Styrylacetic acid

Base Information

• Chemical Name: Styrylacetic acid
• CAS No.: 2243-53-0
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID70871865
• Wikidata: Q105214126
• Mol file: 2243-53-0.mol

Synonyms:4-phenyl-3-butenoic acid;4-phenyl-3-butenoic acid, (E)-isomer;styrylacetic acid

Chemical Property of Styrylacetic acid

Chemical Property:

• Melting Point: 84-86 °C(lit.)
• Refractive Index: 1.5678 (estimate)
• Boiling Point: 302°Cat760mmHg
• PKA: 4.46±0.10(Predicted)
• Flash Point: 215.8°C
• PSA: 37.30000
• Density: 1.145g/cm³
• LogP: 2.17450
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

98%min ^*data from raw suppliers

4-Phenylbut-3-enoicacid 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CCC(=O)O
• General Description: **TRANS-STYRYLACETIC ACID** is a linear carboxylated product derived from the cobalt-catalyzed allylic C(sp3)-H carboxylation of terminal alkenes with CO?. This method efficiently converts allylarenes into **trans-styrylacetic acid** (or its derivatives) with high regioselectivity and functional group compatibility, facilitated by a Co(acac)?/Xantphos/AlMe? catalytic system. The reaction proceeds via a low-valent allylcobalt intermediate, demonstrating its utility in synthesizing unsaturated carboxylic acids. *(If this does not align with the intended focus, please clarify for refinement.)*

Technology Process of Styrylacetic acid

There total 135 articles about Styrylacetic acid 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: 100.0%

trans-3-phenylprop-2-enyl chloride (21087-29-6) + carbon monoxide (201230-82-2) → trans-styrylacetic acid (2243-53-0,59744-46-6,1914-58-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; 18-crown-6 ether; potassium formate; In benzene; at 50 ℃; under 38000 Torr;

DOI:10.1246/bcsj.68.433

Reference yield: 97.0%

carbon monoxide (201230-82-2) + (E)-cinnamyl diethyl phosphate (85669-63-2) → trans-styrylacetic acid (2243-53-0,59744-46-6,1914-58-5)

Guidance literature:

With hexarhodium hexadecacarbonyl; tetrabutyl-ammonium chloride; water; triethylamine; In dimethyl sulfoxide; at 50 ℃; for 10h; under 15200 Torr;

DOI:10.1016/0022-328X(93)83025-Q

Reference yield: 92.0%

malonic acid (141-82-2) + phenylacetaldehyde (122-78-1) → trans-styrylacetic acid (2243-53-0,59744-46-6,1914-58-5)

Guidance literature:

With silica gel; for 0.0666667h; Irradiation;

DOI:10.1016/S0040-4039(99)00113-6

upstream raw materials:

pyridine

(E)-4-phenylbut-2-enoic acid

malonic acid

phenylacetaldehyde

Downstream raw materials:

(E)-4-Phenyl-1-piperidino-3-buten-1-one

2-(4-Phenyl-1,3-butadienyl)thiophen

4-phenyl-but-3-enoic acid methyl ester

styryl-malonic acid

Refernces

Cobalt-Catalyzed Allylic C(sp³)-H Carboxylation with CO₂

10.1021/jacs.7b02775

The study presents a novel catalytic method for the carboxylation of allylic C(sp3)–H bonds in terminal alkenes using CO2. The researchers employed a cobalt/Xantphos complex in conjunction with AlMe3 to achieve this transformation. The Co(acac)2/Xantphos/AlMe3 system was found to be highly effective, enabling the conversion of a wide range of allylarenes and 1,4-dienes into linear styrylacetic acid and hexa-3,5-dienoic acid derivatives with excellent regioselectivity and functional group tolerance. The study highlights the significant role of Xantphos as a hemilabile ligand, facilitating the generation of a low-valent allylcobalt species that reacts with CO2 to form the desired carboxylated products. The developed method not only offers a straightforward route for the synthesis of ?-butyrolactones but also demonstrates potential for further synthetic applications in organic chemistry.