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

Description

Benzyloxyacetaldehyde is a non-natural aldehyde that exists as a pale yellow oil. It is known for undergoing enantioselective Mukaiyama aldol reactions with silylketene acetal nucleophiles in the presence of a C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex, which acts as a catalyst.

Uses

Used in Pharmaceutical Industry:
Benzyloxyacetaldehyde is used as an acceptor for the engineering of 2-deoxyribose 5-phosphate aldolase variants, which are crucial in the enzymic preparation of β-ketols. This application is significant for the development of novel pharmaceutical compounds and the enhancement of existing drug synthesis processes.
Used in Chemical Synthesis:
Benzyloxyacetaldehyde serves as a key intermediate in the synthesis of various complex organic compounds, such as (3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate, (S)-5-benzyloxy-4-hydroxypentan-2-one, and myxothiazols. These synthesized compounds have potential applications in different fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
Due to its unique chemical properties and reactivity, benzyloxyacetaldehyde is also utilized in research and development for the exploration of new synthetic pathways, the study of enantioselective reactions, and the development of novel catalysts and methodologies in organic chemistry.

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 
• 80885-30-9 (E)-4-(benzyloxy)-2-buten-1-ol 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 70677-94-0 1,4-di(benzyloxy)but-2,3-ene 
• 69010-01-1 (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 
• 30379-55-6 benzyloxyacetic acid 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 68973-05-7 (2R*,3S*)-2,3-bis((benzyloxy)methyl)oxirane 
• 100791-51-3 (2R,3R,4R)-1-Benzyloxy-4-methyl-5-hexene-2,3-diol 
• 126568-43-2 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-dihydroxy-1-phenyl-butyl)-carbamic acid tert-butyl ester 
• 71516-48-8 2-((benzyloxy)methyl)-1,3-dioxolane 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 

Downstream Products

• 70350-62-8 phosphonylethanolamine 
• 133281-05-7 5-Hexadecyloxymethyl-2-benzyloxymethyl-1,3-dioxolane 
• 134936-24-6 ethyl (R/S)-2-<(benzyloxyethyl)amino>-3,3-diethoxypropionate 
• 133281-07-9 2-Benzyloxymethyl-4-octadecyloxymethyl-[1,3]dioxolane 
• 79246-52-9 1-Benzyloxy-3-methyl-4-penten-2-ol 
• 221693-47-6 di-tert-butyl (2R,3S)-2-<(1R)-2-(benzyloxy)-1-hydroxyethyl>-1,4-dioxaspiro<4,4>nonane-2,3-dicarboxylate 
• 193957-75-4 di-tert-butyl (2R,3S)-2-<(1S)-2-(benzyloxy)-1-hydroxyethyl>-1,4-dioxaspiro<4,4>nonane-2,3-dicarboxylate 
• 101020-38-6 (Z)-ethyl 4-(benzyloxy)-2-methyl-2-butenoate 
• 101020-38-6 (E)-4-benzyloxy-2-methyl-2-butenoic acid ethyl ester 
• 181633-57-8 (E)-(5S,6R)-7-Benzyloxy-6-tert-butoxycarbonylamino-5-methyl-hept-3-enoic acid methyl ester 
• 94480-29-2 (2S)-2-benzyloxymethyl-2,3-dihydro-4H-pyran-4-one 
• 185614-95-3 racemic 4-benzyloxymethyl-β-propiolactone 
• 101376-74-3 (E)-4-(benzyloxy)-2-methylbut-2-enal 

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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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.

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.