1464-11-5

Basic information

• Product Name: 4-BENZYLOXY-3-INDOLEACETONITRILE
• Synonyms: 4-BENZYLOXY-3-INDOLEACETONITRILE;4-BENZYLOXY-3-INDOLYL ACETONITRILE;4-BENZYLOXYINDOLE-3-ACETONITRILE;4-(PhenylMethoxy)-1H-indole-3-acetonitrile;2-(4-(Benzyloxy)-1H-indol-3-yl)acetonitrile
• CAS NO: 1464-11-5
• Molecular Formula: C₁₇H₁₄N₂O
• Molecular Weight: 262.31
• Product Categories: Aromatics;Indole Derivative;Intermediates
• Mol File: 1464-11-5.mol

Chemical Properties

• Melting Point: 97-100 °C
• Boiling Point: 502.331 °C at 760 mmHg
• Flash Point: 257.601 °C
• Appearance: Light brown solid
• Density: 1.233 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: 2-8°C
• Solubility: DCM, Ethyl Acetate,
• PKA: 16.48±0.30(Predicted)
• CAS DataBase Reference: 4-BENZYLOXY-3-INDOLEACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-3-INDOLEACETONITRILE(1464-11-5)
• EPA Substance Registry System: 4-BENZYLOXY-3-INDOLEACETONITRILE(1464-11-5)

Safety Data

• Hazardous Substances Data: 1464-11-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZYLOXY-3-INDOLEACETONITRILE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, particularly the neurotransmitter agonist 4-Hydroxytryptamine Creatinine. Its role in the synthesis process is crucial for the development of medications targeting neurological and psychiatric disorders.
Used in Chemical Research:
As a tryptamine derivative, 4-BENZYLOXY-3-INDOLEACETONITRILE is also utilized in chemical research for the exploration of new compounds and their potential applications in various fields, including medicine, agriculture, and materials science. Its unique chemical properties make it a valuable component in the development of novel substances with specific functionalities.

InChI:InChI=1/C17H14N2O/c18-10-9-14-11-19-15-7-4-8-16(17(14)15)20-12-13-5-2-1-3-6-13/h1-8,11,19H,9,12H2

Upstream product

• 7042-71-9 4-benzyloxyindole-3-carbaldehyde 
• 143-33-9 sodium cyanide 
• 39731-09-4 4-benzyloxylindole-2-carboxylic acid 
• 773837-37-9 sodium cyanide 
• 100-44-7 benzyl chloride 
• 20876-37-3 2-benzyloxy-6-nitrotoluene 
• 100-39-0 benzyl bromide 
• 20289-26-3 4-benzyloxy-1H-indole 
• 2380-94-1 1H-indol-4-ol 
• 13523-95-0 4-benzyloxy-3-dimethylaminomethylindole 

Downstream Products

• 109249-04-9 2-(4-(benzyloxy)-1H-indol-3-yl)ethanamine 
• 1464-12-6 2-(4-(benzyloxy)-1H-indol-3-yl)acetic acid 
• 118573-52-7 4-hydroxyindole-3-acetonirile 
• 1748-42-1 (4-benzyloxy-indol-3-yl)-acetic acid ethylamide 
• 1467-95-4 ethyl-[2-(4-benzyloxy-indol-3-yl)-ethyl]-amine 
• 1464-13-7 (4-benzyloxy-indol-3-yl)-acetic acid methylamide 
• 1748-41-0 2-(4-(benzyloxy)-1H-indol-3-yl)-N-methylethan-1-amine 
• 404887-95-2 4-benzyloxy-7-bromoindole-3-acetonitrile 
• 152916-20-6 25-<4-benzyloxy-1H-indol-3-yl>-2,2-dimethyl-4,24-dioxo-3-oxa-5,9,13,17,23-pentaazapentacosane-9,13-dicarboxylic acid bis(1,1-dimethylethyl) ester 
• 144923-49-9 N-(5-{3-[3-(3-Amino-propylamino)-propylamino]-propylamino}-pentyl)-2-(4-benzyloxy-1H-indol-3-yl)-acetamide 
• 144923-56-8 4-Nitrophenyl <(4-Benzyloxy)-1H-indol-3-yl>acetate 
• 404888-07-9 4-benzyloxy-7-bromotryptamine 

Relevant articles and documents

Simple one step syntheses of indole-3-acetonitriles from indole-3-carboxaldehydes

One step conversion method of indole-3-carboxaldehydes into indole-3-acetonitriles is developed. Applying the method, 4-nitro- (7 a), 4-phenyl-(7 b), 4-iodo- (7 c), 4-methoxy- (7 d), and 4-benzyloxyindole-3-acetonitrile (7 e) are available in two steps from indole-3-carboxaldehyde (4).

Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE2 productions and was less cytotoxic than arvelexin on macrophage cells.

Facile synthesis of 6-hydroxyindole-3-acetic acid: On the structure of the aromatic subunit of nephilatoxin-1~6

A facile synthesis of 6-hydroxyindole-3-acetic acid 1a, which is the proposed aromatic subunit of NPTX-1~6, is described. Radical cyclization of isonitrile 2 successfully afforded 9 in high yield. The aromatic subunit of NPTX-1~6 was confirmed as 4-hydroxyindole-3-acetic acid 12 by comparison of the 1H-NMR spectra with those of authentic 4- and 6-hydroxyindole-3-acetic acids.

Characterization and synthesis of a new calcium antagonist from the venom of a fishing spider

A new calcium antagonist, CNS 2103, is isolated from the venom of a fishing spider, Dolomedes okefinokensis. The structure of this compound is derived from spectroscopic data, including tandem mass spectrometry. A flexible, convergent synthesis of CNS 2103 is described.