4-Hydroxybutanal

Base Information

• Chemical Name: 4-Hydroxybutanal
• CAS No.: 25714-71-0
• Molecular Formula: C4H8 O2
• Molecular Weight: 88.1063
• Hs Code.: 2912491000
• European Community (EC) Number: 247-205-3
• UNII: 8T59P1Q6NO
• DSSTox Substance ID: DTXSID1067128
• Nikkaji Number: J287.307I
• Wikipedia: Gamma-Hydroxybutyraldehyde
• Wikidata: Q19597550
• Mol file: 25714-71-0.mol

Synonyms:4-hydroxybutanal

Chemical Property of 4-Hydroxybutanal

Chemical Property:

• Vapor Pressure: 0.101mmHg at 25°C
• Refractive Index: 1.4384
• Boiling Point: 196.7°Cat760mmHg
• PKA: 14.89±0.10(Predicted)
• Flash Point: 76.5°C
• PSA: 37.30000
• Density: 0.985g/cm³
• LogP: -0.04220
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 34.5

Purity/Quality:

100% ^*data from raw suppliers

4-Hydroxybutanal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC=O)CO
• Uses: 4-Hydroxybutanal is used in preparation of deoxykeoses and acetonides. 4-Hydroxybutanal is also a metabolite of Tegafur , a prodrug used for various cancer chemotherapies.

Technology Process of 4-Hydroxybutanal

There total 62 articles about 4-Hydroxybutanal 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: 93.0%

4-butanolide (96-48-0) → 4-hydroxybutyraldehyde (25714-71-0)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1016/S0040-4039(99)00895-3

Reference yield: 85.0%

cyclobutanol (2919-23-5) → cyclobutanone (1191-95-3) + 4-hydroxybutyraldehyde (25714-71-0)

Guidance literature:

With C₁₇H₁₉FeN₅O₄⁽¹⁸⁾O^(1-); In acetonitrile; at 26.84 ℃; Reagent/catalyst; Kinetics;

DOI:10.1021/acs.inorgchem.5b01937

Reference yield: 79.1%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 2-methoxytetrahydrofuran (13436-45-8) + 4-butanolide (96-48-0) + propan-1-ol (71-23-8) + 1-methoxy-1,4-butanediol + 2-(4'-hydroxybutoxy)-tetrahydrofuran (64001-06-5) + 4-hydroxy-butanoic acid 4-hydroxybutyl ester + Butane-1,4-diol (110-63-4) + 4-hydroxybutyraldehyde (25714-71-0) + methyl 4-hydroxybutanoate (925-57-5) + butan-1-ol (71-36-3)

Guidance literature:

With hydrogen; at 190 ℃; under 46504.7 Torr; Gas phase;

upstream raw materials:

tetrahydrofuran

2,3-dihydro-2H-furan

2-hydroperoxytetrahydrofuran

triphenylphosphine

Downstream raw materials:

2-ethoxytetrahydrofuran

[1-(Benzhydryl-amino)-4-hydroxy-butyl]-phosphinic acid

(Z)-4-decen-1-ol

2-(3-indole)-ethanol

Refernces

• 1、 Burgé,Flourat,Pollet,Spinnler,Allais. "3-Hydroxypropionaldehyde (3-HPA) quantification by HPLC using a synthetic acrolein-free 3-hydroxypropionaldehyde system as analytical standard". . p. 92619 - 92627. Retrieved 2015.
• 2、 Shi, Min. "Catalytic Oxidation of Tetrahydrofuran in the Presence of Transition Metal Complexes under Aerobic Conditions". . p. 592 - 593. Retrieved 1998.
• 3、 Rocek,Radkowsky. "". . p. 89,90. Retrieved 1973.
• 4、 Shi, Yong-Sen,Liu, Jian-Feng,Wu, Xiao-Lan,Ke, De-Hong,Xu, Sheng. "Synthesis of (E)-α-hydroxyethyl-α,β-unsaturated aldehydes by the reaction of tetrahydrofuran and aromatic aldehydes". supporting information. . Retrieved 2021/08/13.
• 5、 De Geest, Bruno G.,Van Herck, Simon. "Tweaking the acid-sensitivity of transiently thermoresponsive Polyacrylamides with cyclic acetal repeating units". . . Retrieved 2020/03/26.