1,4-Pentadien-3-ol

Base Information

• Chemical Name: 1,4-Pentadien-3-ol
• CAS No.: 922-65-6
• Molecular Formula: C5H8O
• Molecular Weight: 84.1179
• Hs Code.: 29052990
• European Community (EC) Number: 213-080-9
• DSSTox Substance ID: DTXSID00238922
• Nikkaji Number: J298.479B
• Wikidata: Q72499712
• Mol file: 922-65-6.mol

Synonyms:1,4-Pentadien-3-ol;922-65-6;Penta-1,4-dien-3-ol;CCRIS 8963;EINECS 213-080-9;MFCD00008633;divinylcarbinol;DTXSID00238922;AMY14244;BBL103212;STL557022;AKOS015915437;Divinyl carbinol;LS-188213;CS-0064552;FT-0649558;EN300-98370;A844183;1,4-Pentadien-3-ol, contains 0.4% hydroquinone as stabilizer, >=96%

Chemical Property of 1,4-Pentadien-3-ol

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 9.56mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 115.5 °C at 760 mmHg
• PKA: 13.68±0.20(Predicted)
• Flash Point: 30 °C
• PSA: 20.23000
• Density: 0.848 g/cm³
• LogP: 0.71930
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 84.057514874
• Heavy Atom Count: 6
• Complexity: 49

Purity/Quality:

98% min. (GC) ^*data from raw suppliers

1,4-Pentadien-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C=CC(C=C)O
• Uses: Starting material for asymmetric epoxidation.1,2 Substrate employed in a synthesis of amino-substituted dienes via a bismuth-catalyzed SNi displacement of alcohols by sulfonamide nucleophiles.

Technology Process of 1,4-Pentadien-3-ol

There total 17 articles about 1,4-Pentadien-3-ol 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: 92.0%

Triethyl<(1,4-pentadien-3-yl)oxy>silan (62418-65-9) → divinylcarbinol (922-65-6)

Guidance literature:

With Selectfluor; In acetonitrile; at 150 ℃; for 0.05h; Microwave irradiation;

DOI:10.1021/jo802494t

Reference yield: 81.0%

Vinyl bromide (593-60-2,25951-54-6) + formic acid ethyl ester (109-94-4) → divinylcarbinol (922-65-6)

Guidance literature:

Vinyl bromide; With magnesium; iodine; In tetrahydrofuran; at 20 - 40 ℃; Inert atmosphere;

formic acid ethyl ester; In tetrahydrofuran; at 5 - 20 ℃; for 2h;

Reference yield: 73.0%

Vinyl bromide (593-60-2,25951-54-6) + Methyl formate (107-31-3) → divinylcarbinol (922-65-6)

Guidance literature:

Vinyl bromide; With iodine; magnesium; In tetrahydrofuran; for 1h; Heating;

Methyl formate; In tetrahydrofuran; at 20 ℃; for 4h; Further stages.;

DOI:10.1002/hlca.200790169

upstream raw materials:

Methyl formate

vinylmagnesium chloride

1-penten-4-yne-3-ol

vinyl magnesium bromide

Downstream raw materials:

2,4-pentadien-1-ol

1,2,3,4,5-penta-O-acetyl-DL-arabinitol

1,2,3-triacetoxy-4,5-epoxy-pentane

Triethyl<(1,4-pentadien-3-yl)oxy>silan

Refernces

• 1、 Zhang, Zhen,Altaher, Maryam,Zhang, Hefeng,Wang, De,Hadjichristidis, Nikos. "Synthesis of Well-Defined Polyethylene-Based 3-Miktoarm Star Copolymers and Terpolymers". . p. 2630 - 2638. Retrieved 2016.
• 2、 Sugimoto, Kenji,Kobayashi, Ami,Kohyama, Aki,Sakai, Haruka,Matsuya, Yuji. "Divinylcarbinol Desymmetrization Strategy: A Concise and Reliable Approach to Chiral Hydroxylated Fatty Acid Derivatives". . p. 3970 - 3980. Retrieved 2021/03/01.
• 3、 Hori, Hiroto,Arai, Shigeru,Nishida, Atsushi. "Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes". supporting information. p. 1170 - 1176. Retrieved 2017/04/13.