20025
2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine
purum, ≥98.0% (GC)
Sinónimos:
BEMP
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About This Item
Fórmula empírica (notación de Hill):
C13H31N4P
Número de CAS:
Peso molecular:
274.39
Beilstein/REAXYS Number:
5534901
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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grade
purum
Quality Level
assay
≥98.0% (GC)
form
liquid
refractive index
n20/D 1.477 (lit.)
n20/D 1.477
bp
74 °C/0.03 mmHg (lit.)
density
0.948 g/mL at 25 °C (lit.)
SMILES string
CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C
InChI
1S/C13H31N4P/c1-8-17(9-2)18(14-13(3,4)5)15(6)11-10-12-16(18)7/h8-12H2,1-7H3
InChI key
VSCBATMPTLKTOV-UHFFFAOYSA-N
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General description
2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) is a phosphazene base. BEMP participates in the mild base catalyzed nucleophilic ring opening of N-sulfonyl aziridines. BEMP supported on polystyrene (PS-BEMP) has been reported as an efficient catalyst for the ring-opening of epoxides with phenols. BEMP is about 2000 times more basic and also much more sterically hindered than DBU (l,8-diazabicyclo[5.4.0]undecene).
Application
2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP), a organic phosphorine base may be used in the following studies:
- Synthesis of a 2,3-dihydrobenzo[1,4]dioxepin-5-one.
- As catalyst in the alkylation reactions of carbon acids.
- As organocatalyst in the controlled "immortal" ring-opening polymerization (iROP) of six-membered cyclic carbonates.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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N-Mesitylene sulfonyl and N-tosyl aziridines have been identified as effective electrophiles in alkylation reactions of carbon acids catalyzed by the organic phosphorine base BEMP; yields of up to 99% for a range of pro-nucleophiles under mild reaction conditions are reported.
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A short and efficient synthesis of 2'-O-methoxyethylguanosine (8) is described. Central to this strategy is the development of a novel silicon-based protecting group (MDPSCl(2), 2) used to protect the 3',5'-hydroxyl groups of the ribose. Silylation of guanosine with 2 proceeded
2-tert-Butylimino-2-diethylamino-1, 3-dimethylperhydro-1, 3, 2-diazaphosphorine Supported on Polystyrene (PS-BEMP) as an Efficient Recoverable and Reusable Catalyst for the Phenolysis of Epoxides under Solvent-Free Conditions.
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Advanced Synthesis & Catalysis, 352(14-15), 2489-2496 (2010)
Marion Helou et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(46), 13805-13813 (2010-10-15)
Six-membered cyclic carbonates, namely trimethylene carbonate (TMC), 3,3-dimethoxytrimethylene carbonate (DMTMC) and 3-benzyloxytrimethylene carbonate (BTMC), undergo controlled "immortal" ring-opening polymerization (iROP) under mild conditions (bulk, 60-150 °C), by using organocatalysts, including an amine [4-N,N-dimethylaminopyridine (DMAP)], a guanidine [1,5,7-triazabicyclo-[4.4.0]dec-5-ene (TBD)], or a
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Bioorganic & medicinal chemistry letters, 12(7), 1113-1115 (2002-03-23)
First synthesis of a macrocylic cyclophane-based unusual alpha-amino acid derivative 11 by coupling of ethyl isocyanoacetate with 1,2-bis(4-bromomethylphenyl)ethane under phase-transfer catalysis (PTC) conditions. Phosphazene base such as 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) is useful to improve the yield of cyclophane derivative without high
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