405873-05-4

Basic information

• Product Name: (3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE
• Synonyms: (R)-3-(1-METHYL-1H-INDOL-3-YL)-BUTANAL;(3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE;(3R)-(-)-3-(1-Methyl-1H-indol-3-yl)butyraldehyde;(3R)-(-)-3-(1-Methyl-1H-indol-3-yl)butyraldehyde 98%
• CAS NO: 405873-05-4
• Molecular Formula: C13H15NO
• Molecular Weight: 201.26
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Indoles;Aldehydes;Asymmetric Synthesis;Building Blocks;C13-C60;Carbonyl Compounds;Chemical Synthesis;Chiral Building Blocks;Heterocyclic Building Blocks;Organic Building Blocks
• Mol File: 405873-05-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 55.5-59.5 °C(lit.)
• Appearance: /
• CAS DataBase Reference: (3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE(405873-05-4)
• EPA Substance Registry System: (3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE(405873-05-4)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-37/38-41-42/43-36/37/38-25
• Safety Statements: 26-36-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 405873-05-4(Hazardous Substances Data)

Usage

Description

(3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE is a chiral compound characterized by its specific stereochemistry, with the R-configuration at the 3-position and a 1-methyl-1H-indol-3-yl group attached to the butyraldehyde moiety. This unique structure endows it with potential applications in various fields, particularly in the synthesis of complex organic molecules.

Uses

Used in Pharmaceutical Industry:
(3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE is used as a synthetic intermediate for the preparation of tricyclic steroid precursors, which are essential in the development of various pharmaceutical compounds. Its chiral nature and specific functional groups make it a valuable building block in the synthesis of biologically active molecules with potential therapeutic applications.
Used in Chemical Synthesis:
(3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE is used as a substrate in the synthesis of 2-alkyl cyclohexanone intermediates, which are important in the preparation of complex organic molecules and materials. Its unique structure allows for further functionalization and modification, enabling the development of novel compounds with diverse applications in various industries.

Upstream product

• 603-76-9 1-methylindole 
• 123-73-9 trans-Crotonaldehyde 
• 123-73-9 crotonaldehyde 
• 949489-76-3 1-(1-methyl-1H-imidazol-2-yl)-3-(1-methyl-1H-indol-3-yl)-butan-1-ol 
• 860772-44-7 (R)-1-(1-methyl-1H-imidazole-2-yl)-3-(1-methyl-1H-indol-3-yl)butan-1-one 

Downstream Products

• 406920-66-9 (+/-)-3-(1-methyl-1H-indol-3-yl)butanol 
• 406920-66-9 (R)-3-(1-methyl-1H-indol-3-yl)-3-methylpropan-1-ol 

Relevant articles and documents

Highly stereoselective imidazolethiones mediated Friedel-Crafts alkylation of indole derivatives

The asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes was promoted by the novel imidazolethiones to afford the corresponding adducts in moderate to excellent yields and high enantioselectivities under mild reaction conditions.

CaSH organocatalysis: Enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

Enantioselective Friedel-Crafts alkylation of indole with α,β-unsaturated aldehyde was catalyzed by camphor sulfonyl hydrazine (CaSH) with good enantioselectivity (81-88%). Georg Thieme Verlag Stuttgart.

Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold

Indoles react intramolecularly with alkynes in the presence of gold catalysts to give from six- to eight-membered-ring annulated compounds. The cationic AuI complex [Au(P{C6H4-(o-Ph))(tBu) 2)(NCMe)]SbF6 is the best catalyst for the formation of six- and seven-membered rings by 6-endo-dig, 6-exo-dig, and 7-exo-dig cyclizations. Indoloazocines are selectively obtained with AuCl3 as catalyst in a rare 8-endodig process. In this process alienes or tetracyclic annulated derivatives are also formed as a result of an initial fragmentation reaction. The intermolecular reaction of indoles with alkynes proceeds to form 3-alkenylated intermediates that react with a second equivalent of indole to give bisindolyl derivatives. Indoles that are substituted at the 3-position react intermolecularly with alkynes to give 2-alkenylated intermediates that can be trapped intramolecularly with the appropriate nucleophiles.