1971-44-4

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

• 102651-98-9 (1,3-Dimethyl-2-indolyl)ethoxycarbenium-tetrafluoroborat 
• 5257-24-9 2-formyl-3-methylindole 
• 74-88-4 methyl iodide 
• 1971-46-6 1,2,3-trimethylindole 
• 875-30-9 1,3-dimethylindole 
• 75-27-4 bromodichloromethane 
• 67-68-5 dimethyl sulfoxide 
• 875-79-6 1,2-dimethylindole 
• 83-34-1 3-Methylindole 
• 603-76-9 1-methylindole 
• 122-51-0 orthoformic acid triethyl ester 
• 27421-51-8 1-methyl-1H-indole-2-carboxaldehyde 
• 80554-68-3 2-(1,3-dimethylindolyl)acetaldehyde 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 145771-35-3 5-(1',3'-dimethylindol-2'-yl)-4-nitro-1,3-diphenylpentan-1-one 

Relevant academic research and scientific papers

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.

Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.

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.

The ammonium-promoted formylation of indoles by DMSO and H2O

DMSO and H2O is an efficient combination in the NH 4OAc-promoted formylation of indole, where DMSO serves as a C1 carbon source. The mechanism study reveals that the procedure involves a usual and unusual Pummerer reaction.

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.

Microwave-assisted synthesis of photochromic fulgides

The oxazole and indole based heterocyclic photochromic fulgides were synthesized from their corresponding fulgenic acid derivatives by clay catalysed microwave irradiation methodology. Improved yields of fulgides were observed by the microwave irradiation method as compared other chemical methods employed so far. The proportions of clay (montmorillonite KSF) and isopropenyl acetate play a key role in increasing the yields of fulgides. Indian Academy of Sciences.

Fluorine-substituted azobenzene destabilizes polar form of optically switchable fulgimide unit in copolymer system

Fulgimide and various size and electronic nature of substituents on the terminal position of azobenzene in the pendant homo/copolymethacrylates were synthesized. Differential scanning calorimetry analysis indicates the homopolymer possessing C-form fulgimide unit exhibited higher Tm than that of E-form of the homopolymer and revealed C-form is highly ordered. Thermal stability suggests azobenzene homopolymers with electron donating substituents have high thermal stability than electron withdrawing substituents. Polarized optical microscopy observation disclosed homopolymers viz., NI, CY, FL, ME, and T-ME exhibited liquid crystalline mesophases between their Tm and Ti. Optical properties of homo/copolymers were investigated by UV-vis and fluorescence spectroscopy. UV-vis spectroscopy displayed C-form fulgimide absorption in F-co-FL around 482 nm which is around 40 nm lesser than C-form of substituted azobenzene copolymers. Similarly, fluorescence pattern of F-co-FL by UV irradiation exhibited emission intensity slowly increased to certain level then decreases with two new emissions at 430 and 480 nm attributed to terminal position of fluorine atom on azobenzene destabilizes polar form (C-form) fulgimide unit in the copolymer.

THERAPEUTIC AGENTS, AND METHODS OF MAKING AND USING THE SAME

In part, the present invention is directed towards compounds with FabI inhibiting properties. Such compounds may also inhibit other enzymes, including those similar to FabI either structurally or functionally, for example, Fab K. Kits and compositions that include the disclosed compounds are also provided. Methods of treating a subject with a bacterial illness is also disclosed.

THERAPEUTIC AGENTS, AND METHODS OF MAKING AND USING THE SAME

In part, the present invention is directed to antibacterial compounds

FAB I INHIBITORS

Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.