Tiglic aldehyde

Base Information

• Chemical Name: Tiglic aldehyde
• CAS No.: 6038-09-1
• Molecular Formula: C5H8O
• Molecular Weight: 84.1179
• 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: 6038-09-1.mol

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

Chemical Property of Tiglic aldehyde

Chemical Property:

• PSA: 17.07000
• LogP: 1.15150
• 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:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC=C(C)C=O
• Isomeric SMILES: C/C=C(\C)/C=O

Technology Process of Tiglic aldehyde

There total 2 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:

Dichloromethyl methyl ether (4885-02-3) + 1-methylprop-1-enyltributyltin (86633-14-9,86633-15-0,859828-60-7) → 2-methylbut-2-enal (497-03-0) + (Z)-2-methyl-2-butenal (6038-09-1)

Guidance literature:

With aluminium trichloride; In dichloromethane; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/cber.19961290111

Reference yield:

Dichloromethyl methyl ether (4885-02-3) + dibutylbis(1-methyl-1-propenyl)stannane → 2-methylbut-2-enal (497-03-0) + (Z)-2-methyl-2-butenal (6038-09-1)

Guidance literature:

With aluminium trichloride; In dichloromethane; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/cber.19961290111

Reference yield: 98.0%

(Z)-2-methyl-2-butenal (6038-09-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (2E,4E)-4-methylhexa-2,4-dienoate (149400-42-0,90107-62-3)

Guidance literature:

In dichloromethane; at 20 ℃; for 312h;

DOI:10.1021/ol403441c

upstream raw materials:

Dichloromethyl methyl ether

1-methylprop-1-enyltributyltin

Downstream raw materials:

(E)-2-methyl-2-butenal N,N-dimethylhydrazone

(1S,2R,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethyl-2-carboxaldehyde

(1R,2S,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dimethyl-2-carboxaldehyde

(3E,5Z)-1-{(2R,4R,6R)-6-[2-(4-methoxyphenoxy)ethyl]-2-phenyl-1,3-dioxan-4-yl}-5-methylhepta-3,5-dien-2-one

Refernces