CAS 2436-17-1

5-Methoxy-3-indolylacetonitrile

Description:

5-Methoxy-3-indolylacetonitrile, with the CAS number 2436-17-1, is a chemical compound that features an indole structure, which is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring. This compound is characterized by the presence of a methoxy group (-OCH3) at the 5-position of the indole ring and an acetonitrile group (-C≡N) at the 3-position. The methoxy group contributes to the compound's polarity and can influence its reactivity and solubility in various solvents. The acetonitrile moiety introduces a nitrile functional group, which is known for its ability to participate in nucleophilic reactions and can serve as a versatile building block in organic synthesis. 5-Methoxy-3-indolylacetonitrile may exhibit biological activity, making it of interest in medicinal chemistry and pharmacology. Its properties, such as melting point, boiling point, and solubility, can vary based on the specific conditions and purity of the sample.

Formula: C₁₁H₁₀N₂O

InChI: InChI=1/C11H10N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4H2,1H3

SMILES: COc1ccc2c(c1)c(CC#N)c[nH]2

Synonyms:

• 5-Methoxyindole-3-acetonitrile
• (5-methoxy-1H-indol-3-yl)acetonitrile

2-(5-methoxy-1H-indol-3-yl)acetonitrile

CAS: 2436-17-1

Formula: C₁₁H₁₀N₂O

Purity: 98%

Color and Shape: Solid

Molecular weight: 186.2099

Ref: IN-DA006W7A

5-Methoxyindole-3-acetonitrile

CAS: 2436-17-1

Ref: 7W-GK1206

(5-Methoxy-1H-indol-3-yl)acetonitrile

CAS: 2436-17-1

(5-Methoxy-1H-indol-3-yl)acetonitrile

Purity: ≥95%

Color and Shape: Beige Solid

Molecular weight: 186.21g/mol

Ref: 54-OR8748

5-Methoxyindole-3-acetonitrile

CAS: 2436-17-1

5-Methoxyindole-3-acetonitrile is a synthetic compound used as a reference for the synthesis of melatonin. It is produced by the addition of magnesium to 5-methoxyindole, followed by reaction with cyanide and nitrile. The synthesis of this compound was first published in 1938 and has since been used as a reference for many other studies. It has been shown that 5-methoxyindole-3-acetonitrile has high performance liquid chromatography properties, with a linear range from 0.5 to 50 mg/mL and an ultraviolet spectrum that falls within the region between 220 nm and 400 nm. A molecular modeling study was conducted on this compound, which showed that it conforms with 4-hydroxy indole ring systems found in natural products such as tryptophan and serotonin. This product also has fluorescent properties, which are caused by its electron withdrawing group (cyano).

Formula: C₁₁H₁₀N₂O

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 186.21 g/mol

Ref: 3D-FM38506

5-Methoxyindole-3-acetonitrile-d2

Controlled Product

CAS: 2436-17-1

Applications 5-Methoxyindole-3-acetonitrile-d2 is a labelled analogue of 5-Methoxyindole-3-acetonitrile (M262818), which is a versatile reactant used in the preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatment. It is also used in the synthesis of carboline analogs as potent MAPKAP-K2 inhibitors. 5-Methoxyindole-3-acetonitrile-d2 is also an intermediate in synthesizing Melatonin-d4 (M215002), a hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death of cancer cells. Inhibits proliferation/metastasis of breast cancer cells by inhibiting estrogen re
References Barchas, et al.: Nature, 214, 919 (1967); Glass, J.D., et al.: Science, 214, 821 (1981)

Formula: C₁₁D₂H₈N₂O

Color and Shape: Neat

Molecular weight: 188.222

Ref: TR-M262819

5-METHOXYINDOLE-3-ACETONITRILE

CAS: 2436-17-1

Formula: C₁₁H₁₀N₂O

Purity: 98%

Color and Shape: Solid

Molecular weight: 186.214

Ref: 10-F386808

5-Methoxyindole-3-acetonitrile

Controlled Product

CAS: 2436-17-1

Applications 5-Methoxyindole-3-acetonitrile is a versatile reactant used in the preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatment. It is also used in the synthesis of carboline analogs as potent MAPKAP-K2 inhibitors.
References Van Zandt, M., et al.: J. Med. Chem., 48, 3141 (2005); Wu, J., et al.: Bioorg. Med. Chem. Lett., 17, 4664 (2007);

Formula: C₁₁H₁₀N₂O

Color and Shape: Neat

Molecular weight: 186.21

Ref: TR-M262818

5-Methoxyindole-3-acetonitrile

CAS: 2436-17-1

5-Methoxyindole-3-acetonitrile is a versatile building block that can be used for the synthesis of complex compounds. It is a fine chemical that is not commercially available and is sold at high prices as a research chemical. 5-Methoxyindole-3-acetonitrile has been used as a reagent in the synthesis of some pharmaceuticals, such as beta blockers. This compound also has been researched for its potential use as an intermediate in organic syntheses and reactions, including those involving peptides and proteins. The versatility of this chemical makes it useful for the construction of new molecules with medicinal properties.

Formula: C₁₁H₁₀N₂O

Molecular weight: 186.22 g/mol

Ref: 3D-M-3480

Melatonin Impurity 1

CAS: 2436-17-1

Formula: C₁₁H₁₀N₂O

Molecular weight: 186.21

Ref: ST-EA-CP-M166004