25260-60-0

Basic information

• Product Name: CIS-1,4-DIACETOXY-2-BUTENE
• Synonyms: TIMTEC-BB SBB008422;CIS-DIACETOXY-2-BUTENE;CIS-1,4-DIACETOXY-2-BUTENE;CIS-2-BUTENE-1,4-DIOL DIACETATE;CIS-2-BUTENE-1,4-DIACETATE;(Z)-2-Butene-1,4-diol bisacetate;(Z)-2-Butene-1,4-diol diacetate;(Z)-2-Butene-1,4-diyl diacetate
• CAS NO: 25260-60-0
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: -0
• Mol File: 25260-60-0.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 120-121°C 18mm
• Flash Point: >110°C
• Appearance: Clear colorless/Liquid
• Density: 1,09 g/cm3
• Vapor Pressure: 0.064mmHg at 25°C
• Refractive Index: 1.4416
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible in water.
• BRN: 1724379
• CAS DataBase Reference: CIS-1,4-DIACETOXY-2-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,4-DIACETOXY-2-BUTENE(25260-60-0)
• EPA Substance Registry System: CIS-1,4-DIACETOXY-2-BUTENE(25260-60-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 25260-60-0(Hazardous Substances Data)

Usage

Uses

cis-1,4-Diacetoxy-2-butene is used as an organic chemical synthesis intermediate.

General Description

cis-1,4-Diacetoxy-2-butene is an ester. Ruthenium olefin metathesis catalysts having cyclic (alkyl)(amino)carbenes effectively catalyzes the cross-metathesis of cis-1,4-diacetoxy-2-butene with allylbenzene. cis-1,4-Diacetoxy-2-butene on pyrolysis affords 1-acetoxy-1,3-butadiene, a diacetate and an isomeric 1,2-diacetoxy-3-butene. Mechanism of pyrolysis has been investigated.

InChI:InChI=1/C8H12O4/c1-7(9)11-5-3-4-6-12-8(2)10/h3-4H,5-6H2,1-2H3/b4-3-

Upstream product

• 6974-12-5 1,4-dibromo-2-butene 
• 563-63-3 silver(I) acetate 
• 127-09-3 sodium acetate 
• 821-11-4 1,4-butenediol 
• 108-24-7 acetic anhydride 
• 930-22-3 epoxybutene 
• 300-57-2 allylbenzene 
• 64-19-7 acetic acid 
• 108-22-5 Isopropenyl acetate 
• 106-99-0 buta-1,3-diene 
• 5371-49-3 acetoxyacetaldehyde 
• 103204-31-5 4-Sulfamoyl-benzoic acid allyl ester 
• 591-87-7 Allyl acetate 
• 1573-17-7 2-butyn-1,4-diol diacetate 

Downstream Products

• 200628-58-6 Acetic acid 2-(hydroxy-phenyl-methyl)-but-3-enyl ester 
• 114837-56-8 syn-2-(acetoxymethyl)-1-phenylbut-3-en-1-ol 
• 114837-56-8 anti-2-(acetoxymethyl)-1-phenylbut-3-en-1-ol 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 36215-15-3 (Z)-4-Phenyl-2-buten-1-yl acetate 
• 259268-91-2 acetic acid 4-phenyl-but-2-enyl ester 
• 21040-45-9 Cinnamyl acetate 
• 151251-52-4 2-[1-[(4-methylphenyl)sulfonyl]tetrahydro-4(1H)-pyridinyliden]ethyl acetate 
• 91133-05-0 1-nitro-2-(pent-1-en-1-yl)benzene 
• 768392-65-0 (R)-(+)-1-acetoxy-4-(2-nitrophenyl)-2-hexene 
• 792948-34-6 (11aS,E)-acetic acid 3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allyl ester 

Relevant articles and documents

Ionic liquid [BMIM]PF6 as a medium for the selective hydrogenation of 1,4-diacetoxybut-2-yne on the Pd-containing catalysts

A possibility of using a ionic liquid, 1-n-butyl-3-methylimidazolium hexafluorophosphate ([BMIM]PF6), as a reaction medium in the liquid-phase hydrogenation of 1,4-diacetoxybut-2-yne was examined. Two types of catalysts were studied: Pd(10%)/C and the palladium-containing catalytic system based on the biopolymer chitosan supported on silica gel (Pd(1%)/chitosan/SiO2). The data obtained indicate high selectivity of hydrogenation of 1,4-diacetoxybut-2-yne to cis-1,4-diacetoxybut-2-ene under selected conditions.

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.

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.