5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE

Base Information

• Chemical Name: 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE
• CAS No.: 696-68-4
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 2921300090
• Mol file: 696-68-4.mol

Synonyms:NSC 55886;6-(Dimethylamino)fulvene;2,4-Cyclopentadiene-D1,a-methylamine, N,N-dimethyl- (6CI,7CI,8CI);1-(2,4-Cyclopentadien-1-ylidene)-N,N-dimethylmethanamine;1-(Cyclopenta-2,4-dien-1-yliden)-N,N-dimethylmethanamin;1-(Cyclopenta-2,4-dien-1-ylidene)-N,N-dimethylmethanamine;

Chemical Property of 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE

Chemical Property:

• Vapor Pressure: 0.252mmHg at 25°C
• Melting Point: 64-66 °C(lit.)
• Refractive Index: 1.632
• Boiling Point: 205.3 °C at 760 mmHg
• PKA: 6.25±0.20(Predicted)
• Flash Point: 70.3 °C
• PSA: 3.24000
• Density: 1.042 g/cm³
• LogP: 1.55790
• Storage Temp.: Freezer

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-(Dimethylamino)fulvene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 6-(Dimethylamino)fulvene was used in the synthesis of chiral cyclopentadienyllithiums substituted with an N,N-dimethylamino(aryl)methyl group.

Technology Process of 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE

There total 14 articles about 5-(DIMETHYLAMINOMETHYLENE)-1,3-CYCLOPENTADIENE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 6-(dimethylamino)fulvene (696-68-4)

Guidance literature:

for 5h; Heating;

DOI:10.1021/ja012051h

Reference yield: 64.0%

cyclopentadienylthallium (34822-90-7) + (methoxymethylidene)dimethylammonium methyl sulfate (21511-55-7,34643-89-5) → 6-(dimethylamino)fulvene (696-68-4)

Guidance literature:

In tetrahydrofuran; at -10 - 20 ℃;

DOI:10.1021/jo010625v

Reference yield: 50.0%

lithium cyclopentadienide + (methoxymethylidene)dimethylammonium methyl sulfate (21511-55-7,34643-89-5) → 6-(dimethylamino)fulvene (696-68-4)

Guidance literature:

In tetrahydrofuran; at -20 - 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.5b00601

upstream raw materials:

cyclopenta-1,3-diene

N,N-dimethylformamide diethyl diacetal

6,6-bis(dimethylamino)pentafulvene

carbonic acid dimethyl ester

Downstream raw materials:

6-diamino-2,3-diformylfulvene

2-Formyl-6-dimethylamino-fulven

6-Dimethylamino-fulven-dialdehyd-(2,4)

4-(4-methoxy-phenyl)-cyclopenta[d][1,2]oxazine

Refernces

• 1、 Allouch, Fatima,Dwadnia, Nejib,Vologdin, Nikolay V.,Svyaschenko, Yurii V.,Cattey, Hélène,Penouilh, Marie-José,Roger, Julien,Naoufal, Daoud,Ben Salem, Ridha,Pirio, Nadine,Hierso, Jean-Cyrille. "Converging and Diverging Synthetic Strategies to Tetradentate (N,N')-Diaminomethyl,(P,P')-Ferrocenyl Ligands: Influence of tert-Butyl Groups on Ferrocene Backbone Conformation". supporting information. p. 5015 - 5028. Retrieved 2015/11/09.
• 2、 Sanz, Dionisia,Perez-Torralba, Marta,Alarcon, Sergio Hugo,Claramunt, Rosa Maria,Foces-Foces, Concepcion,Elguero, Jose. "Tautomerism in the solid state and in solution of a series of 6-aminofulvene-1-aldimines". . p. 1462 - 1471. Retrieved 2007/10/03.