Methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Name: Methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
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CAS No. 603122-52-7
Cat. No. CS-0007611
Purity≥97%
MDL No.MFCD16996314

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Methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0007611

Structure of 603122-52-7

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General Information

CAS No. 603122-52-7
Cat. No. CS-0007611
Purity ≥97%
MDL No. MFCD16996314
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BFO₄
Molecular Weight 280.10
Synonym(s) Methyl 2-fluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzoate
SMILES O=C(OC)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1F

Description

Methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a bench-stable boronate ester featuring a para-fluorinated aryl moiety. This compound integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, delivering efficient access to functionalized biaryl scaffolds under standard conditions. The tetramethyl-substituted dioxaborolane ring enhances stability and reactivity, enabling reliable coupling with diverse aryl halides.

Application

Methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The ortho-fluorine substituent enables directed metalation and facilitates subsequent functionalization, while the tetramethylboronate group offers excellent stability, ease of handling, and broad functional group tolerance. This reagent is particularly valuable in constructing substituted biaryl scaffolds and heterocyclic systems relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  73183-34-3
- 179232-29-2
- ~%
- In-stock
  
  603122-52-7
References
- Imanishi, Masashi; Tomishima, Yasuyo; Itou, Shinji; Hamashima, Hitoshi; Nakajima, Yutaka; Washizuka, Kenichi; Sakurai, Minoru; Matsui, Shigeo; Imamura, Emiko; Ueshima, Koji; Yamamoto, Takao; Yamamoto, Nobuhiro; Ishikawa, Hirofumi; Nakano, Keiko; Unami, Naoko; Hamada, Kaori; Matsumura, Yasuhiro; Takamura, Fujiko; Hattori, Kouji Journal of Medicinal Chemistry, 2008 , vol. 51, # 6 p. 1925 - 1944
Route2
- In-stock
  
  112704-79-7
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  603122-52-7
References
- FUJISAWA PHARMACEUTICAL CO., LTD. Patent: US2004/6143 A1, 2004 ; US 20040006143 A1

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 44.76
LogP 1.9115
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

CAS No. 603122-52-7

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