7240-90-6

Basic information

• Product Name: 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside
• Synonyms: BCIG;5-BROMO-4-CHLORO-1H-INDOL-3-YL BETA-D-GALACTOPYRANOSIDE;5-BROMO-4-CHLORO-1H-INDOL-3-YL BETA-D-GALACTOSIDE-(1,5);5-BROMO-4-CHLORO-3-INDOLYL-B B-D-GALACTOPYRANOSIDE;5-BROMO-4-CHLORO-3-INDOLYL-B-D-GALACTOPYRANOSIDE;5'-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GALACTO-PYRANOSIDE;5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE;5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE (X-GAL)
• CAS NO: 7240-90-6
• Molecular Formula: C₁₄H₁₅BrClNO₆
• Molecular Weight: 408.63
• EINECS: 230-640-8
• Product Categories: Enzyme substrates;Carbohydrates & Derivatives;Fluorescent Labels & Indicators;Labeling and Diagnostics Reagents;substrate
• Mol File: 7240-90-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 230 °C
• Boiling Point: 698 °C at 760 mmHg
• Flash Point: 375.9 °C
• Appearance: White/Powder
• Density: 1.5563 (rough estimate)
• Vapor Pressure: 4.44E-19mmHg at 25°C
• Refractive Index: 1.6110 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in 100 mM in DMSO.
• PKA: 12.74±0.70(Predicted)
• Sensitive: Moisture & Light Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,10074
• BRN: 1402009
• CAS DataBase Reference: 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside(7240-90-6)
• EPA Substance Registry System: 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside(7240-90-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• F: 8-10-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 7240-90-6(Hazardous Substances Data)

Usage

Description

5-Bromo-4-chloro-3-indolyl-beta-D-galactoside is a synthetic substrate for β-galactosidase, an enzyme involved in the metabolism of lactose. It is a colorless compound that, upon enzymatic conversion by β-galactosidase, forms an intense indigo-blue chromophore with a maximum absorption at 615 nm. This property makes it a useful tool in various applications, particularly in the field of molecular biology and microbiology.

Uses

Used in Molecular Biology:
5-Bromo-4-chloro-3-indolyl-beta-D-galactoside is used as a substrate for β-galactosidase in molecular biology applications. It serves as a colorimetric indicator of enzyme activity, allowing for the detection and quantification of β-galactosidase expression in various systems.
Used in Microbiology:
In microbiology, 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside is used as a substrate for β-galactosidase in the blue-white selection of bacterial colonies with lacZ gene activity during cloning experiments. This method helps in the identification of successfully transformed colonies, streamlining the cloning process.
Used as a magenta β-galactosidase substrate:
5-Bromo-4-chloro-3-indolyl-beta-D-galactoside is also used as a magenta β-galactosidase substrate, providing an alternative color reaction for the detection of β-galactosidase activity. This can be useful in certain applications where the indigo-blue color may interfere with other experimental procedures or when a different color indicator is desired.
Overall, 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside is a versatile compound with applications in molecular biology and microbiology, primarily as a substrate for β-galactosidase to detect and quantify enzyme activity, as well as in the blue-white selection of bacterial colonies during cloning experiments.

InChI:InChI=1/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11+,12+,13-,14-/m1/s1

Upstream product

• 125328-80-5 N-(4-bromo-3-chloro-2-methylphenyl)acetamide 
• 627531-47-9 4-amino-2-chloro-3-methylbromobenzene 
• 125328-75-8 (N-acetyl-5-bromo-4-chloro-indol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 1607828-55-6 C₂₆H₂₇BrClNO₁₂ 
• 1447125-25-8 C₁₅H₁₅BrClNO₄ 
• 1447125-22-5 C₁₃H₉BrClNO₅ 
• 943138-45-2 5-bromo-6-chloro-isatoic anhydride 
• 1447125-28-1 5-bromo-4-chloroindoxylic acid allyl ester 
• 3030-19-1 2-amino-5-bromo-6-chlorobenzoic acid 
• 125328-77-0 N-acetyl-5-bromo-6-chloroanthranilic acid 
• 116270-39-4 1-acetyl-5-bromo-4-chloroindolin-3-one 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 29245-44-1 5,5'-dibromo-4,4'-dichloro-1H,1'H-[2,2']biindolylidene-3,3'-dione 
• 59-23-4 D-Galactose 
• 117887-41-9 5-bromo-4-chloro-3-hydroxyindole 

Relevant articles and documents

Synthesis of precipitating chromogenic/fluorogenic β-glucosidase/β-galactosidase substrates by a new method and their application in the visual detection of foodborne pathogenic bacteria

We developed a new efficient method for the synthesis of important indoxyl glycoside substrates for β-glucosidase and β-galactosidase by using 1-acetylindol-3-ones as intermediates. This method was used to synthesise novel precipitating fluorogenic substrates for β-glucosidase based on 2-(benzothiazol-2′-yl)-phenols. We also assessed the application of these substrates in the detection of foodborne pathogenic bacteria.

Indoxylic acid esters as convenient intermediates towards indoxyl glycosides

Indoxylic acid methyl and allyl esters with varied halide-substitution patterns were obtained in excellent yields using a scalable route. Phase-transfer glycosylation of these key intermediates was carried out with various glycosyl halides. Subsequent mild silver-mediated decarboxylation followed by Zemplen deacetylation led to indoxyl glycosides in good overall yields. Indoxyl glycosides are well-established and widely used tools for enzyme screening and enzyme-activity monitoring. In the past, their synthesis has been difficult, so this new approach has led to a variety of useful structures. Indoxyl glycosides with varied halide-substitution patterns were synthesized using indoxylic acid esters as key intermediates. Glycosylation under phase-transfer conditions, ester cleavage, and mild decarboxylation led to the indoxyl glycosides in good yields. This approach enables access to a number of different indoxyl compounds. Copyright

Novel alizarin-based chromogenic substrates, their uses and composition containing same

The invention concerns a novel chromogenic substrate based on Alizarin. The invention also concerns the uses to which this substrate can be put, and a formulation containing such a substrate. It consists therefore of a substrate to detect the presence of an enzyme activity, with the following general formula: in which: the two ketone groups of the central ring can be replaced by one group R11 (in the upper position), and by OH (in the lower position). R1 is a target part or H, and R2 is a target part or H, with at least one out of R1 and R2 being a target part, R3 is H, SO3H, Cl, Br, F, I, NO2, NH2, NR9R10, or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an a-amino acid residue such as Alanine, R4 is H, SO3H, Cl, Br, F, I, NO2, NH2, NR9R10, OH or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an α-amino acid such as Alanine, according to a modification, R3 and R4 form bonds with one another to create a ring with at least five sides, and preferably six sides. R5, R6, R7 and R8 each consist of one of the following atoms or groups of atoms: H, a halogen (particularly Cl or Br), OH, SO3H, or an Alkyl or Alkoxy group, and R9 a R10 are independently a Methyl, Alkyl, Aryl, Aralkyl group, or one (either R9 or R10) is a ring structure (Piperidine, Pyrrolidine, Morpholine, etc.) with the other (either R10 or R9) being a Hydrogen atom. The invention is particularly applicable in the field of diagnosis.