trans-Styrylacetic acid

Base Information

• Chemical Name: trans-Styrylacetic acid
• CAS No.: 1914-58-5
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.188
• Hs Code.: 29163900
• NSC Number: 172584
• UNII: 77ZO6UV6WY
• Nikkaji Number: J2.507.382G
• Wikidata: Q27266616
• Mol file: 1914-58-5.mol

Synonyms:3-Butenoicacid, 4-phenyl-, (E)- (8CI);(3E)-4-Phenylbut-3-enoic acid;(E)-4-Phenyl-3-butenoic acid;NSC 172584;trans-Styrylacetic acid;

Chemical Property of trans-Styrylacetic acid

Chemical Property:

• Appearance/Colour: white to yellow-brown cryst. powder or needles
• Vapor Pressure: 0.00045mmHg at 25°C
• Melting Point: 84-86 °C(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 302 °C at 760 mmHg
• PKA: 4.46±0.10(Predicted)
• Flash Point: 215.8 °C
• PSA: 37.30000
• Density: 1.145 g/cm³
• LogP: 2.17450
• Storage Temp.: Refrigerator (+4°C)
• 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%,99%, ^*data from raw suppliers

trans-StyrlaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CCC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C\CC(=O)O
• Uses: trans-Styrylacetic acid (4-Phenyl-3-butenoic acid) was used as mechanism-based inhibitor of Peptidylglycine α-hydroxylating monooxygenase.

Technology Process of trans-Styrylacetic acid

There total 53 articles about trans-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: 97.0%

(E)-4-phenyl-3-butenamide (26121-45-9) → trans-styrylacetic acid (2243-53-0,59744-46-6,1914-58-5)

Guidance literature:

With sodium peroxide; In water; at 85 - 100 ℃; for 2h;

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

upstream raw materials:

trans-3-phenylprop-2-enyl chloride

carbon monoxide

bromobenzene

(E)-but-2-enoic acid

Downstream raw materials:

(E)-2,2-dimethyl-4-phenylbut-3-enoic acid

(E)-2-methyl-4-phenylbut-3-enoic acid

ethyl (E)-4-phenylbut-3-enoate

Refernces

• 1、 Gao, Yuzhen,Li, Xueqin,Chen, Weizhu,Tang, Guo,Zhao, Yufen. "Copper-Catalyzed Phosphonation-Annulation Approaches to the Synthesis of β-Phosphonotetrahydrofurans Involving C-P and C-O Bonds Formation". . p. 11398 - 11406. Retrieved 2015.
• 2、 Pan, Chunxiang,Yang, Chunhui,Li, Kangkui,Zhang, Keyang,Zhu, Yuanbin,Wu, Shiyuan,Zhou, Yongyun,Fan, Baomin. "Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles". . p. 7188 - 7193. Retrieved 2021/10/01.