2-Hexyl-3-methylmaleic anhydride

Base Information

• Chemical Name: 2-Hexyl-3-methylmaleic anhydride
• CAS No.: 75052-75-4
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• UNII: VX30JT6S7C
• DSSTox Substance ID: DTXSID90456173
• Nikkaji Number: J875.186B
• Wikidata: Q27292063
• ChEMBL ID: CHEMBL2270567
• Mol file: 75052-75-4.mol

Synonyms:2-Hexyl-3-methylmaleic Anhydride;3-Hexyl-4-methylfuran-2,5-dione;75052-75-4;Maleic anhydride, hexylmethyl-;2,5-Furandione, 3-hexyl-4-methyl-;UNII-VX30JT6S7C;VX30JT6S7C;3-Hexyl-4-methyl-2,5-furandione;starbld0000916;CHEMBL2270567;SCHEMBL10908238;DTXSID90456173;2-nonene-2,3-dicarboxylic acid anhydride;FT-0669207;Q27292063

Chemical Property of 2-Hexyl-3-methylmaleic anhydride

Chemical Property:

• PSA: 43.37000
• LogP: 2.35670
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 196.109944368
• Heavy Atom Count: 14
• Complexity: 276

Purity/Quality:

98% ^*data from raw suppliers

2-Hexyl-3-methylmaleic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCC1=C(C(=O)OC1=O)C
• Uses: An ingredient present in the volatile oils of California raisins and almond hulls, possible insect attractants.

Technology Process of 2-Hexyl-3-methylmaleic anhydride

There total 11 articles about 2-Hexyl-3-methylmaleic anhydride 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: 67.0%

N-benzyl-3-hexyl-4-methylmaleimide → 3-Hexyl-4-methylfuran-2,5-dione (75052-75-4)

Guidance literature:

N-benzyl-3-hexyl-4-methylmaleimide; With potassium hydroxide; In tetrahydrofuran; methanol; for 2h; Heating;

DOI:10.1055/s-2004-829116

Reference yield:

pentylmagnesium iodide (3814-99-1) + 2-(bromomethyl)-3-methyl maleic anhydrate (98453-81-7) → 3-Hexyl-4-methylfuran-2,5-dione (75052-75-4)

Guidance literature:

With copper(l) iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; at -5 - 20 ℃; for 8h;

DOI:10.1021/jo981114k

Reference yield:

2,3-Dimethylmaleic anhydride (766-39-2) → 3-Hexyl-4-methylfuran-2,5-dione (75052-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NBS, benzoyl peroxide / CCl₄ / 10 h / Heating

2: CuI / diethyl ether; hexamethylphosphoric acid triamide / 8 h / -5 - 20 °C

With N-Bromosuccinimide; copper(l) iodide; Perbenzoic acid; In tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether;

DOI:10.1021/jo981114k

upstream raw materials:

citraconic acid anhydride

1-(hexylcarbonyloxy)pyridine-2(1H)-thione

pentylmagnesium iodide

2-(bromomethyl)-3-methyl maleic anhydrate

Refernces

• 1、 De Buyck, Laurent,Cagnoli, Rita,Ghelfi, Franco,Merighi, Giulia,Mucci, Adele,Pagnoni, Ugo M.,Parsons, Andrew F.. "A Simple and efficient route to chaetomellic anhydride A: A potent natural ras farnesyl-protein transferase inhibitor". . p. 1680 - 1686. Retrieved 2007/10/03.
• 2、 Poigny, Stephane,Guyot, Michele,Samadi, Mohammad. "An expeditious synthesis of chaetomellic anhydrides a and B, and analogues". . p. 2175 - 2177. Retrieved 2007/10/03.