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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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1 ML
$142.00
5 ML
$678.00
25 ML
$2,070.00

About This Item

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

$142.00

Available to ship onMay 01, 2025Details

Request a Bulk Order

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.)

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

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General description

2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) is a phosphazene base.[1] BEMP participates in the mild base catalyzed nucleophilic ring opening of N-sulfonyl aziridines.[1] BEMP supported on polystyrene (PS-BEMP) has been reported as an efficient catalyst for the ring-opening of epoxides with phenols.[2] BEMP is about 2000 times more basic and also much more sterically hindered than DBU (l,8-diazabicyclo[5.4.0]undecene).[3][4][5][6]

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.[2]
  • As catalyst in the alkylation reactions of carbon acids.[7]
  • As organocatalyst in the controlled "immortal" ring-opening polymerization (iROP) of six-membered cyclic carbonates.[8]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCF3020
BCCK6375
BCCF0252
BCBW9278

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