90458-77-8

Basic information

• Product Name: 3-(benzyloxy)butanal
• CAS NO: 90458-77-8
• Molecular Weight: 178.231
• Mol File: 90458-77-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-(benzyloxy)butanal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(benzyloxy)butanal(90458-77-8)
• EPA Substance Registry System: 3-(benzyloxy)butanal(90458-77-8)

Safety Data

• Hazardous Substances Data: 90458-77-8(Hazardous Substances Data)

Upstream product

• 40844-09-5 ((pent-4-en-2-yloxy)methyl)benzene 
• 100-52-7 benzaldehyde 
• 774-44-7 (±)-(2S,4R)-2,4-dimethyl-1,3-dioxane 
• 53329-00-3 [(but-3-en-2-yloxy)methyl]benzene 
• 100-39-0 benzyl bromide 
• 52657-84-8 (±)-3-benzyloxybutan-1-ol 

Downstream Products

• 1332329-92-6 (E)-((hepta-4,6-dien-2-yloxy)methyl)benzene 
• 122949-27-3 Cl₃SnOCH(CH₂CHCH₂)CH₂CH(CH₃)OCH₂C₆H₅ 
• 1461-22-9 tributyltin chloride 
• 133621-27-9 Benzoic acid 1-(2-benzyloxy-propyl)-3-phenylsulfanylmethyl-but-3-enyl ester 
• 118377-09-6 3-O-benzyl-1-(2-thiazolyl)-1,3-butanediol 
• 671232-62-5 [(2S,3S)-3-(2-Benzyloxy-propyl)-oxiranyl]-methanol 
• 671232-61-4 (E)-5-Benzyloxy-hex-2-en-1-ol 
• 110410-33-8 (3R,4R,6S)-6-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol 
• 110410-33-8 (3R,4R,6R)-6-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-hept-1-en-4-ol 

Relevant articles and documents

Intramolecular OH...Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif

Fluorination is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogen-bond (HB) properties of adjacent functional groups, as well as the HB-accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH...F intramolecular HBs (IMHBs) has been established for conformationally restricted fluorohydrins, such interaction in flexible compounds remained questionable. Herein is demonstrated for the first time - and in contrast to earlier reports - the occurrence of OH...F IMHBs in acyclic saturated γ-fluorohydrins, even for the parent 3-fluoropropan-1-ol. The relative stereochemistry is shown to have a crucial influence on the corresponding h1JOH...F values, as illustrated by syn- and anti-4-fluoropentan-2-ol (6.6 and 1.9 Hz). The magnitude of OH...F IMHBs and their strong dependence on the overall molecular conformational profile, fluorination motif, and alkyl substitution level, is rationalized by quantum chemical calculations. For a given alkyl chain, the "rule of shielding" applies to OH...F IMHB energies. Surprisingly, the predicted OH...F IMHB energies are only moderately weaker than these of the corresponding OH...OMe. These results provide new insights of the impact of fluorination of aliphatic alcohols, with attractive perspectives for rational drug design.

Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes

The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.

[3+3] Annulation by sequential two electron and one electron allylation

3-phenylthio-2-(trimethylsilymethyl)propene is a convenient conjunctive reagent for the preparation of methylenecyclohexanes via a [3+3] annulation. The trimethylsilyl group facilitates the Lewis acid catalyzed allylation of an aldehyde or acetal while the phenylthio group directs a 6-endo-trig radical cyclization reaction.