Crotonaldehyde

Base Information

• Chemical Name: Crotonaldehyde
• CAS No.: 123-73-9
• Molecular Formula: C4H6O
• Molecular Weight: 70.091
• Hs Code.: 29121990
• European Community (EC) Number: 224-030-0
• ICSC Number: 0241
• UN Number: 1143
• UNII: 6PUW625907
• DSSTox Substance ID: DTXSID6020351
• Nikkaji Number: J118.444J,J9.294K
• Wikipedia: Crotonaldehyde
• Wikidata: Q416036
• NCI Thesaurus Code: C107141
• Pharos Ligand ID: 2CHA95U5Q4ZN
• Metabolomics Workbench ID: 56429
• ChEMBL ID: CHEMBL1086445
• Mol file: 123-73-9.mol

Synonyms:2-Butenal,(E)-;Crotonaldehyde, (E)- (8CI);(2E)-2-Butenal;(E)-2-Butenal;(E)-Crotonaldehyde;2(E)-Butenal;Topanel CA;trans-2-Buten-1-al;trans-2-Butenal;trans-Crotonal;trans-Crotonaldehyde;

Chemical Property of Crotonaldehyde

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 32 mm Hg ( 20 °C)
• Melting Point: - 76 °C(lit.)
• Refractive Index: n20/D 1.437
• Boiling Point: 104 °C at 760 mmHg
• Flash Point: 4.6 °C
• PSA: 17.07000
• Density: 0.819 g/cm³
• LogP: 0.76140
• Storage Temp.: 2-8°C
• Solubility.: water: soluble425.4g/L at 20°C
• Water Solubility.: 150 g/L (20 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 70.041864811
• Heavy Atom Count: 5
• Complexity: 45.6
• Transport DOT Label: Poison Inhalation Hazard Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

(E)-2-Butenal(~0.1%MEHQ) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T+,N
• Hazard Codes: F,T+,N
• Statements: 11-24/25-26-37/38-41-48/22-50-68-R68-R50-R48/22-R41-R37/38-R26-R24/25-R11
• Safety Statements: 26-28-36/37/39-45-61-28A-S61-S45-S36/37/39-S28A-S26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: CC=CC=O
• Isomeric SMILES: C/C=C/C=O
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: Lachrymation. The vapour is severely irritating to the skin, eyes and respiratory tract. Inhalation of high concentrations may cause lung oedema. Exposure far above the OEL could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the liver and respiratory tract. Tumours have been detected in experimental animals but may not be relevant to humans.
• Uses: Crotonaldehyde (2-butenal, β-methyl acrolein, propylene aldehyde) is similar in structure to acrolein, as both are α,β-unsaturated aldehydes. This structural similarity leads to similar sensitizing and irritating properties of the two compounds. Crotonaldehyde is used industrially in the preparation of other chemicals (chiefly sorbic acid), flavoring agents, and can form endogenously and in the environment. Crotonaldehyde is used in the manufacture ofbutyl alcohol, butyraldehyde, and in severalorganic synthesis.

Technology Process of Crotonaldehyde

There total 378 articles about Crotonaldehyde 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: 20.0%

acetaldehyde (75-07-0,9002-91-9) + propionaldehyde (123-38-6) → 2-pentenal (1576-86-9,1576-87-0,764-39-6) + 2-methyl-2-pentenal (14250-96-5,16958-22-8,623-36-9) + crotonaldehyde (123-73-9,4170-30-3)

Guidance literature:

With aniline hydrochloride; In N,N-dimethyl acetamide; at 125 ℃; for 3h; Autoclave;

DOI:10.1134/S0965544118120083

Reference yield:

C3H5Fe(CO)3NO3 → iron pentacarbonyl (13463-40-6,37220-42-1) + 1,4-Pentadiene (591-93-5) + methylallylether (627-40-7) + vinylmethyl ketone (53859-89-5) + crotonaldehyde (123-73-9,4170-30-3)

Guidance literature:

In methanol; water; decompn. in statu nascendi; further products: propene und traces of allyl alcohol;

Reference yield:

→ trans-Crotonaldehyde (123-73-9,4170-30-3) + chloramben (133-90-4)

Guidance literature:

upstream raw materials:

acetaldehyde

2-butenoic acid

formic acid

2H-pyran-2-one-5-carboxylic acid

Downstream raw materials:

trans,trans-2,4-Hexadienal

2,4,6-octatrienal

2,4,6,8-decatetraenal

2,4-hexadienal

Refernces

• 1、 Skattebol,L.. "-". . p. 1554 - 1559. Retrieved 1966.
• 2、 Kaichev, Vasily V.,Chesalov, Yuriy A.,Saraev, Andrey A.,Klyushin, Alexander Yu.,Knop-Gericke, Axel,Andrushkevich, Tamara V.,Bukhtiyarov, Valerii I.. "Redox mechanism for selective oxidation of ethanol over monolayer V2O5/TiO2 catalysts". . p. 82 - 93. Retrieved 2016.
• 3、 Ordomsky,Sushkevich,Ivanova. "Study of acetaldehyde condensation chemistry over magnesia and zirconia supported on silica". . p. 85 - 93. Retrieved 2010.
• 4、 Cvetanovic,Doyle. "". . p. 2187,2189. Retrieved 1960.
• 5、 Raphael,Sondheimer. "-". . p. 2693. Retrieved 1951.
• 6、 Gamez, Patrick,Arends, Isabel W. C. E.,Reedijk, Jan,Sheldon, Roger A.. "Copper(II)-catalysed aerobic oxidation of primary alcohols to aldehydes". . p. 2414 - 2415. Retrieved 2003.
• 7、 Sharma, Priyamvada,Sailani, Riya,Meena, Anita,Khandelwal. "Kinetics and Mechanism of Electron Transfer Reactions: Oxidation of Crotyl Alcohol by Peroxomonosulfate in Aqueous Acidic Medium". . p. 335 - 342. Retrieved 2018.
• 8、 Zeisel,v.Bitto. "-". . p. 591. Retrieved 1908.
• 9、 Bone. "-". . p. 814. Retrieved 1934.
• 10、 Parfenov, Mikhail V.,Pirutko, Larisa V.,Soshnikov, Igor E.,Starokon, Eugeny V.,Kharitonov, Alexander S.,Panov, Gennady I.. "Vinylation of phenol by acetaldehyde: A new reaction for the synthesis of o-vinylphenol". . p. 59 - 62. Retrieved 2016.