21777-15-1

Basic information

• Product Name: 3-(1H-indol-3-yl)acrylaldehyde
• Synonyms: 3-(1H-indol-3-yl)acrylaldehyde
• CAS NO: 21777-15-1
• Molecular Weight: 171.199
• Mol File: 21777-15-1.mol

Chemical Properties

• CAS DataBase Reference: 3-(1H-indol-3-yl)acrylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-indol-3-yl)acrylaldehyde(21777-15-1)
• EPA Substance Registry System: 3-(1H-indol-3-yl)acrylaldehyde(21777-15-1)

Safety Data

• Hazardous Substances Data: 21777-15-1(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 121-44-8 triethylamine 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 360788-02-9 3-(1H-indol-3-yl)propionaldehyde 
• 120-72-9 indole 
• 107-02-8 acrolein 
• 160688-99-3 [tris(3-pyridyl)boroxin] 
• 615-36-1 2-bromoaniline 
• 177202-83-4 2-(pyridin-3-yl)phenylamine 

Relevant articles and documents

Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: A Synthetic Strategy for Discoipyrrole D

Bis-heteroaryl or bis-aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration.

Rare earth triflates/chlorotrimethylsilane-promoted one-pot synthesis of enals

Some heteroaromatic aldehydes were subjected to conditions promoting the rare earth triflates/chlorotrimethylsilane-promoted one-pot synthesis of enals. As a result, diverse α,β-unsaturated aldehydes were obtained in moderate yields.

Formylpyrrole-based heterocycles for nucleic acid attachment to supports

A compound has Formula I: A, B, C, D, W, X, Y, and Z are independently selected from hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C1-C6 alkoxy, aryl, aldehyde, protected aldehyde, CH, N, O, S, null, and bond; Q is selected from aldehyde, protected aldehyde, and null, at least one of A, B, C, D, W, X, Y, Z, or Q is an aldehyde or protected aldehyde; the bonds between each of A-B, B-C, C-D, W-X, X-Y, and Y-Z are selected from single bond, double bond, triple bond, and no bond; L is a linker selected from a C1-C12 alkyl, aralkyl, and aryl, any of which is optionally substituted; one or more methylene unit (CH2) of the C1-C12 alkyl is optionally replaced by any combination of oxygen, carbonyl(C═O), and NH; and R1 and R2 are independently selected from —NR3R4, halogen, C1-C8 alkoxy, aralkoxy, alkenyloxy, alkynyloxy, and OCH2CH2CN; R3 and R4 are independently a C1-C4, straight chain or branched alkyl group.

Morpholine catalyzed direct C3 alkenylation of indoles with α,β-unsaturated aldehydes

Organocatalytic direct C3 alkenylation of indoles has been developed. Simple and readily available morpholine trifluoroacetic acid salt is employed as an efficient catalyst in this oxidative dehydrogenative reaction. Simplicity and practicality constitute

Synthesis of nitrogen heterocycles by the ring opening of pyridinium salts

(Chemical Equation Presented) The century-old ring-opening reaction of pyridinium salts with tethered nucleophiles has been harnessed for a synthesis of substituted indoles and related nitrogen heterocyles. Extension of this method could lead to oxygen- and sulfur-containing heterocycles and carbocycles, as well as to applications in natural product synthesis and medicinal chemistry.