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

Melting point:

249-251 °C

alpha 

-81 º (c=1, DMF)

Boiling point:

673.9±55.0 °C(Predicted)

Density 

1.882±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

DMF: 50 mg/mL, clear, colorless to very faintly yellow

pka

12.74±0.70(Predicted)

form 

Crystalline powder

color 

White to Light yellow

BRN 

1552603

InChI

InChI=1/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-/s3

InChIKey

OPIFSICVWOWJMJ-OTXFOCTGSA-N

SMILES

C12C(Cl)=C(C=CC=1NC=C2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)Br |&1:11,12,14,15,17,r|

CAS DataBase Reference

15548-60-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

8-10-21

HS Code 

29389090

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:5-Bromo-4-chloro-3-indolyl-beta-D-glucopyranoside
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

Substrate for beta-D-glucosidase

Definition

ChEBI: An indolyl carbohydrate that is the beta-D-glucoside of 3-hydroxy-1H-indole in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for th presence of an enzyme, beta-glucosidase, which cleaves the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerises to give an intensely blue product.

Synthesis

Method 1: Take 5-bromo-4-chloro-3-indolyl-2,3,4,6-tetra-O-acetyl-??-D-glucopyranoside dissolved in 15mL of methanol and cooled to 0?? in an ice bath; then add 3mL (0.5 mol/L) of sodium methanol methanol solution dropwise and stirred for 5h at this temperature; at the end of the reaction, the reaction solution was poured into pre-treated cationic exchange resin (cationic). After the reaction, the reaction solution was poured into the pre-treated cation exchange resin (pretreatment method of the resin: firstly, rinse the resin with water; then soak it in 5% hydrochloric acid for about 4h, and wash it to neutral; then soak it in 5% sodium hydroxide solution for about 4h, and wash it to neutral; finally, soak it in 5% hydrochloric acid for 4h, and wash it to neutral), and then it was slowly stirred for 5-10min, and then filtered, and then rinsed by methanol, and then the filtrate was evaporated and removed the solvent, and it was obtained as 0.49g of white solid 5-bromo-4-chloro-3-beta-indolyl-beta-indoline-3-beta-indole. -indolyl-beta-D-glucopyranoside, yield 81.6%, melting point 86.5 ??.

5-Bromo-4-chloro-3-indolyl-beta-D-glucoside(15548-60-4)Related Product Information

• Ascorbyl glucoside
• Indometacin
• Indole-3-acetic acid
• Tetrahydro-4H-pyran-4-one
• Tetrahydropyran
• Decyl glucoside
• 2-acetamido-2-deoxy-4-O-A-L-*fucopyranosyl-D-gluc
• Difluorochloromethane
• 4,6-diamino-2-hydroxy-1,3-cyclohexane3,6’diamino-3,6’-dideoxydi-alpha-d-glu
• Podophyllotoxin
• (6-Chloro-3-indolyl)-β-D-glucuronide cyclohexylammonium salt
• 2-acetamido-2-deoxy-6-O-(beta-D-galactopyranosyl)-D-gluc..
• N,N',N'',N''',N'''',N'''''-Hexaacetylchitohexaose
• Ginsenoside Rg3
• Bromine
• 5-Bromo-4-chloro-3-indolyl-beta-D-glucuronide cyclohexylammonium salt
• X-GLUC, NA,X-GLUC SODIUM SALT,X-GlcA CHA salt, X-Gluc CHA salt,X-GlcA Na salt, X-Gluc Na salt
• 2-ACETAMIDO-1-AZIDO-1-2-DIDEOXY-B-D-GLUC OPYRANOSE