product data sheet: Triethyl phosphite (TEPI) issue A2 2006-06-21 page 1 of 4

TITLE:

Triethyl phosphite (TEPI)

TEXT: TEPI is a versatile reactive intermediate which exerts a phosphorylating, reducing, deoxygenating and desulfurising action.

Chemical name

Phosphonic acid triethylester, Triethyl phosphite (TEPI)

CAS Reg. No.

122-52-1
O C2H5 O O C2H5 C2H5

Structural formula

Empirical formula

C6H15O3P

Molecular weight

166.16 g/mol

Physical form

clear, colorless, low viscosity liquid with a very intensive and unpleasant smell

Health and safety information

Safety data and precautions which must be observed under all circumstances are to be found in EU Safety Data Sheet No. 006479. Hazard label: irritant

Specified Properties Property TEPI (triethyl phosphite) content DEPI (diethyl phosphite) content TEPO (triethyl phosphate) content Ethanol content Hazen (APHA) Nominal Value min. 99.0 max. 0.5 max. 0.2 max. 0.2 max. 25 Unit % by mass % by mass % by mass % by mass Test Method GC GC GC GC ISO 6271

The data given above are of informational character only. Therefore, please request the current valid specification.

product data sheet: Triethyl phosphite (TEPI) issue A2 2006-06-21 page 2 of 4

Additional Information Property Refractive index n20/D Density at 20 C Viscosity at 20 C Boiling temperature at 1013 mbar Flash point (closed up) Typical Value 1.408 0.96 0.7 158 > 52 Unit g/cm mPa . s C C EN 22 719 Test Method DIN 53 491 DIN 51 757 DIN 53 015

These raw material properties are typical properties and, unless specifically indicated otherwise, are not to be considered as delivery specification.

Solubility TEPI is soluble in inert organic solvents such as aliphatic and aromatic hydrocarbons and ethers.

Packaging 190 kg steel drum

Materials Metals such as stainless steel and ceramic apparatus components are ideal. Suitable materials for seals include poly(tetrafluoroethylene) (PTFE), glass-fiber reinforced PTFE and graphite.

Peculiarity The product is one that is subject to international export control measures. In accordance with the international "Responsible Care" initiative, Lanxess AG requires that a declaration of End Use is completed even where not explicitly stipulated by legislation.

Storage In tightly sealed original containers and under proper storage conditions, the product can be stored for at least 2 years without loss in quality.

product data sheet: Triethyl phosphite (TEPI) issue A2 2006-06-21 page 3 of 4

Use in organic synthesis

TEPI is a versatile, reactive intermediate which, in addition to its phosphorylating effect, has pronounced reducing properties. It is used in the manufacturing of flame retardents for rigid polyurethane foam, e.g. diethyl ethane phosphonate (DEEP),
C2H5O P C2H5O C2H5 O

fluorescent whitening agents such as 1,4-bis(o-cyanostyryl)benzene,

HC CN

HC

CH

CH NC

insecticides such as Chlorfenvinphos,

C2H5O P C2H5O Cl O C C H O Cl

Cl

and active ingredients for pharmaceuticals (penicillins, cephalosphorines)

Reaction examples 1. Preparation of vinyl phosphates (Perkow reaction)

R (C2H5O)3P C2H5O - C2H5Cl P C2H5O O O C R CHCl

C CHCl2

Chlorfenvinphos

product data sheet: Triethyl phosphite (TEPI) issue A2 2006-06-21 page 4 of 4

2. Preparation of phosphonates (Michaelis-Arbuzov)

C2H5O - C2H5Br C2H5O O P CH2 C O O C2H5

(C2H5O)3P + Br CH2 C O

C2H5

3. Preparation of olefins (Michaelis-Arbuzov / Horner-Emmons)

O Br Br C2H5O C2H5O

2 (C2H5O)3P - 2 C2H5Br

C2H5O C2H5O

P P O

CH3 2 O C CH(OC2H5)2
(C2H5O)2CH
CH(OC2H5)2

4. Reduction (and subsequent rearrangement) O R1 C HN

O

R1 (C2H5O)3P N S CH2 R2 O N CH R2 C CH3

This information and our technical advice - whether verbal, in writing or by way of trials - are given in good faith but without warranty, and this also applies where proprietary rights of third parties are involved. Our advice does not release you from the obligation to verify the information currently provided - especially that contained in our safety data and technical information sheets - and to test our products as to their suitability for the intended processes and uses. The application, use and processing of our products and the products manufactured by you on the basis of our technical advice are beyond our control and, therefore, entirely your own responsibility. Our products are sold in accordance with the current version of our General Conditions of Sale and Delivery. ____________________________________________________________________________________________ __ editor: Dr. Graupner-von Wolff LANXESS Deutschland GmbH, 51369 Leverkusen www.lanxess.de