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

• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 42783-78-8 benzyloxyacetaldehyde diethyl acetal 
• 64-19-7 acetic acid 
• 14593-43-2 benzyl allyl ether 
• 935-04-6 benzyl vinyl ether 
• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 622-08-2 2-Benzyloxyethanol 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 71516-48-8 2-((benzyloxy)methyl)-1,3-dioxolane 
• 126568-43-2 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-dihydroxy-1-phenyl-butyl)-carbamic acid tert-butyl ester 
• 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 
• 30379-55-6 benzyloxyacetic acid 

Downstream Products

• 14869-00-2 1-(benzyloxy)butan-2-ol 
• 854724-08-6 3-benzyloxy-1-cyclohex-1-enyl-1-nitro-propan-2-ol 
• 62222-04-2 2-(benzyloxy)acrylaldehyde 
• 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 
• 133281-03-5 5-Heptadecyl-2-benzyloxymethyl-1,3-dioxolane 

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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Exploring the dNTP -binding site of HIV-1 reverse transcriptase for inhibitor design

HIV-1 reverse transcriptase (RT) plays a central role in the viral life cycle, and roughly half of the FDA-approved anti-HIV drugs are targeting RT. Nucleoside analogs (NRTIs) require cellular phosphorylation for binding to RT, and to bypass this rate-limiting path, we designed a new series of acyclic nucleoside phosphonate analogs as nucleoside triphosphate mimics, aiming at the chelation of the catalytic Mg2+ ions via a phosphonate and/or a carboxylic acid group. Novel synthetic procedures were developed to access these nucleoside phosphonate analogs. X-ray structures in complex with HIV-1 RT/dsDNA demonstrated that their binding modes are distinct from that of our previously reported compound series. The impact of chain length, chirality and linker atom have been discussed. The detailed structural understanding of these new compounds provides opportunities for designing new class of HIV-1 RT inhibitors.

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.