Tiglic aldehyde

Base Information

• Chemical Name: Tiglic aldehyde
• CAS No.: 497-03-0
• Molecular Formula: C5H8 O
• Molecular Weight: 84.1179
• Hs Code.: 29121990
• European Community (EC) Number: 207-833-0
• NSC Number: 2179
• UNII: 27ZVE2K81C
• DSSTox Substance ID: DTXSID1049308
• Nikkaji Number: J126.513J,J102.093E
• Wikipedia: Trans-2-Methyl-2-butenal
• Wikidata: Q3045687
• Metabolomics Workbench ID: 142349
• ChEMBL ID: CHEMBL53493
• Mol file: 497-03-0.mol

Synonyms:(E)-2-methyl-2-butenal;2-methyl-2-butenal;2-methylbut-2-enal

Chemical Property of Tiglic aldehyde

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Melting Point: -101.15°C (estimate)
• Refractive Index: n20/D 1.448(lit.)
• Boiling Point: 117.9°Cat760mmHg
• Flash Point: 18.3°C
• PSA: 17.07000
• Density: 0.826g/cm³
• LogP: 1.15150
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in water
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 84.057514874
• Heavy Atom Count: 6
• Complexity: 72

Purity/Quality:

98% ^*data from raw suppliers

trans-Methyl-2-butenal ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xi
• Statements: 11-36/37/38-10
• Safety Statements: 16-26-36

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC=C(C)C=O
• Isomeric SMILES: C/C=C(\C)/C=O
• Description: 2-Methyl-2-butenal has a penetrating, powerful green ethereal odor. May be prepared by condensation of acetaldehyde and propionaldehyde.
• Uses: Tiglic aldehyde was used in the concise total synthesis of 7-demethylpiericidin A1. It was used as starting reagent during the synthesis of:alkyl-branched tetraene hydrocarbons, pheromone component for dried fruit beetleE,E-2,4-dimethyl-2,4-hexa dienal, volatile constituents of the defensive secretions of Leiobunum nigripalpi 4-methyl-2,4-hexadiene-1-ol

Technology Process of Tiglic aldehyde

There total 29 articles about Tiglic aldehyde 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: 95.0%

(E)-2-methyl-2-buten-1-ol (497-02-9) → 2-methylbut-2-enal (497-03-0)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol2017802

Reference yield: 87.0%

dimethylacetylene (503-17-3) + carbon monoxide (201230-82-2) → 2-methylbut-2-enal (497-03-0)

Guidance literature:

With C₃₄H₅₁NP₂; hydrogen; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In tetrahydrofuran; at 100 ℃; for 10h; under 30003 Torr; stereoselective reaction; Schlenk technique; Autoclave; Inert atmosphere;

DOI:10.1002/anie.201300759

Reference yield: 81.0%

Tiglic acid (80-59-1) → 2-methylbut-2-enal (497-03-0)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jm960280m

upstream raw materials:

3-ethoxy-2-methylbutanal

(2S,4S)-carveol

(+)-trans-carveol

acetaldehyde

Downstream raw materials:

2,3,6-trimethylquinoline

2-methyl-4-((Ξ)-2-methyl-but-2t-enyliden)-4H-oxazol-5-one

Carbonic acid ethyl ester (E)-2-methyl-buta-1,3-dienyl ester

Diethyl carbonate

Refernces

• 1、 Kumar, Kamlesh,Joshi, Penny,Rawat, Diwan S. "(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols". . . Retrieved 2021/09/02.
• 2、 Fang, Xianjie,Zhang, Min,Jackstell, Ralf,Beller, Matthias. "Selective palladium-catalyzed hydroformylation of alkynes to α,β-Unsaturated Aldehydes". . p. 4645 - 4649. Retrieved 2013/05/22.