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
• Article Data: 3

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

General Description

N,Nμ,Nμμ-Tri-Boc-guanidine, also known as N,N,N′,N′,N′-pentakis(t-butoxycarbonyl) guanidine, is a compound used in organic synthesis and as a reagent in chemical reactions. It is a guanidine derivative with three tert-butoxycarbonyl (Boc) protecting groups, which makes it useful in the synthesis of various organic compounds. It is commonly used for the protection of amines and can be deprotected under mild conditions to reveal the free amine. N,Nμ,Nμμ-Tri-Boc-guanidine is an important building block in organic chemistry and is often utilized in the preparation of pharmaceuticals and other complex molecules. It is a white crystalline solid and should be handled with care as it can be harmful if ingested or inhaled.

Upstream product

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

Downstream Products

• 512173-27-2 C₃₆H₅₅N₃O₇Si 
• 145013-06-5 N,N′-bis(tert-butoxycarbonyl)-N′′-benzylguanidine 
• 204447-02-9 [benzylamino-(3-benzylureido)methylene]carbamic acid tert-butyl ester 

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.

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.