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496871

Sigma-Aldrich

1,3-Bis(tert-butoxycarbonyl)guanidine

98%

Synonym(s):

C,C′-Bis(1,1-dimethylethyl) N,N′-(carbonimidoyl)bis[carbamate], Di-Boc-guanidine, N,N′-Bis(Boc)guanidine, N,N′-Di-Boc-guanidine, N1,N2-Bis(tert-butoxycarbonyl)guanidine, N1,N2-Bis(tert-butyloxycarbonyl)guanidine, tert-Butyl [N-(tert-butoxycarbonyl)carbamimidoyl]carbamate

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About This Item

Linear Formula:
HN=C[NHCO2C(CH3)3]2
CAS Number:
154476-57-0
Molecular Weight:
259.30
MDL number:
MFCD01863604
UNSPSC Code:
12352100
PubChem Substance ID:
24873089
NACRES:
NA.22

Assay

98%

mp

141-144 °C (lit.)

SMILES string

CC(C)(C)OC(=O)NC(=N)NC(=O)OC(C)(C)C

InChI

1S/C11H21N3O4/c1-10(2,3)17-8(15)13-7(12)14-9(16)18-11(4,5)6/h1-6H3,(H3,12,13,14,15,16)

InChI key

VPWFNCFRPQFWGS-UHFFFAOYSA-N

General description

1,3-Bis(tert-butoxycarbonyl)guanidine is a guanidine derivative. The synthesis of N-substituted 2-aminoimidazole inhibitors using 1,3-bis(tert-butoxycarbonyl)guanidine has been reported.

Application

1,3-Bis(tert-butoxycarbonyl)guanidine may be used to produce a guanidinyl derivative during the multi-step synthesis of (-)-crispine E. It may also be used as a reagent during the preparation of 1,6-diphenylnaphthalenes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of (-)-Trolline,(-)-Crispin A and (-)-Crispine E.
Kanemitsu T, et al.
Heterocycles, 74, 199-204 (2008)
Andrew A Yeagley et al.
Organic & biomolecular chemistry, 11(1), 130-137 (2012-10-19)
Antibiotic resistance is a significant problem and is compounded by the ability of many pathogenic bacteria to form biofilms. A library of N-substituted derivatives of a previously reported 2-aminoimidazole/triazole (2-AIT) biofilm modulator was constructed via α-bromoketone cyclization with 1,3-bis(tert-butoxycarbonyl)guanidine, followed
Yongzheng Zhang et al.
Bioorganic & medicinal chemistry letters, 23(7), 2001-2006 (2013-03-14)
Bacterial cell division occurs in conjunction with the formation of a cytokinetic Z-ring structure comprised of FtsZ subunits. Agents that disrupt Z-ring formation have the potential, through this unique mechanism, to be effective against several of the newly emerging multidrug-resistant

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