14918-80-0

Basic information

• Product Name: 3-formylbut-2-enyl acetate
• Synonyms: 3-formylbut-2-enyl acetate;4-Acetyloxy-2-methyl-2-butenal;Acetic acid 3-formyl-2-butenyl ester;Einecs 238-989-8
• CAS NO: 14918-80-0
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.1525
• EINECS: 238-989-8
• Mol File: 14918-80-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 50-55 °C
• Boiling Point: 232.6 °C at 760 mmHg
• Flash Point: 96.5 °C
• Appearance: /
• Density: 1.027 g/cm³
• Vapor Pressure: 0.0586mmHg at 25°C
• Refractive Index: 1.438
• CAS DataBase Reference: 3-formylbut-2-enyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-formylbut-2-enyl acetate(14918-80-0)
• EPA Substance Registry System: 3-formylbut-2-enyl acetate(14918-80-0)

Safety Data

• Hazardous Substances Data: 14918-80-0(Hazardous Substances Data)

Usage

Synthesis

Vitamin A intermediated C5,namely 3- formylbut- 2- enyl acetate,which was used C15 + C5 synthesis route of vitamin A.?2- Chloro- 1- ethanol was used as starting material,esterified by acetic anhydride and protected by phosphate ester,and then reacted with 1,1- dimethoxy- 2propanone,trans- γ- acetoxytiglic aldehyde dimethyl acetal can be obtained,subsequently deprotection and 3- formylbut- 2- enyl acetate can be achieved.

Uses

3-Formylcrotyl Acetate can be used as a vitamin A intermediate.

InChI:InChI=1/C7H10O3/c1-6(5-8)3-4-10-7(2)9/h3,5H,4H2,1-2H3

Upstream product

• 1576-98-3 1,4-diacetoxybut-2-ene 
• 1438-14-8 2-isopropyloxirane 
• 14690-12-1 2-methyl-3-butenal 
• 127-08-2 potassium acetate 
• 29773-17-9 4-acetoxy-2-methylen-butanal 
• 108-24-7 acetic anhydride 
• 88322-53-6 4-hydroxy-2-methyl-2-butenal 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 74549-14-7 (E/Z)-4-Acetoxy-2-methyl-2-butenal-dimethylacetal 
• 3330-25-4 4-chloro-2-methyl-2-buteneal 
• 127-09-3 sodium acetate 
• 10523-96-3 3-methyl-3-butenyl chloride 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 55311-87-0 E,Z-4-bromo-3-methyl-1-acetoxy-2-butene 

Downstream Products

• 1416548-67-8 4-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,7-dien-5-ynyl acetate 
• 51575-59-8 C₁₀H₁₈O₃ 
• 4172-46-7 2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohex-1-enyl)heptadeca-2,4,6,8,10,12,14,16-octaenal 
• 127-47-9 Retinol acetate 
• 27231-36-3 5-methyl-1H-benzoimidazole-2-thiol 

Relevant articles and documents

Synthesis of analogues of citranaxanthin and their activity in free radical scavenging

Citranaxanthin and its analogues were synthesised via a C5 unit elongation to substituted conjugated polyenes. Their free radical scavenging activity was measured by 1,1-diphenyl-2-picrylhydrazinyl spectrophotometric methods. Results indicated that the new compounds exhibited antioxidant activities. Three new analogues had stronger antioxidant activity than citranaxanthin.

Catalytic oxidation method for preparation of 4-acyloxy-2-methyl-2-butenal

The invention provides a preparation method of 4-acyloxy-2-methyl-2-butenal. The preparation method comprises the following steps: preparing raw materials, subjecting the raw materials prepared in thestep 1 to reacting, and carrying out after-treatment to obtain the 4-acyloxy-2-methyl-2-butenal. The preparation method of the 4-acyloxy-2-methyl-2-butenal is simple in process and mild in reaction conditions, and is carried out in the presence of a catalyst; the catalyst is good in catalytic activity, has excellent stability and durability, and can obtain a product with relatively high yield; and preparation cost is low, little waste salt and waste water are generated in the preparation process, the concept of green chemistry is accorded with, and industrial amplification feasibility is high.

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.