“1,3-Indandione”的意思、由来-开放百科全书

词条

1,3-Indandione

释义

Structural properties
Preparation
Chemical properties
Related compounds
See also
References
External links

{{chembox
| Watchedfields = changed
| verifiedrevid = 477205481
| ImageFile = 1,3-indanon.svg
| ImageSize = 130px
| ImageAlt = Skeletal formula
| ImageFile1 = Indandione-3D-balls.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model
|IUPACName=indane-1,3-dione
|OtherNames=Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11322
| InChI = 1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2
| SMILES1 = O=C2c1ccccc1C(=O)C2
| InChIKey = UHKAJLSKXBADFT-UHFFFAOYAR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 283521
| ChEBI = 78877
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UHKAJLSKXBADFT-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=606-23-5
| PubChem=11815
| SMILES=C1C(=O)C2=CC=CC=C2C1=O
|Section2={{Chembox Properties
| C=9|H=6|O=2
| Appearance=Yellow solid
| Density=1.37 g / cm³
| MeltingPtC = 129 to 132
| MeltingPt_ref = ^[1]^[2]
| BoilingPt=
| Solubility=slight
|Section3={{Chembox Hazards
| MainHazards=
| FlashPtC=
| AutoignitionPtC =
}}

1,3-Indandione (indanedione) is an organic compound with the molecular formula C₉H₆O₂. Chemically, it is a β-diketone. In standard conditions it is referred to in different sources as either a colorless or yellowish,^[3] green,^[4] or (most commonly) yellow solid.

Structural properties

In the solid state, 1,3-indandione occurs as a diketone; in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This explains many of chemical properties of the compound.

Preparation

1,3-Indandione can be prepared by decarboxylation of the sodium salt of 2-ethoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and dimethyl phthalate.

Chemical properties

1,3-Indandione is a very strong C-nucleophile. It undergoes self-condensation quite easily, resulting in bindone.

Bromination occurs at the 2-position:

1,3-Indandione could be reduced to indanone, 3-hydroxy-1-indanone, 1,3-indanediol or even indane, depending on the method used.

Related compounds

The related compound 1,2-indandione is used in the first stage of forensic identification of latent fingerprints. It is particularly useful for paper, and for items printed with thermal inks such as receipts. Amino acids left behind by the human hand may be developed into fingerprints by the use of it; the results, photographed with a special filter under a strong yellow-green fluorescent or green laser. It is usually the first method employed in a sequential analysis aimed at the production of evidence of a grade suitable for use in the courtroom. ^[5]

References

1. ^1,3-Indandione at Sigma-Aldrich
2. ^MSDS at Acros Organics, retrieved on June 16, 2011
3. ^{{ref-ru}} Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
4. ^Datapage {{Webarchive|url=https://web.archive.org/web/20140519132940/http://www.alfa.com/de/GP100w.pgm?DSSTK=L01584&rnd=319320352 |date=2014-05-19 }}, AlfaAesar, June 16, 2011
5. ^{{cite video|title=Sequential Processing 2010 : 01 : History of Indanedione|url=https://www.youtube.com/watch?v=5xu_6VpGEu0|work=Sequential Processing of Documents For Fingerprints|publisher=NFSTC|accessdate=August 2, 2013}}

External links

{{Commonscatinline}}

1 : Indandiones

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