5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE

Base Information

• Chemical Name: 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE
• CAS No.: 198402-60-7
• Molecular Formula: C₁₄H₁₅BrClNO₆
• Molecular Weight: 408.633
• Hs Code.: 2938909090
• Mol file: 198402-60-7.mol

Synonyms:5-Bromo-6-chloro-3- indolyl-α-D- galactopyranoside;

Chemical Property of 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 4.44E-19mmHg at 25°C
• Refractive Index: 1.731
• Boiling Point: 673.9 °C at 760 mmHg
• Flash Point: 361.3 °C
• Density: 1.882 g/cm³

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-6-chloro-3-indolyl a-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE

There total 14 articles about 5-BROMO-6-CHLORO-3-INDOXYL-ALPHA-D-GALACTOPYRANOSIDE 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: 99.0%

(N-acetyl-5-bromo-6-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (96414-42-5) → (5-bromo-6-chloroindol-3-yl)-β-D-galactopyranoside (93863-88-8,198402-60-7,878495-64-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1002/ejoc.201301198

Reference yield:

N-(4-bromo-5-chloro-2-methylphenyl)-acetamide (1607828-43-2) → (5-bromo-6-chloroindol-3-yl)-β-D-galactopyranoside (93863-88-8,198402-60-7,878495-64-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux

2.1: sodium hydroxide; water / 4 h / Reflux

3.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice

4.2: Inert atmosphere

5.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere

6.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

7.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C

9.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 95 °C

10.1: sodium methylate / methanol / 20 °C

With morpholine; pyridine; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; water; sodium methylate; silver(I) acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; magnesium sulfate; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 6.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.201301198

Reference yield:

N-(5-chloro-2-methylphenyl)acetamide (5900-55-0) → (5-bromo-6-chloroindol-3-yl)-β-D-galactopyranoside (93863-88-8,198402-60-7,878495-64-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: bromine / acetic acid / 5 h / 20 °C / Cooling with ice

2.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux

3.1: sodium hydroxide; water / 4 h / Reflux

4.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice

5.2: Inert atmosphere

6.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere

7.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

8.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C

10.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 95 °C

11.1: sodium methylate / methanol / 20 °C

With morpholine; pyridine; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; water; bromine; sodium methylate; silver(I) acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; magnesium sulfate; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 7.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.201301198

upstream raw materials:

N-(4-bromo-5-chloro-2-methylphenyl)-acetamide

N-(5-chloro-2-methylphenyl)acetamide

N-acetyl-5-bromo-4-chloroanthranilic acid

2-amino-5-bromo-4-chlorobenzene carboxylic acid

Refernces

• 1、 -. "Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative". Paragraph 0059; 0060; 0066; 0067; 0068; 0069. . Retrieved 2017/08/28.