On September 2, 1960, there was a patent about color photography.Quality Control of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile The title of the patent was Cyanines for color photography. And the patent contained the following:
1-Dicyanomethyleneindan (I), m. 147-8o (MeOH), was prepared in 65% yield as grayish white crystals by refluxing 39.6 g. 1-indanone, 19.8 g. malononitrile, 2.5 g. NH4OAc, 4 cc. AcOH, 40 cc. CHCl3, and simultaneous distillation of 5.4 cc. H2O. 2-Dicyanomethyl- eneindan, m. 190-3, was prepared in 73% yield (brownish), 1-dicyanomethylene-1,2,3,4-tetrahydronaphthalene (colorless), m. 107-8 (EtOH), in 48% yield from 1-tetralone, and 2-dicyanomethylene-1,2,3,4-tetrahydronaphthalene (colorless), m. 102-3 (MeOH), in 22% yield. 1,3-Diethyl-5-(2indanylidene)barbituric acid (colorless), m. 165-7 (EtOH) was prepared in 47% yield by refluxing for 2 h. 19 g. 2-indanone, 26.5 g. 1,3-diethylbarbituric acid, and 2.5 cc. piperidine in 100 cc. EtOH. 1-Dicyanomethylene-2-(3methyl-2-benzothiazolinylidene)indan (orange), m. 245-6 (decomposition) (pyridine/MeOH), was prepared in 35% yield by refluxing for 15 min. 5.4 g. I, 7.4 g. 3-methyl-2-methylthiobenzothiazolium p-toluenesulfonate, 6.06 g. Et3N, 50 cc. EtOH; it sensitized Ag(Br,I) emulsions to 565 mμ, maximum 545 mμ. Similarly were obtained (m.p., % yield, limit and absorption maximum in mμ given): 1-dicyanomethylene-2-(3-ethyl2-benzothiazolinylideneethylidene)indan (green needles), 259-60 (decomposition), -, 680, 660; 1-dicyanomethylene-2[(3 – Et – 2- benzothiazolinylidene) – 2- butenylidene]indan (dark green), 240-1 (decomposition), 36, -, -; 1-dicyanomethylene- 2- (3- methyl-2- benzoxazolinylidene)indan (brownish red ), 230-1 ( decomposition ), -, 510, 490; 1-dicyanomethylene2- ( 1 – methylnaphtho [ 1,2] thiazolin-2- ylidene)indan (red), 265-7 (decomposition), 55, 575, 550; 1-dicyanomethylene-2-(1ethyl-2(1H)-quinolylidene)indan, 227-8 (decomposition), 19, -,-; 1-dicyanomethylene-2-[(1-ethylnaphtho[1,2]thiazolin-2-ylidene)isopropylidene]indan (dark), 191-3 (decomposition), 1, -, -; 2-dicyanomethylene-1-[(3-ethyl-2benzothiazolinylidene)ethylidene]indan (II) (green), 246-50 (decomposition), 21, -, -; 2-dicyanomethylene-1-[(3ethyl-2-benzothiazolinylidene)-2-butenylidene]indan (dark green), 228-30, 22, -, -; 2-dicyanomethylene-1-[(3ethyl-2-benzoxazolinylidene)ethylidene]indan (green), 2145 (decomposition), 28, -, -; 2-dicyanomethylene-1,3-bis(3methyl-2-benzothiazolinylidene )indan (dark needles), <310, 32, 610, 565; 2-dicyanomethylene-1,3-bis[(3-ethyl2-benzothiazollnylidene)ethylidene]indan (dark green), 2889, 33, 780, 690; 2-dicyanomethylene-1,3-bis[(3-ethyl-2benzothiazolinylidene)-2-butenylidene]indan (dark), 2378 (decomposition), 13, 690, 630; 2-dicyanomethylene-1-[(3ethyl-2-benzothiazolinylidene )-2- butenylidene] - 3- [( 3- ethy-2-benzothiazolinylidene)ethylidene]indan (black), 244-5 (decomposition), 35, 840, 810; 2-dicyanomethylene-1-[(3-ethyl2-benzothiazolinylidene)ethylidene]-3- [(3-ethyl-2-benzoxazolinylidene)ethylidene]indan (gray), 255-6° (decomposition), 45,730,685; 1,3-diethyl-5-[1-(3-methyl-2-benzothiazolinylidene)indan-2-ylidene] barbituric acid (brownish red), 272-3 (decomposition) (pyridine), 12, -, -; 1,3-diethyl-5-[1,3-bis(3-methyl- 2- benzothiazolinylidene)indan-2-ylidene] barbituric acid (red), <310, 28, -, -; 1,3-diethyl-5-[1,3-bis(3ethyl - 2 - benzothiazolinylideneethylidene)indan - 2 - ylidene] barbituric acid (green), <310, 61, 770, 750; corresponding benzoxazolinylidene derivative (green), 280-1 (decomposition), 41, 720, 680; 1,3-diethyl-5-[1,3-bis(methylnaphtho [ 1,2] thiazolin-2-ylidene )indan-2-ylidene] barbituric acid (dark), 242-3, 62, 620, 590; 1,3-diethyl-5-[1-(3-ethyl-2benzothiazolinylidene)-2-butadienylidene] -3-(3-methyl-2- benzothiazolinylidene )indan-2-ylidene] barbituric acid (green), 285-43 (decomposition), 27, 810, 730; 1,3-diethyl-5-[1- (3 - methyl- 2- benzothiazolinylidene)- 3- ( 1 -methylnaphtho- [1,2]thiazolinylidene)indan-2-ylidene]barbituric acid (red), 231-2 (decomposition), 54, 575, 555; 1-dicyanomethylene- 1,2,3,4- tetrahydro- 2- (3-methyl- 2- benzothiazolinylidene)- naphthalene (red), 232-3 (decomposition), 76, 555, -; 1-di- cyanomethylene- 1,2,3,4- tetrahydro-2- (1-methylnaphtho- [1,2]thiazolin-2-ylidene)naphthalene (brownish red), 289- 90 (decomposition), 80, 580, 555; 1-dicyanomethylene-2-(1- ethyl-2(1H)-quinolylidene)- 1,2,3,4-tetrahydronaphthalene (red), 285-6 (decomposition), 33, -, -; 1-dicyanomethylene- 2-[(3-ethyl-2-benzoxazolinylidene)ethylidene]- 1,2,3,4-tetra- hydronaphthalene (green needles), 213-14 (decomposition), 19, 690, 600; and 1-dicyanomethylene-1,2,3,4-tetrahydro-2-[(3-methyl-2-benzothiazolinylidene)ethylidene] naphthalene (green needles), 231-2 ( decomposition ), 5, 690, 580. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Quality Control of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile
2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Quality Control of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts