2,2,6,6-Tetramethylheptane-3,5-dione

Base Information

• Chemical Name: 2,2,6,6-Tetramethylheptane-3,5-dione
• CAS No.: 1118-71-4
• Deprecated CAS: 139996-82-0,61346-74-5,82846-74-0,61346-74-5,82846-74-0
• Molecular Formula: C11H20O2
• Molecular Weight: 184.279
• Hs Code.: 29141900
• European Community (EC) Number: 214-268-3
• NSC Number: 174296
• UNII: R8UI909HOY
• DSSTox Substance ID: DTXSID7049396
• Nikkaji Number: J4.487C
• Wikidata: Q27287980
• ChEMBL ID: CHEMBL3186481
• Mol file: 1118-71-4.mol

Synonyms:2,2,6,6,-tetramethyl-3,5-heptanedione;dipivaloylmethane

Chemical Property of 2,2,6,6-Tetramethylheptane-3,5-dione

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 0.00138mmHg at 25°C
• Melting Point: >400 °C (decomp)
• Refractive Index: n20/D 1.459(lit.)
• Boiling Point: 202.8 °C at 760 mmHg
• PKA: 11.60±0.10(Predicted)
• Flash Point: 67.2 °C
• PSA: 34.14000
• Density: 0.901 g/cm³
• LogP: 2.60690
• Storage Temp.: Store below +30°C.
• Solubility.: Difficult to mix.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

99%+, ^*data from raw suppliers

2,2,6,6-Tetramethyl-3,5-heptanedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-40-36/37/38
• Safety Statements: 24/25-36-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(C)(C)C(=O)CC(=O)C(C)(C)C
• Uses: suzuki reaction 2,2,6,6-tetramethyl-3,5-heptanedione was used in the synthesis of α-aryl-β-diketones1 and dicyanamidobenzene-bridge diruthenium complex. 2,2,6,6-Tetramethyl-3,5-heptanedione is a beta diketone with antibacterial activity.

Technology Process of 2,2,6,6-Tetramethylheptane-3,5-dione

There total 15 articles about 2,2,6,6-Tetramethylheptane-3,5-dione 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%

2,2,6,6-tetramethylhepta-4-yn-3-one (62688-81-7) → 2,2,6,6-tetramethylheptane-3,5-dione (1118-71-4)

Guidance literature:

With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate; In methanol; at 25 ℃; for 12h;

Reference yield: 88.0%

pinacolone enolate anion (64723-95-1) + pivaloyl chloride (3282-30-2) → 2,2,6,6-tetramethylheptane-3,5-dione (1118-71-4)

Guidance literature:

pinacolone enolate anion; pivaloyl chloride; In toluene; at 0 - 20 ℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique;

With hydrogenchloride; In water; Solvent;

DOI:10.1021/acs.joc.9b00433

Reference yield: 64.0%

3,3-dimethyl-butan-2-one (75-97-8) + Methyl pivalate (598-98-1) → 2,2,6,6-tetramethylheptane-3,5-dione (1118-71-4)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 50 ℃; for 5h;

DOI:10.1080/00397910701572803

upstream raw materials:

3,3-dimethyl-butan-2-one

pivalic acid phenyl ester

pivaloyl chloride

Methyl pivalate

Downstream raw materials:

4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-2,2,6,6-tetramethyl-3,5-heptanedione

1,3-di-t-butyl-2-methylpropan-1,3-dione

2,2,4,4-Tetramethyl-4-(phenylselenenyl)heptane-3,5-dione

C₃₄H₄₈O₄Te

Refernces

• 1、 Roitburd,G.V. et al.. "-". . p. 4935 - 4940. Retrieved 1972.
• 2、 Kollenz, Gert,Kappe, C. Olivier,Nabey, Hesham Abd el. "ON THE REACTION OF 2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONE ("DIPIVALOYLMETHANE") WITH OXALYL CHLORIDE". . p. 669 - 673. Retrieved 1991.
• 3、 Arnett,De Palma. "". . p. 5828. Retrieved 1977.
• 4、 -. "Method of preparing 1,3-diketone compound by acetyenic ketone". Paragraph 0236-0241. . Retrieved 2019/06/12.