1-tert-Butylpropadiene

Base Information

• Chemical Name: 1-tert-Butylpropadiene
• CAS No.: 26981-77-1
• Molecular Formula: C7H12
• Molecular Weight: 96.1723
• Hs Code.: 2901299090
• Mol file: 26981-77-1.mol

Synonyms:4,4-Dimethylpenta-1,2-diene;NSC 147137; tert-Butylallene

Chemical Property of 1-tert-Butylpropadiene

Chemical Property:

• Vapor Pressure: 65.4mmHg at 25°C
• Boiling Point: 89.7°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.697g/cm³
• LogP: 2.37360

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-tert-Butylpropadiene

There total 5 articles about 1-tert-Butylpropadiene 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: 54.0%

μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine] (88016-29-9) + 4,4-dimethyl-1-(tributylstannyl)-2-pentyne (144241-73-6) → t-butylallene (26981-77-1) + 4,4-dimethyl-1-(2-iodophenyl)-2-pentyne (131251-47-3) + tributylstannyl trifluoromethanesulfonate (68725-14-4)

Guidance literature:

In chloroform; at -30 ℃;

DOI:10.1021/jo00050a024

Reference yield:

diethyl ether (60-29-7,927820-24-4) + 4-chloro-4-methylpent-2-yne (999-79-1) + methylmagnesium bromide (75-16-1) → 2,4-dimethyl-2,3-pentadiene (1000-87-9) + t-butylallene (26981-77-1)

Guidance literature:

at 60 ℃; reagiert analog mit Phenylmagnesiumbromid;

Reference yield:

propargyl iodide (659-86-9) → tetramethyl-2,2,3,3 butane (594-82-1) + 4,4-Dimethyl-1-pentyne (13361-63-2) + t-butylallene (26981-77-1) + tert-Butyl iodide (558-17-8) + hexa-1,5-diyne (628-16-0) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With (t-Bu)2CuLi; In diethyl ether; at -78 ℃; Mechanism; Product distribution; also at 0 deg C;

DOI:10.1021/ja00195a054

upstream raw materials:

diethyl ether

4-chloro-4-methylpent-2-yne

methylmagnesium bromide

μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine]

Downstream raw materials:

(S)-3-(4,4-Dimethyl-pent-2-ynyl)-1-phenyl-pyrrolidine-2,5-dione

(1R,5R)-6-[2,2-Dimethyl-prop-(E)-ylidene]-3-phenyl-3-aza-bicyclo[3.2.0]heptane-2,4-dione

(1S,5S,6R)-6-tert-Butyl-7-methylene-3-phenyl-3-aza-bicyclo[3.2.0]heptane-2,4-dione

(1S,5S,6S)-6-tert-Butyl-7-methylene-3-phenyl-3-aza-bicyclo[3.2.0]heptane-2,4-dione

Refernces

Palladium Catalyzed Reactions of Neopentylidenesiliranes

10.1246/cl.1988.1567

The research investigates palladium-catalyzed reactions of neopentylidenesiliranes with various unsaturated compounds. The study focuses on how the nature of ligands on palladium influences the ring expansion products obtained. Key chemicals involved include 1,1-dimesityl-2-Z-neopentylidenesilirane and its E-isomer, which serve as the main reactants. Dimethyl acetylenedicarboxylate, acetylene, t-butylallene, and methyl acrylate are among the unsaturated compounds that react with the neopentylidenesiliranes to produce different adducts. Palladium complexes, such as Pd(PPh3)4 and Pd(II) complexes with varying ligands, act as catalysts to facilitate these reactions. The products formed, like insertion product 3 and trace amount of 4, are analyzed through techniques like NMR, mass spectra, and elemental analysis to confirm their structures. The research highlights the unusual ring expansion reaction modes and the role of reactants in activating the catalyst, as well as the influence of steric and electronic factors on the reaction pathways and product formation.

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