6282-65-1

Usage

Physical state

Colorless liquid

Odor

Benzene-like

Uses

a. Solvent in industrial applications
b. Fragrance ingredient in cosmetic and personal care products
c. Precursor in the synthesis of pharmaceuticals, agrochemicals, and dyes
d. Crosslinking agent in the production of polymers

Derivation

Reaction of 1,4-butanediol with benzyl chloride

Chemical stability

High

Solubility

Soluble in both organic solvents and water

Upstream product

• 110-63-4 Butane-1,4-diol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 93877-21-5 1,4-dibenzyloxybut-2-yne 
• 100-52-7 benzaldehyde 
• 105966-45-8 2-[4-(benzyloxy)butoxy]tetrahydro-2H-pyran 

Downstream Products

• 137299-14-0 2-(3-(benzyloxy)propyl)-1,3-dithiane 
• 5470-84-8 4-benzyloxybutanal 

Relevant academic research and scientific papers

Efficient Generation and Synthetic Applications of Alkyl-Substituted Siloxycarbenes: Suppression of Norrish-Type Fragmentations of Alkanoylsilanes by Triplet Energy Transfer

Acylsilanes have been known to undergo isomerization to siloxycarbenes under photoirradiation and the thus generated carbenes can be utilized for various synthetic reactions. But this carbene formation is not necessarily efficient with some alkanoylsilanes because Norrish-type fragmentations compete, which limit the synthetic utility of alkanoylsilanes as carbene precursors. In this study, generation of siloxycarbenes from alkanoylsilanes by visible-light-induced energy transfer was examined by using an Ir complex, [Ir{dF(CF3)ppy}2(dtbpy)]PF6, and was successfully applied to the C?C coupling reactions with boronic esters or aldehydes. This methodology efficiently suppressed undesired Norrish-type reactions and broadened synthetic utility of alkanoylsilanes.

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

Tandem ring-closing metathesis/transfer hydrogenation: Practical chemoselective hydrogenation of alkenes

An operationally simple chemoselective transfer hydrogenation of alkenes using ruthenium metathesis catalysts is presented. Of great practicality, the transfer hydrogenation reagents can be added directly to a metathesis reaction and effect hydrogenation of the product alkene in a single pot at ambient temperature without the need to seal the vessel to prevent hydrogen gas escape. The reduction is applicable to a range of alkenes and can be performed in the presence of aryl halides and benzyl groups, a notable weakness of Pd-catalyzed hydrogenations. Scope and mechanistic considerations are presented.

Palladium-supported ionic liquid catalyst (Pd-SH-SILC) immobilized on mercaptopropyl silica gel as a chemoselective, reusable and heterogeneous catalyst for catalytic hydrogenation

Palladium acetate was immobilized as Pd-SH-SILC (Pd-supported ionic liquid catalyst) in the pores of amorphous mercaptopropyl silica gel with the aid of an ionic liquid [bmim]BF4. The heterogeneous Pd-SH-SILC was effective for catalytic hydrogenation of a variety of olefins at atmospheric pressure and room temperature. It withstood recycling up to 10 times by decantation.

First evidence for the formation of a geminal dizinc carbenoid: A highly stereoselective synthesis of 1,2,3-Substituted cyclopropanes

Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate

A highly efficient and convenient method for the direct conversion of alkyl THP ethers into the corresponding alkyl benzyl ethers

Direct conversion of alcohol tetrahydropyranyl (THP) ethers into the corresponding benzyl ethers can be conveniently performed by reaction with triethylsilane and benzaldehyde in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfona

Intramolecular benzyl-benzyl interactions in protonated benzyl diethers in the gas phase. Effects of internal hydrogen bonding

Protonated molecules of a variety of benzyl diethers, produced by chemical ionization (CI), undergo a unique rearrangement yielding relatively abundant mlz 181 C14H13+ ions, both in the ion source and under collision-induc

Highly selective Silver(I) oxide mediated monoprotection of symmetrical diols

Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.

Monobenzylation of 1,n-diols via dibutylstannylene intermediates

Symmetrical primary 1,n-diols, HO(CH2)(n)OH, of any chain length from n = 2-10, can be selectively monobenzylated via sequential treatment with dibutyltin oxide and benzyl bromide.

Novel Ammonium Ionophores Based on Glycol Dibenzyl Ethers for an Ion-Selective Electrode

Based on the finding that dibenzyl ether (DBE) exhibited a relatively high selectively for ammonium ion relative to potassium ion, four types of dibenzyl ethers were synthesized and their ammonium ion selectivities over alkali and alkali-earth metal ions