5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside

Base Information

• Chemical Name: 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside
• CAS No.: 15548-60-4
• Molecular Formula: C14H15BrClNO6
• Molecular Weight: 408.633
• Hs Code.: 29389090
• European Community (EC) Number: 239-603-0
• DSSTox Substance ID: DTXSID701245955
• Nikkaji Number: J317.907I
• Wikidata: Q27145297
• Mol file: 15548-60-4.mol

Synonyms:5-Br-4-Cl-3-indoxyl-alpha-D-glucoside;5-bromo-4-chloro-3-indolyl-beta-glucoside;5-bromo-4-chloro-3-indoxylglucoside

Chemical Property of 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 4.44E-19mmHg at 25°C
• Melting Point: 249-251 °C
• Refractive Index: 1.731
• Boiling Point: 698 °C at 760 mmHg
• PKA: 12.74±0.70(Predicted)
• Flash Point: 375.9 °C
• PSA: 115.17000
• Density: 1.882 g/cm3
• LogP: 0.76250
• Storage Temp.: −20°C
• Solubility.: DMF: 50 mg/mL, clear, colorless to very faintly yellow
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 406.97713
• Heavy Atom Count: 23
• Complexity: 421

Purity/Quality:

99%, ^*data from raw suppliers

5-Bromo-4-chloro-3-indolyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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
• Uses: Substrate for beta-D-glucosidase

Technology Process of 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside

There total 8 articles about 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(N-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 (15548-60-4,1174456-59-7)

Guidance literature:

With potassium hydroxide; In methanol; at 25 - 28 ℃; for 1h;

DOI:10.1039/c6cc07522c

Reference yield: 25.0%

(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 (15548-60-4,1174456-59-7)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 18h;

Reference yield:

C26H27BrClNO12 (1607828-53-4) → (5-bromo-4-chloroindol-3-yl)-β-D-glucopyranoside (15548-60-4,1174456-59-7)

Guidance literature:

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

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; silver(I) acetate; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1002/ejoc.201301198

upstream raw materials:

C₂₆H₂₇BrClNO₁₂

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

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

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

Downstream raw materials:

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

Refernces

• 1、 -. "Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative". Paragraph 0043; 0044; 0045; 0046. . Retrieved 2017/08/28.