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5-Bromo-4-chloro-3-indolyl beta-D-glucopyranoside

HCID 84982
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Basic information

CAS
15548-60-4
Standard SMILES
OC[C@H]1O[C@@H](Oc2c[nH]c3ccc(Br)c(Cl)c23)[C@H](O)[C@@H](O)[C@@H]1O
InChIKey
OPIFSICVWOWJMJ-LNNRFACYSA-N
Molecular formula
C14H15BrClNO6
Average molar mass
408.63 g/mol
Monoisotopic mass
406.97713

Overview

5-bromo-4-chloro-3-indolyl beta-D-glucoside is 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 the 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. It has a role as a chromogenic compound. It is a beta-D-glucoside, an indolyl carbohydrate, an organochlorine compound, an organobromine compound and a D-aldohexose derivative. It is functionally related to an indoxyl.

Names & identifiers

Preferred name
5-Bromo-4-chloro-3-indolyl beta-D-glucopyranoside
IUPAC
(2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
English name
5-Bromo-4-chloro-3-indolyl-beta-D-glucoside
Molecular formula
C14H15BrClNO6
Molecular weight
408.63

Names & synonyms

15548-60-45-Bromo-4-chloro-3-indolyl beta-D-glucopyranoside5-Bromo-4-chloro-3-indoxylglucosideDTXSID701245955RefChem:533659DTXCID001676806X-GlcX-glucoside5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside(2S,3R,4S,5S,6R)-2-((5-Bromo-4-chloro-1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolMFCD000636905-BROMO-4-CHLORO-3-INDOLYL-beta-D-GLUCOPYRANOSIDE
Show more names
X-GLUGLUC(X-)X-BETA-D-GLCX-BETA-D-GLUCOSIDEX-Glc, X-glucosideX-Gluc(5-Bromo-4-Chloro-3-Indolyl-5-Bromo-4-chloroindolylglucopyranoside
(2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol5-Bromo-4-chloro-3-indolyl |A-D-glucopyranoside5-Bromo-4-chloro-3-indolyl-beta-D-glucosideEINECS 239-603-05-bromo-4-chloro-1H-indol-3-yl beta-D-glucopyranosidebeta-D-Glucopyranoside, 5-bromo-4-chloro-1H-indol-3-yl5-bromo-4-chloro-3-indolyl beta-d-glucoside5-Bromo-4-chloro-3-indoxyl-beta-D-glucopyranoside

Database identifiers

CAS
15548-60-4
PubChem CID
84982
DTXSID
DTXSID701245955
ChEBI
CHEBI:75424
EC Number
239-603-0
Nikkaji
J317.907I

Properties

Computed structural propertiesFilling in

XLogP
1.2
Topological polar surface area
115 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
23
Formal charge
0
Complexity
421

Physicochemical properties

Melting point
249 · 249-251 °C
alpha
-81 · -81 º (c=1, DMF)
Boiling point
673.9 · 673.9±55.0 °C(Predicted)
Density
1.882 · 1.882±0.06 g/cm3(Predicted)
storage temp.
20 °C · −20°C
solubility
50 mg/mL, · DMF: 50 mg/mL, clear, colorless to very faintly yellow
pka
12.74 · 12.74±0.70(Predicted)
form
Crystalline powder
color
White to Light yellow
BRN
1552603 · 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 · 15548-60-4(CAS DataBase Reference)
UNSPSC Code
12352204 · 12352204
NACRES
83 · NA.83
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
24 · 24/25
WGK Germany
3 · 3
F
8 · 8-10-21
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

F
8-10-21
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29389090
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Chemistry & industry

Applications

UsesSubstrate for beta-D-glucosidase

Additional notes · 1 item

DefinitionChEBI: 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.

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