BOP

Other Names:

(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium

hexafluorophosphate

Castro's reagent

General Information:

Structure:

CAS Number: 56602-33-6

Molecular Weight: 442.287 g/mol

Appearance: White crystalline powder

BOP is a reagent used occasionally in amide coupling reactions. The use of BOP forms Hexamethylphosphoramide (HMPA) as a by-pdt which is a known carcinogen. PyBOP is considered a safer alternative to BOP.

Common Uses:

Reagents for amide coupling reactions

Procedure excerpt:

To a mixture of the acid (0.3 g, 0.85 mmol) and BOP (442 mg, 1 mmol) in DMF at 0 C was added TEA (0.3 mL 2.14 mmol). The resulting mixture was stirred for . . .

[full procedure]

Safety:

BOP forms Hexamethylphosphoramide (HMPA) as a by-pdt which is a known carcinogen.

References:

1) Patent Reference: WO2010038081, page 133, (33.8 MB)

2) Wikipedia: BOP reagent (link)

3) www.sigmaaldrich.com: (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (link)

4) www.alfa.com: A16140 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 98% (link)