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

Bezeichnung:1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE

CAS-Nr207857-15-6

Englisch Name:1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE

CBNumberCB2339467

SummenformelC12H20F3N3O6S

Molgewicht391.36

MOL-Datei207857-15-6.mol

1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE physikalisch-chemischer Eigenschaften

Schmelzpunkt	113 °C (dec.)(lit.)
Dichte	1.36
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Acetonitrile, Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
Aggregatzustand	Solid
pka	-4.76±0.40(Predicted)
Farbe	White to Off-White
BRN	7947176
Major Application	peptide synthesis
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

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
F	10-21
HS Code	29350090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
White solid
Verwenden
1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine is a guanidinylation reagent for amines and peptides.
Synthese

358-23-6

332882-82-3

207857-15-6

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.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

1,3-DI-BOC-2-(TRIFLUOROMETHYLSULFONYL)GUANIDINE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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