156281-11-7

Usage

Chemical Properties

White Solid

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 87188-50-9 para-tert-butoxycarbonyloxybenzaldehyde 

Downstream Products

• 1419942-88-3 C₁₇H₁₇NO₈ 
• 390815-79-9 tert-butyl (4-(chloromethyl)phenyl)carbonate 

Relevant academic research and scientific papers

Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide

A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO has been developed. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.

Cellular protection of SNAP-25 against botulinum neurotoxin/A: Inhibition of thioredoxin reductase through a suicide substrate mechanism

Botulium neurotoxins (BoNTs) are among the most lethal toxins known to man. They are comprised of seven serotypes with BoNT/A being the most deadly; yet, there is no approved therapeutic for their intoxication or one that has even advanced to clinical trials. Botulinum neurotoxicity is ultimately governed through light chain (LC) protease SNARE protein cleavage leading to a loss of neurotransmitter release. Pharmacological attempts to ablate BoNT/A intoxication have sought to either nullify cellular toxin entry or critical biochemical junctions found within its intricate mechanism of action. In these regards, reports have surfaced of nonpeptidic small molecule inhibitors, but few have demonstrated efficacy in neutralizing cellular toxicity, a key prerequisite before rodent lethality studies can be initiated. On the basis of a lead discovered in our BoNT/A cellular assay campaign, we investigated a family of N-hydroxysuccinimide inhibitors grounded upon structure activity relationship (SAR) fundamentals. Molecules stemming from this SAR exercise were theorized to be protease inhibitors. However, this proposition was overturned on the basis of extensive kinetic analysis. Unexpectedly, inhibitor data pointed to thioredoxin reductase (TrxR), an essential component required for BoNT protease translocation. Also unforeseen was the inhibitors' mechanism of action against TrxR, which was found to be brokered through a suicide-mechanism utilizing quinone methide as the inactivating element. This new series of TrxR inhibitors provides an alternative means to negate the etiological agent responsible for BoNT intoxication, the LC protease.

General solvent-free highly selective N-tert-butyloxycarbonylation strategy using protic ionic liquid as an efficient catalyst

A simple, rapid and solvent-free protocol is described for the chemo-selective transformation of amines to tert-butyloxycarbonyl protected derivatives (NHBoc) using Boc2O and imidazolium trifluoroacetate protic ionic liquid (5-20 mol%). Unwanted side products such as isocyanate, urea or N,N-di-Boc were not detected. The scope of the protection strategy was successfully explored for substrate alcohols, phenols and thiol at elevated temperatures. Optically pure amino acids, amino acid esters and amino alcohols were efficiently converted to the corresponding N-Boc protected derivatives in excellent yields without racemization at the chiral center. The distinct advantages of this method are: operational simplicity, cleaner reaction, high selectivity, excellent yield, rapid reaction convergence, easy preparation and recyclability of the catalyst.

Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst

The chemoselective O-tert-butoxycarbonylation of phenols using low levels (5-0.1 mol %) of 6,7-dimeth-oxyisoquinoline as a reusable organocatalyst is described.

Organocatalytic methods for chemoselective O-tert-butoxycarbonylation of phenols and their regeneration from the O-t-Boc derivatives

(Chemical Equation Presented) Carbon tetrabromide (CBr4) catalyzes O-tert-butoxycarbonylation of functionalized phenols without any side reactions (bromination, addition of CBr3 to a double bond, and formation of symmetrical diaryl carbonates, cyclic carbonates, or carbonic-carbonic anhydrides). The parent phenols are regenerated from the O-t-Boc derivatives by the catalyst system CBr4-PPh3 without affecting other protecting groups (aryl alkyl ether, alkyl ester, and thioacetal) or competitive side reaction such as bromination, nitrene (from NO2) and α,α-dibromoolefine (with CHO/COMe) formation, and transesterification (with CO2Me/Et) taking place.

Triphenylphosphine as a novel organocatalyst for chemoselective O-tert-butoxycarbonylation of phenols

A novel organocatalytic procedure for the chemoselective O-tert-butoxycarbonylation of phenols under neutral and neat conditions is described. Georg Thieme Verlag Stuttgart.

A novel tert-butoxycarbonylation reagent: 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)

The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a tert-butoxycarbonylation reagent for acidic proton-containing substrates such as phenols, aromatic and aliphatic amines hydrochlorides, and aromatic carboxylic acids in the absence of a base is described. The reactions proceed chemoselectively in high yield under mild conditions.

PHOTORESIST BASE MATERIAL, METHOD FOR PURIFICATION THEREOF, AND PHOTORESIST COMPOSITIONS

A photoresist base material comprising an extreme ultra-violet reactive organic compound of the following formula (1), ???wherein A is a central structure that is an aliphatic group having 1 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atom

1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline: A novel and chemoselective tert-butoxycarbonylation reagent

(formula presented) The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as tert-butoxycarbonylation reagent for aromatic and aliphatic amine hydrochlorides and phenols in the absence of a base has been demonstrated. The reactions proceed chemoselectively in high yield under mild conditions.