622-08-2

Basic information

• Product Name: 2-Benzyloxyethanol
• Synonyms: RARECHEM AL BD 0628;2-(benzyloxy)-ethano;2-(phenylmethoxy)-ethano;Benzylcelosolv;Ethanol, 2-(benzyloxy)-;Glycol benzyl ether;Glycol monobenzyl ether;glycolmonobenzylether
• CAS NO: 622-08-2
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 210-719-3
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols;Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 622-08-2.mol

Chemical Properties

• Melting Point: <-75 °C
• Boiling Point: 265 °C(lit.)
• Flash Point: 110 °C
• Appearance: Clear colorless/Liquid
• Density: 1.071 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00895mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.40±0.10(Predicted)
• Water Solubility: 4.282g/L(23 oC)
• BRN: 2043566
• CAS DataBase Reference: 2-Benzyloxyethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzyloxyethanol(622-08-2)
• EPA Substance Registry System: 2-Benzyloxyethanol(622-08-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: KJ7550000
• Hazardous Substances Data: 622-08-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Benzyloxyethanol is used as a reagent in the base-free iridium-catalyzed direct alkylation of active methylene compounds with alcohols, enabling the formation of new chemical bonds and the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
2-Benzyloxyethanol is used as a building block in the synthesis of 9-(2-hydroxyethyl)-linked 2,6-diaminopurines, which are important for the development of pharmaceutical compounds with potential therapeutic applications.
Used in Polymer Science:
2-Benzyloxyethanol is used in the synthesis of benzyloxy ethyl methacrylate monomer by esterification with methacryloyl chloride. This monomer can be polymerized to form polymers with specific properties, such as hydrophilicity and biocompatibility, for use in various applications, including drug delivery systems and biomaterials.
Used in Organic Chemistry Research:
2-Benzyloxyethanol serves as a versatile intermediate in organic chemistry, allowing for the development of new synthetic methods and the exploration of novel chemical reactions. Its acid-labile benzyl protecting group and reactive primary alcohol make it a valuable tool for researchers in the field of organic chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 389, 1990 DOI: 10.1016/S0040-4039(00)94562-3

Hazard

Toxic by ingestion.

InChI:InChI=1/C9H12O2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2

Upstream product

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• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 107-21-1 ethylene glycol 
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• 2403-54-5 2-(4-chlorophenyl)-1,3-dioxolane 
• 128702-33-0 4-((2-(benzyloxy)ethoxy)methyl)aniline 
• 128702-36-3 N-[4-(2-Benzyloxy-ethoxymethyl)-phenyl]-acetamide 
• 136057-07-3 1-Azido-4-(2-benzyloxy-ethoxymethyl)-benzene 
• 107-07-3 2-chloro-ethanol 
• 100-51-6 benzyl alcohol 
• 75-21-8 oxirane 
• 128702-30-7 O-(4-Nitrobenzyl)-2-benzyloxyethanol 

Downstream Products

• 13808-07-6 lactic acid-(2-benzyloxy-ethyl ester) 
• 4995-22-6 acrylic acid-(2-benzyloxy-ethyl ester) 
• 58841-52-4 2-(benzyloxy)ethyl methanesulfonate 
• 5312-10-7 2-(benzyloxy)ethyl acetate 
• 53256-85-2 1-(1,1,1-Trichlor-2-hydroxyethoxy)-2-benzyloxy-ethan 
• 123455-81-2 Pyridine-2-sulfonic acid 2-benzyloxy-ethyl ester 
• 146860-52-8 4-(2-benzyloxyethoxy)-pyridine-2,6-dimethanol 
• 97431-31-7 2-(benzyloxy)ethyl 2-bromohexadecanoate 
• 112882-05-0 2-Methyl-propane-2-sulfonic acid 2-benzyloxy-ethyl ester 
• 93206-15-6 <2-(benzyloxy)ethoxy>acetic acid methylester 
• 118638-76-9 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 622-22-0 1,2-dibenzyloxyethane 
• 91905-99-6 Isopropyloxymethyloxyaethyl-benzyl-aether 
• 92372-19-5 Butyloxymethyloxyaethyl-benzyl-aether 

Relevant articles and documents

3-(5-METHOXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF

The present disclosure relates to compounds of formula (I') and pharmaceutical compositions and their use in reducing Widely Interspaced Zinc Finger Motifs (WIZ) expression levels, or inducing fetal hemoglobin (HbF) expression, and in the treatment of inherited blood disorders (e.g., hemoglobinopathies, e.g., beta-hemoglobinopathies), such as sickle cell disease and beta-thalassemia.

Highly selective reductive catalytic fractionation at atmospheric pressure without hydrogen

Reductive catalytic fractionation (RCF) is an efficient and selective way to produce phenolic monomers from lignin. However, this strategy is difficult to scale up due to its high operating pressure. In this work, we investigated RCF reaction at or near atmospheric pressure and without the use of hydrogen. The atmospheric RCF (ARCF) was conducted in acidified ethylene glycol in glass vessels at 185-195 °C catalyzed by 5% Ru/C. The products mainly include propylguaiacol and propylsyringyl (up to 95.6% among the lignin monomers) and do not contain propanolguaiacol, propanolsyringyl, or H monomers. Although the total yield of lignin monomers in ARCF is about one-quarter less than that of RCF, the operation of ARCF is much easier, milder, safer, and cheaper due to the atmospheric condition and the feasibility of the semi-continuous operation.

4-Acyl Pyrrole Capped HDAC Inhibitors: A New Scaffold for Hybrid Inhibitors of BET Proteins and Histone Deacetylases as Antileukemia Drug Leads

Multitarget drugs are an emerging alternative to combination therapies. In three iterative cycles of design, synthesis, and biological evaluation, we developed a novel type of potent hybrid inhibitors of bromodomain, and extra-terminal (BET) proteins and histone deacetylases (HDACs) based on the BET inhibitor XD14 and well-established HDAC inhibitors. The most promising new hybrids, 49 and 61, displayed submicromolar inhibitory activity against HDAC1-3 and 6, and BRD4(1), and possess potent antileukemia activity. 49 induced apoptosis more effectively than the combination of ricolinostat and birabresib (1:1). The most balanced dual inhibitor, 61, induced significantly more apoptosis than the related control compounds 62 (no BRD4(1) affinity) and 63 (no HDAC inhibition) as well as the 1:1 combination of both. Additionally, 61 was well tolerated in an in vivo zebrafish toxicity model. Overall, our data suggest an advantage of dual HDAC/BET inhibitors over the combination of two single targeted compounds.

Nematicidal activity of benzyloxyalkanols against pine wood nematode

Pine wilt disease (PWD) is caused by the pine wood nematode (PWN; Bursaphelenchus xylophilus) and causes severe environmental damage to global pine forest ecosystems. The current strategies used to control PWN are mainly chemical treatments. However, the continuous use of these reagents could result in the development of pesticide-resistant nematodes. Therefore, the present study was undertaken to find potential alternatives to the currently used PWN control agents abamectin and emamectin. Benzyloxyalkanols (BzOROH; R = C2–C9 ) were synthesized and the nematicidal activity of the synthetic compounds was investigated. Enzymatic inhibitory assays (acetylcholinesterase (AChE) and glutathione S-transferase (GST)) were performed with BzOC8OH and BzOC9OH to understand their mode of action. The benzyloxyalkanols showed higher nematicidal activity than did benzyl alcohol. Among the tested BzOROHs, BzC8OH and BzC9OH showed the strongest nematicidal activity. The LD50 values of BzC8OH and BzC9OH were 246.1 and 158.0 ppm, respectively. No enzyme inhibitory activity was observed for BzC8OH and BzC9OH. The results suggested that benzyloxyalcohols could be an alternative nematicidal agent.

Composition for controlling pine wood nematode containing benzyloxyalcohol

The present invention relates to a composition for controlling pine nematode comprising a benzyloxyalcohol compound and a method for controlling pine nematode using the same.

Design, Synthesis, and Evaluation of VHL-Based EZH2 Degraders to Enhance Therapeutic Activity against Lymphoma

Traditional EZH2 inhibitors are developed to suppress the enzymatic methylation activity, and they may have therapeutic limitations due to the nonenzymatic functions of EZH2 in cancer development. Here, we report proteolysis-target chimera (PROTAC)-based EZH2 degraders to target the whole EZH2 in lymphoma. Two series of EZH2 degraders were designed and synthesized to hijack E3 ligase systems containing either von Hippel-Lindau (VHL) or cereblon (CRBN), and some VHL-based compounds were able to mediate EZH2 degradation. Two best degraders, YM181 and YM281, induced robust cell viability inhibition in diffuse large B-cell lymphoma (DLBCL) and other subtypes of lymphomas, outperforming a clinically used EZH2 inhibitor EPZ6438 (tazemetostat) that was only effective against DLBCL. The EZH2 degraders displayed promising antitumor activities in lymphoma xenografts and patient-derived primary lymphoma cells. Our study demonstrates that EZH2 degraders have better therapeutic activity than EZH2 inhibitors, which may provide a potential anticancer strategy to treat lymphoma.

Protein degradation targeting chimera for degrading androgen receptor

The invention relates to a novel difunctional molecule compound based on VHL ligand induction and application of the difunctional molecule compound in synthesis of the compounds and pharmaceutical compositions thereof. The compound is shown as a formula I. The compound can selectively induce AR protein degradation and can be used for treating cancers such as prostatic cancer and breast cancer.

IDEBENONE COMPOUNDS

The present application provides idebenone derivatives or analogues useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating the disease or disorder are also provided.

CONDENSED PYRROLES AS NOVEL BROMODOMAIN INHIBITORS

Compounds of formula (1) or (2) and their use in the treatment of diseases or conditions for which a bromodomain inhibitor is indicated.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.