1971-44-4

Basic information

• Product Name: 1,3-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE
• Synonyms: AKOS BC-1816;1,3-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE;1H-Indole-2-carboxaldehyde, 1,3-diMethyl-
• CAS NO: 1971-44-4
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21
• Mol File: 1971-44-4.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE(1971-44-4)
• EPA Substance Registry System: 1,3-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE(1971-44-4)

Safety Data

• Hazardous Substances Data: 1971-44-4(Hazardous Substances Data)

Usage

Physical state

Pale yellow liquid

Odor

Strong, sweet floral

Primary use

Fragrance ingredient in perfumes, soaps, and personal care products

Source

Derived from indole, a heterocyclic aromatic organic compound found in natural sources like jasmine and orange flowers

Additional use

Chemical intermediate in the synthesis of pharmaceuticals and other organic compounds

Industry relevance

Fragrance and chemical industries due to its unique odor profile and structural properties

Upstream product

• 875-30-9 1,3-dimethylindole 
• 1478-41-7 diethoxycarbonium fluoroborate 
• 68-12-2 N,N-dimethyl-formamide 
• 1971-46-6 1,2,3-trimethylindole 
• 80554-68-3 2-(1,3-dimethylindolyl)acetaldehyde 
• 102651-98-9 (1,3-Dimethyl-2-indolyl)ethoxycarbenium-tetrafluoroborat 
• 27421-51-8 1-methyl-1H-indole-2-carboxaldehyde 
• 74-88-4 methyl iodide 
• 5257-24-9 2-formyl-3-methylindole 
• 122-51-0 orthoformic acid triethyl ester 
• 83-34-1 3-Methylindole 
• 603-76-9 1-methylindole 
• 875-79-6 1,2-dimethylindole 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 253325-56-3 2-[1,3-dimethylindol-2-ylmethylidene]-3-isopropylidene-N-phenylsuccinimide 
• 253325-53-0 N-benzyl-2-[1,3-dimethylindol-2-ylmethylidene]-3-isopropylidenesuccinimide 
• 253325-55-2 2-[1,3-dimethylindol-2-ylmethylidene]-3-isopropylidene-N-(4-vinylphenyl)succinimide 
• 322475-94-5 2-[1,3-dimethylindol-2-ylmethylidene]-3-isopropylidene-N-(4-ethoxycarbonylphenyl)succinimide 
• 145771-35-3 5-(1',3'-dimethylindol-2'-yl)-4-nitro-1,3-diphenylpentan-1-one 

Relevant articles and documents

First electrophilic substitutions of 3-substituted indoles with diethoxycarbenium tetrafluoroborate: Functionalized indole derivatives

The indoles 2a-2c react with diethoxycarbenium tetrafluoroborate (1) to furnish the indolecarbaldehydes 3a-3d. In the thermodynamically controlled reaction of 3-methylindole (2a) with 1 the tris(indolyl)methane 4 and diskatole (5), are formed in addition. The limitations of these reactions are discussed and evidence is presented for a C-3-ipso-attack and a Wagner-Meerwein rearrangement, respectively, leading to the formation of 3b or 3d.

Organocatalytic asymmetric reaction of indol-2-yl carbinols with enamides: Synthesis of chiral 2-indole-substituted 1,1-diarylalkanes

The chiral phosphoramide-catalyzed asymmetric reaction of indol-2-yl carbinols with enamides is presented. The method provided an efficient and novel way for the synthesis of chiral 2-indole-substituted 1,1-diarylalkane derivatives.

Copper-catalyzed aerobic methyl/methylene oxygenation and C-H formylation with a DABCO-DMSO system for the synthesis of carbonyl indoles and pyrroles

Copper-catalyzed aerobic methyl/methylene oxygenation of substituted indoles and pyrroles was developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additive in dimethyl sulfoxide (DMSO). Similar aerobic catalytic conditions could also be utilized for direct C-H formylation of C(3) on indoles and C(2) on pyrroles.