3-Formylbut-2-enyl acetate

Base Information

• Chemical Name: 3-Formylbut-2-enyl acetate
• CAS No.: 26586-02-7
• Molecular Formula: C7H10 O3
• Molecular Weight: 142.155
• European Community (EC) Number: 247-825-4,238-989-8
• DSSTox Substance ID: DTXSID201031492
• Nikkaji Number: J227.231H,J248.979A
• Wikidata: Q76324381
• Mol file: 26586-02-7.mol

Synonyms:3-Formylbut-2-enyl acetate;(E)-3-Formylbut-2-enyl acetate;26586-02-7;14918-80-0;EINECS 247-825-4;EC 247-825-4;2-Butenal, 4-(acetyloxy)-2-methyl-;Crotonaldehyde, 4-hydroxy-2-methyl-, acetate;SCHEMBL3137231;4-acetoxy-2-methylcrotonaldehyde;4-Acetyloxy-2-methyl-2-butenal;LPDDKAJRWGPGSI-ZZXKWVIFSA-N;DTXSID201031492;(E)-2-Methyl-4-acetoxy-2-butenal;(E)-3-Methyl-4-oxobut-2-en-1-ylacetate;(E)-3-Methyl-4-oxobut-2-en-1-yl acetate;2-Butenal, 4-(acetyloxy)-2-methyl-, (2E)-;W-110398

Chemical Property of 3-Formylbut-2-enyl acetate

Chemical Property:

• Vapor Pressure: 0.0586mmHg at 25°C
• Boiling Point: 232.6°Cat760mmHg
• Flash Point: 96.6°C
• PSA: 43.37000
• Density: 1.027g/cm³
• LogP: 0.69470
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCOC(=O)C)C=O
• Isomeric SMILES: C/C(=C\COC(=O)C)/C=O

Technology Process of 3-Formylbut-2-enyl acetate

There total 45 articles about 3-Formylbut-2-enyl acetate 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: 91.0%

acetoxyacetaldehyde (5371-49-3) + 2-(triphenylphosphoranylidene)propionaldehyde (24720-64-7) → (E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + (Z)-4-Acetoxy-2-methyl-2-butenal (69551-41-3)

Guidance literature:

In benzene; for 23h; Yields of byproduct given. Title compound not separated from byproducts; Heating;

Reference yield: 88.0%

4-acetoxy-1-chloro-2-methyl-2-butene (38872-49-0) → (E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7)

Guidance literature:

With N-ethylmorpholine N-oxide; In N,N-dimethyl-formamide; r.t., 1 h, 50 deg C, 4 h;

DOI:10.1246/bcsj.59.3287

Reference yield: 86.0%

(E)-4-hydroxy-3-methylbut-2-en-1-yl acetate (57152-93-9,70473-55-1,132032-87-2) → (E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7)

Guidance literature:

With oxygen; tris(triphenylphosphine)ruthenium(II) chloride; In 1,2-dichloro-ethane; under 760 Torr; Ambient temperature;

DOI:10.1039/c39810000907

upstream raw materials:

1,1-Diethoxy-4-acetoxy-2-methyl-2-buten

(E)-1,4-diacetoxy-2-methyl-2-butene

γ-Acetoxy-tiglinaldehyd-oxim

(E)-4,4-diethoxy-3-methyl-but-2-en-1-ol

Downstream raw materials:

(11Ξ)-O-acetyl-retinol

1,3,3-trimethyl-2-[(1E,3E)-3-methyl-1,3-pentadienyl]cyclohexene

(2E,6E,8E)-4-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatriene acetate

Retinol acetate

Refernces

• 1、 Babler et al.. "". . p. 1716. Retrieved 1979.
• 2、 -. "Synthetic method of trans-4-acetoxyl-2-methyl-2-butene-1-aldehyde". Paragraph 0026; 0039; 0040. . Retrieved 2016/12/22.
• 3、 Yang, Fanglong,Newsome, Jeffery J.,Curran, Dennis P.. "Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers". . p. 14200 - 14205. Retrieved 2008/02/10.