(S)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile

CAS No. 207557-35-5
Cat. No. CS-D1786
Purity≥98%
MDL No.MFCD08689902

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(S)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile|CS-D1786

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Description

(S)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile is a chiral building block featuring a pyrrolidine core with strategically positioned chloroacetyl and nitrile functionalities. This configuration enables selective derivatization in asymmetric synthesis, particularly for bioactive molecule construction. The molecule exhibits enhanced reactivity due to the electron-withdrawing nitrile group adjacent to the acyl chloride, facilitating nucleophilic substitution under mild conditions. Its bench-stable nature simplifies handling in multi-step synthetic sequences.

Application

(S)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile serves as a versatile chiral building block for the synthesis of pyrrolidine-based scaffolds in medicinal chemistry. Its dual functionality—reactive chloroacetyl electrophile and nitrile group—enables sequential transformations, including nucleophilic substitution and ring formation. The stereochemistry at the C2 position is retained under standard reaction conditions, facilitating access to enantiopure heterocycles. Bench-stable and amenable to purification by chromatography or recrystallization, it functions effectively in modular synthetic sequences targeting bioactive molecules.

General Information

CAS No. 207557-35-5
Cat. No. CS-D1786
Purity ≥98%
MDL No. MFCD08689902
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₉ClN₂O
Molecular Weight 172.62
Synonym(s) (2S)-1-(2-Chloroacetyl)-2-pyrrolidinecarbonitrile; (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile; (2S)-1-chloroacetylpyrrolidine-2-carbonitrile; s-2-cyanopyrrolidine-1-carbonylchloride
SMILES N#C[C@H]1N(C(CCl)=O)CCC1

Computational Chemistry Data

TPSA 44.1
LogP 0.73978
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: 3261
Class : 8	Packing Group : Ⅱ
Hazard Statements : H302+H312+H332-H314
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P330+P331-P302+P352-P304+P340-P330-P362+P364-P363-P405-P501

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Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Building Blocks for Pharmaceutical Ingredients

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(S)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile

CAS No. 207557-35-5

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