(5E,8E,11E,14E)-10,10-difluoroicosa-5,8,11,14-tetraenoic acid

Base Information

• Chemical Name: (5E,8E,11E,14E)-10,10-difluoroicosa-5,8,11,14-tetraenoic acid
• CAS No.: 108212-58-4
• Molecular Formula: C₂₀H₃₀F₂O₂
• Molecular Weight: 340.454
• Hs Code.: 2916190090
• Mol file: 108212-58-4.mol

Synonyms:10,10-difluoroarachidonic acid

Chemical Property of (5E,8E,11E,14E)-10,10-difluoroicosa-5,8,11,14-tetraenoic acid

Chemical Property:

• Vapor Pressure: 9.78E-10mmHg at 25°C
• Boiling Point: 459.9°Cat760mmHg
• Flash Point: 232°C
• PSA: 37.30000
• Density: 1.005g/cm³
• LogP: 6.46190
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 340.22138652
• Heavy Atom Count: 24
• Complexity: 435

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC(C=CCC=CCCCC(=O)O)(F)F
• Isomeric SMILES: CCCCC/C=C/C/C=C/C(/C=C/C/C=C/CCCC(=O)O)(F)F

Technology Process of (5E,8E,11E,14E)-10,10-difluoroicosa-5,8,11,14-tetraenoic acid

There total 12 articles about (5E,8E,11E,14E)-10,10-difluoroicosa-5,8,11,14-tetraenoic 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:

methyl hex-5-ynoate (77758-51-1) → 10,10-difluoroarachidonic acid (108212-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h

2: H₂ / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature

3: H₂O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02

With ammonium hydroxide; Rhisopus arrhizus lipase; hydroxylamine hydrochloride; sodium cyanide; water; hydrogen; copper(II) sulfate; quinoline; Lindlar's catalyst; In toluene;

DOI:10.1021/ja00246a027

Reference yield:

4,4-difluorotetradeca-2,5-dien-8-yn-1-ol (108234-89-5) → 10,10-difluoroarachidonic acid (108212-58-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: LiBr / tetrahydrofuran / Ambient temperature

3: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h

4: H₂ / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature

5: H₂O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02

With ammonium hydroxide; Rhisopus arrhizus lipase; hydroxylamine hydrochloride; sodium cyanide; water; hydrogen; copper(II) sulfate; triethylamine; lithium bromide; quinoline; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00246a027

Reference yield:

1-bromo-4,4-difluorotetradeca-2,5-dien-8-yne (108234-91-9) → 10,10-difluoroarachidonic acid (108212-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h

2: H₂ / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature

3: H₂O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02

With ammonium hydroxide; Rhisopus arrhizus lipase; hydroxylamine hydrochloride; sodium cyanide; water; hydrogen; copper(II) sulfate; quinoline; Lindlar's catalyst; In toluene;

DOI:10.1021/ja00246a027

upstream raw materials:

methyl 10,10-difluoroarachidonate

methyl hex-5-ynoate

4,4-difluorotetradeca-2,5-dien-8-yn-1-ol

1-bromo-4,4-difluorotetradeca-2,5-dien-8-yne

Refernces