Cas no 400777-00-6 (tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate)

Tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate is a versatile pyridine-based intermediate used in organic synthesis and pharmaceutical research. Its key structural features—a chloro and iodo substituent on the pyridine ring, along with a tert-butyl carbamate protecting group—make it valuable for selective functionalization and further derivatization. The iodine moiety facilitates cross-coupling reactions, such as Suzuki or Sonogashira couplings, while the carbamate group provides stability under various reaction conditions. This compound is particularly useful in the development of bioactive molecules, offering precise control over molecular architecture. Its high purity and well-defined reactivity profile ensure reliable performance in complex synthetic pathways.
tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate structure
400777-00-6 structure
Product Name:tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate
CAS No:400777-00-6
MF:C10H12ClIN2O2
MW:354.571953773499
MDL:MFCD11977418
CID:324771
PubChem ID:53415320
Update Time:2025-10-29

tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate Chemical and Physical Properties

Names and Identifiers

    • tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate
    • Carbamic acid, (6-chloro-4-iodo-3-pyridinyl)-, 1,1-dimethylethyl ester
    • Carbamicacid, N-(6-chloro-4-iodo-3-pyridinyl)-, 1,1-dimethylethyl ester
    • tert-Butyl 6-chloro-4-iodopyridin-3-ylcarbaMate
    • tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate
    • (6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester
    • AK103176
    • (6-Chloro-4-iodo-3-pyridinyl)-carbamic acid 1,1-dimethylethyl ester
    • tert-butyl(6-chloro-4-iodopyridin-3-yl)carbamate
    • YCBOUHLCYYKTFG-UHFFFAOYSA-N
    • BCP27803
    • (6-Chloro-4-iodopyridin-3-yl)carbamic acid tert-butyl ester
    • F30210
    • 400777-00-6
    • N-(6-chloro-4-iodo-3-pyridinyl)carbamic acid tert-butyl ester
    • 1,1-dimethylethyl (6-chloro-4-iodo-3-pyridinyl)carbamate
    • SY068667
    • tert-butyl N-(6-chloranyl-4-iodanyl-pyridin-3-yl)carbamate
    • SB83680
    • N-Boc-6-chloro-4-iodopyridin-3-amine
    • AKOS016005339
    • A824908
    • DTXSID40697039
    • FT-0698384
    • DS-4034
    • 3-(Boc-amino)-6-chloro-4-iodopyridine
    • CS-W007089
    • MFCD11977418
    • SCHEMBL1581324
    • MDL: MFCD11977418
    • Inchi: 1S/C10H12ClIN2O2/c1-10(2,3)16-9(15)14-7-5-13-8(11)4-6(7)12/h4-5H,1-3H3,(H,14,15)
    • InChI Key: YCBOUHLCYYKTFG-UHFFFAOYSA-N
    • SMILES: IC1C=C(N=CC=1NC(=O)OC(C)(C)C)Cl

Computed Properties

  • Exact Mass: 353.96300
  • Monoisotopic Mass: 353.963
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 258
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 51.2
  • XLogP3: 3

Experimental Properties

  • Density: 1.723±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Very slightly soluble (0.11 g/l) (25 o C),
  • PSA: 54.71000
  • LogP: 3.70020

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tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate Production Method

Additional information on tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate

tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate: A Comprehensive Overview

The compound with CAS No 400777-00-6, commonly referred to as tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate, is a highly specialized organic compound that has garnered significant attention in the fields of pharmaceutical chemistry and agricultural science. This compound is notable for its unique structural features, which include a pyridine ring substituted with chlorine and iodine atoms, as well as a tert-butyl carbamate group. These structural elements contribute to its diverse applications and intriguing chemical properties.

Recent studies have highlighted the potential of tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate in the development of novel drug delivery systems. Researchers have explored its ability to act as a stabilizing agent in drug formulations, particularly in the context of biodegradable polymers. The presence of the tert-butyl group enhances the compound's solubility in organic solvents, making it an ideal candidate for use in lipid-based drug delivery systems. This application is particularly promising for delivering hydrophobic drugs, which often pose challenges in traditional delivery methods.

In addition to its role in pharmaceuticals, this compound has also been investigated for its potential in pesticide development. The pyridine ring, with its electron-withdrawing substituents, imparts insecticidal properties to the molecule. Recent experiments have demonstrated that tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate exhibits potent activity against agricultural pests such as aphids and whiteflies. Its effectiveness is attributed to its ability to disrupt the nervous system of these insects, leading to paralysis and eventual death.

The synthesis of this compound involves a multi-step process that requires precise control over reaction conditions. The key steps include the formation of the pyridine ring through a nucleophilic aromatic substitution reaction, followed by the introduction of the chlorine and iodine substituents via electrophilic substitution. The final step involves the attachment of the tert-butyl carbamate group, which is achieved through a coupling reaction using appropriate coupling agents. This synthesis pathway has been optimized in recent studies to improve yield and purity, making it more feasible for large-scale production.

One of the most exciting developments involving this compound is its application in material science. Scientists have discovered that when incorporated into polymer matrices, tert-butyl N-(6-chloro-4-iodopyridin-3-yl)carbamate significantly enhances the mechanical properties of the resulting materials. This is particularly relevant for applications requiring high tensile strength and flexibility, such as in biodegradable plastics used in packaging and agriculture.

The unique combination of properties exhibited by this compound makes it a valuable tool in various research domains. Its ability to function as both a stabilizing agent and an active ingredient underscores its versatility. Furthermore, ongoing research continues to uncover new applications for this compound, particularly in areas such as bioimaging and sensors. For instance, recent studies have explored its potential as a contrast agent in magnetic resonance imaging (MRI), where its electronic properties enable enhanced image resolution.

In conclusion, CAS No 400777-00-6 represents a significant advancement in chemical synthesis and application. Its structural features provide a foundation for diverse functionalities, making it an invaluable asset across multiple industries. As research into this compound progresses, it is anticipated that new applications will continue to emerge, further solidifying its importance in both academic and industrial settings.

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