5-Methyl-3-methylene-2-hexanone

Base Information

• Chemical Name: 5-Methyl-3-methylene-2-hexanone
• CAS No.: 1187-87-7
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 2914190090
• DSSTox Substance ID: DTXSID40152214
• Nikkaji Number: J113.164H
• Mol file: 1187-87-7.mol

Synonyms:5-METHYL-3-METHYLENE-2-HEXANONE;1187-87-7;5-Methyl-3-methylenehexan-2-one;5-methyl-3-methylidenehexan-2-one;2-Hexanone, 5-methyl-3-methylene-;3-Isobutyl-3-buten-2-one #;SCHEMBL12447513;DTXSID40152214;AGMJVYMZEAWWND-UHFFFAOYSA-N;BAA18787;MFCD18205964;AKOS022182574;BS-26045;H11904;A905477

Chemical Property of 5-Methyl-3-methylene-2-hexanone

Chemical Property:

• Vapor Pressure: 1.5mmHg at 25°C
• Refractive Index: 1.419
• Boiling Point: 170 °C at 760 mmHg
• Flash Point: 54.1 °C
• PSA: 17.07000
• Density: 0.824 g/cm³
• LogP: 2.17770
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 123

Purity/Quality:

98% ^*data from raw suppliers

5-Methyl-3-methylene-2-hexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=C)C(=O)C
• Uses: 5-Methyl-3-methylene-2-hexanone is an impurity of Tetrabenazine (T284000), an antipsychotic.

Technology Process of 5-Methyl-3-methylene-2-hexanone

There total 11 articles about 5-Methyl-3-methylene-2-hexanone 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: 62.1%

trimethyl[2-(2-methylpropyl)-3-oxobutyl]azanium iodide (1069-62-1) → 5-methyl-3-methylidenehexan-2-one (1187-87-7)

Guidance literature:

With potassium hydroxide; In diethyl ether; water; at 20 ℃; for 18h;

DOI:10.1021/acs.joc.1c01098

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-Methyl-2-hexanone (110-12-3) → 5-methyl-3-methylidenehexan-2-one (1187-87-7)

Guidance literature:

With hydrogenchloride; diethyl amine hydrochloride;

DOI:10.1021/ja00796a019

Reference yield:

(2-acetyl-2-methoxycarbonyl-4-methyl-pentyl)-trimethyl-ammonium; iodide (51756-13-9) → 5-methyl-3-methylidenehexan-2-one (1187-87-7)

Guidance literature:

In N,N-dimethyl-formamide; at 75 ℃;

upstream raw materials:

3-bromo-5-methyl-3-(trimethylsilanyl-methyl)-hexan-2-one

(2-acetyl-2-methoxycarbonyl-4-methyl-pentyl)-trimethyl-ammonium; iodide

formaldehyd

5-Methyl-2-hexanone

Downstream raw materials:

(3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(+/-)-9,10-dihydroxy-3c-isobutyl-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one