2,2-dihydroxy-5-(methylthio)-1,3-indanedione

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Properties of substance:

2,2-dihydroxy-5-(methylthio)-1,3-indanedione

skc-file

Synonyms:

2,2-dihydroxy-5-(methylthio)-1H-indene-1,3(2H)-dione
5-(methylthio)ninhydrin

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₁₀H₈O₄S

Synthesis 1:

Reference: Heffner, R. J., & Joullie, M. M. Synthetic Routes to Ninhydrins. Preparation of Ninhydrin, 5-Methoxyninhydrin, and 5-(Methylthio)Ninhydrin / Synthetic Communications. - 1991. - Vol. 21, No. 21 pp. 2253 [doi: 10.1080/00397919108055457]

To a solution containing 3-bromo-6-(methylthio)-1-indenone (0.72 g, 2.8 mmol) and 2,3-dibromo-6-(methylthio)-1-indenone (1.64 g, 4.91 mmol) in benzene (20 mL) at 5 °C, was added dimethylsulfoxide (20 mL), followed by the addition of bromine (0.368 g, 2.23 mmol). This solution was heated at reflux for 5 hours, after which it was cooled to 5 °C, water (30 mL) was added, and a solid precipitated. The solid was removed by filtration, washed with water, and dried by filtration under reduced pressure to provide 2,2-dihydroxy-5-(methylthio)-1,3-indanedione (1.19 g, 69 % yield): mp 189—191 °C.

R_f 0.47 petroleum ether : ethyl acetate (50 : 50), and 0.56 methylene chloride : methanol : acetic acid (90 : 10 : 1).

HRMS calcd. for C10H8O4S (M+): 224.014. Found: 224.013.

IR (KBr): 3500-2900 (broad), 1745 (strong), 1705 (strong), 1585 (strong), 1565 (medium), 1400 (weak), 1420 (weak), 1390 (medium), 1325 (medium), 1270 (medium), 1200 (medium), 1175 (strong), 1075 (medium), 1055 (strong), 1005 (medium), 970 (medium), 950 (medium), 900 (medium), 855 (medium), 770 (medium) cm^-1.

1H NMR (DMSO-6): δ 2.65 (3H, s), 7.51 (2H, s), 7.71 (1H, s), 7.88 (2H, s); 1H NMR (DMSO-d6, D2O): 2.64 (3H, S), 7.89 (1H, s), 7.90 (2H, s).

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