(2Z,4E)-5-phenylpenta-2,4-dienoic acid

Base Information

• Chemical Name: (2Z,4E)-5-phenylpenta-2,4-dienoic acid
• CAS No.: 1552-94-9
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 174.199
• Hs Code.: 2916399090
• NSC Number: 109408,63972
• DSSTox Substance ID: DTXSID401281877
• Mol file: 1552-94-9.mol

Synonyms:(2Z,4E)-5-phenylpenta-2,4-dienoic acid;2, 5-phenyl- (VAN8C;28010-13-1;(2Z,4E)-5-Phenyl-2,4-pentadienoic acid;2, 5-Phenyl-(VAN8C;SCHEMBL144680;DTXSID401281877;NSC63972;NSC-63972;NSC109408;NSC-109408

Chemical Property of (2Z,4E)-5-phenylpenta-2,4-dienoic acid

Chemical Property:

• Vapor Pressure: 1.09E-05mmHg at 25°C
• Melting Point: 165-166 °C
• Refractive Index: 1.616
• Boiling Point: 356.1 °C at 760 mmHg
• PKA: 4.56±0.10(Predicted)
• Flash Point: 257.6 °C
• PSA: 37.30000
• Density: 1.148 g/cm³
• LogP: 2.34060
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

5-Phenylpenta-2,4-dienoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC=CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C=C\C(=O)O
• Uses: 5-Phenyl-2,4-pentadienoic acid is used as Synthetic building block, anti-malarial agent.

Technology Process of (2Z,4E)-5-phenylpenta-2,4-dienoic acid

There total 37 articles about (2Z,4E)-5-phenylpenta-2,4-dienoic 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: 60.0%

malonic acid (141-82-2) + 3-phenyl-propenal (104-55-2) → 5-phenyl-2,4-pentadienoic acid (1552-94-9,28010-12-0,28010-13-1,38446-98-9,54352-97-5)

Guidance literature:

With piperidine; In pyridine; at 100 ℃; for 4h;

DOI:10.1007/s11172-020-2980-7

Reference yield:

3-phenyl-propenal (104-55-2) + ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate (188945-44-0) → 5-phenyl-2,4-pentadienoic acid (1552-94-9,28010-12-0,28010-13-1,38446-98-9,54352-97-5)

Guidance literature:

3-phenyl-propenal; ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate; With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; toluene; at -78 ℃; for 1.33333h; Inert atmosphere;

With sodium hydroxide; In ethanol; water; at 20 ℃; for 2h;

Reference yield:

methyl 5-phenylpenta-2,4-dienoate (1516-24-1,24196-39-2,38447-05-1,38448-84-9,101934-35-4,121411-05-0) → 5-phenyl-2,4-pentadienoic acid (1552-94-9,28010-12-0,28010-13-1,38446-98-9,54352-97-5)

Guidance literature:

With water; potassium hydroxide; In methanol; at 20 ℃; for 48h;

DOI:10.1002/anie.202000838

upstream raw materials:

piperidine

pyridine

(E)-3-phenylpropenal

malonic acid

Downstream raw materials:

buta-1,3-dien-1-ylbenzene

5-Phenylpentanoic acid

5-phenyl-penta-2,4-dienoyl chloride

2-bromo-5-phenyl-penta-2,4-dienoic acid

Refernces

• 1、 Dominguez,X.A. et al.. "-". . p. 2617 - 2618. Retrieved 1974.
• 2、 Bernadat, Guillaume,Gelis, Coralie,Masson, Géraldine,Neuville, Luc,Retailleau, Pascal,Varlet, Thomas. "Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions". . p. 8491 - 8496. Retrieved 2020/04/10.