Ethidium bromide CAS 1239-45-8

Introduction：Basic information about Ethidium bromide CAS 1239-45-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Ethidium bromide Basic information

• Product Name: Ethidium bromide
• Synonyms: 3,8-diaMino-5-ethyl-6-phenylphenanthridin-5-iuM broMide;EthidiuM broMide dropper bottle,5Ml;2,7-Diamino-10-ethyl-9-phenylphenanthridinium bromide, 1% aqueous solution;Ethidinium bromide, 3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide;EthidiuM BroMide, OMniPur(R);EthidiuM broMide, pure, 95% 1GR;EthidiuM broMide, pure, 95% 5GR;Dromilac
• CAS: 1239-45-8
• MF: C21H20BrN3
• MW: 394.32
• EINECS: 214-984-6
• Product Categories: marker;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Phenanthridine;Purines
• Mol File: 1239-45-8.mol

Ethidium bromide Chemical Properties

• Melting point: 260-262 °C (dec.)(lit.)
• bulk density: 340kg/m3
• density: 1.3739 (rough estimate)
• refractive index: 1.6700 (estimate)
• Fp: >100°C
• storage temp.: 2-8°C
• solubility: H₂O: 10 mg/mL, opaque, strongly red
• form: powder
• color: Red to dark purple
• Odor: Odorless solid
• PH: 4.4 (20°C, 10g/L in H2O)
• Water Solubility: 40 g/L (25 ºC)
• λmax: 518 nm, 210 nm, 285 nm, 316 nm,343 nm, 480 nm, 525 nm
• Merck: 14,4731
• BRN: 3642536
• Stability: Stable. Incompatible with strong oxidizing agents.
• Major Application: Electroluminescent displays;photoresists
• Biological Applications: Nucleic acid hybridization; detecting nucleic acids,cells,cancer cells,human cytomegalovirus,hydrogenase A (hydA) of Clostridia,influenza A virus,oligonucleotides,viable Plesiomonas shigelloides; apoptosis assay; nucleic acid quantification
• InChI: 1S/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H
• InChIKey: ZMMJGEGLRURXTF-UHFFFAOYSA-N
• SMILES: [Br-].CC[n+]1c(-c2ccccc2)c3cc(N)ccc3c4ccc(N)cc14
• CAS DataBase Reference: 1239-45-8(CAS DataBase Reference)
• EPA Substance Registry System: Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide (1239-45-8)

Safety Information

• Hazard Codes: T,T+
• Risk Statements: 23-68-36/37/38-26-21/22-22
• Safety Statements: 36/37-45-36/37/39-28A-26-22-28-63
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: SF7950000
• F: 8-9
• HazardClass: 6.1
• PackingGroup: I
• HS Code: 29339990
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
• Hazard Classifications: Acute Tox. 1 Inhalation Acute Tox. 4 Oral Muta. 2
• Hazardous Substances Data: 1239-45-8(Hazardous Substances Data)
• Toxicity: Intercalating dye widely used to stainDNA in gels and gradients. The DNA can be visualized readilyby irradiation with ultraviolet light, as little as 0.5 μg of DNAbeing detectable by such methods. Ethidium bromide is alsoadded to cesium chloride density gradients, since as an intercalatingmolecule it binds more readily to linear DNA than toclosed collinear circles of DNA (such as plasmids). Binding ofethidium bromide reduces the density of DNA, thus covalentcircles of DNA have higher densities at saturating concentrationsof ethidium bromide, permitting the separation of plasmidDNA. Ethidium bromide is a putative carcinogen.

Ethidium bromide Usage And Synthesis

description

Ethidium Bromide (EtBr), commonly used in research laboratories as a stain for the visualization of nucleic acids in electrophoresis gels, is a toxic chemical and a potent mutagen. When used in nucleic acid staining, ethidium bromide fluoresces a red-orange to pink color under ultraviolet light and with increased fluorescence when bound to double-stranded DNA. While it is not specifically regulated as a hazardous waste, the mutagenic properties may present health hazards and disposal concerns if it is not managed properly in the laboratory.

Uses

Ethidium bromide (EtBr) is a fluorescent dye widely used in molecular biology research. Early usage was as a veterinary trypanocide. It is a mutagenic compound that intercalates double-stranded DNA and RNA. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA, 25-fold on binding double-stranded DNA (although histones block binding of EtBr to DNA). Ethidium bromide has been used in multiple fluorimetric assays for nucleic acids. It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA. Because of the binding to DNA, EtBr is a powerful inhibitor of DNA polymerase.
Molecular Biology-grade Powder is suitable for use in gel electrophoresis and DNA isolation procedures.
Aqueous Solution (10 mg/mL) is suitable for use in gel electrophoresis and DNA isolation procedures.
Molecular Biology-grade Aqueous Solution (500 mg/mL) is suitable for use in gel electrophoresis.

Health Hazards

EtBr is a potent mutagen (may cause genetic damage), and moderately toxic after an acute exposure. EtBr can be absorbed through skin, so it is important to avoid any direct contact with the chemical. EtBr is an irritant to the skin, eyes, mouth, and upper respiratory tract. It should be stored away from strong oxidizing agents in a cool, dry place, and the container must be kept undamaged and tightly closed.

Description

Ethidium bromide is an intercalating reagent that is used for double-stranded DNA and RNA in agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 ug/ml). Ethidium bromide acts as an inhibitor of DNA polymerase.

Chemical Properties

Purple/maroon crystalline powder

Uses

Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids. It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA. Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase. Antiprotozoal (Trypanosoma).

Uses

Intercalating agent and fluorescent label for DNA.

Uses

antiprotozoal, intercalcates with DNA

Definition

ChEBI: Ethidium bromide is the organic bromide salt of ethidium. It has a role as a trypanocidal drug, a geroprotector and an intercalator. It contains an ethidium.

Health Hazard

Acute toxic effects from exposure to ethidium bromide have not been thoroughlyinvestigated. Ethidium bromide is irritating to the eyes, skin, mucous membranes,and upper respiratory tract.Although there is no evidence for the carcinogenicity or teratogenicity of thissubstance in humans, ethidium bromide is strongly mutagenic and therefore shouldbe regarded as a possible carcinogen and reproductive toxin

Flammability and Explosibility

Ethidium bromide does not pose a flammability hazard (NFPA rating = 1).

Biochem/physiol Actions

Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.

Safety Profile

Because ethidium bromide can bind with DNA, it is highly toxic as a mutagen. It may potentially cause carcinogenic or teratogenic effects, although no scientific evidence showing either health effect has been found. Exposure routes of ethidium bromide are inhalation, ingestion, and skin absorption. An acute exposure to ethidium bromide causes irritation of the mouth, upper respiratory tract, skin, and eyes.

storage

Because of its mutagenicity, stock solutions of this compound should be prepared in a fume hood, and protective gloves should be worn at all times while handling this substance. Operations capable of generating ethidium bromide dust or aerosols of ethidium bromide solutions should be conducted in a fume hood to prevent exposure by inhalation.

Purification Methods

Crystallise it from MeOH or EtOH [Lamos et al. J Am Chem Soc 108 4278 1986]. Its solubility in H2O is 1%. [Beilstein 22/11 V 352.] POSSIBLE CARCINOGEN.

Incompatibilities

No incompatibilities are known.

Waste Disposal

Excess ethidium bromide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.