| 词条 | Indene |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443871788 | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Indene.png | ImageSize = 150px | ImageName = Skeletal formula | ImageFile1 = Indene 3D ball.png | ImageAlt1 = Ball-and-stick model of the indene molecule | PIN = 1H-Indene | SystematicName=Bicyclo[4.3.0]nona-1,3,5,7-tetraene | OtherNames= Benzocyclopentadiene Indonaphthene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6949 | InChI = 1/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2 | InChIKey = YBYIRNPNPLQARY-UHFFFAOYAJ | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 192812 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YBYIRNPNPLQARY-UHFFFAOYSA-N | CASNo=95-13-6 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem=7219 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB02815 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 41921 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C11565 | SMILES = c1ccc2c(c1)CC=C2 | Beilstein = 635873 | Gmelin = 27265 }} |Section2={{Chembox Properties | Formula=C9H8 | MolarMass=116.16 | Appearance=Colorless liquid[1] | Density=0.997 g/mL | MeltingPtC= -1.8 | BoilingPtC= 181.6 | Solubility= Insoluble | pKa = 20.1 (in DMSO)[1] | MagSus = -80.89·10−6 cm3/mol |Section3={{Chembox Hazards | MainHazards=Flammable | FlashPtC = 78.3 | AutoignitionPtC = | IDLH = N.D.[2] | REL = TWA 10 ppm (45 mg/m3)[2] | PEL = none[2] | Section8 = {{Chembox Related | OtherAnions = | OtherCations = | OtherFunction_label = | OtherFunction = | OtherCompounds = Benzofuran, Benzothiophene, Indole }} Indene is a flammable polycyclic hydrocarbon with chemical formula C9H8. It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins. IsolationIndene occurs naturally in coal-tar fractions boiling around 175–185 °C. It can be obtained by heating this fraction with sodium to precipitate solid "sodio-indene." This step exploits indene's weak acidity evidenced by its deprotonation by sodium to give the indenyl derivative. The sodio-indene is converted back to indene by steam distillation.[3] ReactivityIndene readily polymerises. Oxidation of indene with acid dichromate yields homophthalic acid (o-carboxylphenylacetic acid). It condenses with diethyl oxalate in the presence of sodium ethoxide to form indene-oxalic ester, and with aldehydes or ketones in the presence of alkali to form benzofulvenes. The latter are highly coloured. Treatment of indene with organolithium reagents give lithium indenyl compounds: C9H8 + RLi → LiC9H7 + RH Indenyl is a ligand in organometallic chemistry, giving rise to many transition metal indenyl complexes. See also
References1. ^{{cite journal| author = Bordwell FG| year = 1988| title = Equilibrium acidities in dimethyl sulfoxide solution| journal = Accounts of Chemical Research| volume = 21| issue = 12| pages = 456–463| doi = 10.1021/ar00156a004}}Bordwell pKa Table in DMSO {{webarchive|url=https://web.archive.org/web/20081009060809/http://www.chem.wisc.edu/areas/reich/pkatable/ |date=2008-10-09 }} 2. ^1 2 3 {{PGCH|0340}} 3. ^Gerd Collin, Rolf Mildenberg, Mechthild Zander, Hartmut Höke, William McKillip, Werner Freitag, Wolfgang Imöhl “Resins, Synthetic” Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2000. External links
| title = Zur Synthese von Indenderivaten | author = W. v. Miller, Rohde | journal = Berichte der deutschen chemischen Gesellschaft | volume = 23 | issue = 2 | pages = 1881–1886 | year = 1890 | doi = 10.1002/cber.18900230227 }}
| title = Zur Synthese von Indenderivaten | author = W. v. Miller, Rohde | journal = Berichte der deutschen chemischen Gesellschaft | volume = 23 | issue = 2 | pages = 1887–1902 | year = 1890 | doi = 10.1002/cber.18900230228 }}
| title = Organic Chemistry | last = Finar | first = I. L. | publisher = Longman Scientific & Technical | isbn = 0-582-44257-5 | year = 1985 }}{{Authority control}} 1 : Indenes |
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