16423-76-0

Basic information

• Product Name: ethyl 3,5-dimethyl-1H-indole-2-carboxylate
• Synonyms: ethyl 3,5-dimethyl-1H-indole-2-carboxylate;1H-indole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester;3,5-dimethyl-1H-indole-2-carboxylic acid ethyl ester
• CAS NO: 16423-76-0
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.2637
• Mol File: 16423-76-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 131-133 °C
• Boiling Point: 357.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.150±0.06 g/cm3(Predicted)
• PKA: 15.49±0.30(Predicted)
• CAS DataBase Reference: ethyl 3,5-dimethyl-1H-indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3,5-dimethyl-1H-indole-2-carboxylate(16423-76-0)
• EPA Substance Registry System: ethyl 3,5-dimethyl-1H-indole-2-carboxylate(16423-76-0)

Safety Data

• Hazardous Substances Data: 16423-76-0(Hazardous Substances Data)

Upstream product

• 31750-57-9 ethyl (E)-2-chloro-3-(phenylamino)but-2-enoate 
• 106-49-0 p-toluidine 
• 607-97-6 ethyl 2-ethyl-3-oxobutanoate 
• 95239-03-5 tert-butyl 2-(4-ethoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate 
• 15933-07-0 Ethyl 2-oxobutanoate 
• 621-94-3 1-(4-methylphenyl)-2-phenylhydrazine 

Downstream Products

• 132870-72-5 1-(4-Chloro-2-nitro-phenyl)-3,5-dimethyl-1H-indole-2-carboxylic acid ethyl ester 
• 78580-36-6 3,5-Dimethyl-1-(2-nitro-phenyl)-1H-indole-2-carboxylic acid ethyl ester 

Relevant articles and documents

Ethyl 1-(2-cyanoethyl)-3,5-dimethyl-1Hindole-2-carboxylate

The title compound, C16H18N2O2, is an important precursor in the synthesis of 1,2,3,4-tetrahydropyrazinoindoles, which show excellent antihistamine, antihypertensive and central nervous system depressant properties. The carbethoxy group attached to C2 and the planar cyanoethyl group attached to N1 make dihedral angles of 11.0(4) and 75.0(3) °, respectively, with the mean plane of the indole ring. The C - C=N chain is linear with a bond angle of 179.3(4) °.

Cytotoxic N-unsubstituted indoles and cyclopent(b)indoles and method of making and using same

The merits of N-unsubstituted indoles and cyclopent[b]indoles as DNA-directed reductive alkylating agents are described. These systems represent a significant departure from N-substituted and pyrrolo[1,2-a] fused systems such as the mitomycins and mitosenes. The cyclopent[b]indole—based aziridinylquinone, when bearing an acetate leaving group, was found to be cytotoxic and displayed significant in vivo activity against syngeneic tumor implants. This particular analogue was unexpectedly superior to the others studied, both in terms of high specificity for the activating enzyme DT-diaphorase and in high % DNA alkylation. Alkylation by a quinone methide intermediate as well as by the aziridinyl group were examined for crosslinking. The possible metabolites of the most active indole species were prepared and found to retain cytotoxicity, strongly suggesting that in vivo activity could also be sustained. The indole systems in the present invention display selectivity for melanoma and for non small cell lung, colon, renal, and prostate cancers when administered in an effective amount. The cancer specificity observed is believed to pertain to differential substrate specificity for DT-diaphorase.

3-(Arylamino)quinolin-2(1H)- and -4(1H)-ones: Reinvestigation of the reaction between ethyl 2-chloro-3-(phenylamino)but-2-enoate and arylamines

The reaction between ethyl 2-chloro-3-(phenylamino)but-2-enoate (5) and aniline gave 4-methyl-3-(phenylamino)quinolin-2(1H)-one (6) and not, as reported earlier in the literature, the isomeric 2-methyl-3- (phenylamino)quinolin-4(1H)-one (1). The latter co