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92730

Sigma-Aldrich

Trimethyl phosphite

≥97%

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Synonym(s):
TMP, Methyl phosphite, P(OMe)3, Trimethoxyphosphine
Linear Formula:
(CH3O)3P
CAS Number:
121-45-9
Molecular Weight:
124.08
Beilstein:
956570
MDL number:
MFCD00008350
UNSPSC Code:
12350000
PubChem Substance ID:
329770160
NACRES:
NA.22

vapor density

4.3 (vs air)

Quality Level

200

vapor pressure

17 mmHg ( 20 °C)

Assay

≥97%

form

liquid

refractive index

n20/D 1.408 (lit.)
n20/D 1.408

bp

111-112 °C (lit.)

mp

−78 °C (lit.)

density

1.052 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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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Application

Trimethyl phosphite is an organophosphorus ester with flame retardant property. It is generally used as a ligand to form coordinate complexes with transition metals.
Some of its other applications include:
  • For N-alkylation of amino-9,10-anthraquinones in imidazolium-based ionic liquids without the use of base and highly polar organic solvents.
  • To synthesize dimethyl phenylphosphonate by reacting with phenyl radical generated by the thermal decomposition of phenylazotriphenylmethane (PAT).
  • To synthesize aryl phosphonates via P-arylation reaction with silyl triflates.

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 3 - Muta. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

WGK

WGK 1

Flash Point(F)

82.4 °F

Flash Point(C)

28 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Free-radical chemistry of organophosphorus compounds. I. Reactions of phenyl radicals from phenylazotriphenylmethane with trimethyl phosphite.
Fu JJL & Bentrude WG.
Journal of the American Chemical Society, 94(22), 7710-7717 (1972)
Ionic liquids as novel and recyclable reaction media for N-alkylation of amino-9, 10-anthraquinones by trialkyl phosphites.
Yavari I & Kowsari E.
Tetrahedron Letters, 48(21), 3753-3756 (2007)
P-Arylation: Arynes to Aryl-Phosphonates,-Phosphinates, and-Phosphine Oxides.
Dhokale RA & Mhaske SB.
Organic Letters, 15(9), 2218-2221 (2013)
The chemistry of cyclopentadienyl-ruthenium and-osmium complexes. 1. The preparation and substitution reactions of (. eta. 4-cycloocta-1, 5-diene)(. eta. 5-cyclopentadienyl) haloruthenium (II) complexes. Versatile new synthetic precursors to open-face cyclopentadienylruthenium (II) chemistry.
Albers MO, et al.
Organometallics, 5(11), 2199-2205 (1986)
Comparative study of trimethyl phosphite and trimethyl phosphate as electrolyte additives in lithium ion batteries.
Yao XL, et al.
Journal of Power Sources, 144(1), 170-175 (2005)
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