17026-49-2

Usage

Uses

Used in Chemical Synthesis:
5-chloro-m-xylene-2,alpha,alpha'-triol is used as an intermediate in the synthesis of Ochratoxin A (O148490), a toxic metabolite produced by Aspergillus ochraceus. It plays a crucial role in the production of this environmental and food contaminant.
Used in Environmental and Food Contaminant Analysis:
5-chloro-m-xylene-2,alpha,alpha'-triol is used as a reference compound in the analysis and detection of ochratoxins, which are harmful substances that can contaminate food products and pose health risks to humans and animals. Its presence in the synthesis process helps in understanding the formation and distribution of these contaminants in the environment.

Upstream product

• 50-00-0 formaldehyd 
• 106-48-9 4-chloro-phenol 
• 123-31-9 hydroquinone 
• 64-19-7 acetic acid 

Downstream Products

• 133167-92-7 2-(4-chloro-2,6-bis-hydroxymethyl-phenoxymethyl)-5-methoxy-pyran-4-one 
• 71643-08-8 4-chloro-2,6-bis[(5-bromo-2-hydroxyphenyl)methyl]phenol 
• 127679-80-5 4-Chloro-2,6-bis<(5-nitro-2-hydroxyphenyl)methyl>phenol 
• 92436-45-8 6-Chlor-8-chlormethyl-2-phenyl-benzo-1.3-dioxan 
• 114302-75-9 (4-chloro-2,6-bis-hydroxymethyl-phenoxy)-acetic acid 
• 92253-01-5 3-anilinomethyl-5-chloro-2-hydroxy-benzyl alcohol 
• 6641-05-0 2,6-bis-hydroxymethyl-4-chloro-anisole 
• 6640-95-5 4-chloro-2,6-bis-(2-hydroxy-3,5-dimethyl-benzyl)-phenol 
• 65302-49-0 4-chloro-2,6-bis[(3,5-dichloro-2-hydroxyphenyl)methyl]phenol 
• 71642-88-1 2,6-bis-(5-fluoro-2-hydroxybenzyl)-4-chlorophenol 
• 71643-54-4 4-Chloro-2,6-bis-(2-hydroxy-5-iodo-benzyl)-phenol 
• 75445-37-3 4-Chlor-2,6-bis(2-methyl-2-nitropropyl)phenol 
• 89553-17-3 2,6-Bis<(5-tert-butyl-2-hydroxyphenyl)methyl>-4-chlorophenol 
• 41403-44-5 6,6′-[(5-chloro-2-hydroxy-1,3-phenylene)bis(methylene)]bis(2-tert-butyl-4-methylphenol) 

Relevant academic research and scientific papers

A New Synthesis of Oxacalixarene Macrocycles and Alkali-Metal-Binding Studies

The title oxacalixarene macrocycles 1 have been synthesized in yields of 12-32percent by an acid-catalyzed, high-dilution condensation of 2,6-bis(hydroxymethyl)-p-subtituted-phenols, where R = t-Bu, i-Pr, Et, Me, and Cl.The macrocycles are isolated in high purity without chromatography, as the sodium or potassium salts of their monoanions.Metal-binding studies indicate that, like the related calixarenes, the oxacalixarenes bind alkali metals only in the presence of base (Na(1+) ca.K(1+) > Li(1+)).

Synthesis, structure, luminescent property and theoretical studies of 4-chloro-2,6-bis[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]phenol

4-Chloro-2,6-bis[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]phenol has been synthesised and characterised, including by single-crystal X-ray diffraction. The benzene ring system is planar and makes dihedral angles of 88.90°(0.14) and 59.84°(0.11) with two pyrazole rings, respectively, and the two pyrazole rings are arranged trans to each other with the dihedral angles 87.22°(0.15). The luminescent property of the title compound was investigated. The molecular structure of the title compound has been optimised by density functional theory with B3LYP/6-31G (d, p) level, the optimised geometer parameters and vibrational frequencies are consistent with the experiment data.

Magnetic and structural properties of dinuclear singly bridged-phenoxido metal(II) complexes

The reaction of a methanolic solution containing the bi-compartmental phenolic ligand 2,6-bis[bis(2-pyridylmethyl)aminomethyl]-4-chlorophenol (LCl-OH) with MCl2·nH2O in the presence of NH4PF6 or NaClO4 afforded the dinuclear bridged-phenoxido dichlorido-metal(ii) complexes [Co2(μ-LClO)(H2O)2Cl2][Co2(μ-LClO)(MeOH)2Cl2](PF6)2 (1), [Ni2(μ-LClO)(MeOH)2Cl2]PF6 (2), [Ni2(μ-LClO)(MeOH)(H2O)Cl2]ClO4·1.25H2O (3), [Cu2(μ-LClO)Cl2]PF6·1/2MeOH (4) and [Zn2(μ-LClO)Cl2]PF6·MeOH (5). The complexes were characterized by elemental microanalyses, conductivity measurements, IR and UV-Vis spectroscopy, mass spectrometry and single crystal X-ray crystallography. Each M(ii) center within the dinuclear complex cations is octahedrally coordinated in complexes 1-3, and five-coordinated distorted square pyramidal in 4 and 5. Magnetic susceptibility measurements at variable temperature of the complexes 1-4 revealed weak to moderate antiferromagnetic coupling with |J| values = 8.38, 39.0, 30.2 and 0.79 cm-1, respectively. The results of DFT calculations correlate well with the experimentally determined antiferromagnetic coupling and show that the magnetic exchange coupling occurs mainly through the phenoxido bridge M-O-M. Implications of geometry around the central metal ion, M...M distance, M-O-M bond angle and overlapping of magnetic orbitals on the magnetic exchange coupling are discussed.

Coordination cluster analogues of the high-Spin [Mn19] system with functionalized 2,6-Bis(hydroxymethyl)phenol ligands

A series of 2,6-bis(hydroxymethyl)-4-R-phenol ligands (H3LR; R = H, F, Cl, Br, I, Ph, NH2, NO2, SMe) have either been newly synthesized or the existing syntheses have been significantly improved to investigate ligand-functionalized analogues of the previously published coordination cluster [MnIII12MnII7(μ4-O)8(μ3-N3)8(HLMe)12(MeCN)6]Cl2·10MeOH·MeCN (1) with S = 83/2. The crystal structures and magnetic properties of three such Mn19 clusters, namely, [MnIII12MnII7(μ4-O)8(HLH)12(μ3-Cl)7(μ3-OMe)(MeOH)6]Cl2·16H2O·10MeOH·MeCN (3), [MnIII12MnII7(μ4-O)8(HLI)12(μ3-N3)8(MeOH)6](O2CH)2·16MeOH·10MeCN (4) and [MnIII12MnII7(μ4-O)8(μ3-Cl)7.7(μ3-OMe)0.3(HLSMe)12(MeOH)6]Cl2·27MeOH (5) are reported and compared to those of the parent cluster. When these ligands are functionalized with substituents of moderate electronegativity, it is possible to synthesize Mn19 analogues; however, when such ligands bear highly electron-donating (amino) or -withdrawing (nitro) substituents, the Mn19 analogues are no longer accessible. The Mn19 cluster framework is both magnetically and structurally robust with respect to the electron-donor/acceptor characteristics of the ligand substituent; therefore, the Mn19 system is an excellent platform for peripheral chemical engineering. The robustness of the inorganic {MnIII12MnII7(μ4-O)8} core of Mn19 systems with variously functionalized encapsulating ligands is demonstrated by the invariance of the record S = 83/2 spin state. Chemical modification aimed towards attaching the molecule to various substrates does not interfere with the electronic structure.

Efficient synthesis of (R)-ochratoxin alpha, the key precursor to the mycotoxin ochratoxin A

Two new routes for the synthesis of enantiomerically pure ochratoxin alpha ((3R)-OTα) are presented, which is the key intermediate for the synthesis of ochratoxin A (OTA) by coupling reaction with the amino acid l-phenylalanine. The key step of both routes is the one pot directed ortho-metalation/alkylation/ lactonization of unprotected and suitably functionalized aromatic carboxylic acids, using lithium tetramethylpiperidide (LTMP) and (R)-propylene oxide.

VISIBLE LIGHT ABSORBERS FOR OPHTHALMIC LENS MATERIALS

Azo compounds that block visible light are disclosed. These light absorbers are particularly suitable for use in intraocular lens materials.

Mononuclear copper(ii) complexes with 3,5-substituted-4-salicylidene-amino- 3,5-dimethyl-1,2,4-triazole: Synthesis, structure and potent inhibition of protein tyrosine phosphatases

Six copper complexes of Schiff base ligands containing 3,5-substituted-4- salicylideneamino-3,5-dimethyl-1,2,4-triazole have been synthesized and well characterized. The structures of complexes 1 and 2 were determined by X-ray crystal analysis. Fluorescence and potentiometric study indicated that in the physiological pH range, one ligand was dissociated from the complexes to form 1:1 mononucleus copper complexes. The complexes potently inhibit protein tyrosine phosphatase 1B (PTP1B), T-cell protein tyrosine phosphatase (TCPTP), megakaryocyte protein tyrosine phosphatase 2 (PTP-MEG2) and Src homology phosphatase 1 (SHP-1) with 3-4 fold selectivity against PTP1B over TCPTP and PTP-MEG2, and 3-9 fold over SHP-1, but display almost no inhibition against Src homology phosphatase 2 (SHP-2). Complex 1 inhibits PTP1B with a competitive model with Ki of 30 nM. Substitution with small groups at the phenyl of the ligand does not obviously influence the inhibitory ability of the complexes.

VISIBLE LIGHT ABSORBERS FOR OPHTHALMIC LENS MATERIALS

Azo compounds that block visible light are disclosed. These light absorbers are particularly suitable for use in intraocular lens materials.

Self-assembly from metal-organic vesicles to globular networks: Metallogel-mediated phenylation of indole with phenyl boronic acid

Self-assembly of the conformationally flexible bismethylimidazolyl ligands with Pd(OAc)2 is described. Depending on whether the ligands provide the hydrogen bonding donor, a switching of metal-organic vesicles to globular networks gelating solvents is achieved. The metallogels exhibit catalytic activity for the cross-coupling of indole with phenyl boronic acid.

Preparation of new phenol-based acyclic ligands with double set of coordination sites

A convenient four-step preparation of the two compartmental ligands 1,6-bis(2-pyridyl)-2,5-bis(2-hydroxy-3-hydroxymethyl-5-chlorobenzyl)-2, 5-diazahexane 3a and 1,7-bis (2-pyridyl)-2,6-bis(2-hydroxy-3-hydroxymethyl-5- chlorobenzyl)-2,6-diazaheptane 3b starting from 4-chlorophenol 4 is reported. Compound 4 was converted to triol 5 which was then protected to 2,2-dimethyl-6-chloro-8-(hydroxymethyl)benzo-1,3-dioxin 6 with 2-methoxy propene. Compound 6 was chlorinated to 2,2-dimethyl-6-chloro-8-(chloromethyl) benzo-1,3-dioxin 7 and then reacted with 1,6-bis(2-pyridyl)-2,5-diazahexane or 1,7-bis(2-pyridyl)-2,6-diazaheptane in the presence of Na2CO 3 in dioxane. Subsequent acid hydrolysis gave 3a and 3b, respectively. The total yields were 38%.