2 contains indigotine (also known as indigo carmine), which is a sulfonated sodium salt of indigo. As textile dye. In sutures. Indigo is a chemical compound used as a dye in industrial clothing and textile processes. Also used in the synthesis of organic semiconductors. Dyes and metabolites.
• Production method: It is a kind of edible natural blue pigment made from the leaves of Polygonum tinctorium. The indigo leaves are piled up and frequently subject to watering, to ferment 2 to 3 months to become a black clod like. After ramming using mortar, it is known as the ball indigo with the indigo pigment being 2% to 10%. The wood ash, lime and bran are incorporated into ball indigo and further subject to water mixing, heated to 30~40 ℃, exposed to the air to become insoluble blue indigo. Phenylglycine is taken as raw material and form indole phenol after subjecting to alkali melting, followed by air oxidation to derive the products. There are many ways to synthesize phenylglycine. In our country, the condensation method of aniline and chloroacetic acid is adopted. For the convenience of the refining of phenylglycine, we can first make its insoluble iron salt to remove the impurities before converting into soluble sodium salt and entering into alkali melting process. . (1) indigo preparation. Edible indigo is actually indigo disulfonic acid disodium. Indigo is subject to sulfonation with concentrated sulfuric acid, followed by dilution with and then soda ash neutralization. Finally add sodium chloride for salting out, filter, wash and dry to get the finished product. (2) Preparation of indigo aluminum precipitate. First have aluminum chloride and aluminum sulfate have reaction with alkali such as sodium carbonate for preparation of aluminum hydroxide. Then add it to the indigo water solution for precipitation to derive the products.
• Description: Indigo, known chemically as indigotin, is a common blue dye that has been highly valued throughout history and has played a major role in trade and commerce since ancient times. The term indigo is often used to describe many blue dyes produced from a number of plants. For example, woad, a blue dye obtained from the plant Isatis tinctoria, was used throughout the Mediterannean and Europe and is often identified as indigo. True indigo comes from the leguminous plant of the genus Indigofera. The Indigofera genus includes several hundred species, and indigo has been obtained from a number of these, but the dominant species for the dye are Indigofera tinctoria grown mainly in India and tropical Asia and Indigofera suff ructiosa from the tropical Americas. The name indigo comes from the Greek indikon and Latin indicum meaning “dye from India.” There is evidence that indigo was used several thou sand years b.c.e. Persian rugs containing indigo color exist from several thousand years b.c.e. Textile artifacts from Egyptian tombs provide evidence of indigo’s use by royalty from as far back as 2500 b.c.e. The writings of Herodotus from approximately 450 b.c.e. mention indigo’s use in the Mediterranean area.

Technology Process of Indigo

There total 297 articles about Indigo 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: 90.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 1H,1H'-2,2'-Biindolylidene-3,3'-dione (482-89-3,12626-73-2)

Guidance literature:

With tetraphosphorus decasulfide; In pyridine; at 85 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)77084-5

Reference yield: 88.8%

1-acetyl-2,3-dihydro-1H-indol-3-one (16800-68-3) + N,O-diacetylindoxyl (16800-67-2) → 1,1'-(3-oxoindoline-1,2-diyl)bis(ethan-1-one) (110912-08-8) + 1H,1H'-2,2'-Biindolylidene-3,3'-dione (482-89-3,12626-73-2)

Guidance literature:

With sulfuric acid; In acetic anhydride; at 20 ℃; for 20h;

Reference yield: 86.4%

1-acetyl-2-propionyl-3-indolinone (110912-09-9) → 1-(3-Hydroxy-1H-indol-2-yl)-propan-1-one (110912-10-2) + 1H,1H'-2,2'-Biindolylidene-3,3'-dione (482-89-3,12626-73-2)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 2h;

upstream raw materials:

indole

indoxyl

3-indoxyl acetate

2-ethynyl-1-nitrobenzene

Downstream raw materials:

leucoindigo

phenylglyoxylic acid ethyl ester

2,3-dimethylindole

5,14b-diaza-benzo[b]benzo[5,6]cyclohepta[1,2,3-lm]fluorene-10,15-dione

Refernces

• 1、 -. "CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF". Page/Page column 50-51. . Retrieved 2021/01/29.
• 2、 Rousseau, Olivier,Ebert, Maximilian C. C. J. C.,Quaglia, Daniela,Fendri, Ali,Parisien, Adem H.,Besna, Jonathan N.,Iyathurai, Saathanan,Pelletier, Joelle N.. "Indigo Formation and Rapid NADPH Consumption Provide Robust Prediction of Raspberry Ketone Synthesis by Engineered Cytochrome P450 BM3". . p. 837 - 845. Retrieved 2019/12/15.