|
|
| | 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside Basic information |
| Product Name: | 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside | | Synonyms: | 5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GLUCOPYRANOSIDE (X-GLU);5-BROMO-4-CHLORO-3-INDOLYL-β-D-GLUCOPYRANOSIDE (X-GLC);5-BROMO-4-CHLORO-3-INDOLYL-b-D-GLUCO-PYRANOSIDE (X-GLU) extrapure;X-Glc, X-glucoside;(2S,3R,4S,5S,6R)-2-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol;4-Chloro-5-bromo-1H-indole-3-yl β-D-glucopyranoside;5-Bromo-4-chloro-1H-indol-3-yl β-D-glucopyranoside;5-Bromo-4-chloro-3-indolyl-beta-D-glucoside,98% | | CAS: | 15548-60-4 | | MF: | C14H15BrClNO6 | | MW: | 408.63 | | EINECS: | 239-603-0 | | Product Categories: | substrate | | Mol File: | 15548-60-4.mol |  |
| | 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 Statements | 24/25 | | WGK Germany | 3 | | F | 8-10-21 | | HS Code | 29389090 | | Storage Class | 11 - Combustible Solids |
| | 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 . Method 2: 40 mg of compound 5 was dissolved in 5 mL of methanol, cooled to 0 C in an ice bath, then 5 mL (0.2 mol/L) of methanol solution of sodium methanol was added dropwise and stirred for 3 h at this temperature; at the end of the reaction, the reaction solution was poured into pre-treated cation-exchange resin (pre-treatment method as in section 1.2.1) and stirred slowly for 5~10 min; filtered, rinsed with methanol, the filtrate was evaporated to remove the solvent to obtain 10mg of white solid, i.e., 5-bromo-4-chloro-3-indolyl-beta-D-glucopyranoside, with a yield of 40.3% and a melting point of 82.1C. The reaction was completed by pouring the reaction solution into the pre-treated cation exchange resin (pretreatment method as in section 1.2.1). |
| | 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside Preparation Products And Raw materials |
|