2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethan-1-one

Name: 2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethan-1-one
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 141095-78-5
Cat. No. CS-0045281
Purity≥95%
MDL No.None

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2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethan-1-one|CS-0045281

Structure of 141095-78-5

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General Information

CAS No. 141095-78-5
Cat. No. CS-0045281
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₁₁BrO₂
Molecular Weight 207.07
Synonym(s) 2-Bromo-1-(oxan-4-yl)ethan-1-one
SMILES BrCC(C1CCOCC1)=O

Description

2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethan-1-one features a bromo-substituted ketone scaffold integrated with a tetrahydropyran ring, offering enhanced stability and selective reactivity. This functionalized building block enables efficient access to complex molecular architectures in synthetic organic chemistry, particularly in the development of chiral intermediates and bioactive compounds under standard bench conditions.

Application

2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethan-1-one serves as a versatile building block in synthetic organic chemistry, enabling efficient construction of functionalized carbonyl and halogen-containing intermediates. The tetrahydropyranyl group provides robust protection for alcohols under acidic conditions, while the α-bromo ketone moiety facilitates nucleophilic substitution, cross-coupling, or enolate-based transformations. Its bench-stable nature and compatibility with standard reaction conditions make it ideal for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

Route1
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References
- EISAI RandD MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; EATHERTON, Andrew John Patent: WO2014/13076 A1, 2014 ; Location in patent: Page/Page column 100; 101 ;
Route2
- In-stock
  
  137052-08-5
- ~%
- In-stock
  
  141095-78-5
References
- Bischoff, Francois; Berthelot, Didier; De Cleyn, Michel; MacDonald, Gregor; Minne, Garrett; Oehlrich, Daniel; Pieters, Serge; Surkyn, Michel; Trabanco, Andres A.; Tresadern, Gary; Van Brandt, Sven; Velter, Ingrid; Zaja, Mirko; Borghys, Herman; Masungi, Chantal; Mercken, Marc; Gijsen, Harrie J. M. Journal of Medicinal Chemistry, 2012 , vol. 55, # 21 p. 9089 - 9106,18
Route3
- 40191-32-0
- ~%
- In-stock
  
  141095-78-5
References
- Harnest; Burger Journal of the American Chemical Society, 1943 , vol. 65, p. 370

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05
Signal Word : Danger	UN#: 3261
Class : 8	Packing Group : Ⅱ
Hazard Statements : H290-H314
Precautionary Statements : P234-P260-P264-P280-P301+P330+P331-P304+P340-P363-P390-P405-P406-P501

Quality Control

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Computational Chemistry Data

TPSA 26.3
LogP 1.377
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydropyran compounds

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2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethan-1-one

CAS No. 141095-78-5

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