30379-55-6

Basic information

• Product Name: Benzyloxyacetic acid
• Synonyms: PHENYLMETHOXY ACETIC ACID;RARECHEM AL BE 0628;BENZYLOXYACETIC ACID;ACETIC ACID, (PHENYLMETHOXY)-;benzyloxy acctic acid;2-(benzyloxy)acetic acid;Acetic acid, 2-(phenylMethoxy)-;Benzyloxyacetic acid 95%
• CAS NO: 30379-55-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• Product Categories: C9;Carbonyl Compounds;Carboxylic Acids;Building Blocks/Intermediates;NULL
• Mol File: 30379-55-6.mol

Chemical Properties

• Melting Point: 80-81 °C
• Boiling Point: 137-139 °C0.6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.162 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.33E-05mmHg at 25°C
• Refractive Index: n20/D 1.526(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.52±0.10(Predicted)
• CAS DataBase Reference: Benzyloxyacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyloxyacetic acid(30379-55-6)
• EPA Substance Registry System: Benzyloxyacetic acid(30379-55-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 30379-55-6(Hazardous Substances Data)

Usage

Uses

1. Used in Proteomics Research:
Benzyloxyacetic acid is used as a compound for proteomics research, which is essential for understanding the structure, function, and interactions of proteins within a biological system.
2. Used in Chemical Synthesis:
Benzyloxyacetic acid is used as a key component in the synthesis of various compounds, such as mixed benzyloxyacetic pivalic anhydride, chiral glycolates, and 1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl benzyloxyacetate. These syntheses are achieved through esterification, a chemical reaction that involves the formation of an ester from an alcohol and an acid.
3. Used in the Preparation of Metal Complexes:
Benzyloxyacetic acid serves as a ligand in the preparation of diaquabis(benzyloxyacetato)copper(II) complex. This complex is a coordination compound that consists of a central metal ion (copper in this case) surrounded by ligands, which are molecules or ions that donate electrons to the metal center.
4. Used in Pharmaceutical Industry:
The in vitro activities of phenoxy and benzyloxyacetic acid derivatives as antisickling agents have been investigated, which could potentially lead to the development of new treatments for sickle cell disease and other related conditions.

InChI:InChI=1/C9H10O3/c10-9(11)7-12-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)

Upstream product

• 32122-09-1 ethyl benzyloxyacetate 
• 2785-29-7 benzyl potassium 
• 105-39-5 chloroacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 
• 100-51-6 benzyl alcohol 
• 3926-62-3 sodium monochloroacetic acid 
• 20194-18-7 sodium phenyl-methanolate 
• 124-38-9 carbon dioxide 
• 66222-28-4 (benzyloxymethyl)tributylstannane 
• 622-08-2 2-Benzyloxyethanol 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 14690-00-7 2-O-benzylglycerol 
• 51164-00-2 4-Benzyloxymethyl-2-phenyl-[1,3]dioxolane 
• 68728-34-7 5-benzyloxy-2-phenyl-1,3-dioxane 

Downstream Products

• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 97077-22-0 benzyloxy-acetic acid-(2-indol-3-yl-ethylamide) 
• 19810-31-2 Benzyloxyacetyl chloride 
• 5774-77-6 2-(benzyloxy)acetamide 
• 94915-11-4 2-(benzyloxy)-N-(3,4-dimethoxyphenethyl)acetamide 
• 19348-63-1 N-benzyl-2-(benzyloxy)acetamide 
• 60359-64-0 Benzyloxy-acetic acid 2-phenoxy-ethyl ester 
• 97416-41-6 trimethylsilyl 2-(benzyloxy)acetate 
• 70258-22-9 1-Benzyloxy-9b-phenyl-1,4,5,9b-tetrahydro-azeto[2,1-a]isoquinolin-2-one 
• 81017-16-5 3-Benzyloxy-4-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-azetidin-2-one 
• 61458-01-3 3-benzyloxy-4-(4-methoxy-phenyl)-1-p-tolyl-azetidin-2-one 
• 154710-30-2 Benzyloxy-acetic acid 2-bromo-3-methyl-cyclohex-2-enyl ester 
• 66922-43-8 formaldehyde benzyl t-butyl acetal 
• 88920-28-9 benzyloxymethyl benzyloxyacetate 

Relevant articles and documents

On the electron withdrawing nature of ethers in glycosylation chemistry

The present paper is a commentary on the electronic effects that protecting groups exert on glycosylation chemistry. Specifically, its purpose is to rectify the misguided use of the term electron donating benzyl groups, which hardly makes sense in the context of protecting groups on alcohols in saturated systems such as carbohydrates. It is argued that benzyl ethers (OBn) should rightfully be referred to as being inductively electron withdrawing, even if they are less so than benzoyl esters (OBz).

Toward the stereoselective synthesis of zaragozic acid framework: A desilylation-aldol reaction approach

A convergent synthesis of the C3-C8 fragment of zaragozic acids is described. The key reactions include desilylation-aldol reaction, rearrangement induced by regioselective reductive cleavage, BAIB/TEMPO-Pinnick oxidation, esterification, silylation, and hydrogenolysis.

Oxidative carbon-carbon bond cleavage of 1,2-diols to carboxylic acids/ketones by an inorganic-ligand supported iron catalyst

The carbon-carbon bond cleavage of 1,2-diols is an important chemical transformation. Although traditional stoichiometric and catalytic oxidation methods have been widely used for this transformation, an efficient and valuable method should be further explored from the views of reusable catalysts, less waste, and convenient procedures. Herein an inorganic-ligand supported iron catalyst (NH4)3[FeMo6O18(OH)6]·7H2O was described as a heterogeneous molecular catalyst in acetic acid for this transformation in which hydrogen peroxide was used as the terminal oxidant. Under the optimized reaction conditions, carbon-carbon bond cleavage of 1,2-diols could be achieved in almost all cases and carboxylic acids or ketones could be afforded with a high conversion rate and high selectivity. Furthermore, the catalytic system was used efficiently to degrade renewable biomass oleic acid. Mechanistic insights based on the observation of the possible intermediates and control experiments are presented.

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Glycerol conversion to high-value chemicals: The implication of unnatural α-amino acid syntheses using natural resources

Glycerol derivatives are an important class of compounds, which have great applications as basic structural building blocks in organic synthesis. O-Benzylglycerol was oxidised to produce a high-value compound in high yield using a NaOtBu-O2 system. Furthermore, the synthetic utility of the resulting product was demonstrated by its transformation into unnatural α-amino acids, thus showing the valorisation of glycerol biomass.

A Triazolotriazine-Based Dual GSK-3β/CK-1δ Ligand as a Potential Neuroprotective Agent Presenting Two Different Mechanisms of Enzymatic Inhibition

Glycogen synthase kinase 3β (GSK-3β) and casein kinase 1δ (CK-1δ) are emerging targets for the treatment of neuroinflammatory disorders, including Parkinson's disease. An inhibitor able to target these two kinases was developed by docking-based design. Compound 12, 3-(7-amino-5-(cyclohexylamino)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-2-yl)-2-cyanoacrylamide, showed combined inhibitory activity against GSK-3β and CK-1δ [IC50(GSK-3β)=0.17 μm; IC50(CK-1δ)=0.68 μm]. In particular, classical ATP competition was observed against CK-1δ, and a co-crystal of compound 12 inside GSK-3β confirmed a covalent interaction between the cyanoacrylamide warhead and Cys199, which could help in the development of more potent covalent inhibitors of GSK-3β. Preliminary studies on in vitro models of Parkinson's disease revealed that compound 12 is not cytotoxic and shows neuroprotective activity. These results encourage further investigations to validate GSK-3β/CK-1δ inhibition as a possible new strategy to treat neuroinflammatory/degenerative diseases.

A colourful azulene-based protecting group for carboxylic acids

An intensely blue-coloured protecting group for carboxylic acids has been developed. The protecting group is introduced through a Steglich esterification that couples 6-(2-hydroxyethyl)azulene (AzulE) and the carboxylic acid substrate. Deprotection is effected under basic conditions by the addition of the amidine base DBU, whereupon cleavage occurs, accompanied by a colour change. A two-step deprotection methodology comprising activation with oxalyl chloride and deprotection with a very mild base was developed for use with base-sensitive substrates. The AzulE esters were found to be compatible with other commonly employed protecting groups – silyl ethers, MOM acetals – by studying their orthogonal and concomitant deprotections. The stability of the new protecting group towards various synthetic processes – oxidation, reduction, cross-coupling, olefination and treatment with base – provided the basis of a versatility profile. This indicated that AzulE esters are sensitive to strongly oxidising and basic agents while being compatible with reducing conditions and selected other reactions. The convenience of a highly coloured protecting group for tracking material (and avoiding loss of compound) through laboratory processes warrants further investigation of this and/or related species.

4,5-Disubstituted N-Methylimidazoles as Versatile Building Blocks for Defined Side-Chain Introduction

Fungerin is a 1,4,5-trisubstituted imidazole natural product characterised by a broad spectrum of antifungal activities. We planned to develop flexible strategies to access to such compounds. Imidazoles bearing suitable anchor groups at C-4 and C-5 allow the introduction of various substituted side-chains, generating libraries of fungerin derivatives for biological tests. Starting from commercially available reactants, two N-methyl 4,5-substituted imidazole core units were synthesised. Derivatives of type 1 contained two orthogonally protected C-1 anchors. Selective side-chain introduction was achieved through a sequence of Grignard coupling at C-5 to replace a tosylate and a Horner olefination through an aldehyde attached to C-4. Two target fungerin derivatives were synthesised. Since the organometallic substitution of the C-5-CH2-positioned leaving group proved to suffer from limitations concerning potential competing side-reactions, a type 2 imidazole core was built up. These structures had a halogen centre at C-4 and a hydroxyethyl anchor at C-5. Now, selective side-chain introduction allowed us to use Julia olefination to form the allyl side-chain at C-5 and Heck reactions to introduce the C-4 acryl substituents. Eight derivatives, including fungerin, were synthesised by this latter strategy, without producing any regioisomers. The second approach had the advantage that various side-chains could be coupled at C-4 and C-5 in two final steps. Thus, this strategy represents a versatile way to build up libraries of fungerin derivatives for biological testing.

PREPARATION METHOD FOR CHIRAL INTERMEDIATE FOR USE IN STATINS

The present invention relates to a preparation method for a chiral intermediate for use in statins, acquired with chloroacetic acid and benzyl alcohol as starting materials via a series of reactions, namely etherification, condensation, substitution, and asymmetric reduction. The preparation method provided in the present invention has a novel route of synthesis, allows an intermediate compound to be introduced conveniently into the chiral center of a glycol via enzyme reduction, and not only is low in costs, but also is reliable in quality. The route of synthesis provided in the present invention uses raw materials of low costs, has an easy to operate process, and provides a final product of great purity and high yield.