• Name

  5-Bromo-4-chloro-3-indolyl-beta-D-glucoside

• EINECS 239-603-0
• CAS No. 15548-60-4
• Article Data4
• CAS DataBase
• Density 1.882 g/cm3
• Solubility
• Melting Point 249-251 °C
• Formula C₁₄H₁₅BrClNO₆
• Boiling Point 698 °C at 760 mmHg
• Molecular Weight 408.633
• Flash Point 375.9 °C
• Transport Information
• Appearance white to off-white powder
• Safety 24/25
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Indole,5-bromo-4-chloro-3-(b-D-glucopyranosyloxy)- (7CI,8CI);4-Chloro-5-bromo-3-indolyl-b-D-glucoside;5-Bromo-4-chloro-3-indolyl b-D-glucopyranoside;5-Bromo-4-chloro-3-indolyl b-D-glucoside;X-Glucoside;
• PSA 115.17000
• LogP 0.76250

Synthetic route

125328-74-7

(1-acetyl-5-bromo-4-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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%

3252-36-6

(5-bromo-4-chloroindol-3-yl) acetate

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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

1607828-53-4

C26H27BrClNO12

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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

116270-39-4

1-acetyl-5-bromo-4-chloroindolin-3-one

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

15548-60-4

(5-bromo-4-chloroindol-3-yl) β-D-glucopyranoside

Conditions

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

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside Chemical Properties

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside Safety Profile

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside Specification