15548-60-4

Basic information

• Product Name: 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside
• Synonyms: GLUC(X-);5-BROMO-4-CHLORO-3-INDOXYL-BETA-D-GLUCOPYRANOSIDE;5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GLUCOPYRANOSIDE;5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GLUCOSIDE;X-BETA-D-GLUCOSIDE;X-BETA-D-GLC;X-GLC;X-GLU
• CAS NO: 15548-60-4
• Molecular Formula: C₁₄H₁₅BrClNO₆
• Molecular Weight: 408.63
• EINECS: 239-603-0
• Product Categories: substrate
• Mol File: 15548-60-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 249-251 °C
• Boiling Point: 698 °C at 760 mmHg
• Flash Point: 375.9 °C
• Appearance: white to off-white powder
• Density: 1.882 g/cm3
• Vapor Pressure: 4.44E-19mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: −20°C
• Solubility: DMF: 50 mg/mL, clear, colorless to very faintly yellow
• PKA: 12.74±0.70(Predicted)
• BRN: 1552603
• CAS DataBase Reference: 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside(15548-60-4)
• EPA Substance Registry System: 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside(15548-60-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 15548-60-4(Hazardous Substances Data)

Usage

Description

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside, also known as X-Glc, is an indolyl carbohydrate that is the beta-D-glucoside of 3-hydroxy-1H-indole. It is characterized by the presence of chlorine and bromine substitutions at positions 4 and 5 of the indole moiety, respectively. 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside is a white to off-white powder and is primarily used as a substrate for the detection and measurement of beta-D-glucosidase enzyme activity.

Uses

1. Used in Enzyme Assays:
5-Bromo-4-chloro-3-indolyl-beta-D-glucoside is used as a substrate for beta-D-glucosidase enzyme assays. The application reason is that when the enzyme cleaves the glycosidic bond, it generates 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerizes to form an intensely blue product. This color change allows for the detection and quantification of beta-D-glucosidase activity in various samples.
2. Used in Research and Diagnostics:
In the field of research and diagnostics, 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside is used as a tool to study the presence and activity of beta-D-glucosidase. This enzyme plays a crucial role in the breakdown of glucosides, and its activity can be indicative of certain metabolic processes or conditions. The compound's ability to produce a visible color change upon enzyme interaction makes it a valuable tool for researchers and diagnosticians.
3. Used in Pharmaceutical Development:
5-Bromo-4-chloro-3-indolyl-beta-D-glucoside may also be utilized in the development of pharmaceuticals targeting beta-D-glucosidase or related enzymes. By understanding the compound's interaction with the enzyme, researchers can potentially design drugs that modulate enzyme activity, leading to therapeutic benefits in various conditions.
4. Used in Environmental Testing:
In environmental testing, 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside can be employed to assess the presence and activity of beta-D-glucosidase in soil, water, or other samples. This information can be valuable for understanding the ecological balance and the role of this enzyme in natural processes.
5. Used in Food Industry:
In the food industry, 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside may be used to evaluate the activity of beta-D-glucosidase in various food products, such as wine, cheese, or fermented beverages. This can help in optimizing the fermentation process and improving the quality of the final product.

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-/m0/s1

Synthetic route

(1-acetyl-5-bromo-4-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (125328-74-7) → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
With potassium hydroxide In methanol at 25 - 28℃; for 1h;	89%
With potassium hydroxide In methanol at 20℃; for 1h;	89%
With sodium methylate In methanol at 20℃;	75%

(5-bromo-4-chloroindol-3-yl) acetate (3252-36-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
With sodium methylate In methanol at 0℃; for 18h;	25%

C26H27BrClNO12 (1607828-53-4) → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); morpholine / tetrahydrofuran / 20 °C 2: potassium carbonate; silver(I) acetate / 0.58 h / 105 °C 3: sodium methylate / methanol / 20 °C View Scheme

C23H23BrClNO12 → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; silver(I) acetate / 0.58 h / 105 °C 2: sodium methylate / methanol / 20 °C View Scheme

C16H17BrClNO8 → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 40 - 45 °C 2: potassium carbonate; silver(I) acetate / 1 h / 110 °C 3: sodium methylate / methanol / 20 °C View Scheme

C15H15BrClNO8 → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; silver(I) acetate / 1 h / 110 °C 2: sodium methylate / methanol / 20 °C View Scheme

1-acetyl-5-bromo-4-chloroindolin-3-one (116270-39-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside (15548-60-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide / dichloromethane / 0.17 h / 25 - 28 °C / Inert atmosphere 1.2: 3 h / 25 - 28 °C / Inert atmosphere 2.1: potassium hydroxide / methanol / 1 h / 25 - 28 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetra(n-butyl)ammonium hydrogensulfate; potassium phosphate / water-d2; dichloromethane / 0.17 h / 20 °C / Inert atmosphere 1.2: 10 h 2.1: potassium hydroxide / methanol / 1 h / 20 °C View Scheme

Upstream product

• 3252-36-6 (5-bromo-4-chloroindol-3-yl) acetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 125328-74-7 (N-acetyl-5-bromo-4-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1607828-53-4 C₂₆H₂₇BrClNO₁₂ 
• 116270-39-4 1-acetyl-5-bromo-4-chloroindolin-3-one 

Downstream Products

• 29245-44-1 5,5'-dibromo-4,4'-dichloro-1H,1'H-[2,2']biindolylidene-3,3'-dione 

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