Benzeneacetaldehyde, alpha-(2-methylpropylidene)-

Base Information

• Chemical Name: Benzeneacetaldehyde, alpha-(2-methylpropylidene)-
• CAS No.: 26643-91-4
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Hs Code.: 2912299000
• European Community (EC) Number: 247-869-4
• UNII: GL417RMH5C
• Nikkaji Number: J121.847F
• Wikidata: Q27279166
• Mol file: 26643-91-4.mol

Synonyms:4-Methyl-2-phenyl-2-pentenal, (E)+(Z);26643-91-4;4-methyl-2-phenylpent-2-enal;4-Methyl-2-phenyl-2-pentenal;1809814-97-8;cocoa pentenal;(E)-4-methyl-2-phenylpent-2-enal;4 - methyl - 2 - phenyl - 2 - pentenal;Benzeneacetaldehyde, ?-(2-methylpropylidene)-;Benzeneacetaldehyde, .alpha.-(2-methylpropylidene)-;GL417RMH5C;SCHEMBL872649;2-Phenyl-4-methyl-2-pentenal;FEMA NO. 3200, E-;MFCD08533235;(2e)-4-methyl-2-phenyl-2-pentenal;AKOS024348941;4-METHYL-2-PHENYL-2-PENTENAL, (2E)-;Q27279166

Chemical Property of Benzeneacetaldehyde, alpha-(2-methylpropylidene)-

Chemical Property:

• Vapor Pressure: 0.00156mmHg at 25°C
• Refractive Index: n20/D 1.536(lit.)
• Boiling Point: 295.1 °C at 760 mmHg
• Flash Point: 113.9 °C
• PSA: 17.07000
• Density: 0.962 g/cm³
• LogP: 2.92490
• Sensitive.: Air Sensitive
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 174.104465066
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

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

4-Methyl-2-phenyl-2-pentenal, mixture of cis and trans ≥88%, stabilized ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C=C(C=O)C1=CC=CC=C1
• Isomeric SMILES: CC(C)/C=C(/C=O)\C1=CC=CC=C1
• Description: 4-Methyl-2-phenyl-2-pentenal has a cocoa aroma. It is often used in chocolate and cocoα-type flavors. May be prepared by aldolic condensation of the corresponding aldehydes in the presence of a basic catalyst.

Technology Process of Benzeneacetaldehyde, alpha-(2-methylpropylidene)-

There total 6 articles about Benzeneacetaldehyde, alpha-(2-methylpropylidene)- 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: 66.0%

4-methyl-2-phenylpent-2-en-1-ol → 4-methyl-2-phenyl-2 pentenal (26643-91-4)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 1.5h; Schlenk technique;

DOI:10.1002/anie.201809333

Reference yield:

→ 4-methyl-2-phenyl-2 pentenal (26643-91-4)

Guidance literature:

Phenylacetaldehyd, Isobutyraldehyd;

DOI:10.1021/jf60160a011

Reference yield:

2-bromophenylacetic acid (4870-65-9,31302-84-8) → 4-methyl-2-phenyl-2 pentenal (26643-91-4)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / 2 h / 0 - 20 °C

2: neat (no solvent) / 2 h / Reflux

3: sodium hydride / mineral oil; tetrahydrofuran / 7 h / 0 - 20 °C

4: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Schlenk technique

5: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.5 h / 0 - 20 °C / Schlenk technique

With thionyl chloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; mineral oil;

DOI:10.1002/anie.201809333

upstream raw materials:

2-bromophenylacetic acid

ethyl 2-phenyl-2-bromoacetate

ethyl 2-diethoxyphosphoryl-2-phenylacetate

Refernces