$N,N\'-Bis-tert-butoxycarbonylthiourea$

N,N\'-Bis-tert-butoxycarbonylthiourea

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Cat Number

INT145013054

CAS Number

145013-05-4

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CAS Number

145013-05-4

EINECS

215-888-7

Storage

Store at room temperature

Synonyms

N,Nμ-Di-Boc-thiourea;Diboc-thiourea;N,N'-bis(1,1-diMethylethoxycarbonyl)thiourea

Molecular Formula

C11H20N2O4S

Molecular Weight

276.35

Smiles

C(C)(C)(C)OC(=O)NC(=S)NC(=O)OC(C)(C)C

Appearance

White to off-white solid

Melting Point

131-135℃

Relative Density

1.152

pKa

5.55

General Description

N,N'-Bis-tert-butoxycarbonylthiourea is a symmetric, dual-Boc protected thiourea reagent. It serves as a highly efficient and stable electrophilic source for the synthesis of protected guanidine derivatives.

Mechanism of Action

It functions as a powerful guanylating agent. The two Boc groups enhance the reactivity and stability of the thiourea core, allowing for the smooth transfer of the guanidine moiety to primary and secondary amines, often mediated by Mukaiyama's reagent or metal catalysts.

Application

It is widely used in medicinal chemistry to convert amino groups into Boc-protected guanidines, a common functional group found in many pharmaceuticals and bioactive natural products.