6117-91-5

Basic information

• Product Name: Crotonyl alcohol
• Synonyms: 1-Hydroxy-2-butylene;2-buten-1-ol (crotyl alcohol);2-Butenol;2-Butenyl alcohol;2-butenylalcohol;CH3CH=CHCH2OH;Crotyl alcohol,c&t;Krotylalkohol
• CAS NO: 6117-91-5
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• EINECS: 207-996-8
• Product Categories: Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 6117-91-5.mol
• Article Data: 166

Chemical Properties

• Melting Point: -91.3°C (estimate)
• Boiling Point: 121-122 °C(lit.)
• Flash Point: 37 °C
• Appearance: Clear light yellow liquid
• Density: 0.845 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.24mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: Flammables area
• PKA: 14.70±0.10(Predicted)
• Water Solubility: Miscible with water.
• Merck: 14,2601
• BRN: 1719374
• CAS DataBase Reference: Crotonyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: Crotonyl alcohol(6117-91-5)
• EPA Substance Registry System: Crotonyl alcohol(6117-91-5)

Safety Data

• Hazard Codes: Xn,F
• Statements: 10-21/22
• Safety Statements: 36/37
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• RTECS: EM9275000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 6117-91-5(Hazardous Substances Data)

Usage

Description

Crotyl alcohol, also known as 3-buten-2-ol, is a primary alcohol with the hydroxy function bonded to a CH3CH2CHCH2 group. It is characterized by its clear light yellow liquid appearance and is recognized for its versatile applications across various industries.

Uses

Used in Chemical Industry:
Crotyl alcohol is used as a chemical intermediate for the synthesis of various compounds and as a source of monomers, which are essential building blocks for creating polymers and other complex molecules.
Used in Pharmaceutical Industry:
Crotyl alcohol is used as a starting material in the synthesis of antitumor agents such as 14-azacamptothecin and 10,11-methylenedioxy-14-azacamptothecin. These compounds have potential applications in cancer treatment, making crotonyl alcohol a valuable precursor in the development of novel therapeutics.
Used in Agriculture:
Crotyl alcohol serves as a herbicide and soil fumigant, helping to control the growth of unwanted plants and improve crop yields. Its application in agriculture contributes to more efficient and effective pest management strategies.

Hazard

Toxic by ingestion, strong eye and skin irritant. Moderate fire risk.

Safety Profile

Moderately toxic by ingestion and skin contact. Mutation data reported. Dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also ALCOHOLS.

InChI:InChI=1/C4H8O/c1-2-3-4-5/h2-3,5H,4H2,1H3/b3-2+

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 598-32-3 2-hydroxy-3-butene 
• 563-52-0 2-chloro-3-butene 
• 18826-95-4 1.3-butanediol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 4894-61-5 trans-but-2-enyl chloride 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 2203-35-2 3-chloro-1-butanol 
• 4435-50-1 butane-1,2,3-triol 
• 144-62-7 oxalic acid 
• 98-88-4 benzoyl chloride 
• 64-19-7 acetic acid 
• 123-73-9 crotonaldehyde 
• 591-97-9 1-chloro-2-butene 

Downstream Products

• 82259-92-5 but-2-enyl 3-oxobutanoate 
• 94291-54-0 (E)-2-butenyl hexanoate 
• 872-38-8 2,3-epoxybutan-1-ol 
• 4784-77-4 (E/Z)-crotyl bromide 
• 22037-73-6 3-bromo-1-butene 
• 598-32-3 2-hydroxy-3-butene 
• 4435-50-1 butane-1,2,3-triol 
• 4021-75-4 2,3-dibromo-1-butanol 
• 63467-43-6 4-hydroxy-butane-2-sulfonic acid 
• 60626-96-2 4-nitro-benzoic acid but-2-enyl ester 
• 563-52-0 2-chloro-3-butene 
• 10487-71-5 crotonyl chloride 
• 106-99-0 buta-1,3-diene 
• 591-97-9 1-chloro-2-butene 

Relevant articles and documents

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

Selective production of 1,3-butadiene from 1,3-butanediol over Y2Zr2O7 catalyst

The vapor-phase dehydration of 1,3-butanediol (1,3-BDO) to produce 1,3-butadiene (BD) was evaluated over yttrium zirconate, which was prepared through a hydrothermal aging process. 1,3-BDO was initially dehydrated to three unsaturated alcohols, namely 3-buten-2-ol, 3-buten-1-ol, and 2-buten-1-ol, followed by the further dehydration to BD. The catalytic activity of yttrium zirconate was greatly dependent on the calcination temperature. Also, the reaction temperature was one of the important factors to produce BD efficiently. The selectivity to BD was increased with increasing reaction temperature up to 375°C, while coke formation resulted in catalyst deactivation together with by-product formation at higher temperatures. Yttrium zirconate catalyst calcined at 900°C showed a high BD yield of 95% at 375°C and 10 hr on stream.

Preparation method of 2-butenol

The invention discloses a preparation method of 2-butenol, which comprises the following steps of: reacting 2-butenol and isopropanol serving as reaction raw materials, aluminum isopropoxide serving as a catalyst I and metal chloride or metal oxide servin