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Home > Encyclopedia > Indigo Blue

Indigo Blue

Indigo Blue structure

Indigo Blue 

structure
  • CAS No:

    482-89-3

  • Formula:

    C16H10N2O2

  • Chemical Name:

    Indigo Blue

  • Synonyms:

    3H-Indol-3-one,2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-;[Δ2,2′-Biindoline]-3,3′-dione;Indigo Pure BASF;2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one;11669 Blue;C.I. 73000;[Δ2,2′(3H,3′H)-Biindole]-3,3′-dione;Δ2,2′-Bipseudoindoxyl;D+C Blue No. 6;C.I. Vat Blue 1;Diindogen;Indigo J;Indigo N;Indigo P;Indigo Ciba;Indigo Ciba SL;Indigo NAC;Indigo NACCO;Indigo PLN;Indigo Powder W;Indigo Pure BASF Powder K;Indigo Synthetic;Indigotin;Indigo VS;Lithosol Deep Blue B;Mitsui Indigo Paste;Mitsui Indigo Pure;Monolite Fast Navy Blue BV;Synthetic indigo;Synthetic Indigo TS;Vulcafix Blue R;Vulcafor Blue A;Vulcanosine Dark Blue L;Vulcol Fast Blue GL;Vynamon Blue A;Vat Blue 1;Indigo;Blue No. 201;Cystoceva;Indigo Blue;D and C Blue No. 6;Indigotin (natural);Indigotine;C.I. Pigment Blue 66;Pigment Indigo;Pigment Indigo V;Pigment Blue 66;C Blue 22;Natural blue indigotin;C.I. Natural Blue 1;Natural Blue 1;Mitsui Indigo Pure EXN;Japan Blue 201;Vat Dark Blue VB;D&C Blue No. 6;Reduced Dark Blue VB;Dystar Indigo Gr;2,2′-Bis(2,3-dihydro-3-oxoindolylidene);Bezema Indigo AXX-FL;AXX-FL;2,2′-Biindolylidene-3,3′-dione;2-(3-Oxo-1H-indol-2-ylidene)-1H-indol-3-one;AT 01;Dystar Indigo Gran;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

  • Categories:

    Cosmetic Ingredient  >  Cosmetic Colorant

Description

Indigo is a deep and rich color dye for indole stain, isolated from the plant Indigofera tinctoria and related species[1].


C.i. vat blue 1 is a dark blue powder with coppery luster. Occurs in isomeric forms (cis and trans). In solid state it is in the trans form. (NTP, 1992)


C.i. vat blue 1 is a dark blue powder with coppery luster. Occurs in isomeric forms (cis and trans). In solid state it is in the trans form. (NTP, 1992)|Indigo dye is a member of hydroxyindoles.|Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.

Indigo Blue Basic Attributes

262.26300

262.26

207-586-9

1G5BK41P4F

8645

DTXSID3026279

DARK-BLUE POWDER WITH COPPERY LUSTER

3204151000

Characteristics

58.20000

3.09080

C.i. vat blue 1 is a dark blue powder with coppery luster. Occurs in isomeric forms (cis and trans). In solid state it is in the trans form. (NTP, 1992)

1.35 g/cm3

390 °C (decomp)

400.4ºC at 760mmHg

158.2ºC

1.709

SOL IN ANILINE, NITROBENZENE, CHLOROFORM, GLACIAL ACETIC ACID, CONCN SULFURIC ACID

Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

1.27E-06mmHg at 25°C

LD50 oral in mouse: > 32gm/kg

SUBLIMES @ ABOUT 300 °C; DECOMPOSES @ 390 °C; DISSOLVES IN NONPOLAR SOLVENTS WITH RED & IN POLAR SOLVENTS WITH BLUE COLOR; WITH FUMING H2SO4 IT FORMS A SOL SULFONIC ACID; OCCURS AS CIS & TRANS ISOMER; TRANS ISOMER IS SOLID|INDIGO...IS A DYE WHICH IS ESSENTIALLY INSOLUBLE IN WATER IN ITS COLORED OXIDIZED FORM, BUT IS SOLUBLE WHEN REDUCED TO A COLORLESS FORM.

Insoluble in water.

Amines, Phosphines, and Pyridines

Safety Information

UN 3264 8/PG 3

1

R36/37/38

S26-S36

DU2988400

Xi

Stable. Incompatible with strong oxidizing agents.

P260

H373

D & C BLUE NO 6 (INDIGO) MAY BE USED UNDER FEDERAL FOOD, DRUG, & COSMETIC ACT IN COLORING POLY(ETHYLENE TEREPHTHALATE) NONABSORBABLE SUTURES FOR USE IN GENERAL & OPHTHALMIC SURGERY. SPECIFICATIONS FOR CERTIFICATION ARE GIVEN.

A REVIEW OF THE CHARACTERISTICS OF VARIOUS SYNTHETIC ORGANIC DYES USED AS ADDITIVES IN DRUGS (125 REFERENCES).[HELOU JH; ADDITIVES IN DRUGS. CHARACTERISTICS OF VARIOUS SYNTHETIC ORGANIC DYES; AN FARM QUIM SAO PAULO 18(1) 157 (1979)]

Flash point data for this compound are not available but it is probably combustible. (NTP, 1992)

Fires involving this compound should be controlled using a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

INDIGO IS RECOVERED FROM WASTEWATER CONTAINING 0.1 KG/CU M BY FLOCCULATION WITH 0.03 KG/CU M CACL2-MGCL2 & 2.3 KG/CU M NAOH.|WASTEWATER FROM INDIGO DYEING IS FILTERED AT 62 L/MIN ON STAINLESS STEEL SCREEN (128 MESH/CM) & CONCN 100-FOLD BY REVERSE OSMOSIS AT 4.75 M/SEC & 65 DEG/69 BAR THROUGH POROUS STAINLESS STEEL TUBES TO GIVE 4600 L/SQ M/DAY EFFLUENT.

Toxicity

PROBABLY THE OLDEST KNOWN COLORING MATTER. ORIGINALLY OBTAINED FROM VARIOUS SPECIES OF INDIGOFERA, LEGUMINOSAE, INDIGENOUS TO BENGAL, JAVA, GUATEMALA, IN WHICH IT OCCURS AS A GLUCOSIDE.

Drug Information

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

WAS OBSERVED IN 24-HR URINE SAMPLES COLLECTED AT 14-DAY INTERVALS FROM 6 SHEEP GRAZING PASTURE OF OESTROGENIC CLOVER FROM JULY TO LATE OCTOBER. GENERALLY IT OCCURRED IN ONLY 1 URINE SAMPLE AT EACH COLLECTION BUT FROM MID-AUGUST TO MID-SEPTEMBER IT WAS PRESENT IN 3 OR 4 SAMPLES.

TWO MOLECULES OF INDOLE WERE OXIDIZED TO FORM ONE MOLECULE OF INDIGOTIN (INDIGO) IN PSEUDOMONAS INDOLOXIDANS, WITH INDOXYL BEING DETECTED AS INTERMEDIATE.

ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin and mucous membranes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

...MAN SPLASHED 7% ALKALINE SOLN OF REDUCED FORM INTO HIS EYES, CONJUNCTIVA APPEARED BLUE SEVERAL HR LATER; CORNEA WAS SOMEWHAT TURBID BUT NOT STAINED. IN COURSE OF 10 DAYS CORNEA GRADUALLY CLEARED & SOME FINE BLUE DOTS WERE SEEN IN STROMA. ...DYE APPEARED TO BE RATHER INERT & NONTOXIC IN TISSUES...

(delta-2,2'-biindole)-3,3'-dione

Indigo Blue Use and Manufacturing

Methods of Manufacturing

FIRST SYNTHESIS: BAEYER, BER 11: 1296 (1878); 12: 456 (1879). FIRST COMMERCIAL PROCESS: HEUMANN, BER 23: 3043, 3431 (1890).|HARLEY-MASON, J CHEM SOC 1950, 2907; ZIEGLER, KAPPE, MONATSH 96: 889 (1965).|FROM ANILINE & CHLOROACETIC ACID, & FUSING RESULTING PHENYLGLYCINE WITH ALKALI & SODIUM AMIDE. FORMERLY FROM PLANTS OF GENUS INDIGOFERA.|Condensation of aniline, formaldehyde, and hydrocyanic acid to form N-phenylglycinonitrile, followed by alkaline hydrolysis to yield N-phenylglycine which gives indigo in 94% yields. This is the major commercial route used throughout the world

Uses

Indigo dye is an organic compound with a distinctive blue color (see indigo). Historically, indigo was a natural dye extracted from plants, and this process was important economically because blue dyes were once rare. A large percentage of indigo dye produced today – several thousand tons each year – is synthetic. It is the blue often associated with blue jeans.


Dyes

Production

< 25,000 lb|(1986) No Data

GRADES: TECHNICAL; PURE

Textiles, apparel, and leather manufacturing|3H-Indol-3-one, 2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-: ACTIVE|A DOUBLE INDOLE DERIVATIVE

COLUMN CHROMATOGRAPHIC-SPECTROPHOTOMETRIC DETERMINATION OF INDIGO IN CHINESE TRADITIONAL MEDICINE QING-DAI PREPD FROM LEAF OR STEM OF ISATIS TINCTORIA, BAPHICACANTHES CUSIA, INDIOFERA SUFFRUICOSA OR POLYGONUM TINCTORUM.

TLC WAS USED TO SHOW PRESENCE OF INDIGO IN URINE SAMPLES COLLECTED FROM SHEEP.

Cosmetics -> Cosmetic colorant; Masking; Tonic

Computed Properties

Molecular Weight:262.26
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:262.074227566
Monoisotopic Mass:262.074227566
Topological Polar Surface Area:65.4
Heavy Atom Count:20
Complexity:448
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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