Dibutyl tartrate

Base Information

• Chemical Name: Dibutyl tartrate
• CAS No.: 87-92-3
• Deprecated CAS: 15763-01-6,201280-88-8,60484-38-0,305322-71-8
• Molecular Formula: C12H22O6
• Molecular Weight: 262.303
• Hs Code.: 29181300
• European Community (EC) Number: 201-784-9
• UNII: 2D1V32IF1E
• DSSTox Substance ID: DTXSID10883265
• Nikkaji Number: J148.056A
• Wikipedia: Dibutyl_tartrate
• Wikidata: Q27254585
• Mol file: 87-92-3.mol

Synonyms:dibutyl tartrate

Chemical Property of Dibutyl tartrate

Chemical Property:

• Appearance/Colour: clear colourless to yellowish liquid after melting
• Melting Point: 20-22 °C
• Refractive Index: 1.446-1.448
• Boiling Point: 182 °C (11 mmHg)
• PKA: 11.42±0.20(Predicted)
• Flash Point: 167 °C
• PSA: 93.06000
• Density: 1.09 g/cm³
• LogP: 0.39480
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: 4.827g/L(temperature not stated)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 262.14163842
• Heavy Atom Count: 18
• Complexity: 227

Purity/Quality:

97% ^*data from raw suppliers

Dibutyl L-(+)-Tartrate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCCCOC(=O)C(C(C(=O)OCCCC)O)O
• Isomeric SMILES: CCCCOC(=O)[C@@H]([C@H](C(=O)OCCCC)O)O
• Uses: L-(+)-TARTARIC ACID DI-N-BUTYL ESTER is used as resolving agent

Technology Process of Dibutyl tartrate

There total 3 articles about Dibutyl tartrate 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: 68.0%

L-Tartaric acid (87-69-4,138508-61-9) + butan-1-ol (71-36-3) → (+)-(2R,3R)-dibutyl tartrate (87-92-3,15763-01-6)

Guidance literature:

With H+ resin; Zerolit 225; In benzene; for 8h; Heating;

DOI:10.1080/00397919608003611

Reference yield:

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate (622-00-4) + butan-1-ol (71-36-3) → (+)-(2R,3R)-dibutyl tartrate (87-92-3,15763-01-6)

Guidance literature:

In various solvent(s); at 39 ℃; for 24h; lipase from Pseudomonas fluorescens;

DOI:10.1016/S0040-4020(01)89450-3

Reference yield:

tartaric acid (87-69-4,138508-61-9) + butan-1-ol (71-36-3) → (+)-(2R,3R)-dibutyl tartrate (87-92-3,15763-01-6)

Guidance literature:

durch Destillation;

upstream raw materials:

tartaric acid

butan-1-ol

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate

L-Tartaric acid

Downstream raw materials:

threitol

butyl glyoxalate

butyl {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl)phenyl-3,7-dimethylnona-2,4,6.8}tetraenoate

dibutyl-2,3-bis(dibenzylphospho)-L-tartrate

Refernces

Enantioselective metallo-organocatalyzed preparation of cyclopentanes bearing an all-carbon quaternary stereocenter

10.1039/c2cc32823b

The research aimed to develop an enantioselective metallo-organocatalyzed method for the preparation of cyclopentanes that incorporate an all-carbon quaternary stereocenter, a significant challenge in organic chemistry due to the steric repulsion between the four carbon substituents. The researchers employed a cooperative catalytic strategy that combined aminocatalysis with a chiral copper(I) complex, leading to the enantio-enriched formation of cyclopentanes. Key chemicals used in this process included formyl-alkynes, chiral phosphorus ligands (A–F), copper(II) trifluoromethanesulfonate, cyclohexylamine, and various substrates such as gem-dimethylmalonate, gem-dimethoxymethyl, and gem-dibenzyloxymethyl groups. The study concluded that the cooperative enamine catalysis and copper(I)-4-MeO-3,5-(t-Bu)2-MeO-BIPHEP activation of alkynes resulted in enantioenriched cyclopentane carbaldehydes with moderate to excellent enantioselectivities, demonstrating the efficiency of this novel metallo-organocatalytic approach for constructing all-carbon quaternary stereogenic centers.

Combined experimental and theoretical investigation into C-H activation of cyclic alkanes by Cp′Rh(CO)₂ (Cp′ = η⁵- C₅H₅ or η⁵-C₅Me₅)

10.1039/c0dt00661k

The study investigates the C–H activation of cyclic alkanes by the rhodium complexes Cp'Rh(CO)? (Cp' = η?-C?H? or η?-C?Me?) using fast time-resolved infrared spectroscopy and density functional theory (DFT) calculations. The research explores how the rate of oxidative cleavage varies among different complexes and alkanes, specifically focusing on cyclopentane, cyclohexane, and neopentane. Unlike linear alkanes, where activation occurs at primary C–H bonds with rate dependence on chain hopping, cyclic alkanes exhibit activation controlled mainly by alkane binding strength. The study highlights that steric hindrance slows down the activation of neopentane compared to cyclic alkanes. The findings contribute to understanding transition metal-mediated C–H bond activation, a crucial step for applications like alkane functionalization and catalytic transformations.