1576-98-3

Basic information

• Product Name: 1,4-DIACETOXY-2-BUTENE
• Synonyms: 2-BUTENE-1,4-DIOL DIACETATE;1,4-DIACETOXY-2-BUTENE;TRANS-2-BUTENE-1,4-DIACETATE;TRANS-1,4-DIACETOXY-2-BUTENE;Butene-1,4-diolDiacetate,trans-2-;trans-2-Butene-1,4-dioldiacetate;1,4-Diacetoxy-trans-2-butene;(2E)-1,4-Diacetoxy-2-butene
• CAS NO: 1576-98-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• Mol File: 1576-98-3.mol

Chemical Properties

• Melting Point: 14-16 °C
• Boiling Point: 114 °C(Press: 9 Torr)
• Appearance: /
• Density: 1.0842 g/cm3
• CAS DataBase Reference: 1,4-DIACETOXY-2-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIACETOXY-2-BUTENE(1576-98-3)
• EPA Substance Registry System: 1,4-DIACETOXY-2-BUTENE(1576-98-3)

Safety Data

• Hazardous Substances Data: 1576-98-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-DIACETOXY-2-BUTENE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to facilitate the creation of complex organic molecules that are integral to drug development.
Used in Organic Chemical Production:
In the organic chemical industry, 1,4-DIACETOXY-2-BUTENE is employed as a versatile building block for the production of a range of organic chemicals, leveraging its reactivity and functional groups to form diverse chemical entities.
Used as a Solvent:
1,4-DIACETOXY-2-BUTENE is utilized as a solvent in various chemical processes, capitalizing on its ability to dissolve a wide array of substances and facilitate reactions in a controlled environment.
Used in Synthesis of Other Organic Compounds:
It is also used as a reagent in the synthesis of other organic compounds, where its unique structure and properties enable the formation of new chemical entities for various applications across different industries.

Upstream product

• 108-24-7 acetic anhydride 
• 106-99-0 buta-1,3-diene 
• 6974-12-5 1,4-dibromo-2-butene 
• 563-63-3 silver(I) acetate 
• 127-09-3 sodium acetate 
• 930-22-3 epoxybutene 
• 300-57-2 allylbenzene 
• 25260-60-0 cis-1,4-bis(acetyloxy)but-2-ene 
• 108-22-5 Isopropenyl acetate 
• 821-11-4 1,4-butenediol 
• 64-19-7 acetic acid 
• 5371-49-3 acetoxyacetaldehyde 
• 103204-31-5 4-Sulfamoyl-benzoic acid allyl ester 
• 591-87-7 Allyl acetate 

Downstream Products

• 126544-40-9 racemic-1,4-Dibenzyl-2-vinylpiperazine 
• 14918-80-0 3-methyl-4-oxobut-2-enyl acetate 
• 68480-27-3 undec-2-en-1-yl acetate 
• 53627-36-4 3-vinylbutyrolactone 
• 18085-02-4 1,2-diacetoxy-3-butene 

Relevant articles and documents

Influence of the N→Ru Coordinate Bond Length on the Activity of New Types of Hoveyda-Grubbs Olefin Metathesis Catalysts Containing a Six-Membered Chelate Ring Possessing a Ruthenium-Nitrogen Bond

An efficient approach to the synthesis of new types of Hoveyda-Grubbs catalysts containing an N→Ru bond in a six-membered chelate ring is proposed. The synthesis of the organometallic compounds is based on the interaction of ready accessible 2-vinylbenzylamines and 1,3-bis(2,4,6-trimethylphenyl)-2-trichloromethylimidazolidine ligands with dichloro(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphane)ruthenate, and it afforded the target ruthenium complexes in 70-80% yields. Areas of practical utility and potential applications of the obtained chelates were highlighted by tests of the catalysts in different olefin cross-metathesis (CM) and ring-closing-metathesis (RCM) reactions. These experiments revealed a high catalytic performance (up to 10-2 mol %) of all the synthesized structures in a broad temperature range. The structural peculiarities of the resultant ruthenium catalysts were thoroughly investigated by X-ray crystallography, which allowed making a reliable correlation between the structure of the metallo-complexes and their catalytic properties. It was proved that the bond length between ruthenium and nitrogen in the six-membered chelate ring has the greatest effect on the stability and efficiency of the catalyst. As a rule, the shorter and stronger the N→Ru bond, the higher the stability of the complex and the worse its catalytic characteristics. In turn, the coordination N→Ru bond length can be finely tuned and varied over a wide range of values by changing the steric volume of the cyclic substituents at the nitrogen atom, which will make it possible, as appropriate, to obtain in the future metal complexes with predictable stability and the required catalytic activity. Also, it was found that complexes in which the nitrogen atom is included in the morpholine or isoquinoline rings are the most efficient catalysts in this series. An attempt to establish a correlation between the N→Ru bond length and the 1H and 13C chemical shifts in the Ru═CH fragment has been made.

Palladium(II)-catalyzed isomerization of (Z)-1,4-diacetoxy-2-butene: Solvent effects

The isomerization of (Z)-1,4-diacetoxy-2-butene (1) catalyzed by PdCl 2(MeCN)2 was studied in THF and DMF. The reaction occurs more rapidly in THF than in DMF, but in both solvents it did not proceed to complete consumption of the substrate and led to a mixture of 1, (E)-1,4-diacetoxy-2-butene (2), and 1,2-diacetoxy-3-butene (3). The formation of 2 is more favored in DMF than in THF. The reactivity of 1 and the solvent effect differ strongly from those previously obtained with Pd(PPh 3)4 as the catalyst. Interpretations are provided for the crucial role of the nature of both solvent and intermediates on the course of the isomerizations. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Effect of a proximal oxygen substituent on the efficacy of ruthenium-catalyzed cross-metathesis and RCM

Ruthenium-catalyzed cross-metathesis of various derivatives of 1,2-dihydroxy-3-butene reveals that cyclic acetals are best suited as substrates compared to acyclic diethers or diacetates, while RCM is relatively insensitive to the presence of allylic or homoallylic hydroxy or acetoxy groups.

Palladium(0)-catalyzed isomerization of (Z)-1,4-diacetoxy-2-butene - Dependence of η1- or η3-allylpalladium as a key intermediate on the solvent polarity

In the presence of Pd(PPh3)4, (Z)-1,4-diacetoxy-2-butene is selectively isomerized to (E)-1,4-diacetoxy-2-butene in THF while both (E)-1,4-diacetoxy-2-butene and 1,2-diacetoxy-3-butene are obtained in DMF. Evidence to support the involvement of an η1-allylpalladium in the former solvent and of a cationic η3-allylpalladium in the latter as the keys intermediates is presented.

Preparation method of 4-acetoxy-2-methyl-2-butenal

The invention discloses a method for preparing 4-acetoxyl-2-methyl-2-butenal, and the method comprises the following steps: forming a catalyst system by using a cobalt acid complex and a metal chloride, mixing 4-acetoxyl-2-methylene butyraldehyde (III) with hydrogen, and performing heating to react to obtain the 4-acetoxyl-2-methyl-2-butenal. In the prior art, precious metal needs to be used as a catalyst in the step, and the yield and the selectivity are not high. The method does not need to use a noble metal catalyst, is lower in cost, high in double-bond isomerization reaction speed and high in reaction yield, and is easy to realize industrial production.

Process for preparation of 4-acetoxy-2-methyl-2-butene-1-aldehyde and intermediates thereof

The invention relates to the technical field of organic synthesis, and discloses a method for preparing 4-acetoxy-2-methyl-2-butene-1-aldehyde and an intermediate thereof. The method comprises the following steps: (1) in the presence of an esterification reagent, carrying out esterification reaction on 1, 4-butenediol to obtain 1, 4-butenediol diacetate; (2) in the optional presence of a first catalyst, carrying out an isomerization reaction on the 1, 4-butenediol diacetate to obtain 3, 4-diacetoxy-1-butene; (3) in the presence of a phosphorus-containing ligand and a rhodium catalyst and/or a cobalt catalyst, carrying out hydroformylation reaction on the 3, 4-diacetoxy-1-butene, carbon monoxide and hydrogen to obtain 2-methyl-3, 4-diacetoxy-1-butyraldehyde; (4) in the optional presence of a third catalyst, carrying out an elimination reaction on the 2-methyl-3, 4-diacetoxyl-1-butyraldehyde to obtain the 4-acetoxyl-2-methyl-2-butene-1-aldehyde. The method provided by the invention has the advantages of mild reaction conditions, environmental friendliness and high yield.

Protection of COOH and OH groups in acid, base and salt free reactions

We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.

Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines

This report describes the stereoselective synthesis of 3-azido-tetralins, -chromanes, and -tetrahydroquinolines via a tandem allylic azide rearrangement/Friedel-Crafts alkylation. Exposure of allylic azides with a pendant trichloroacetimidate to catalytic quantities of AgSbF6 proved optimal for this transformation. This cascade successfully differentiates the equilibrating azide isomers, providing products in excellent yield and selectivity (>25 examples, up to 94% yield and >25:1 dr). In many cases, the reactive isomer is only a trace fraction of the equilibrium mixture, keenly illustrating the dynamic nature of these systems. We demonstrate the utility of this process via a synthesis of hasubanan.

Preparation method of 3,4-diacetoxy-1-butene

The invention discloses a preparation method of 3,4-diacetoxy-1-butene. The preparation method comprises steps as follows: an esterification step: 1,4-butylene glycol and acetic acid are subjected to an esterification reaction in the presence of acid, a solution containing 1,4-diacetoxy-2-butene and acetic acid is obtained, acetic acid is removed and 1,4-diacetoxy-2-butene is obtained; an isomerization step: cuprous catalysts are added to 1,4-diacetoxy-2-butene obtained in the esterification step, the mixture is heated for an isomerization rearrangement reaction, and a mixed solution containing 3,4-diacetoxy-1-butene is obtained; a purification step: the mixed solution obtained in the isomerization step is purified, and 3,4-diacetoxy-1-butene is obtained. The preparation method adopts easy-to-realize reaction conditions and has the characteristic of high yield.

OLEFIN METATHESIS CATALYSTS

This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.