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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.)

functional group

amine

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000234773
0000253221
0000193399
BGBC4884V
BGBB9347

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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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