(2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate

Basic Information

View in Editor

CAS Number

15548-60-4

Molecular Formula

C14H14BrClNO6

Molecular Weight

408.63 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Agricultural Chemicals Pesticides Herbicides

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

243°C

Boiling Point

673.9 °C at 760 mmHg

Density

1.882

Flash Point

361.3 °C

Solubility

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

Refractive Index

1.731

Specific Rotation

-81 º (c=1, DMF)

SMILES

View in Editor

C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br

InChI

InChI=1S/C14H14BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-13-12(20)11(19)8(4-18)23-14(13)21/h1-3,8,11-14,17-20H,4H2/q-1/t8-,11-,12+,13-,14-/m1/s1

InChIKey

VFKCDXJDSDJFQU-LNNRFACYSA-N

LogP

0.7624999999999993

Topological Polar Surface Area

115.17000000000002 Å²

Hydrogen Bond Donor/Acceptor

5 / 7

Complexity

421

Synonyms & References

English

CS-0141886
(2S,3R,4S,5S,6R)-2-(5-bromo-4-chloro-1H-indol-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Indoxyl-Glucoside
5-Bromo-4-chloro-3-indolyl beta-D-glucopyranoside, >=97%
5-Br-4-Cl-3-indoxyl-alpha-D-glucoside
5-bromo-4-chloro-3-indolyl beta-glucoside
5-BROMO-4-CHLORO-3-INDOLYLB-D-GLUCOPYRAN OSIDE
EINECS 239-603-0
5-Bromo-4-chloro-3-indolyl beta-D-glucopyranoside
MFCD00063690
5-bromo-4-chloro-3-indolyl-beta-glucoside
(-)-5-BROMO-4-CHLORO-3-INDOLYL BETA-D-GLUCOSIDE
HY-137779
beta-D-Glucopyranoside, 5-bromo-4-chloro-1H-indol-3-yl
15548-60-4
A-D-glucopyranoside
A-D-glucoside
5-Bromo-4-chloro-3-indolyl beta -D-glucopyranoside
X-Glc
5-BROMO-4-CHLORO-3-INDOLYL-beta-D-GLUCOPYRANOSIDE
5-bromo-4-chloro-3-indolyl beta-d-glucoside
5-bromo-4-chloro-1H-indol-3-yl beta-D-glucopyranoside
CHEBI:75424
DTXSID701245955
5-Bromo-4-chloro-3-indolyl
Q27145297
(2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
5-bromo-4-chloro-3-indolyl
5-Bromo-4-chloro-3-indoxylglucoside
AS-11177
(-)-5-bromo-4-chloro-3-indolyl-beta-D-glucoside

MDL Number

MFCD00063690

Customs Code

29389090

FAQ

What are the physical and chemical properties of (2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate (CAS: 15548-60-4)?

The compound is a crystalline solid with a molecular weight of approximately 525.14 g/mol. It has a low solubility in water but is soluble in organic solvents. The compound is reactive towards nucleophiles and can undergo ring-opening reactions. It also shows acidity which can affect its reactivity in aqueous solutions.

How is (2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate (CAS: 15548-60-4) typically synthesized?

This compound is typically synthesized through a multistep process involving the protection of the indole ring, followed by introduction of the bromo and chloro substituents, and subsequent coupling with a tetrahydro-2H-pyran derivative. The synthesis involves the use of protecting groups, such as tert-butyldimethylsilyl (TBS) group, and the use of base catalysts like sodium hydride. The overall yield is moderate, around 50-60%.

What industries use (2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate (CAS: 15548-60-4)?

This compound is primarily used in pharmaceutical research and development, particularly for the synthesis of indole-based drugs. It is also of interest in polymer chemistry for its potential as a monomer and in sensor technology for its ability to interact with specific analytes.

What precautions should be taken when handling (2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate (CAS: 15548-60-4)?

When handling this compound, appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coat should be worn. It should be stored in a cool, dry place away from direct sunlight and heat sources. Spills should be cleaned up with appropriate absorbent materials and disposed of according to local regulations. Always refer to the Safety Data Sheet (SDS) for specific handling and disposal instructions.