4-Nitrophenyl 2-fluoropropanoate

Name: 4-Nitrophenyl 2-fluoropropanoate
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CAS No. 178181-33-4
Cat. No. CS-0094397
Purity≥98%
MDL No.None

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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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4-Nitrophenyl 2-fluoropropanoate|CS-0094397

Structure of 178181-33-4

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General Information

CAS No. 178181-33-4
Cat. No. CS-0094397
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₈FNO₄
Molecular Weight 213.16
Synonym(s) 4-Nitrophenyl 2-fluoropropionate
SMILES CC(F)C(OC1=CC=C([N+]([O-])=O)C=C1)=O

Description

4-Nitrophenyl 2-fluoropropanoate is a bench-stable fluorinated ester featuring a para-nitrophenol leaving group and a chiral α-fluoro carbonyl moiety. This combination enables selective acylation in synthetic workflows, particularly in peptide coupling and bioconjugation chemistry. The electron-withdrawing nitro group enhances leaving group ability, while the fluorine atom imparts steric and electronic modulation for controlled reactivity.

Application

4-Nitrophenyl 2-fluoropropanoate serves as a stable, bench-ready acylating agent that facilitates efficient esterification and peptide coupling reactions. Its ortho-activated aryl leaving group enables reliable displacement under mild conditions, while the fluorinated aliphatic moiety enhances electrophilic reactivity without compromising shelf stability. Functions effectively in nucleophilic substitution protocols and provides clean reaction profiles with minimal side products.

Synthesis

Route1
- In-stock
  
  57965-29-4
- In-stock
  
  5070-13-3
- ~56%
- In-stock
  
  178181-33-4
References
- Jiang, Han; Moore, Sarah J.; Liu, Shuanglong; Liu, Hongguang; Miao, Zheng; Cochran, Frank V.; Liu, Yang; Tian, Mei; Cochran, Jennifer R.; Zhang, Hong; Cheng, Zhen Amino Acids, 2013 , vol. 44, # 2 p. 673 - 681 Title/Abstract Full Text View citing articles Show Details Liu, Hongguang; Liu, Shuanglong; Miao, Zheng; Jiang, Han; Deng, Zixin; Hong, Xuechuan; Cheng, Zhen Molecular Pharmaceutics, 2013 , vol. 10, # 9 p. 3384 - 3391

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 69.44
LogP 1.8582
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Nitrophenyl 2-fluoropropanoate

CAS No. 178181-33-4

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