5396-50-9

Usage

Uses

Used in Organic Synthesis:
2-(tert-butylthio)ethanol is utilized as an intermediate in organic synthesis, playing a crucial role in the formation of various complex organic compounds. Its reactivity and stability contribute to its value in this application.
Used as a Solvent:
In the chemical industry, 2-(tert-butylthio)ethanol is employed as a solvent, leveraging its ability to dissolve a wide range of substances, which is essential for numerous chemical reactions and processes.
Used in Metalworking Fluids:
2-(tert-butylthio)ethanol is used as a corrosion inhibitor in metalworking fluids, helping to prevent the degradation of metal surfaces during manufacturing processes, thereby extending the life of machinery and tools.
Used in Pharmaceutical Products:
In the pharmaceutical industry, 2-(tert-butylthio)ethanol serves as a stabilizer, ensuring the consistency and longevity of active pharmaceutical ingredients, which is vital for maintaining the efficacy and safety of medications.
It is important to handle 2-(tert-butylthio)ethanol with care, using appropriate personal protective equipment to minimize any potential risks associated with its use.

InChI:InChI=1/C6H14OS/c1-6(2,3)8-5-4-7/h7H,4-5H2,1-3H3

Upstream product

• 75-21-8 oxirane 
• 75-66-1 2-methylpropan-2-thiol 
• 540-51-2 2-bromoethanol 
• 107-07-3 2-chloro-ethanol 
• 29364-29-2 sodium tert-butyl thiolate 
• 594-01-4 1-chloroethanol 

Downstream Products

• 4303-44-0 2-(2-chloro-ethylsulfanyl)-2-methyl-propane 
• 55791-33-8 2-(2-Methyl-propane-2-sulfinyl)-ethanol 
• 362707-25-3 C₇H₁₆O₃S₂ 
• 118893-31-5 diethyl 2-(2-methyl-2-cyclohexen-1-yl)-2-<2-bromo-2-<(1,1-dimethylethyl)sulfonyl>ethyl>propane-1,3-dioate 
• 14094-13-4 vinyl (2-methyl-2-propyl) sulfide 
• 179612-04-5 (+/-)-2-(tert-butylsulfonyl)-3-phenyl-propan-1-ol 

Relevant academic research and scientific papers

Activatable fluorescent probes for hydrolase enzymes based on coumarin-hemicyanine hybrid fluorophores with large Stokes shifts

We show that the equilibrium of intramolecular spirocyclization of coumarin-hemicyanine hybrid fluorophores can be finely tuned by means of chemical modifications. We used this scaffold to develop activatable fluorescent probes with large Stokes shifts for γ-glutamyltranspeptidase and esterase.

Molecular addition compounds. 18. Borane adducts with hydroxydialkyl sulfide borates for hydroboration. New, essentially odorless, water-soluble sulfide borane acceptors for hydroboration

Hydroxydialkyl sulfides of general formula RS(CH2CH2)nH (R = Et, t-Bu, i-Am; n = 1-3) and thiodiethanol monomethyl ether (9) have been synthesized and used as borane carriers. The compounds 3 and 6 (R = Et, n = 2, 3), 7 (R = t-Bu, n = 3), and 9 are completely miscible with water and exhibit only very mild odor. The sulfides were transformed into the corresponding borates by treatment either with boric acid or with diborane. The borates complex 3 mol of borane per 1 mol of borate to give highly reactive, stable, liquid adducts, hydroborating 1-octene in 15 min at room temperature. The adducts derived from water soluble sulfides 3 and 9, selected for the hydroboration of more hindered olefins, reacted readily with (-)-β-pinene, 1-methyleyclohexene, and 2,3-dimethyl-2-butene. The carrier borates liberated from the adducts during hydroboration are readily hydrolyzed to give 3 and 9, which can be washed off with water from trialkylboranes or oxidation products. Consequently, hydroxydialkyl sulfides 3 and 9 are the first completely water-soluble sulfide borane carriers that can be washed off in the workup of hydroboration products. The adducts derived from 3 and 9 are new, highly promising reagents suitable for large scale hydroborations and reductions.

Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis

The Candida antarctica lipase catalyzed esterification of the hydroxymethyl sulfones rac-1a and rac-1b led to the isolation of ent-1a (92% ee) and 1b (≤99% eel, respectively. The acyloxymethyl sulfone ent-7a (≤99% ee) was obtained by the Candida antarctica lipase catalyzed hydrolysis of rac-7a. Not only Candida antarctica lipase but also Pseudomonas cepacia lipase showed the opposite enantiomer differentiation in the esterification of the methyl substituted alcohol rac-1a and the benzyl substituted alcohol rac-1b. The absolute configuration of ent-1a and 1b was determined by measurement of their circular dichroism and the calculation of the CD spectra of 1a and 1b by semiempirical methods. The configurational assignment was verified by X-ray structure analysis of 1b and ent-7a.

Preparation of enantiomerically pure α-hydroxymethyl S-tert-butyl sulfones by Candida antarctica lipase catalyzed resolution

Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of racemic methyl and benzyl substituted hydroxy sulfones rac-3a and rac-3d, respectively, with vinyl acetate either neat or in ether solvents proceeded with E-values of 18 and 49. For the CAL catalyzed hydrolysis of methyl substituted acetoxy sulfone rac-4a in an emulsion of phosphate buffer and methyl tert-butyl ether at pH 7.0 an E-value of 22 was found. Acetate (+)-ent-4a as well as alcohols (-)-3a and (-)-(S)-3d were obtained with ee-values of 99% on a gram scale.

SYNTHESIS OF POLYSULFIDES, SULFOXIDES AND SULFONES CONTAINING REACTIVE GROUPS

Preparation of polysulfides, sulfoxides and sulfones (containing reactive groups: OH, Cl, COOR, CN, SO3Na) are presented; 13C chemical shifts of these compounds have been recorded.Keywords: Sulfide; sulfoxide; sulfone; chlorosulfide; 1H NMR; 13C NMR.