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Indigo

HCID 10215
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
482-89-3
Standard SMILES
O=C1C(c2[nH]c3ccccc3c2O)=Nc2ccccc21
InChIKey
COHYTHOBJLSHDF-BUHFOSPRSA-N
Molecular formula
C16H10N2O2
Average molar mass
262.26 g/mol
Monoisotopic mass
262.07422757

Overview

Indigo dye is a member of hydroxyindoles.

Names & identifiers

Preferred name
Indigo
IUPAC
2-(3-hydroxy-1H-indol-2-yl)indol-3-one
English name
Indigo
Molecular formula
C16H10N2O2
Molecular weight
262.26

Names & synonyms

INDIGO482-89-3IndigotinIndigo BlueVat blue 1CystocevaDiindogenIndigo (synthetic)Vulcafix Blue RIndigo Pure BASFIndigo CibaIndigo Synthetic
Show more names
(2,2’-biindoline)-3,3’-dioneCI 73000C.I, vat blue 1C.I. pigment blue 66delta(sup2,2’)-bipseudoindoxyl
Synthetic IndigoIndigo Powder WVulcafor Blue AIndigo JIndigo NIndigo PVynamon Blue AIndigo VS

Database identifiers

CAS
482-89-3、64784-13-0、68651-46-7
PubChem CID
10215
DTXSID
DTXSID3026279
ChEMBL
CHEMBL35479
ChEBI
CHEBI:177687
UNII
1G5BK41P4F
EC Number
207-586-9
Nikkaji
J1.210.939C、J2.292.935F、J3.724.732D、J5.983H

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
65.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
20
Formal charge
0
Complexity
448

Experimental & physicochemical properties

Chemical ClassesDye
CosmeticsCosmetic colorant
SpringerMaterials PropertiesBoiling point
LogP2.63

Physicochemical properties

Melting point
300 °C · >300 °C(lit.)
Boiling point
405.51 °C · 405.51°C (rough estimate)
Density
1.01 g/mL · 1.01 g/mL at 20 °C
vapor pressure
0 Pa · 0Pa at 100℃
refractive index
1.58 · 1.5800 (estimate)
Flash point
220 ℃ · >220℃
storage temp.
Sealed in dry,Room Temperature
solubility
DMSO (Slightly, Heated, Sonicated), DMF (Slightly)
form
Powder

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 6.2% (11 of 176) of reports.

Warning

H373 (90.9%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P319, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 176 reports by companies from 13 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: 3H-Indol-3-one, 2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-

REACH registered substance: 2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one (EC: 207-586-9)

Hazard Classes and CategoriesSTOT RE 2 (90.9%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
DU2988400
ridadr
UN 3264 8/PG 3
hs_code
32041510
Toxicity
LD50 oral in mouse: > 32gm/kg
risk_code
36/38-36/37/38-48/20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-36

Chemistry & industry

Uses & manufacturing

Use ClassificationCosmetics -> Cosmetic colorant
General Manufacturing Information3H-Indol-3-one, 2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-: ACTIVE
Applications · 8 items

Uses1. 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.

DescriptionIndigo, 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.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Colour Index
73000 · 73000
pka
-3.83 · -3.83±0.20(Predicted)
color
Dark blue to violet
Water Solubility
0.1 g/100 · <0.1 g/100 mL
λmax
602 nm · 602 nm
ε(extinction coefficient)
8000 at · ≥8000 at 599-605nm in chloroform
Merck
14 · 14,4943
BRN
88275 · 88275
Stability
Stable. Incompatible with strong oxidizing agents.
Major Application
diagnostic assay manufacturinghematologyhistology
Cosmetics Ingredients Functions
COLORANT
InChI
1S/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/b14-13+
InChIKey
COHYTHOBJLSHDF-BUHFOSPRSA-N
SMILES
O=C1C(\Nc2ccccc12)=C3/Nc4ccccc4C3=O
LogP
2.7 at · 2.7 at 23℃
FDA 21 CFR
74.3106 · 74.3106
CAS DataBase Reference
482 · 482-89-3(CAS DataBase Reference)
EWG's Food Scores
1 · 1-3
FDA UNII
1 G5BK41P4F · 1G5BK41P4F
NIST Chemistry Reference
1 · c.i. Vat blue 1(482-89-3)
EPA Substance Registry System
1 · C.I. Vat Blue 1 (482-89-3)
UNSPSC Code
41116107 · 41116107
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
302 · P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/38-36/37/38-48/20/21/22
Safety Statements
26 · 26-36
RIDADR
3264 · UN 3264 8/PG 3
WGK Germany
1 · 1
RTECS
2988400 · DU2988400
TSCA
TSCA listed
HS Code
32041510 · 32041510
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
482 · 482-89-3(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in mouse: > 32gm/kg
REACH Registrations
Active
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H315-H319-H335
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P302+P352-P305+P351+P338
Hazardous Substances Data
482-89-3(Hazardous Substances Data)

OccurrenceIndigo is a perennial shrub found in several regions of the world.

HistoryIndigotin. The blue dye of the ancient world was derived from indigo and woad. Which plant is the oldest is a matter of conjecture. That indigo was known at least four thousand years ago is evident from ancient Sanskrit writings. Cloth dyed with indigotin (CI Natural Blue; CI 75780) has been found in Egyptian tombs and in the graves of the Incas in South America. Indigo belongs to the legume family. The two most important species are Indigo tinctoria and I. suffruticosa, found in India and the Americas, respectively. The leaves of the indigo plant do not contain the dye as such, but in the form of its precursor, a glycoside known as indican.

UsesIn 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.

UsesIndigo 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.

UsesAs textile dye. In sutures.

General DescriptionDark blue powder with coppery luster. Occurs in isomeric forms (cis and trans). In solid state Indigo is in the trans form.

Upstream & downstream products

Upstream raw materials

Chloroacetic acidPotassium hydroxidePhenyl glycineSodium chlorideDisodiumSodiumFood Blue 1:1Concentrated sulfuric acidAnilineSodium hydroxideIndigo CarmineIndoleAluminum sulfateAluminum hydroxideSodium carbonateAmmonia3H-Indol-3-one, 1,2,4,5,6,7-hexahydro-2-Phenylimino-3-indolinoneN-(2-Carboxyphenyl)glycine

Downstream products

Vat Blue 4BIsatinFood Blue 1:1Indigo CarmineIndoleEthanone, 1-(3-hydroxy-1H-indol-2-yl)- (9CI)C.I.Vat Blue 35Vat Blue 4B

Additional notes

DefinitionA double indole derivative.

Definitionindigo: A blue vat dye, C16H10N2O2.It occurs as the glucoside indican inthe leaves of plants of the genus Indigofera,from which it was formerlyextracted. It is now made synthetically.