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

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

 EINECS 239-603-0
CAS No. 15548-60-4 Density 1.882 g/cm3
PSA 115.17000 LogP 0.76250
Solubility N/A 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 N/A Appearance white to off-white powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 15548-60-4 (5-Bromo-4-chloro-3-indolyl-beta-D-glucoside) Hazard Symbols N/A
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;

Article Data 4

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

Product Name: beta-D-Glucopyranoside,5-bromo-4-chloro-1H-indol-3-yl (CAS NO.15548-60-4)

Molecular Formula: C14H15BrClNO6
Molecular Weight: 408.63g/mol
Mol File: 15548-60-4.mol
EINECS: 239-603-0
Appearance: white to off-white powder
Melting Point: 249-251 °C
Flash Point: 375.9 °C 
Enthalpy of Vaporization: 107.33 kJ/mol 
Boiling Point: 698 °C at 760 mmHg 
Vapour Pressure: 1.89E-20 mmHg at 25°C 
XLogP3-AA: 1.2
H-Bond Donor: 5
H-Bond Acceptor: 6
Structure Descriptors of beta-D-Glucopyranoside,5-bromo-4-chloro-1H-indol-3-yl (CAS NO.15548-60-4):
  IUPAC Name: (2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  Canonical SMILES: C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br
  Isomeric SMILES: C1=CC(=C(C2=C1NC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl)Br
  InChI: InChI=1S/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 
  InChIKey: OPIFSICVWOWJMJ-LNNRFACYSA-N

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

Safety Information of beta-D-Glucopyranoside,5-bromo-4-chloro-1H-indol-3-yl (CAS NO.15548-60-4):
Safety Statements: 24/25 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
F: 8-10-21

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

 beta-D-Glucopyranoside,5-bromo-4-chloro-1H-indol-3-yl , its CAS NO. is 15548-60-4, the synonyms are  5-Bromo-4-chloro-3-indoxylglucoside ; 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside .

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