Ethyl 3-(3-bromophenyl)-3-oxopropanoate

Name: Ethyl 3-(3-bromophenyl)-3-oxopropanoate
Brand: ChemScene
Availability: InStock
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CAS No. 21575-91-7
Cat. No. CS-W022666
Purity≥97%
MDL No.MFCD03424812

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Ethyl 3-(3-bromophenyl)-3-oxopropanoate|CS-W022666

Structure of 21575-91-7

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General Information

CAS No. 21575-91-7
Cat. No. CS-W022666
Purity ≥97%
MDL No. MFCD03424812
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₁BrO₃
Molecular Weight 271.11
Synonym(s) ETHYL (3-BROMOBENZOYL)ACETATE
SMILES O=C(OCC)CC(C1=CC=CC(Br)=C1)=O

Description

Ethyl 3-(3-bromophenyl)-3-oxopropanoate features a brominated aromatic ring paired with an α,β-unsaturated ester motif, enabling direct participation in palladium-catalyzed cross-coupling reactions. This electrophilic enone derivative integrates readily into complex molecular architectures under standard conditions.

Application

Ethyl 3-(3-bromophenyl)-3-oxopropanoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted phenylalkyl scaffolds via Michael addition and aldol-type transformations. The ortho-bromo substituent provides a handle for subsequent palladium-catalyzed cross-coupling reactions, facilitating the construction of complex biaryl systems. Its stability under standard bench conditions and compatibility with common functional groups make it well-suited for multi-step synthesis in medicinal chemistry and process development workflows.

Synthesis

Route1
- 95-92-1
- ~92%
- In-stock
  
  21575-91-7
References
- MERCK and CO., INC. Patent: WO2004/92140 A1, 2004 ; Location in patent: Page 56-57 ; WO 2004/092140 A1
Route2
- In-stock
  
  1711-09-7
- In-stock
  
  6148-64-7
- ~97%
- In-stock
  
  21575-91-7
References
- Iwanowicz, Edwin J.; Watterson, Scott H.; Dhar, T.G. Murali; Pitts, William J.; Gu, Henry H. Patent: US2002/40022 A1, 2002 ;
Route3
- 51699-41-3
- ~72%
- In-stock
  
  21575-91-7
References
- Kafle, Bhooshan; Aher, Nilkanth G.; Khadka, Deegendra; Park, Hwangseo; Cho, Hyeongjin Chemistry - An Asian Journal, 2011 , vol. 6, # 8 p. 2073 - 2079

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 43.37
LogP 2.585
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Ethyl 3-(3-bromophenyl)-3-oxopropanoate

CAS No. 21575-91-7

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