Basic information
- Standard SMILES
O=c1c2ccccc2[nH]c2cc3c(=O)c4ccccc4[nH]c3cc12- InChIKey
NRCMAYZCPIVABH-UHFFFAOYSA-N- Molecular formula
- C20H12N2O2
- Average molar mass
- 312.3 g/mol
- Monoisotopic mass
- 312.08987762
Overview
Quinacridone is an organonitrogen heterocyclic compound and an organic heterotetracyclic compound.
Names & identifiers
- Preferred name
- Quinacridone
- IUPAC
- 5,12-dihydroquinolino[2,3-b]acridine-7,14-dione
- English name
- Quinacridone
- Molecular formula
- C20H12N2O2
- Molecular weight
- 312.32
Names & synonyms
Show more names
Database identifiers
- CAS
1047-16-1- PubChem CID
- 13976
- DTXSID
DTXSID5027354- ChEBI
CHEBI:174977- UNII
- 11P487375P
- EC Number
- 213-879-2
- Nikkaji
- J8.584G
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 58.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 500
Experimental & physicochemical properties
Polymers
Plastics -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PET; PMMA; PA; PC; (E)PS
Plastics -> Pigments agents
Color/Form
Red to violet solid with blueish or yellowish tint depending upon crystalline form.
particle characteristics: thin plates
Solubility
Insoluble in water
Insoluble in organic solvents and dispersion media.
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
Physical Description
Liquid; Other Solid; Dry Powder; Other Solid; CBI
Red to violet solid; Bluish or yellowish tint depending of form; [HSDB] Red odorless powder; [MSDSonline]
Solid
Physicochemical properties
- Melting point
- 390 °C · 390 °C
- Boiling point
- 568.5 · 568.5±50.0 °C(Predicted)
- Density
- 1.5 g/cm3 · 1.5 g/cm3
- storage temp.
- Sealed in dry,Room Temperature
- form
- Solid:nanomaterial
- pka
- -2.96 · -2.96±0.20(Predicted)
- Colour Index
- 46500 · 46500
- color
- Orange to Amber to Dark red
- Cosmetics Ingredients Functions
- COLORANTHAIR DYEING
- LogP
- 2.2 at · 2.2 at 24℃ and pH7
- CAS DataBase Reference
- 1047 · 1047-16-1(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- QUINACRIDONE RED (C.I. PIGMENT VIOLET 19, C.I. NO. 73900)
- FDA 21 CFR
- 175.3 · 175.300; 178.3297
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 11 P487375P · 11P487375P
- NIST Chemistry Reference
- 2 · Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-(1047-16-1)
- EPA Substance Registry System
- Quinacridone (1047-16-1)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319
- Precautionary statements
- 261 · P261-P302+P352-P305+P351+P338
- Safety Statements
- 24 · 24/25
- RTECS
- 8533500 · VA8533500
- TSCA
- TSCA listed
- HS Code
- 29339900 · 29339900
- Hazardous Substances Data
- 1047 · 1047-16-1(Hazardous Substances Data)
- Toxicity
- 50 oral · LD50 oral in rat: > 20mL/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 99.6% (760 of 763) of all reports.
Not Classified
Aggregated GHS information provided per 763 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-
Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14755
Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Skin reactions have been reported: inflammation in a tattoo after sun exposure and acne-like changes on the face of a child colored with a red felt-tip pen; Also acne-like reaction on the skin of rabbits after coloring with red felt-tip pen; [HSDB] No known adverse effects on human health; Not an irritant; Not a sensitizer; [MSDSonline] See Acridine.
Special Reports
A BRIEF DESCRIPTION OF THE CHEMICAL PROPERTIES, DEVELOPMENT, & EFFORTS TOWARD GAINING APPROVAL OF THE QUINACRIDONE PIGMENT VIOLET #19 (LINEAR TRANS QUINACRIDONE) BY THE FDA IS PRESENTED.[VIOLET #19--POTENTIAL NEW COSMETIC COLOR; COSMET TOILET 94(MAY) 19 (1979)]
[ITC/USEPA; Information Review #315 (Draft) Cinquasia Red 1982]
Toxicology
Environmental Fate
Much of cinquasia red will be bound up in the components of landfills, junkyards, and general dump sites.
Terrestrial: The insolubility of cinquasia red will cause it to collect in soils and sediments.
Aquatic: Due to its insolubility, cinquasia red may reside in the water column for a substantial period, long enough to become part of deep sea sediments.
Human Toxicity Excerpts
Two different red pigments used for tattooing were found to give rise to inflammatory reactions in the skin. No inorganic component was found in the pigments. NMR and MS analyses elucidated the molecular structures ... a red-violet pigment was found to be linear quinacridone. A strong exposure to UV-light was reported in most cases prior to the onset of the inflammation.
Acne-like changes were observed on a child's cheek after coloring them with a red felt tip pen. Numerous comedos appeared around a red tattoo colored with felt tip pen ink on a 16-yr-old girl.
Artificial Pollution Sources
Released to the environment as fugitive dust during manufacturing and end use.
EPA reported that the waste streams from the manufacture of cinquasia red are brines which contain small amounts of organic chemicals and strong acid wastes.
Non-Human Toxicity Excerpts
Pigment Violet #19 was nonmutagenic by Ames test.
In rabbits ... /pigment violet 19/ in felt tip pens produced a comedo type reaction.
Regulatory information
Safety data
- tsca
- TSCA listed
- rtecs
- VA8533500
- hs_code
- 29339900
- Toxicity
- LD50 oral in rat: > 20mL/kg
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Hazard statements
- H302-H315-H319
- REACH Registrations
- Active
- Precautionary statements
- P261-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 1047-16-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used as pigment (paints, printing inks, plastics, rubber, alkyd resin enamels, textile emulsion inks, textiles, nitrocellulose, vinyl, and acrylic lacquers) and sensitizing dye in color photo electrophoresis; Used to tone and make other pigments; [HSDB]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
PAINTS, PRINTING INKS, PLASTICS, RUBBER
Cinquasia red is used a sensitizing dye in color photoelectrophoresis.
Pigment in textiles
As colorants for plastics, quinacridone pigments may be used in all resins except nylon-66 and polystyrene./Quinacridone Pigments/
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) 2.49X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1981) 6.21X10+6 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
2023: 1,000,000 - <2,500,000 lb
1.2 million lbs.
(1979) 7.11X10+8 GRAMS
(1981) 6.25X10+8 GRAMS
Consumption Patterns
Quinacridone pigment use in automotive finishes accounts for the majority of the consumption of cinquasia red, with lesser quantities finding end uses in PVC manufacturing and the textile industry.
ESSENTIALLY 100% AS A PIGMENT
Methods of Manufacturing
The major commercial production methods involve cyclization of 2,5-di(arylamino)terephthalic acids and esters.
The manufacturing process /of cinquasia red/ required three steps: (1) halogenation of terephthalic acid, (2) reaction of aniline with 2,5-dihaloterephthalic acid, and (3) cyclization of 2,5-dianilinoterephthalic acid to finished pigment.
HEATING OF DIALKYL(C1-C3)-2,5-DIARYLAMINO-3,6-DIHYDROTEREPHTHALATE IN AN INERT, HIGH-BOILING MEDIUM FOLLOWED BY OXIDATION
Use Classification
Plastics -> Polymer Type -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PET; PMMA; PA; PC; (E)PS
Plastics -> Pigments agents
Cosmetics -> Hair dyeing; Cosmetic colorant
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-: ACTIVE
Importer: American Hoechst Corporation, Rte 202-206 North, Bridgewater, NJ, 08876
Importer: Dainippon Ink & Chems. America Inc., 200 Park Avenue, New York, NY, 10017
Importer: BASF Wyandotte Corp., 100 Cherry Hill Rd., Parsippany, NJ, 07054.
Applications
DescriptionCI 73900 is classed chemically as a quinacridone colour.
UsesQuinacridone is mainly used for coloring plastics, coatings, resins, coating printing, inks, paints, rubber (including synthetic rubber) and plexiglass, and can also be used for dope (slurry) coloring of synthetic fibers.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionA lightfast pigment used in paints, printing inks, plastics, etc.
Related reactions
Linked notes
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