5-Bromo-4-chloro-3-indolyl beta-galactoside

Base Information

• Chemical Name: 5-Bromo-4-chloro-3-indolyl beta-galactoside
• CAS No.: 7240-90-6
• Molecular Formula: C14H14BrClNO6
• Molecular Weight: 408.633
• Hs Code.: 2934999090
• European Community (EC) Number: 230-640-8
• UNII: V595OG374W
• Nikkaji Number: J212.257J
• Wikipedia: X-gal
• Wikidata: Q238475
• ChEMBL ID: CHEMBL1242856
• Mol file: 7240-90-6.mol

Synonyms:5-bromo-4-chloro-3-indolyl beta-galactoside;5-bromo-4-chloro-3-indolyl-beta D-galactopyranoside;5-bromo-4-chloro-3-indolyl-beta-D-galactoside;X-gal

Chemical Property of 5-Bromo-4-chloro-3-indolyl beta-galactoside

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.44E-19mmHg at 25°C
• Melting Point: 230 °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: 1.882g/cm3
• LogP: 0.76250
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Soluble in 100 mM in DMSO.
• 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

X-Gal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• 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: A substrate for β-Galactosidase that is converted by the enzyme into an intense indigo-blue chromophore (615 nm). magenta b-galactosidase substrate A substrate for -Galactosidase that is converted by the enzyme into an intense indigo-blue chromophore (615 nm) In histochemical staining, in blue-white selection of bacterial colonies with lacZ gene activity during cloning experiments.

Technology Process of 5-Bromo-4-chloro-3-indolyl beta-galactoside

There total 17 articles about 5-Bromo-4-chloro-3-indolyl beta-galactoside 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: 87.0%

(N-acetyl-5-bromo-4-chloro-indol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (125328-75-8) → 5-bromo-4-chloro-3-indolyl β-D-galactopyranoside (7240-90-6,1174456-59-7)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1002/ejoc.201301198

Reference yield:

N-acetyl-5-bromo-6-chloroanthranilic acid (125328-77-0) → 5-bromo-4-chloro-3-indolyl β-D-galactopyranoside (7240-90-6,1174456-59-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydroxide; water / 4 h / Reflux

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

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

3.2: Inert atmosphere

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

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

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

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

8.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C

9.1: sodium methylate / methanol / 20 °C

With morpholine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; water; sodium methylate; silver(I) acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 5.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.201301198

Reference yield:

2-amino-5-bromo-6-chlorobenzoic acid (3030-19-1) → 5-bromo-4-chloro-3-indolyl β-D-galactopyranoside (7240-90-6,1174456-59-7)

Guidance literature:

Multi-step reaction with 8 steps

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

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

2.2: Inert atmosphere

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

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

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

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

7.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C

8.1: sodium methylate / methanol / 20 °C

With morpholine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; sodium methylate; silver(I) acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.201301198

upstream raw materials:

N-acetyl-5-bromo-6-chloroanthranilic acid

2-amino-5-bromo-6-chlorobenzoic acid

5-bromo-4-chloroindoxylic acid allyl ester

5-bromo-6-chloro-isatoic anhydride

Downstream raw materials:

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

D-Galactose

5-bromo-4-chloro-3-hydroxyindole

Refernces

• 1、 -. "Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative". Paragraph 0054; 0055; 0056; 0057. . Retrieved 2017/08/28.
• 2、 Reyes Martinez, Juana Elizabeth,Sardzik, Robert,Voglmeir, Josef,Flitsch, Sabine L.. "Enzymatic synthesis of colorimetric substrates to determine α-2,3- and α-2,6-specific neuraminidase activity". . p. 21335 - 21338. Retrieved 2013/11/06.