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20025

Sigma-Aldrich

2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine

purum, ≥98.0% (GC)

Synonym(s):

BEMP

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About This Item

Empirical Formula (Hill Notation):
C13H31N4P
CAS Number:
98015-45-3
Molecular Weight:
274.39
Beilstein:
5534901
MDL number:
MFCD00043143
UNSPSC Code:
12352005
PubChem Substance ID:
329751970
NACRES:
NA.22

grade

purum

Quality Level

200

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

Phosphazene Bases: a Family of Extremely Strong, Non-Ionic, Non-Charged Nitrogen–Bases
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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF3020
BCCK6375
BCCF0252
BCBW9278
1390279V

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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
Thomas A Moss et al.
Chemical communications (Cambridge, England), (21)(21), 2474-2476 (2008-05-21)
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.
Ke Wen et al.
The Journal of organic chemistry, 67(22), 7887-7889 (2002-10-26)
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
Tommaso Angelini et al.
Organic & biomolecular chemistry, 11(30), 5042-5046 (2013-06-28)
An efficient protocol for the hydrophosphonylation of aromatic and aliphatic aldehydes catalyzed by PS-BEMP under solvent-free conditions (SolFC) has been reported. Addition reactions were performed by using equimolar amounts of reagents and the resulting α-hydroxyphosphonates were isolated with simple workup
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.
Zvagulis A, et al.
Advanced Synthesis & Catalysis, 352(14-15), 2489-2496 (2010)
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