3-Benzyl-2,4-pentanedione

Base Information

• Chemical Name: 3-Benzyl-2,4-pentanedione
• CAS No.: 1134-87-8
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Hs Code.: 2914399090
• NSC Number: 35139
• UNII: WC38C3PH26
• DSSTox Substance ID: DTXSID50150403
• Nikkaji Number: J103.857E
• Wikidata: Q83016491
• Mol file: 1134-87-8.mol

Synonyms:3-Benzyl-2,4-pentanedione;1134-87-8;3-benzylpentane-2,4-dione;2,4-Pentanedione, 3-benzyl-;2,4-Pentanedione, 3-(phenylmethyl)-;NSC-35139;NSC35139;NSC 35139;2,4-Pentandedione, 3-(phenylmethyl);2,4-Pentanedione, 3-benzyl- (8CI);2, 3-benzyl-;AI3-18949;2, 3-(phenylmethyl)-;3-benzyl-pentane-2,4-dione;SCHEMBL1896075;WC38C3PH26;DTXSID50150403;BAA13487;3-(Phenylmethyl)-2,4-pentanedione;MFCD00544307;AKOS004907979;3-Benzyl-2,4-pentanedione, AldrichCPR;BS-37035

Chemical Property of 3-Benzyl-2,4-pentanedione

Chemical Property:

• Vapor Pressure: 0.00282mmHg at 25°C
• Melting Point: 203-205 °C
• Refractive Index: 1.506
• Boiling Point: 285.317 °C at 760 mmHg
• PKA: 10.26±0.46(Predicted)
• Flash Point: 106.212 °C
• PSA: 34.14000
• Density: 1.04 g/cm³
• LogP: 2.02330
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 190.099379685
• Heavy Atom Count: 14
• Complexity: 200

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Benzyl-2,4-pentanedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(CC1=CC=CC=C1)C(=O)C

Technology Process of 3-Benzyl-2,4-pentanedione

There total 47 articles about 3-Benzyl-2,4-pentanedione 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: 98.0%

acetylacetone (123-54-6,81235-32-7) + benzyl alcohol (100-51-6,185532-71-2) → 3-benzyl-pentane-2,4-dione (1134-87-8)

Guidance literature:

With rice husk ash nano silica supported 12-tungstophosphoric acid; at 80 ℃; for 0.0833333h; Neat (no solvent);

DOI:10.1016/j.molcata.2011.10.008

Reference yield: 94.0%

3-benzylidene acetylacetone (4335-90-4) → 3-benzyl-pentane-2,4-dione (1134-87-8)

Guidance literature:

With triethylsilane; iron(III) chloride hexahydrate; In dichloromethane; at 20 ℃; for 3.5h; chemoselective reaction;

DOI:10.1016/j.tetlet.2018.07.041

Reference yield: 91.0%

acetylacetone (123-54-6,81235-32-7) + benzyl alcohol (100-51-6,185532-71-2) → 3-benzyl-pentane-2,4-dione (1134-87-8) + dibenzyl ether (103-50-4)

Guidance literature:

With 12-tungestocobaltic acid supported on nano silica; at 80 ℃; for 0.0333333h; neat (no solvent);

DOI:10.1016/j.molcata.2012.03.005

upstream raw materials:

sodium acetoacetonate

benzyl chloride

sodium acetylacetonate

acetylacetone

Downstream raw materials:

4-benzyl-3,5-dimethyl-1H-pyrazole

4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione

3,3-dibenzyl-pentane-2,4-dione

4-Phenyl-2-butanone

Refernces

• 1、 Scully,F. et al.. "-". . p. 7352 - 7364. Retrieved 1978.
• 2、 Ridvan, Ludek,Zavada, Jiri. "Mono- vs. dialkylation of carbanions. Effects of absolute and relative acidity of the conjugate carbon acids in selectivity control". . p. 14793 - 14806. Retrieved 1997.
• 3、 Bloomfield,J.J.. "-". . p. 4112 - 4115. Retrieved 1961.
• 4、 Zhai, Guifa,Wang, Wenyan,Xu, Wei,Sun, Guo,Hu, Chaoqun,Wu, Xiangming,Cong, Zisong,Deng, Liang,Shi, Yanrong,Leadlay, Peter F.,Song, Heng,Hong, Kui,Deng, Zixin,Sun, Yuhui. "Cross-Module Enoylreduction in the Azalomycin F Polyketide Synthase". . p. 22738 - 22742. Retrieved 2020.
• 5、 Christoffers, Jens. "Facile nBu4NF mediated benzylation of congested 1,3-diketones". . p. 117 - 122. Retrieved 1999.
• 6、 Shimizu, Ken-Ichi,Yamamoto, Takumi,Tai, Yutaka,Okumura, Kazu,Satsuma, Atsushi. "Addition of olefins to acetylacetone catalyzed by cooperation of Br?nsted acid site of zeolite and gold cluster". . p. 171 - 175. Retrieved 2011.
• 7、 Ning, Yongquan,Song, Qingmin,Sivaguru, Paramasivam,Wu, Lizuo,Anderson, Edward A.,Bi, Xihe. "Ag-Catalyzed Insertion of Alkynyl Carbenes into C-C Bonds of β-Ketocarbonyls: A Formal C(sp2) Insertion". supporting information. p. 631 - 636. Retrieved 2022/01/20.
• 8、 Hilker, Simon,Posevins, Daniels,Unelius, C. Rikard,B?ckvall, Jan-E.. "Chemoenzymatic Dynamic Kinetic Asymmetric Transformations of β-Hydroxyketones". supporting information. p. 15623 - 15627. Retrieved 2021/10/07.