216584-22-4

Basic information

• Product Name: N,Nμ,Nμμ-Tri-Boc-guanidine
• Synonyms: N,Nμ,Nμμ-Tri-Boc-guanidine;1,2,3-Tris(tert-butoxycarbonyl)guanidine (This product is only available in Japan.)
• CAS NO: 216584-22-4
• Molecular Formula: C₁₆H₂₉N₃O₆
• Molecular Weight: 359.41796
• Product Categories: Guanidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 216584-22-4.mol

Chemical Properties

• Melting Point: 190-196 °C
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 5.88±0.46(Predicted)
• CAS DataBase Reference: N,Nμ,Nμμ-Tri-Boc-guanidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,Nμ,Nμμ-Tri-Boc-guanidine(216584-22-4)
• EPA Substance Registry System: N,Nμ,Nμμ-Tri-Boc-guanidine(216584-22-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 216584-22-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N,Nμ,Nμμ-Tri-Boc-guanidine is used as a reagent in organic synthesis for the protection of amines. The Boc protecting groups enable the compound to be used in various chemical reactions without the reactivity of the amine group interfering, allowing for the synthesis of complex organic compounds.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, N,Nμ,Nμμ-Tri-Boc-guanidine is used as a building block for the preparation of pharmaceuticals. Its ability to protect amines and be deprotected under mild conditions makes it a valuable tool in the synthesis of various drug molecules.
Used in Chemical Reactions:
N,Nμ,Nμμ-Tri-Boc-guanidine is used as a reagent in chemical reactions to facilitate the synthesis of various organic compounds. Its Boc protecting groups allow for the controlled deprotection of amines, enabling the formation of desired products in a controlled manner.
Safety Precautions:
N,Nμ,Nμμ-Tri-Boc-guanidine should be handled with care as it can be harmful if ingested or inhaled. Proper safety measures, such as wearing protective clothing and using appropriate ventilation, should be taken during its use in laboratories and industrial settings.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 145013-06-5 N,N′-bis(tert-butoxycarbonyl)-N′′-benzylguanidine 
• 204447-02-9 [benzylamino-(3-benzylureido)methylene]carbamic acid tert-butyl ester 
• 1092657-95-8 C₃₄H₄₅N₃O₆ 

Relevant articles and documents

Process for the preparation of substituted pyrimidine derivatives

The present invention is directed to processes for the preparation of substituted pyrimidine derivatives, useful as intermediates in the synthesis of histamine H4 receptor modulators, and to intermediates in H4 modulator synthesis.

Optimisation of the synthesis of guanidines from amines via nitroguanidines using 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine

The synthesis of the useful reagent for the preparation of guanidines, 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine (DMNPC), has been optimised. A detailed protocol for using this reagent for the preparation in pure form of a range of guanidines via nitroguanidines is described. A comparison has been made regarding efficiency between DMNPC and the guanidinylating reagents N,N′-bis-Boc-1-pyrazole-1-carboxamidine (2) and N,N′-bis-Boc- N′-triflylguanidine (3).

Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions

New guanidinylation reagents are reported. These reagents consist of N,N',N''-tri-Boc-guanidine (1) and N,N',N''-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions, to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents N,N'-di-Boc-N''- triflylguanidine (3) and N,N'-di-Cbz-N''-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.