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[4-[4-(Diethylamino)benzhydrylen]cyclohexa-2,5-dien-1-yliden]diethylammoniumhydrogensulfat

Brilliant Green

HCID 12449
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
633-03-4
Standard-SMILES
CCN(CC)c1ccc(C(=C2C=CC(=[N+](CC)CC)C=C2)c2ccccc2)cc1.O=S(=O)([O-])O
InChIKey
NNBFNNNWANBMTI-UHFFFAOYSA-M
Summenformel
C27H33N2.HO4S
Durchschnittliche Molmasse
482,6 g/mol
Monoisotopische Masse
482,22392857

Überblick

Brilliant green is an organic hydrogensulfate salt having 4-{[4-(diethylamino)phenyl](phenyl)methylidene}-N,N-diethylcyclohexa-2,5-dien-1-iminium as the counterion. It has a role as an antibacterial agent, an antiseptic drug, a fluorochrome, a poison, a histological dye and an environmental contaminant. It contains a brilliant green cation.

Namen und Bezeichner

Bevorzugter Name
Brilliant Green
IUPAC
[4-[[4-(diethylamino)phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-diethylazanium;hydrogen sulfate
Lokaler Name
[4-[4-(Diethylamino)benzhydrylen]cyclohexa-2,5-dien-1-yliden]diethylammoniumhydrogensulfat
Englischer Name
Basic Green 1
Summenformel
C27H34N2O4S
Molmasse
482.63

Namen und Synonyme

Brilliant green633-03-4Basic green 1Malachite Green GDiamond Green GC.I. Basic Green 1Fast Green JSolid GreenBasic Brilliant GreenBasic Green VGreen ENBrilliant Green B
Weitere Namen anzeigen
BrilliantBrillant blueBRILLIANT GREEN CERTIFIEDgreenenCI 42040Nsc 5011Certified12415greenfastgreenj
Brilliant Green GBrilliant Green PBrilliant Green YFast Green JJOBasic Bright GreenBrilliant Green GXBrilliant Green YNDeorlene Green JJO

Datenbank-Bezeichner

CAS
633-03-4
PubChem CID
12449
DTXSID
DTXSID1048700
ChEMBL
CHEMBL1181633、CHEMBL1790039

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
92,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
7
Schwere Atome
34
Formalladung
0
Komplexität
642

Experimentelle und physikochemische Eigenschaften

Chemical ClassesDyes -> Di- and Triaryl Dyes
CosmeticsHair dyeing
Color/Form · 2 Einträge

Minute, glistening, golden crystals

Green crystalline powder

Solubility40 mg/ml in water; 60 mg/ml in 2-methoxyethanol; 50 mg/ml in ethanol
DecompositionWhen heated to decomposition it emits very toxic fumes of /nitrogen oxides, ammonia and sulfur oxides/.
Melting Point210 °C, decomposes.
Physical DescriptionGold crystals; [Merck Index] Hygroscopic; [MSDSonline]
Ionization Efficiency · 6 Einträge

Positive

4.79

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Other Experimental PropertiesC.I. Basic Green 1 has indicator properties with a visual-transition interval of pH 0.0 (yellow) to pH 2.6 (green).

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 3.4% (6 of 175) of reports.

Danger

H301 (12.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 175 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Ethanaminium, N-[4-[[4-(diethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-ethyl-, sulfate (1:1)

Status: Active Update: 04-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17567

C.I. Basic green 1: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Malachite green and related chemicals: Human health tier II assessment
Hazards SummaryA severe eye irritant; [HSDB] A skin, eye, and respiratory tract irritant; May cause eye injury; Toxic by ingestion; LD50 (rat) = 313 mg/kg; [MSDSonline]
Special Reports · 2 Einträge

Hatch KL, Maibach HI; J Am Acad Dermatol 32 (4): 631-9 (1995). The literature concerning textile dye dermatitis published during the last decade was reviewed. ... The 10 new dye allergens /included/ ... the basic dye brilliant green. ...

USEPA; Chemical Profile: C.I. Basic Green 1 (1985). Chemical safety information sheet /details toxicological information concerning this dye/.

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.

Verwendung und Herstellung

Uses · 6 Einträge

Used in the treatment of intestinal worms, mycotic infections, and wound antisepsis; Also used as a dye (wool, cotton, man-made fibers, and paper), ink, and wood stain; [HSDB] Used as an indicator and biological stain; [Merck Index]

Pulp and Paper Processing [Category: Industry]

Use as an agriculture fungicide.

Industrial applications include dyeing wool, acrylic, cotton, bast fibers, acetate, nylon, PVC fibers and paper and preparing spirit inks, wood stains and pigments.

C.I. Basic Green 1 is used along with Gentian Violet and Proflavine hemisulfate to prepare a triple-dye, broad-spectrum, antiseptic solution for neonatal nursery use. It finds limited use as a stain for bacteria; its most important use in bacteriology is as a component of culture media...

Pigment Green 2 component; dye (wool, silk, polyamide, polyvinyl chloride, jute, cotton, leather, polyacrylonitrile)

Methods of Manufacturing · 2 Einträge

C.I. Basic Green 1 is made by condensing one mole of benzaldehyde with two moles of diethylaniline, in the presence of either hydrochloric or sulfuric acid to form the leuco dye. The leuco dye is oxidized and converted to the acid sulfate.

Prepn: Doebner, Ber. 13, 2222 (1880); Fischer, ibid. 14, 2521 (1881); Colour Index, vol. 4 (3rd ed., 1971) p. 4382.

Use ClassificationCosmetics -> Hair dyeing
General Manufacturing InformationEthanaminium, N-[4-[[4-(diethylamino)phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-N-ethyl-, sulfate (1:1): ACTIVE

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEBI
CHEBI:88173
UNII
G0L543D370
EC Number
211-190-1

Physikochemische Eigenschaften

Schmelzpunkt
210 °C · 210 °C (dec.)(lit.)
Siedepunkt
100 · 100.0
Dichte
1.1016 · 1.1016 (rough estimate)
Dampfdichte
16.6 · 16.6 (vs air)
Dampfdruck
0 Pa · 0Pa at 25℃
Brechungsindex
1.651 · 1.6510 (estimate)
storage temp.
room temp
Löslichkeit
100 g/l · 100g/l
Aggregatzustand
Powder/Solid
Farbe
Metallic green
PH
2.5 · 2.5 (10g/l, H2O, 25℃)
Geruch (Odor)
Odorless
Wasserlöslichkeit
100 G/L · 100 G/L (25 ºC)
Merck
14 · 14,1374
BRN
3901207 · 3901207
Stabilität
Stable. Incompatible with strong oxidizing agents, reducing agents.
Major Application
Black matrix, color filter, photoresists, sensors, inks, rodenticide, dyes, cosmetics, detecting dental carious tissue, Escherichia coli, antimalarial agent, dressing material, treatment of cancer, medical devices
Kosmetik-Inhaltsstoffe Funktionen
HAIR DYEING
InChI
1S/C27H33N2.H2O4S/c1-5-28(6-2)25-18-14-23(15-19-25)27(22-12-10-9-11-13-22)24-16-20-26(21-17-24)29(7-3)8-4;1-5(2,3)4/h9-21H,5-8H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1
InChIKey
UURSSPGMJADCAU-UHFFFAOYSA-N
SMILES
OS([O-])(=O)=O.CCN(CC)c1ccc(cc1)C(\c2ccccc2)=C3/C=CC(\C=C3)=[N+](/CC)CC
LogP
0.765 at · 0.765 at 20℃
CAS Datenbank
633 · 633-03-4(CAS DataBase Reference)
EPA chemische Informationen
1 · C.I. Basic Green 1 (633-03-4)
Toxic Combustion ProductsWhen heated to decomposition it emits very toxic fumes of NOx and SOx.
Hazard Classes and Categories · 2 Einträge

Acute Tox. 3 (12.6%)

Germ cell mutagenicity - category 2

Skin, Eye, and Respiratory IrritationsA skin irritant
Hazardous Reactivities and IncompatibilitiesIncompatible with anionic, oxidizing and reducing substances. Incompatible with aqueous suspensions of bentonite.

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 13(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(3), indicates that C.I. Basic Green 1 will have very high mobility in soil(SRC). Due to the ionic nature of C.I. Basic Green 1, the retention of the dye by ion-exchange processes(4,SRC), particularly on clay surfaces, and adsorption at mineral surfaces such as geothite(5,SRC), may slow down or prevent leaching(SRC). As C.I. Basic Green 1 is an ionic compound, volatilization of this compound will not be important from moist soil surfaces(4,SRC). Based on limited data, C.I. Basic Green 1 is expected to be resistant to aerobic biodegradation in soil(SRC). In an aqueous screening test, only 1.3% of the theoretical BOD was reached in 5 days(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 13(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(1), indicates that C.I. Basic Green 1 should not adsorb to suspended solids and sediment in water(SRC). However, due to the ionic nature of C.I. Basic Green 1, the retention of the dye by ion-exchange processes(3,SRC), particularly on clay surfaces, and adsorption at mineral surfaces such as geothite(4,SRC), may lead to increased adsorption on some surfaces(SRC). As C.I. Basic Green 1 is an ionic compound, volatilization from water surfaces is not expected(3,SRC). According to a classification scheme(5), an estimated BCF value of 2(1,SRC), from a measured water solubility(2), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited data, C.I. Basic Green 1 is expected to be resistant to aerobic biodegradation in water(SRC). In an aqueous screening test, only 1.3% of the theoretical BOD was reached in 5 days(6).

ATMOSPHERIC FATE: The ionic state of C.I. Basic Green 1 makes this compound essentially non-volatile(1,SRC); therefore, this compound should exist in the particulate phase in the ambient atmosphere. Particulate-phase C.I. Basic Green 1 may be physically removed from the air, mainly by wet deposition(SRC).

Soil Adsorption/Mobility · 1 Eintrag

The Koc of C.I. Basic Green 1 is estimated as approximately 13(SRC), using a measured water solubility of 40,000 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that C.I. Basic Green 1 has very high mobility in soil(SRC). Due to the ionic nature of the dye, the retention of C.I. Basic Green 1 by ion-exchange processes(4,SRC), particularly on clay surfaces and adsorption at mineral surfaces such as geothite(5,SRC), may slow down or prevent leaching(SRC).

Human Toxicity Excerpts · 3 Einträge

Brilliant green ... has been employed topically on the skin as an antiseptic, but in contact with the eye is severely injurious. In one instance an attempt to treat conjunctivitis with 1% solution of this dye resulted in destructive keratitis with hypopyon and terminated in bilateral blindness due to corneal opacification.

Ingestion causes diarrhea & abdominal pain.

Eczema, cross-reaction with gentian violet and malachite green.

Artificial Pollution Sources · 1 Eintrag

C.I. Basic Green 1's production and use as a dye, in the preparation of spirit inks, wood stains and pigments, and in antiseptic solutions used for neonatal nurseries(1) may result in its release to the environment through various waste streams(SRC).

Environmental BiodegradationC.I. Basic Green 1 was resistant to aerobic biodegradation in the BOD5 test using an activated sludge inoculum; 1.3% of the theoretical BOD was reached in 5 days(1).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF value of 2 was calculated for C.I. Basic Green 1(SRC), using a measured water solubility of 40,000 mg/l(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/SoilSince C.I. Basic Green 1 is an ionic compound, evaporation from water and moist soil surfaces will not be important(1,SRC).
Non-Human Toxicity Excerpts · 2 Einträge

Experimentally in rabbit eyes the dye is severely injurious.

The haploid strain 15B-II4 of Saccharomyces cerevisiae was used to study in an acute experiment the toxic and mutagenic effects of /three/ arilmethan dyes ... /including/ brilliant green (C.I. 42040). ...High biological activity of all the dyes tested was found, based on such toxic effects as cell killing and growth inhibition. ... It was shown that the dyes could incr the frequency of appearance of nuclear point mutations and cytoplasmic mutations of respiratory deficiency.

Probable Routes of Human Exposure · 1 Eintrag

NIOSH (NOES Survey 1981-1983) has statistically estimated that 42,531 workers (28,804 of these are female) are potentially exposed to C.I. Basic Green 1 in the US(1). Occupational exposure may be through inhalation of dust particles and dermal contact with this compound at workplaces where C.I. Basic Green 1 is produced or used. The general population may be exposed to C.I. Basic Green 1 via dermal contact with products containing C.I. Basic Green 1(SRC).

Environmental Fate/Exposure Summary · 1 Eintrag

C.I. Basic Green 1's production and use as a dye, in the preparation of spirit inks, wood stains and pigments, and in antiseptic solutions used for neonatal nurseries may result in its release to the environment through various waste streams. The ionic state of C.I. Basic Green 1 makes this compound essentially non-volatile, therefore C.I. Basic Green 1 should exist solely in the particulate phase in the ambient atmosphere. Particulate-phase C.I. Basic Green 1 may be physically removed from the air, mainly by wet deposition. An estimated Koc of 13 suggests that C.I. Basic Green 1 will have very high mobility in soil although its ionic nature may result in ion-exchange processes with clay that would retard leaching. The volatilization of the dye from moist soil surfaces to air will not be important as C.I. Basic Green 1 is an ionic compound. Based on limited data, this compound is expected to be resistant to aerobic biodegradation in both soil and water; in an aqueous screening test, only 1.3% of the theoretical BOD was reached in 5 days. It may adsorb to clay sediments and particulate matter in the water due to ion-exchange processes. The loss of the dye from water by evaporation should not be important due to its ionic nature. The potential for bioconcentration in aquatic organisms should be low based on an estimated BCF value of 2. Occupational exposure may be through inhalation of dust particules and dermal contact with this compound at workplaces where C.I. Basic Green 1 is produced or used. (SRC)

Non-Human Toxicity Values · 5 Einträge

LDLo Rat intraperitoneal 8 mg/kg

LDLo Mouse oral 25 mg/kg

LDLo Mouse intraperitoneal 5 mg/kg

LDLo Mouse intravenous 3 mg/kg

For more Non-Human Toxicity Values (Complete) data for C.I. BASIC GREEN 1 (6 total), please visit the HSDB record page.

Sicherheitsdaten

F
10-21
wgk
3
tsca
TSCA listed
ridadr
2811
hs_code
3204 13 00
RTECS-Nr.
BP6825000
risk_code
22-36-36/37/38-20/21/22
Toxizität
LD100 i.v. in mice: 3 mg/kg (Anderson)
hazard_code
Xn
safety_code
26-39-36-24/25
hazard_class
6.1(a)
packing_group
II
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
633-03-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2Skin Sens. 1

Anwendungen

VerwendenDyeing silk, wool, leather, jute and cotton yellowish-green; manufacture of green ink; biological stain; indicator.

Darstellung · 1 Eintrag

synthetischein the presence of sulfuric acid hydrochloric acid or, Benzaldehydeand N,N-diethylbenzenamine condensation, and then will product oxidation, and translated into sulfate. The first generation of resin mixture will suddenly for curing crystalline good crystals.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

BleidioxidBenzaldehydN,N-Diethylanilin

Anbieter100 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: An organic hydrogensulfate salt having 4-{[4-(diethylamino)phenyl](phenyl)methylidene}-N,N-diethylcyclohexa-2,5-dien-1-iminium as the counterion.