Cas no 876589-13-8 (tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate)

Tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate is a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. Its key structural features include a reactive chloromethyl group and a Boc-protected pyrrolidine ring, making it valuable for further functionalization. The Boc group enhances stability and facilitates selective deprotection under mild acidic conditions, while the chloromethyl moiety allows for nucleophilic substitution reactions. This compound is commonly employed in the synthesis of complex molecules, including active pharmaceutical ingredients (APIs) and bioactive compounds. Its well-defined reactivity and compatibility with a range of synthetic conditions make it a preferred choice for researchers requiring precise modifications to the pyrrolidine scaffold.
tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate structure
876589-13-8 structure
Product Name:tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate
CAS No:876589-13-8
MF:C10H18ClNO2
MW:219.70842218399
MDL:MFCD08059338
CID:94750
PubChem ID:51358284
Update Time:2025-06-08

tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-Boc-3-Chloromethylpyrrolidine
    • tert-Butyl3-(chloromethyl)-1-pyrrolidinecarboxylate
    • 3-Chloromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
    • tert-Butyl 3-(chloromethyl)pyrrolidine-1-carboxylate
    • 1,1-Dimethylethyl 3-(chloromethyl)-1-pyrrolidinecarboxylate (ACI)
    • tert-Butyl 3-(chloromethyl)-1-pyrrolidinecarboxylate
    • AS-30202
    • MFCD08059338
    • 1-Pyrrolidinecarboxylic acid, 3-(chloromethyl)-, 1,1-dimethylethyl ester
    • 1-Boc-3-(chloromethyl)pyrrolidine
    • AC-28285
    • AB43113
    • 3-Chloromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, AldrichCPR
    • t-butyl 3-(chloromethyl)-1-pyrrolidinecarboxylate
    • AB43110
    • MFCD08059336
    • AKOS015898150
    • ZCOBWMKNMWVILV-UHFFFAOYSA-N
    • CS-0005407
    • 876589-13-8
    • AB43107
    • (S)-1-Boc-3-(chloromethyl)pyrrolidine
    • SCHEMBL4940891
    • DTXSID70679929
    • SY344415
    • DB-077067
    • tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate
    • MDL: MFCD08059338
    • Inchi: 1S/C10H18ClNO2/c1-10(2,3)14-9(13)12-5-4-8(6-11)7-12/h8H,4-7H2,1-3H3
    • InChI Key: ZCOBWMKNMWVILV-UHFFFAOYSA-N
    • SMILES: O=C(N1CC(CCl)CC1)OC(C)(C)C

Computed Properties

  • Exact Mass: 219.103
  • Monoisotopic Mass: 219.103
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 213
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 29.5A^2
  • XLogP3: 2.1

Experimental Properties

  • Density: 1.101
  • Boiling Point: 284.3°C at 760 mmHg
  • Flash Point: 125.7°C
  • Refractive Index: 1.477
  • Vapor Pressure: 0.0±0.6 mmHg at 25°C

tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate Security Information

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tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Carbon tetrachloride ,  Triphenylphosphine Solvents: Dichloromethane ;  rt
Reference
Novel N-substituted benzimidazole CXCR4 antagonists as potential anti-HIV agents
Miller, John F.; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(7), 2125-2128

tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate Raw materials

tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate Preparation Products

tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate Related Literature

Additional information on tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate

Introduction to tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate (CAS No. 876589-13-8)

tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate (CAS No. 876589-13-8) is a versatile organic compound that has garnered significant attention in the fields of chemical synthesis, medicinal chemistry, and pharmaceutical research. This compound is characterized by its unique structural features, which include a tert-butyl group, a pyrrolidine ring, and a chloromethyl substituent. These features contribute to its utility in various synthetic transformations and its potential as a building block in the development of novel pharmaceuticals.

The tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate molecule is a chiral compound, which means it can exist in two enantiomeric forms. The ability to control the stereochemistry of this compound is crucial for its applications in asymmetric synthesis and the development of enantiomerically pure drugs. Recent advancements in chiral catalysis and asymmetric synthesis have significantly enhanced the efficiency and selectivity of producing this compound, making it more accessible for research and industrial applications.

In the realm of medicinal chemistry, tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate has been explored for its potential as a prodrug precursor. Prodrugs are biologically inactive compounds that are converted into their active forms through metabolic processes within the body. The chloromethyl group in this compound can be readily functionalized to introduce various bioactive moieties, making it an attractive candidate for prodrug design. Studies have shown that derivatives of this compound exhibit improved pharmacokinetic properties, such as enhanced solubility and reduced toxicity, compared to their parent compounds.

The pyrrolidine ring in tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate is known for its ability to form stable complexes with metal ions, which has led to its use in coordination chemistry and metal-catalyzed reactions. This property is particularly useful in the synthesis of metallo-drugs and other metal-containing pharmaceuticals. Recent research has focused on developing new catalysts based on this compound to improve the efficiency and selectivity of various chemical transformations.

The tert-butyl group in tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate provides steric protection to the pyrrolidine ring, which can be advantageous in protecting sensitive functional groups during synthetic sequences. This feature makes the compound a valuable protecting group in organic synthesis, particularly in multistep syntheses where maintaining the integrity of specific functional groups is critical.

In addition to its synthetic utility, tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate has been investigated for its biological activities. Studies have shown that certain derivatives of this compound exhibit potent inhibitory effects on various enzymes and receptors, making them potential leads for drug discovery. For example, some derivatives have been found to inhibit protein kinases, which are key targets in cancer therapy. Other derivatives have shown promise as modulators of G protein-coupled receptors (GPCRs), which are involved in numerous physiological processes and are targets for many therapeutic agents.

The versatility of tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate extends beyond its use as a synthetic intermediate or drug candidate. It has also found applications in materials science and polymer chemistry. The chloromethyl group can be used to introduce reactive functionalities into polymers, enabling the creation of novel materials with tailored properties. These materials have potential applications in areas such as drug delivery systems, coatings, and adhesives.

In conclusion, tert-butyl 3-(chloromethyl)pyrrolidine-1-carboxylate (CAS No. 876589-13-8) is a multifaceted compound with a wide range of applications in chemical synthesis, medicinal chemistry, pharmaceutical research, materials science, and polymer chemistry. Its unique structural features and versatile reactivity make it an invaluable tool for researchers and chemists working across these fields. Ongoing research continues to uncover new possibilities for this compound, further solidifying its importance in modern scientific endeavors.

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