(E)-4-hydroxybut-2-enal

Base Information

• Chemical Name: (E)-4-hydroxybut-2-enal
• CAS No.: 18445-71-1
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.0904
• DSSTox Substance ID: DTXSID201346326
• Nikkaji Number: J1.177.129G,J128.593I
• Mol file: 18445-71-1.mol

Synonyms:4-hydroxycrotonaldehyde;penitricin B

Chemical Property of (E)-4-hydroxybut-2-enal

Chemical Property:

• Vapor Pressure: 0.00748mmHg at 25°C
• Boiling Point: 238.5°Cat760mmHg
• Flash Point: 97.4°C
• PSA: 37.30000
• Density: 1.037g/cm³
• LogP: -0.26620
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 86.036779430
• Heavy Atom Count: 6
• Complexity: 56.6

Purity/Quality:

99% ^*data from raw suppliers

(2E)-4-Hydroxy-2-butenal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C=CC=O)O
• Isomeric SMILES: C(/C=C/C=O)O
• Uses: (2E)-4-Hydroxy-2-butenal has been used as a reactant for organic reactions such as Henry reaction, [4+2] annulation (Robinson annulation) and asymmetric Michael addition.

Technology Process of (E)-4-hydroxybut-2-enal

There total 5 articles about (E)-4-hydroxybut-2-enal 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: 80.0%

glycolaldehyde dimer (23147-58-2,110822-84-9,110822-85-0,77431-49-3) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → trans-4-hydroxy-2-butenal (29343-64-4,122093-66-7,18445-71-1)

Guidance literature:

In tetrahydrofuran; for 8h; Reflux;

DOI:10.1039/c2cc33309k

Reference yield: 48.3%

trans-4,4-dimethoxy-2-butenol (152522-71-9) → trans-4-hydroxy-2-butenal (29343-64-4,122093-66-7,18445-71-1)

Guidance literature:

With Amberlyst-15 ion exchange resin; In water; acetone; at 20 ℃; for 0.5h;

DOI:10.1021/tx00044a014

Reference yield:

2,5-dihydrofuran (1708-29-8) → cis-butenedial (3675-13-6) + trans-4-hydroxy-2-butenal (29343-64-4,122093-66-7,18445-71-1) + 2-buten-4-olide (497-23-4) + maleic acid (110-16-7,26099-09-2)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; at 20 ℃; for 3h; anodic oxidation on PbO₂;

DOI:10.1002/prac.19943360708

upstream raw materials:

2,5-dihydrofuran

trans-4,4-dimethoxy-2-butenol

glycolaldehyde dimer

(triphenylphosphoranylidene)acetaldehyde

Downstream raw materials:

C₁₂H₁₄O₂

C₁₃H₁₆O₃

4-(4-Methoxy-phenyl)-tetrahydro-furan-2-ol

4-(4-dimethylaminophenyl)-tetrahydrofuran-2-ol