Skip to Content
Merck
All Photos(1)

Key Documents

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


About This Item

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

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.)

functional group

amine

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

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

Signal Word

Danger

Hazard Statements

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

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.

Already Own This Product?

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

Visit the Document Library

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
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
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.
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

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