15258-73-8

Usage

Uses

Used in Organic Synthesis:
2,6-Dichlorobenzyl alcohol is used as a reagent in the chemical industry for its ability to participate in a wide range of organic synthesis reactions. Its chemical properties allow it to be a versatile building block for creating more complex molecules and compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Dichlorobenzyl alcohol is used as an intermediate in the synthesis of various drugs and medicinal compounds. Its unique structure and reactivity make it a valuable component in the development of new pharmaceuticals.
Used in Chemical Research:
2,6-Dichlorobenzyl alcohol is also utilized in chemical research as a model compound for studying reaction mechanisms and exploring new synthetic pathways. Its predictable and well-understood reactivity make it an ideal candidate for such investigations.
Used in Agrochemicals:
In the agrochemical industry, 2,6-Dichlorobenzyl alcohol is employed as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its properties contribute to the development of effective and targeted products for agricultural use.
Used in Dyes and Pigments:
The chemical properties of 2,6-Dichlorobenzyl alcohol also make it suitable for use in the production of dyes and pigments. Its ability to form a variety of compounds allows for the creation of a wide range of colors and shades in the dye and pigment industry.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 707, 1988 DOI: 10.1016/S0040-4039(00)80190-2

InChI:InChI=1/C7H6Cl2O/c8-6-2-1-3-7(9)5(6)4-10/h1-3,10H,4H2

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 20443-98-5 2,6-Dichlorobenzyl bromide 
• 61875-53-4 2,6-dichlorophenylacetylchloride 
• 80257-11-0 2,6-dichloro-3-iodobenzoic acid 
• 50-30-6 2,6-dichlorobenzoic acid 
• 14920-87-7 2,6-dichlorobenzoic acid methyl ester 
• 766-77-8 Dimethylphenylsilane 
• 37532-04-0 N'-(2,6-dichlorobenzylidene)-4-methylbenzene-1-sulfonohydrazide 
• 81-19-6 2,6-dichlorobenzalchloride 

Downstream Products

• 62031-35-0 1,3-dichloro-2-(iodomethyl)benzene 
• 33486-90-7 1,3-dichloro-2-methoxymethylbenzene 
• 1035797-94-4 trichloroacetamidate de dichloro-2,6 benzyle 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 251537-54-9 3-(2,6-dichloro-benzyloxy)-quinoxalin-2-ylamine 
• 71172-54-8 acetic acid 2,6-dichloro-benzyl ester 
• 134164-35-5 tris(2,6-dichlorobenzyl)sulfonium tetrafluoroborate 
• 1033617-98-9 C₁₄H₁₁Cl₂NOS 
• 66496-55-7 2-(2,6-dichlorobenzyloxy)pyridine 
• 642085-69-6 5-(2,6-dichloro-benzyloxy)-pyrazine-2-carboxylic acid 
• 756503-71-6 5-bromo-3-((2,6-dichlorobenzyl)oxy)pyrazin-2-amine 
• 503068-36-8 (5R)-3-{6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one 
• 1254709-07-3 (2S,3R)-tert-butyl 2-(2,6-dichlorobenzyloxy)-3-(4-methoxyphenyl)-3-(4-methoxyphenylamino)propanoate 
• 1254709-00-6 (2S,3R)-tert-butyl 2-(2,6-dichlorobenzyloxy)-3-(4-ethoxyphenylamino)-3-phenylpropanoate 

Relevant academic research and scientific papers

Syntheses and catalytic application of hydrido iron(ii) complexes with [P,S]-chelating ligands in hydrosilylation of aldehydes and ketones

Four hydrido iron(ii) complexes (1-4) with [P,S]-chelating ligands were synthesized by the reactions of (2-diphenylphosphanyl)thiophenols, C6H3(1-SH) (2-PPh2) (4-R1) (6-R2), abbreviated as (P^SH), with Fe(PMe3)4. (1: R1 = R2 = H; 2: R1 = H, R2 = SiMe3; 3: R1 = CH3, R2 = H; 4: R1 = SiMe3, R2 = H). Among them, complexes 2-4 are new and were completely characterized by spectroscopic methods. The molecular structures of complexes 2, 3, and 4 were confirmed by X-ray single crystal diffraction. The catalytic properties of hydrido iron(ii) complexes 1-4 were explored in the hydrosilylation of aldehydes and ketones. They showed a good activity in catalytic hydrosilylation of aldehydes and ketones by using (EtO)3SiH as a hydrogen source under mild conditions.

Hydrosilylation of aldehydes and ketones catalyzed by hydrido iron complexes bearing imine ligands

Two new hydrido iron complexes (2 and 4) were synthesized by the reactions of (4-methoxyphenyl)phenylketimine ((4-MeOPh)PhCNH) with Fe(PMe 3)4 or FeMe2(PMe3)4. The molecular structures of complexes 2 and 4 were confirmed by X-ray single crystal diffraction. Using hydrido iron complexes (1-4) as catalysts, the hydrosilylations of aldehydes and ketones were investigated. The four complexes were effective catalysts for this reduction reaction. Complex 1 among them is the best catalyst. This journal is the Partner Organisations 2014.

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones

A novel silylene supported iron hydride [Si, C]FeH (PMe3)3 (1) was synthesized by C (sp3)-H bond activation with zero-valent iron complex Fe (PMe3)4. Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp3)?H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.

Homoleptic Zinc-Catalyzed Hydroboration of Aldehydes and Ketones in the Presence of HBpin

Here, we report the reaction between N-phenyl-o-phenylenediamine and pyrrole-2-carboxaldehyde to afford the N-phenyl-o-phenyl-enediiminopyrrole ligand {L-H2} in quantitative yield. A one-pot reaction between {L-H2} and diethylzinc (ZnEt2) in a 2:1 ratio afforded the homoleptic zinc metal complex [{L-H}2Zn] (1). The solid-state structures of ligand {L-H2} and zinc complex 1 were confirmed using X-ray crystallography. Further, complex 1 was used for chemoselective hydroboration of aldehydes and ketones in the presence of pinacolborane (HBpin) at ambient temperature to produce the corresponding boronate esters in high yield.

A tunable synthesis of either benzaldehyde or benzoic acid through blue-violet LED irradiation using TBATB

In this paper, a highly efficient, metal-free, and homogeneous method for the selective aerobic photooxidation of alcohols and photooxidative-desilylation of tert-butyldimethylsilyl ethers (TBDMS) in the presence of tetrabutylammonium tribromide (TBATB) under irradiation of visible light was reported. The light source: blue (460 nm) and violet (400 nm) LED, can control selective oxidation to aldehyde or carboxylic acid.

Reduction of Aldehydes with Formic acid in Ethanol using Immobilized Iridium Nanoparticles on a Triazine-phosphanimine Polymeric Organic Support

A novel triazine-phosphanimine polymeric organic support (TPA) was synthesized successfully by a controllable one-pot method using melamine (1,3,5-triazine-2,4,6-triamine) and trichlorophosphane (PCl3). The TPA substrate is a material incorporating P and N atoms which can coordinate with metals as a pincer ligand to stabilize them, providing an efficient heterogeneous support to prepare recyclable transition metal catalyst systems. In this study, TPA was used as support to immobilize iridium nanoparticles in the range of ~8 nm on its surface, resulting in the generation of a novel iridium nanocatalyst system (INP-TPA-POP). This catalyst system was characterized using different microscopic and spectroscopic techniques such as FT-IR, TEM, XPS, XRD, SEM, EDX, elemental analysis, ICP and BET analysis. The INP-TPA-POP nanocatalyst exhibited remarkable activity in reduction of aldehydes to alcohols using formic acids as reducing agent in ethanol as solvent.

Pyridine: N-oxide promoted hydrosilylation of carbonyl compounds catalyzed by [PSiP]-pincer iron hydrides

Five [PSiP]-pincer iron hydrides 1-5, [(2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (2), (2-Ph2PC6H4)2PhSiFe(H)(PMe3)2 (3), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3) (4), and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (5)], were used as catalysts to study the effects of pyridine N-oxide and the electronic properties of [PSiP]-ligands on the catalytic hydrosilylation of carbonyl compounds. It was proved for the first time that this catalytic process could be promoted with pyridine N-oxide as the initiator at 30 °C because the addition of pyridine N-oxide is beneficial for the formation of an unsaturated hydrido iron complex, which is the key intermediate in the catalytic mechanism. Complex 4 as the best catalyst shows excellent catalytic performance. Among the five complexes, complex 3 was new and the molecular structure of complex 3 was determined by single crystal X-ray diffraction. A proposed mechanism was discussed.

Synthesis and Catalytic Activity of Iron Hydride Ligated with Bidentate N-Heterocyclic Silylenes for Hydroboration of Carbonyl Compounds

We report the synthesis of a novel bidentate N-heterocyclic silylene (NHSi) ligand, N-(LSi:)-N-methyl-2-pyridinamine (1) (L = PhC(NtBu)2), and the first bischelate disilylene iron hydride, [(Si,N)(Si,C)Fe(H)(PMe3)] (2), and monosilylene iron hydride, [(Si,C)Fe(H)(PMe3)3] (2′), through Csp2-H activation of the NHSi ligand. Compounds 1 and 2 were fully characterized by spectroscopic methods and single-crystal X-ray diffraction analysis. Density functional theory calculations indicated the multiple-bond character of the Fe-Si bonds and the π back-donation from Fe(II) to the Si(II) center. Moreover, the strong donor character of ligand 1 enables 2 to act as an efficient catalyst for the hydroboration reaction of carbonyl compounds at room temperature. Chemoselective hydroboration is attained under these conditions. This might be the first example of hydroboration of ketones and aldehydes catalyzed by a silylene hydrido iron complex. A catalytic mechanism was suggested and partially experimentally verified.

Method of fluorination using iodonium ylides

A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

Efficient transfer hydrogenation of carbonyl compounds catalyzed by selenophenolato hydrido iron(II) complexes

Selenophenolato hydrido iron(II) complexes 1–3 cis-[(H)(SeAr)Fe(PMe3)4] (Ar = C6H5 (1), p-MeOC6H4 (2) and o-MeC6H4 (3)) could catalyze transfer hydrogenation of aldehydes and ketones. Among the three complexes, catalyst 1 exhibited the highest catalytic activity. The catalytic reactions took place under very mild conditions, using isopropanol as solvent and hydrogen source, tBuONa as base under 60–80 °C. This catalytic system has good tolerance for many functional groups, such as halides, C[dbnd]C double bonds, nitro groups and cyano groups at the phenyl ring of the substrates.