215050-11-6

Basic information

• Product Name: 1 3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE
• Synonyms: [(2-Hydroxyethyl)carbonimidoyl]biscarbamic acid bis(1,1-dimethylethyl) ester;1,3-Di-Boc-2-(2-hydroxyethyl)guanidine, >=99%
• CAS NO: 215050-11-6
• Molecular Formula: C₁₃H₂₅N₃O₅
• Molecular Weight: 303.35
• Product Categories: Guanidine Protection/Guanidinylation;Peptide Synthesis;Specialty Synthesis;amino acids
• Mol File: 215050-11-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 121-126 °C
• Appearance: /
• Density: 1.13g/cm³
• Refractive Index: 1.489
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1 3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE(215050-11-6)
• EPA Substance Registry System: 1 3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE(215050-11-6)

Safety Data

• WGK Germany: 3
• F: 4.5-10
• Hazardous Substances Data: 215050-11-6(Hazardous Substances Data)

Usage

Description

1,3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE is a guanidine derivative used in organic synthesis and pharmaceutical research. It features protective tert-butoxycarbonyl (BOC) groups on the nitrogen atoms and a 2-(2-hydroxyethyl) group that enhances stability and solubility. 1 3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE has potential applications in medicinal chemistry, particularly for the synthesis of guanidine-based drugs and inhibitors. Its unique structure and reactivity make it a valuable building block for creating new compounds with biological activity. The BOC groups can be easily removed under mild conditions, making it a versatile intermediate in organic synthesis.

Uses

Used in Pharmaceutical Research:
1,3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE is used as a key intermediate in the synthesis of guanidine-based drugs and inhibitors, contributing to the development of novel therapeutic agents.
Used in Organic Synthesis:
1,3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE is used as a versatile building block for creating new compounds with biological activity, thanks to its unique structure and reactivity.
Used in Medicinal Chemistry:
1,3-DI-BOC-2-(2-HYDROXYETHYL)GUANIDINE is used as a valuable precursor in the design and synthesis of innovative pharmaceutical compounds, facilitating advancements in drug discovery and development.

InChI:InChI=1/C13H25N3O5/c1-12(2,3)20-10(18)15-9(14-7-8-17)16-11(19)21-13(4,5)6/h17H,7-8H2,1-6H3,(H2,14,15,16,18,19)

Upstream product

• 141-43-5 ethanolamine 
• 145013-05-4 tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate 
• 332882-82-3 1,3-bis(t-butoxycarbonyl)guanidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 207857-15-6 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine 
• 322474-21-5 N,N'-bis-Boc-S-methyl-isothiourea 

Downstream Products

• 1563178-41-5 C₃₄H₅₄N₆O₁₃ 
• 1201582-63-9 5-acetyl-6-(2-(N,N'-di-Boc-guanidino)ethoxy)-7-[3-(4-fluorophenyl)butoxy]-2,4-dimethylbenzooxazole 
• 215050-18-3 C₃₇H₄₈N₆O₁₂S 
• 215050-15-0 C₃₃H₄₆N₆O₁₂S 

Relevant articles and documents

Synthesis of New Guanidine-Containing Amphiphiles and Their Pyrene Analog for Liposomal Delivery Systems and Visualization in Target Cells

New cationic amphiphiles with a guanidine head group have been synthesized starting from lipoamino acids with the goal of creating drug and genetic material delivery systems. Their analog containing a pyrene fragment has also been obtained as a potential agent for visualization of liposome transport in various cells.

ANTIMICROBIAL GUANIDINIUM AND THIOURONIUM FUNCTIONALIZED POLYMERS

Antimicrobial cationic polycarbonates and polyurethanes have been prepared comprising one or more pendent guanidinium and/or isothiouronium groups. Additionally, antimicrobial particles were prepared having a silica core linked to surface groups comprising a guanidinium and/or isothiouronium group. The cationic polymers and cationic particles can be potent antimicrobial agents against Gram-negative microbes, Gram-positive microbes, and/or fungi.

Investigation of mechanism-based thrombin inhibitors: Implications of a highly conserved water molecule for the binding of coumarins within the S pocket

The synthesis of novel coumarins bearing on the lateral side chain in the 3-position an amine or a guanidine group is described. In vitro evaluation highlighted 14d which possesses a meta aniline side chain as a very potent THR inhibitor. Surprisingly, the introduction of a guanidine moiety always led to a decrease in THR inhibiting properties. We, thus, used docking experiments to rationalize the SAR in the series. This study showed the crucial role of a conserved water molecule in the specificity pocket of THR during docking simulation in order to explain the inactivity of guanidine derivatives.