2819-05-8

Usage

Uses

Used in Chemical Synthesis:
2-TERT-BUTYLPROPANE-1,3-DIOL is used as a building block in the synthesis of other organic compounds due to its versatile chemical structure and reactivity.
Used in Solvent Applications:
2-TERT-BUTYLPROPANE-1,3-DIOL is used as a solvent in various industrial applications, taking advantage of its high boiling point and low volatility, which make it suitable for use in high-temperature processes.
Used in Commercial and Industrial Settings:
2-TERT-BUTYLPROPANE-1,3-DIOL is used in commercial and industrial settings due to its relatively low toxicity and safety profile, making it a preferred choice for applications where chemical safety is a concern.

InChI:InChI=1/C7H16O2/c1-7(2,3)6(4-8)5-9/h6,8-9H,4-5H2,1-3H3

Upstream product

• 5340-78-3 ethyl 3,3-dimethylbutanoate 
• 1070-83-3 tert-Butylacetic acid 
• 6802-75-1 diethyl isopropylidenemalonate 
• 1184-53-8 methylcopper 
• 67-64-1 acetone 
• 105-53-3 diethyl malonate 
• 55740-28-8 2-(tert-butyl)malonaldehyde 
• 759-24-0 tert-butylmalonic acid diethyl ester 

Downstream Products

• 36976-68-8 2-(hydroxymethyl)-3,3-dimethylbutyl 4-methylbenzenesulfonate 
• 39536-50-0 (5-tert-Butyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-dimethyl-amine 
• 39536-49-7 (5-tert-Butyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-dimethyl-amine 
• 138741-39-6 (S)-2-Benzyloxymethyl-3,3-dimethyl-butan-1-ol 
• 252954-90-8 4,4-dimethyl-1-phenyl-3-triethylsilanyloxymethyl-pentan-2-one 
• 443284-59-1 (S)-2-(4-Methoxy-benzyloxymethyl)-3,3-dimethyl-butan-1-ol 
• 443284-35-3 2-tert-butyl-1-p-methoxybenzyloxypropan-3-ol 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Synthesis and acidity of conformationally constrained 1,3-oxathiane S-oxides

Conformationally constrained 5-tert-butyl 1,3-oxathiane was synthesized and oxidation led to the diastereoisomeric sulfoxides and the respective sulfone. Stereoelectronic effects are discussed for these compounds and their corresponding 2-carbanions. pKavalues are calculated for these compounds and compared with the respective 1,3-dithiane-derived sulfide, the sulfoxides, and the sulfone.

Conformationally constrained 2-methylidene 1,3-oxathiane S-oxides: Synthesis and nucleophilic additions

The properties of vinyl sulfoxides are significantly influenced by stereoelectronic effects, where the relative orientation of sulfoxide group and alkene moiety is responsible for reactivity and selectivity, e.g., in the addition of nucleophiles. Conformationally constrained derivatives of 2-methylidene 1,3-oxathiane S-oxides allow the quantification of stereoelectronic effects. Suitable substrates were prepared by oxidation of 2-hydroxymethyl-1,3-oxathianes and pyrolysis of the respective xanthogenates. Nucleophilic additions of ethyl thiolate, piperidine, and dimethyl malonate anion are over 100 times faster to axial sulfoxides than to the respective equatorial substrates. The oxathiane derivatives turned out to be about 1000 times less reactive than the respective 1,3-dithianes.

Esters of 2,5-multisubstituted-1,3-dioxane-2-carboxylic acid: their conformational analysis and selective hydrolysis

The carbomethoxy group at the C2 position of the 2,5-multisubstituted 1,3-dioxanes prefers the axial conformation rather than the equatorial one due to an anomeric effect. The trans isomers of the 5-monosubstituted compounds are more selectively hydrolyzed than the cis isomers. Based on the calculated results, hydrolysis to the trans isomers is attributed to the larger carbonyl charges of the trans than those of the cis isomers. The anomeric and homoanomeric effects will explain the axial preference of the carbomethoxy group and selective hydrolysis to the trans isomers. Furthermore, the calculated stability between the cis and trans isomers is in good agreement with the experimental results in the equilibrium state.

Conformational analysis and selective hydrolysis of 2,5-disubstituted-1,3-dioxane-2-carboxylic acid esters

5-Alkyl-2-methyl-2-carbomethoxy-1,3-dioxanes were found to have a cis preferential configuration in the equilibrium state, and the ester hydrolysis rate of the trans-isomers was faster than that of the cis-isomers. Conformational analysis and charge calculation of the carbomethoxy group in both dioxanes elucidated this selectivity.

Spiropiperidine derivatives and their use as fungicides

The invention provides spiropiperidine derivatives of the general formula or an acid-addition salt thereof, in which R1 represents a hydrogen atom or an optionally substituted alkyl, aryl or aralkyl group; R2 represents a hydrogen atom or an optionally su

A solution and solid state conformation of 2-diphenylphosphinoyl-1,3-dioxanes. The nature of O-C-P anomeric interactions

Diastereoisomeric 2-diphenylphosphinoyl-1,3-dioxanes 1-4 were synthesized either via the Arbuzov reaction of isopropyl diphenylphosphinite with (1,3-dioxan-2-yl) trimethylammonium iodides or via the transacetalization reaction between 1,3-diols and diphenyl (diethoxymethyl) phosphine oxide. The latter reaction afforded less thermodynamically stable isomers of 3 and 4 in a good yield (44 and 56%, respectively). The magnitude of the anomeric effect in this system determined according to the Franck's equation was found to be 19.7 kJ/mol. Both the NMR and X-ray structural data concerning cis-4,6-dimethyl-1,3-dioxane derivatives 4 suggest that the anomeric effect could stem from several interaction, including the no-δ* C-P negative hyper-conjugation and intramolecular hydrogen bond formation.

Cycloalkylmethyl Radicals. Part 8. A Conformational Study of Dioxa- and Dithia-cyclohexylmethyl Radicals by EPR Spectroscopy

The conformations of some six-membered oxygen- and sulphur-containing heterocyclic rings have been investigated by EPR spectroscopy using the methylenyl group, CH2., directly attached to a ring carbon atom as a 'spin probe'.For the 2-oxacyclohexylmethyl radical the CH2. group has a 'conformational free energy' preference for the equatorial position, -ΔG0273 = 1.4 kcal mol-1, which is about twice as large as the 0.7 kcal mol-1 found previously for cyclohexylmethyl.The equatorial preference of the CH2. group is still greater in (1,3-dioxan-2-yl)methylradicals; indeed, even with the cis-(5-tert-butyl-1,3-dioxan-2-yl)methyl radical the CH2. group was equatorial and the tert-butyl group axial.The CH2. group in (1,3-dioxan-5-yl)methyl also exhibits a strong preference for the equatorial position (ΔG0 > ca. 1.5 kcal mol-1), but with cis-(2-methyl-1,3-dioxan-5-yl)methyl it is the methyl group which is equatorial and the CH2. group axial.These and other axial/equatorial conformational preferences and the rotational conformational preference of the plane of the CH2. group with respect to the Cβ-Hβ bond are rationalized in terms of subtle steric factors which involve 1,3-axial/axial interactions, or lack thereof, and the variation in the lengths of C-C, C-O and C-S bonds.

ANALYSE STRUCTURALE EN SERIE CYCLOBUTANIQUE. Partie 1. Derives monosubstitues et gem disubstitues du cyclobutane

Methylene bending mode analysis of some cyclobutane-d2 molecules reveals that in the dissolved state (solvent CCl4), bromocyclobutane occurs exclusively in a pseudo-equatorial form, whereas, under the same conditions, cyclobutanol and 1-bromocyclobutane carbonitrile exist both in pseudo-axial and pseudo-equatorial conformations.NMR spectroscopy confirms the results obtained for bromocyclobutane and leads to the conclusion that the pseudo-equatorial conformer is predominant in the case of cyclobutanol as well as in that of cyclobutane carbonitrile.A theoretical study of cyclobutanol in the gaseous state by the P.C.I.L.O. method gives results which are consistent with a pseudo-equatorial conformer.

2-Oxo-1,3,2-dioxathianes. I. Preparation of the Alkyl-substituted Derivatives

2-Oxo-1,3,2-dioxathiane, all methyl- and several other alkyl-substituted 2-oxo-1,3,2-dioxathianes have been synthesized by condensing 1,3-alkanediols and thionyl chloride.The amount of the S==O-axial and S==O-equatorial isomers can be controlled by adding pyridine to the reaction mixture.