76089-59-3

Basic information

• Product Name: 1,2,3,4-tetramethyl-5-methylidene-cyclopenta-1,3-diene
• Synonyms: 1,2,3,4-tetramethyl-5-methylidene-cyclopenta-1,3-diene;2,3,4,5-tetramethylfulvene
• CAS NO: 76089-59-3
• Molecular Formula: C₁₀H₁₄
• Molecular Weight: 134.22
• Mol File: 76089-59-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 173.7°C at 760 mmHg
• Flash Point: 43.3°C
• Appearance: /
• Density: 0.85g/cm³
• Vapor Pressure: 1.68mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: 1,2,3,4-tetramethyl-5-methylidene-cyclopenta-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetramethyl-5-methylidene-cyclopenta-1,3-diene(76089-59-3)
• EPA Substance Registry System: 1,2,3,4-tetramethyl-5-methylidene-cyclopenta-1,3-diene(76089-59-3)

Safety Data

• Hazardous Substances Data: 76089-59-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 4811, 1989 DOI: 10.1016/S0040-4039(01)80514-1

InChI:InChI=1/C10H14/c1-6-7(2)9(4)10(5)8(6)3/h1H2,2-5H3

Upstream product

• 69446-48-6 decamethylfulvalene 
• 115795-91-0 (η5-C5Me5)W(O)2(OC5Me5) 
• 104-15-4 toluene-4-sulfonic acid 
• 102869-71-6 bis(pentamethylcyclopentadienyl)dimercaptotitanium 
• 108-48-5 2,6-dimethylpyridine 
• 116889-30-6 5-bromo-1,2,3,4,5-pentamethyl-1,3-cyclopentadiene 
• 486-25-9 9-fluorenone 
• 7719-09-7 thionyl chloride 
• 1148-79-4 2,2':6,2''-terpyridine 
• 1423076-68-9 (η⁵-pentamethylcyclopentadienyl)Fe(CO)(acetonitrile)Ph 
• 503027-47-2 N,N'-bis(trimethylsilyl)sulfurdiimide 
• 128541-33-3 (C5Me5)2Ti(η(2)-bis(trimethylsilyl)acetylene) 
• 72443-18-6 neopentylisonitrile 

Downstream Products

• 1131695-27-6 dilithium 1,1'-[phenylphosphanediylbis(methyl)]bis(η⁵-2,3,4,5-tetramethylcyclopenta-2,4-dienide) 
• 34074-16-3 Dimethyl-phenyl-(2-phenyl-propyl)-silane 
• 1015254-21-3 C₅H(CH₃)4CH₂CH(C₆H₅)NCHCHN(CH₃)CH⁽¹⁺⁾*I^(1-)=(C₅H(CH₃)4CH₂CH(C₆H₅)NCHCHN(CH₃)CH)I 
• 1446473-97-7 ansa-(C₂H₄)(C₅Me₄)₂Ca(THF)₂ 
• 1122571-45-2 C₂₀H₂₂ 
• 1353756-72-5 C₂₀H₂₂ 
• 1353756-71-4 1-[(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)methyl]naphthalene 
• 1353756-73-6 1-[(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)methyl]naphthalene potassium salt 
• 190076-36-9 tris(pentamethylcyclopentadienyl)uranium(III) 
• 1192225-30-1 C₂₁H₂₆N₂ 
• 916178-11-5 (C₅(CH₃)5)2Lu(CHC₅(CH₃)4) 

Relevant articles and documents

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5-Bromo-1,2,3,4,5-pentamethylcyclopenta-1,3-diene, which is available in good yield from 1,2,3,4,5-pentamethylcyclopenta-1,3-diene, reacts with potassium tert-butoxide in the presence of catalytic amounts of 18-crown-6 under dehydrobromination to give 1,2

Gallium Methylene

Despite the eminent importance of metal alkylidene species for organic synthesis and industrial catalytic processes, molecular homoleptic metal methylene compounds [M(CH2)n] as the simplest representatives, have remained elusive. Reports on this topic date back to 1955 when polymeric [Li2(CH2)]n and [Mg(CH2)]n were accessed by pyrolysis of methyllithium and dimethylmagnesium, respectively. However, the insoluble salt-like composition of these compounds has impeded their application as valuable reagents. We report that rare-earth metallocene methyl complexes [(C5Me5)2Ln{(μ-Me)2GaMe2}] (Ln=Lu, Y) trigger the formation of homoleptic gallium methylene [Ga8(μ-CH2)12] from trimethylgallium [GaMe3] (Me=methyl) via a cascade C?H bond activation involving the dodecametallic clusters [(C5Me5)6Ln3(μ3-CH2)6Ga9(μ-CH2)9] as crucial intermediates. Such gallium methylene compounds feature a reversible [Ga8(μ-CH2)12]/[Ga6(μ-CH2)9] oligomer switch in donor solvents and act as Schrock-type methylene-transfer reagents.

Chemoselective dehydrogenative esterification of aldehydes and alcohols with a dimeric rhodium(II) catalyst

Dehydrogenative cross-coupling of aldehydes with alcohols as well as dehydrogentive cross-coupling of primary alcohols to produce esters have been developed using a Rh-terpyridine catalyst. The catalyst demonstrates broad substrate scope and good functional group tolerance, affording esters highly selectively. The high chemoselectivity of the catalyst stems from its preference for dehydrogenation of benzylic alcohols over aliphatic ones. Preliminary mechanistic studies suggest that the active catalyst is a dimeric Rh(ii) species, operating via a mechanism involving metal-base-metal cooperativity.

Synthesis and characterization of cyclopentadienylgallium amide compounds as potential single source precursors to GaN

The synthesis, spectroscopic characterization, and single crystal X-ray structures of [(η5-C5Me4H)2Ga(μ2-NH2)] (1), [(η5-C5Me5)2Ga(μ2-