1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE Chemical Properties

Melting point:

113 °C (dec.)(lit.)

Density 

1.36

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetonitrile, Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)

form 

Solid

pka

-4.76±0.40(Predicted)

color 

White to Off-White

BRN 

7947176

InChI

InChI=1S/C12H20F3N3O6S/c1-10(2,3)23-8(19)16-7(17-9(20)24-11(4,5)6)18-25(21,22)12(13,14)15/h1-6H3,(H2,16,17,18,19,20)

InChIKey

GOQZIPJCBUYLIR-UHFFFAOYSA-N

SMILES

C(/NC(=O)OC(C)(C)C)(=N\C(=O)OC(C)(C)C)\NS(=O)(=O)C(F)(F)F

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

29350090

MSDS

• Language:English Provider:SigmaAldrich

1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE Usage And Synthesis

Chemical Properties

White solid

Uses

1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine is a guanidinylation reagent for amines and peptides.

Synthesis

N,N'-Bis(tert-butoxycarbonyl)guanidine (S6; 4.38 g, 16.9 mmol, 1.00 eq.) was dissolved in dichloromethane (CH2Cl2, 84.4 mL) at room temperature. The reaction mixture was cooled to -78°C and stirred for 10 minutes. Subsequently, freshly distilled triethylamine (Et3N; 1.79 g, 17.7 mmol, 1.05 eq.) was added slowly and dropwise. Trifluoromethanesulfonic anhydride (5.00 g, 17.7 mmol, 1.05 eq.) was added dropwise over 15 min at -78 °C while maintaining vigorous stirring. The reaction mixture was gradually warmed up to room temperature. After 6 hours of reaction, the reaction mixture was washed with 1.0 M potassium bisulfate (KHSO4) solution followed by water (H2O). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and filtered. The solvent was removed by concentration under reduced pressure. Purification by silica gel fast column chromatography (eluent: 100% dichloromethane) afforded 1,3-di-BOC-2-(trifluoromethylsulfonyl)guanidine (S7; 5.51 g, 14.1 mmol, 83% yield) as a colorless solid.

References

[1] Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 1038 - 1042
[2] Organic Syntheses, 2002, vol. 78, p. 91 - 91
[3] Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 3804 - 3805
[4] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8432 - 8439
[5] ChemMedChem, 2014, vol. 9, # 1, p. 129 - 150

1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE(207857-15-6)Related Product Information

• 1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE
• BOC-GUANIDINE
• 1 3-BIS(TERT-BUTOXYCARBONYL)GUANIDINE
• METHYLENE DIURETHANE