696-68-4

Basic information

• Product Name: 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE
• Synonyms: N-CYCLOPENTA-2,4-DIENYLIDENMETHYL-N,N-DIMETHYLAMINE;SPECS AO-840/40768031;2,4-Cyclopentadiene-delta1,alpha-methylamine, N,N-dimethyl-;Methanamine, 1-(2,4-cyclopentadien-1-ylidene)-N,N-dimethyl-;N-(2,4-Cyclopentadien-1-ylidenemethyl)-N,N-dimethylamine;5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE;6-(DIMETHYLAMINO)FULVENE;AIDS051095
• CAS NO: 696-68-4
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• Mol File: 696-68-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 64-66 °C(lit.)
• Boiling Point: 205.3 °C at 760 mmHg
• Flash Point: 70.3 °C
• Appearance: /
• Density: 1.042 g/cm³
• Vapor Pressure: 0.252mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Freezer
• PKA: 6.25±0.20(Predicted)
• CAS DataBase Reference: 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE(696-68-4)
• EPA Substance Registry System: 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE(696-68-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 696-68-4(Hazardous Substances Data)

Usage

Description

5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE is an organic compound with the chemical formula C8H10N. It is characterized by its cyclopentadiene core, which is a five-membered ring with alternating double and single bonds, and a dimethylaminomethylene group attached to the 5th position. 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE is used as a key intermediate in the synthesis of various organic compounds, particularly those with chiral centers. Its unique structure allows for the formation of new bonds and the creation of complex molecular architectures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE is used as a building block for the development of novel drugs. Its chiral nature and reactivity make it a valuable component in the design and synthesis of new pharmaceutical compounds with potential therapeutic applications.
Used in Material Science:
5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE is also utilized in the field of material science for the development of new materials with specific properties. Its incorporation into polymers and other materials can lead to enhanced performance characteristics, such as improved stability, reactivity, or selectivity.
Used in the Synthesis of Chiral Cyclopentadienyllithiums:
5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE is used as a starting material for the synthesis of chiral cyclopentadienyllithiums substituted with an N,N-dimethylamino(aryl)methyl group. These chiral cyclopentadienyllithiums are important intermediates in the preparation of various organometallic compounds and catalysts, which are widely used in the chemical industry for the production of fine chemicals and pharmaceuticals.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 1615, 1975 DOI: 10.1021/ja00839a078

InChI:InChI=1/C8H11N/c1-9(2)7-8-5-3-4-6-8/h3-7H,1-2H3

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 703-24-2 6,6-bis(dimethylamino)pentafulvene 
• 616-38-6 carbonic acid dimethyl ester 
• 77-78-1 dimethyl sulfate 
• 124-40-3 dimethyl amine 
• 68-12-2 N,N-dimethyl-formamide 
• 4984-82-1 sodium cyclopentadienylide 
• 30868-74-7 ethoxymethylene-dimethyl-ammonium; tetrafluoroborate 
• 34822-90-7 cyclopentadienylthallium 
• 21511-55-7 (methoxymethylidene)dimethylammonium methyl sulfate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 17513-08-5 6-Dimethylamino-N-benzolsulfonyl-fulven-thiocarbonsaeure-⁽²⁾-amid 
• 36381-73-4 4-phenyl-cyclopenta[d][1,2]oxazine 
• 17513-06-3 6-Dimethylamino-N-(p-chlorphenyl)-fulven-carbonsaeure-⁽²⁾-amid 
• 17513-07-4 6-Dimethylamino-N-(p-toluolsulfonyl)-fulven-thiocarbonsaeure-2-amid 
• 17513-05-2 6-Dimethylamino-N-benzoyl-fulven-carbonsaeure-⁽²⁾-amid 
• 1654-52-0 6-methylazulene 
• 1654-55-3 5-methyl-azulene 
• 10556-12-4 5,6-Dimethylazulen 
• 56594-78-6 4,6-dimethyl-azulene 
• 23781-82-0 6-phenylazulene 
• 28007-60-5 5,6-Diphenylazulen 
• 15763-93-6 6-diamino-2,3-diformylfulvene 
• 15763-91-4 2-Formyl-6-dimethylamino-fulven 
• 90921-88-3 6-Dimethylamino-fulven-dialdehyd-(2,4) 

Relevant articles and documents

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PTP-1B inhibitors: Cyclopenta[d][1,2]-oxazine derivatives

A series of novel cyclopenta[d][1,2]-oxazine derivatives was prepared and evaluated for their inhibitory activity toward protein tyrosine phosphatase 1B (PTP-1B). Compound 6s was found to be an inhibitor of PTP-1B with nanomolar IC50 value and

Octachloroazulene

The title compound, the first perhaloazulene, has been synthesized from hexachlorobutadiene and cyclopentadiene. Further chlorination of 1,3,4,5,6,7-hexachloroazulene results in addition, rot substitution, under electrophilic as well as free radical conditions. Radical chlorination of the hexachloro-azulene affords in good yield a single decachlorotetrahydroazulene. Treatment of this Cl10 compound with one equiv of a phosphazene base gives a nonachlorodihydroazulene, but the addition of a second equiv results in dechlorination to 1,2,3,4,5,6,7-heptachloroazulene as well as dehydrochlorination to octachloro-azulene. The former azulene is obtained cleanly from the Cl9 compound with acid catalysis or by reduction with mercury. In the presence of calcium carbonate, however, the Cl9 intermediate yields the dark green octachloroazulene. Although octachloronaphthalene is readily converted into its octafluoro counterpart, the isomeric octachloroazulene is far too sensitive to undergo the analogous transformation.