60656-87-3

Basic information

• Product Name: BENZYLOXYACETALDEHYDE
• Synonyms: BENZYLOXYACETALDEHYDE;(phenylmethoxy)acetaldehyde;2-Benzyloxyacetaldehyde;Benzyloxyacetaldehyde, stabilized, 95%;Benzyloxyacetaldehyde CAS;2-(Benzyloxy)ethanal;2-(Phenylmethoxy)acetaldehyde;a-(Benzyloxy)acetaldehyde
• CAS NO: 60656-87-3
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 262-349-7
• Product Categories: Aromatics Compounds;Aromatics;Aldehydes;C9;Carbonyl Compounds
• Mol File: 60656-87-3.mol
• Article Data: 103

Chemical Properties

• Boiling Point: 118-120 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.069 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.174mmHg at 25°C
• Refractive Index: n20/D 1.518(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Solubility: Chloroform, Ethyl Acetate
• Stability: Temperature, Moisture Sensitive
• CAS DataBase Reference: BENZYLOXYACETALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLOXYACETALDEHYDE(60656-87-3)
• EPA Substance Registry System: BENZYLOXYACETALDEHYDE(60656-87-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 60656-87-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

Different sources of media describe the Uses of 60656-87-3 differently. You can refer to the following data:
1. Acceptor; engineering of 2-deoxyribose 5-phosphate aldolase variants for enzymic preparation of β-ketols
2. Benzyloxyacetaldehyde may be used in the following syntheses:(3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate(S)-5-benzyloxy-4-hydroxypentan-2-one myxothiazols
3. Acceptor; engineering of 2-deoxyribose 5-phosphate aldolase variants for enzymic preparation of -ketols

General Description

Benzyloxyacetaldehyde is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).

InChI:InChI=1/C9H10O2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-6H,7-8H2

Upstream product

• 42783-78-8 benzyloxyacetaldehyde diethyl acetal 
• 64-19-7 acetic acid 
• 14593-43-2 benzyl allyl ether 
• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 71516-48-8 2-((benzyloxy)methyl)-1,3-dioxolane 
• 100791-51-3 (2R,3R,4R)-1-Benzyloxy-4-methyl-5-hexene-2,3-diol 
• 68973-05-7 (2R*,3S*)-2,3-bis((benzyloxy)methyl)oxirane 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 69010-01-1 (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 
• 80885-30-9 (E)-4-(benzyloxy)-2-buten-1-ol 
• 70677-94-0 1,4-di(benzyloxy)but-2,3-ene 
• 100-51-6 benzyl alcohol 
• 622-08-2 2-Benzyloxyethanol 

Downstream Products

• 14869-00-2 1-(benzyloxy)butan-2-ol 
• 62987-20-6 3'-benzyloxymethyl-1'-thioxo-2',3',6',7'-tetrahydro-1'H-spiro[[1,3]dioxane-2,5'-pyrrolo[1,2-c]pyrimidine]-4'-carboxylic acid methyl ester 
• 71841-10-6 (E)-2-(2-Benzyloxy-1-hydroxy-ethyl)-6,10-dimethyl-2-phenylsulfanyl-undeca-5,9-dienoic acid methyl ester 
• 66646-70-6 2-amino-4-benzyloxy-3-hydroxy-butyric acid methyl ester 
• 65577-51-7 [1-(Benzhydryl-amino)-2-benzyloxy-ethyl]-phosphinic acid 
• 70350-62-8 phosphonylethanolamine 
• 94776-34-8 Diphenyl 1-benzyloxycarbonylamino-2-benzyloxyethanephosphonate 
• 101062-05-9 2-benzyloxy-N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)ethanimine 
• 70150-60-6 ethyl 2E-4-(benzyloxy)-2-butenoate 
• 157542-41-1 (2R,3R)-1-benzyloxy-3-methyl-4-penten-2-ol 
• 80127-39-5 2-benzyloxymethyl-2,3-dihydropyran-4-one 
• 84304-03-0 5-Benzyloxymethyl-4-bromo-5H-furan-2-one 
• 133281-05-7 5-Hexadecyloxymethyl-2-benzyloxymethyl-1,3-dioxolane 
• 77358-94-2 1-Benzyloxy-2,5-heptandion 

Relevant articles and documents

Biosynthesis of sulfur compounds. Elucidation of the stereochemistry of the conversion of [3-(Methylthio)propyl]glucosinolate into allylglucosinolate (Sinigrin)

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Bio-derived nanosilica-anchored Cu(II)-organoselenium complex as an efficient retrievable catalyst for alcohol oxidation

A new copper(II) complex supported onto rice-husk-derived nanosilica was prepared from 2,6-bis((phenylselanyl)methyl)pyridine, salicylaldehyde and copper acetate monohydrate, Cu(OAc)2·H2O. The as-synthesized complex Cu(II)SeNSe@imine-nanoSiO2 (Complex I) was extensively characterized with FT-IR, powder XRD, SEM-EDX, solid-state UV-Vis, ESR, XPS, TGA and BET surface area analysis. The catalytic activity of the complex was explored for alcohol oxidation reactions using H2O2 as oxidant and acetonitrile as solvent. For comparison, we have also prepared an analogous homogeneous catalyst (Complex II) and characterized it with FT-IR, UV-Vis, LC-MS and ESR analyses. Its catalytic activity was also screened to the same reaction. The immobilized catalyst showed better efficiency with 75%–95% isolated yield compared with the homogeneous one for alcohol oxidation with at least five times recyclability without profound loss in activity.

General Asymmetric Synthetic Strategy for the α-Alkylated 2,5,6-Trisubstituted Pyran of Indanomycin and Related Natural Products

A general synthetic strategy for convergent asymmetric synthesis of C1–C10 fragment of tetraene-containing natural product indanomycin was achieved starting from 2-(benzyloxy)acetaldehyde which in turn was obtained from very inexpensive material cis-1,4-butene-diol. Key steps include Evans' aldol reaction, HWE olefination, iodine-catalyzed tandem isomerization followed by C–O and C–C bond formation similar to our earlier report in constructing the trans-2,6-disubstituted dihydropyran ring and Evans' asymmetric alkylation.