Indan-1,3-dion

Indan-1,3-dion
Strukturní vzorec
Strukturní vzorec
Model molekuly
Model molekuly
Obecné
Systematický názevIndan-1,3-dion
Ostatní názvyindandion, 1,3-indanon
Anglický název1,3-Indandione
Německý název1,3-Indandion
Sumární vzorecC9H6O2
Vzhledbílá, zelená nebo žlutá pevná látka
Identifikace
Registrační číslo CAS606-23-5
PubChem11815
SMILESC1C(=O)C2=CC=CC=C2C1=O
InChIInChI=1S/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2
Vlastnosti
Molární hmotnost146,146 g/mol
Teplota tání129 až 132 °C (402 až 405 K)
Hustota1,37 g/cm3
Rozpustnost ve voděmírně rozpustný
Bezpečnost
GHS07 – dráždivé látky
GHS07
[1]
Varování[1]
Není-li uvedeno jinak, jsou použity
jednotky SI a STP (25 °C, 100 kPa).
Některá data mohou pocházet z datové položky.

Indan-1,3-dion je dicyklický diketon odvozený od indanu.

Struktura

V pevném skupenství se tato látka vyskytuje jako diketon; ve vodném roztoku přechází asi 2 % molekul do tautomerní enolové formy. Enolátový anion vykazuje silnou delokalizaci a nejvyšší elektronovou hustotu na druhém uhlíku, čímž se dá vysvětlit řada chemických vlastností sloučeniny.

Výroba

Indan-1,3-dion lze vyrobit dekarboxylací sodné soli 2-ethoxykarbonyl-indan-1,3-dionu, který se získá Claisenovou kondenzací ethylacetátu a dimethylftalátu.

Chemické vlastnosti

Indan-1,3-dion je velmi silný C-nukleofil. Dochází u něj k poměrně snadné autokondenzaci za vzniku bindonu:

Bromace probíhá na druhém uhlíku:

Indan-1,3-dion může být v závislosti na použitém postupu redukován na indanon, 3-hydroxy-indan-1-on, indan-1,3-diol nebo indan.

Podobné sloučeniny

Podobný indan-1,2-dion se používá na identifikaci skrytých otisků prstů a jako přísada do některých druhů papíru.

Nivimedon působí jako antialergen.

Odkazy

Související články

Externí odkazy

Reference

V tomto článku byl použit překlad textu z článku 1,3-Indandione na anglické Wikipedii.

  1. ↑ a b 1,3-Indandione. pubchem.ncbi.nlm.nih.gov [online]. PubChem [cit. 2021-05-24]. Dostupné online. (anglicky) 

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