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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

20025-25ML:
20025-5ML:
20025-BULK:
20025-1ML:
20025-INTR:
20025-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF3020
BCCF0252
BCBW9278
1390279V
1387061V

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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)
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
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.
M.J. O'Donnell et al.
Tetrahedron Letters, 39, 8775-8775 (1998)
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