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240907

Sigma-Aldrich

Trimethyl phosphite

≥99%

Synonym(s):

Methyl phosphite, P(OMe)3, Trimethoxyphosphine

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About This Item

Linear Formula:
(CH3O)3P
CAS Number:
121-45-9
Molecular Weight:
124.08
Beilstein:
956570
EC Number:
204-471-5
MDL number:
MFCD00008350
UNSPSC Code:
12352108
PubChem Substance ID:
24854442
NACRES:
NA.22
Pricing and availability is not currently available.

vapor density

4.3 (vs air)

Quality Level

200

vapor pressure

17 mmHg ( 20 °C)

Assay

≥99%

form

liquid

reaction suitability

reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

refractive index

n20/D 1.408 (lit.)

bp

111-112 °C (lit.)

mp

−78 °C (lit.)

density

1.052 g/mL at 25 °C (lit.)

SMILES string

COP(OC)OC

InChI

1S/C3H9O3P/c1-4-7(5-2)6-3/h1-3H3

InChI key

CYTQBVOFDCPGCX-UHFFFAOYSA-N

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General description

Trimethyl phosphite is an organophosphorus compound commonly used as a polymerization catalyst, coating additive, and as an intermediate in the synthesis of flame retardants. In addition, it is also used as an activating reagent in amide formation.[1]

Application

Trimethyl phosphite can be used as a ligand in the synthesis of allyliridium phosphite complexes by direct reaction with allyliridium 1,5-cyclooctadiene complex.[2]

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

82.4 °F - closed cup

Flash Point(C)

28 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5684
BCCJ4640
BCCG9674
BCCG1632
BCCF7329

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An efficient protocol for the amidation of carboxylic acids promoted by trimethyl phosphite and iodine
Luo QL, et al.
European Journal of Organic Chemistry (2011)
Allyliridium phosphite complexes. Synthesis and chemistry
Muetterties EL, et al.
Organometallics, 1(12), 1562-1567 (1982)
Bangwei Ding et al.
Journal of the American Chemical Society, 125(11), 3248-3259 (2003-03-13)
Trimethyl phosphite, (MeO)(3)P, is introduced as an efficient and selective trap in oxiranylcarbinyl radical (2) systems, formed from haloepoxides 8-13 under thermal AIBN/n-Bu(3)SnH conditions at about 80 degrees C. Initially, the transformations of 8-13, in the absence of phosphite, to
D H Barton et al.
Bioorganic & medicinal chemistry, 2(4), 259-266 (1994-04-01)
In harmony with our studies on the activation of hydrocarbons by Gif chemistry, we have, in the first part of this paper, studied the mechanism of the lipoxygenase enzymes using soybean lipoxygenase as a model. We have shown with trimethyl
Shinichi Yamabe et al.
The journal of physical chemistry. A, 114(43), 11699-11707 (2010-10-15)
Density functional theory calculations of the title reaction, P(OCH₃)₃ + (H₂O)(n) in CH₃CN, were conducted, where n is the number of water molecules. Two routes, the routes suggested by (A) Aksnes and (B) Arbuzov, were traced with various n values.
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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