tert-Butyl 6-chloro-3,5-dioxohexanoate

Base Information

• Chemical Name: tert-Butyl 6-chloro-3,5-dioxohexanoate
• CAS No.: 276249-18-4
• Molecular Formula: C10H15 Cl O4
• Molecular Weight: 234.68
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID30439647
• Nikkaji Number: J1.476.615D
• Wikidata: Q82255658
• Mol file: 276249-18-4.mol

Synonyms:tert-Butyl 6-chloro-3,5-dioxohexanoate;276249-18-4;6-Chloro-3,5-dioxo hexanic acid, 1,1-dimethyl ethyl ester;t-butyl 6-chloro-3,5-dioxohexanoate;SCHEMBL5443383;6-Chloro-3,5-dioxo hexanic acid,1,1-dimethyl ethyl ester;DTXSID30439647;BCP29771;AKOS015961480;AC-14056;F79421;3,5-Dioxo-6-chlorohexanoic acid tert-butyl ester;6-Chloro-3,5-dioxo-hexanoic acid,tert-butyl ester;J-016828;Hexanoic acid, 6-chloro-3,5-dioxo-, 1,1-dimethylethyl ester;6-Chloro-3,5-dioxo hexanic acid, 1,1-dimethyl ethyl ester pound>>t-butyl 6-chloro-3,5-dioxohexanoate

Chemical Property of tert-Butyl 6-chloro-3,5-dioxohexanoate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 301.3°Cat760mmHg
• PKA: 6?+-.0.10(Predicted)
• Flash Point: 116.3°C
• PSA: 60.44000
• Density: 1.157g/cm³
• LogP: 1.48530
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 234.0658866
• Heavy Atom Count: 15
• Complexity: 265

Purity/Quality:

≥99.0% ^*data from raw suppliers

tert-Butyl6-chloro-3,5-dioxohexanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of tert-Butyl 6-chloro-3,5-dioxohexanoate

There total 2 articles about tert-Butyl 6-chloro-3,5-dioxohexanoate 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: 97.0%

C10H11ClO6 (1401896-78-3) + tert-butyl alcohol (75-65-0) → tert-butyl 6-chloro-3,5-dioxohexanoate (276249-18-4)

Guidance literature:

for 2.5h; Product distribution / selectivity; Reflux;

Reference yield: 70.0%

methyl chloroacetate (96-34-4) + tert-Butyl acetoacetate lithium bis-enolate → tert-butyl 6-chloro-3,5-dioxohexanoate (276249-18-4)

Guidance literature:

In tetrahydrofuran; at -60 ℃;

DOI:10.1002/1521-3773(20001201)39:23<4306::AID-ANIE4306>3.0.CO;2-G

Reference yield: 95.5%

tert-butyl 6-chloro-3,5-dioxohexanoate (276249-18-4) → 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate (154026-93-4)

Guidance literature:

With hydrogen; (R)-[RuCl₂(BINAP)]n; In ethanol; at 95 - 105 ℃; for 0.666667 - 480h; under 67506.8 - 75007.5 Torr; Conversion of starting material;

upstream raw materials:

methyl chloroacetate

C₁₀H₁₁ClO₆

tert-butyl alcohol

Downstream raw materials:

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate

(S)-6-chloromethyl-5,6-dihydropyran-2-one

1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate

Refernces

• 1、 Wolberg, Michael,Hummel, Werner,Wandrey, Christian,Mueller, Michael. "Highly regio- and enantioselective reduction of 3,5-dioxocarboxylates". . p. 4306 - 4308. Retrieved 2007/10/03.