3-Pentyl Acetoacetate

Base Information

• Chemical Name: 3-Pentyl Acetoacetate
• CAS No.: 13562-81-7
• Molecular Formula: C9H16O3
• Molecular Weight: 172.2215
• Hs Code.: 2918300090
• European Community (EC) Number: 672-728-2
• DSSTox Substance ID: DTXSID60562917
• Nikkaji Number: J235.978B
• Mol file: 13562-81-7.mol

Synonyms:3-Pentyl Acetoacetate;13562-81-7;PENTAN-3-YL 3-OXOBUTANOATE;Acetoacetic Acid 3-Pentyl Ester;Acetoacetic acid sec-amyl ester;ACETOACETICACID3-PENTYLESTER;3-Amyl Acetoacetate;Acetoacetic Acid 3-Amyl Ester;SCHEMBL7321395;DTXSID60562917;PFTIWTQFHWICDR-UHFFFAOYSA-N;A0813;CS-0445426;D88330

Chemical Property of 3-Pentyl Acetoacetate

Chemical Property:

• Vapor Pressure: 0.167mmHg at 25°C
• Refractive Index: 1.424
• Boiling Point: 213.2 °C at 760 mmHg
• Flash Point: 82.4 °C
• PSA: 43.37000
• Density: 0.967 g/cm³
• LogP: 1.69730
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 172.109944368
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

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

AcetoaceticAcid3-PentylEster ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC(=O)CC(=O)C

Technology Process of 3-Pentyl Acetoacetate

There total 1 articles about 3-Pentyl Acetoacetate 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:

2-pentanol (584-02-1) + ethyl acetoacetate (141-97-9) → pentan-3-yl 3-oxobutanoate (13562-81-7)

Guidance literature:

With sodium; Heating;

Reference yield: 76.0%

pentan-3-yl 3-oxobutanoate (13562-81-7) + 4-ethynyl-6-methyl-1-tosyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one → pentan-3-yl (Z)-2-(2,5-dimethyl-1-tosyl-1H-indol-3-yl)-3-hydroxybut-2-enoate

Guidance literature:

With sodium pivalate hydrate; copper(II) bis(trifluoromethanesulfonate); In N,N-dimethyl-d₆-formamide; at 60 ℃; for 22h; Inert atmosphere;

DOI:10.1039/c8cc04499f

Reference yield:

pentan-3-yl 3-oxobutanoate (13562-81-7) → (2S,3R)-pentan-3-yl 3-(4-methoxyphenoxy)-2-methylpentanoate

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Reflux; Inert atmosphere

2: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 - 20 °C / Inert atmosphere

3: C₃H₄F₅NO₄S₂*C₃₁H₃₂BNO / toluene / 1 h / -95 °C / Inert atmosphere

4: zinc borohydride / tetrahydrofuran; chloroform; toluene / 5 h / -45 °C / Inert atmosphere

5: pyridine / 12 h / 20 °C / Inert atmosphere

With pyridine; 4-acetamidobenzenesulfonyl azide; zinc borohydride; C₃H₄F₅NO₄S₂*C₃₁H₃₂BNO; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; chloroform; toluene; acetonitrile; mineral oil; 3: Roskamp reaction;

DOI:10.1002/anie.201204350

upstream raw materials:

2-pentanol

ethyl acetoacetate

Downstream raw materials:

(3-Pentyl)-dihydro-orsellinat

(S)-pentan-3-yl 2-methyl-3-oxopentanoate