Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

20025

Sigma-Aldrich

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

purum, ≥98.0% (GC)

Synonym(s):

BEMP

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCF3020
BCCK6375
BCCF0252
BCBW9278
1390279V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

M.J. O'Donnell et al.
Tetrahedron Letters, 39, 8775-8775 (1998)
Sambasivarao Kotha et al.
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
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
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)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service