22607-11-0

Usage

Physical state

Colorless, odorless liquid

Uses

Solvent, dispersant, emulsifier in industrial and consumer products; improves stability and performance in coatings, adhesives, and personal care products; raw material for synthesis of other chemicals; potential applications in pharmaceutical and agricultural industries

Toxicity

Low toxicity, generally regarded as safe for use in intended applications.

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 4723-10-8 racem. 2,5-dimethyl-hexa-1,5-diene-3,4-diol 
• 815-77-0 isobutyroin 
• 94098-84-7 2,5-dimethyl-3-hydroperoxy-1,4-hexadiene 
• 67-63-0 isopropyl alcohol 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 97-62-1 Ethyl isobutyrate 
• 71-43-2 benzene 
• 1068-55-9 isopropylmagnesium chloride 
• 412346-29-3 (R)-1-((S)-3,3-Dimethyl-oxiranyl)-2-methyl-prop-2-en-1-ol 
• 78-84-2 isobutyraldehyde 
• 692-70-6 (E)-2,5-dimethylhex-3-ene 
• 75-09-2 dichloromethane 

Downstream Products

• 82343-38-2 C₂₂H₂₈N₂O₄ 

Relevant academic research and scientific papers

A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay

A colorimetric indicator displacement assay (IDA) amenable to high-throughput experimentation was developed to determine the percentage of cis and trans alkenes. Using 96-well plates two steps are performed: a reaction plate for dihydroxylation of the alkenes followed by an IDA screening plate consisting of an indicator and a boronic acid. The dihydroxylation generates either erythro or threo vicinal diols from cis or trans alkenes, depending upon their syn- or anti-addition mechanisms. Threo diols preferentially associate with the boronic acid due to the creation of more stable boronate esters, thus displacing the indicator to a greater extent. The generality of the protocol was demonstrated using seven sets of cis and trans alkenes. Blind mixtures of cis and trans alkenes were made, resulting in an average error of ±2 % in the percentage of cis or trans alkenes, and implementing E2 and Wittig reactions gave errors of ±3 %. Furthermore, we developed variants of the IDA for which the color may be tuned to optimize the response for the human eye.

Efficient diastereoselective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species

Reductive coupling reaction of aromatic and aliphatic aldehydes proceeded under mild conditions to give the corresponding pinacols in moderate to high yields and DL-diastereoselectivities by using combinations of either low valent titanium(II) bromide and copper or titanium(IV) iodide and copper in a mixed solvent of dichloromethane and pivalonitrile. In the case of using titanium(IV) iodide and copper, pinacols were obtained in good to high yields with moderate to high diastereoselectivities irrespective of the number of substitutuents at α-position of aliphatic aldehydes.

Dichloromethane as a source of the CH22-synthon: A combination of an arene-catalysed lithiation and a barbier-type reaction

The reaction of dichloromethane 1 with an excess of lithium powder (1:7 molar ratio) and catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of a carbonyl compound 2 (1:2 molar ratio) in tetrahydrofuran at -40°C yields, after hydrolysis, the corresponding 1,3-diols 3 in moderate yields. The process can be also applied to more complicated gem-dichloro derivatives such as 7,7-dichlorobicyclo[4.1.0]heptane 6 or methyl dichloromethyl ether 9.

Pinacol Coupling of Aliphatic Aldehydes Promoted by Niobium (III) Reagent

NbCl3 (DME) was found to be a useful reagent for the intermolecular pinacol coupling of aliphatic aldehydes.The high anti diastereoselectivity of this reaction (dl / meso >/= 9 / 1) did not depend on the variation in the aldehyde alkyl chain.With respect to intramolecular pinacolization, the loss of the stereoselectivity observed is consistent with the mechanism involving an insertion of the oxo-group into the metal-carbon bond of the intermediate niobiooxirane. - Key Words: Nb(III) reagent; Pinacol coupling; Acetalization; Stereoselectivity

REGIO-CONTROLLED FUNCTIONALIZATION OF 2,5-DIMETHYL-2,4-HEXADIENE INTO EPOXY ALCOHOLS BY PHOTOOXYGENATION IN THE PRESENCE OF TITANIUM(IV) OR VANADIUM(V)

Using Ti(OiPr)4 as oxygen transfer catalyst, the diene 1 afforded exclusively the epoxy alcohol 1c, but VO(acac)2 gave exclusively the isomerized epoxy alcohol 2c during its ene reaction with singlet oxygen.

PHOTOCHEMICAL REACTION OF ALCOHOLS-I IRRADIATION OF ALIPHATIC ALCOHOLS

The UV irradiation of aliphatic alcohols gave α-glycols as the principal products.The values of the dl-α-glycol to meso-α-glycol ratios obtained in each example were analyzed.The stereochemical course of the formation of α-glycols, their conformations and configurations were established on basis of 1H NMR data.