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Merck

92730

Trimethyl phosphite

≥97%, liquid

Synonym(s):

TMP, 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
NACRES:
NA.22
PubChem Substance ID:
329770160
UNSPSC Code:
12350000
MDL number:
MFCD00008350
Beilstein/REAXYS Number:
956570

Key Documents

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Product Name

Trimethyl phosphite, ≥97%

InChI

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

SMILES string

COP(OC)OC

InChI key

CYTQBVOFDCPGCX-UHFFFAOYSA-N

vapor density

4.3 (vs air)

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

Quality Level

200

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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.

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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

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

82.4 °F - closed cup

flash_point_c

28 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9504
BCCN7816
BCCN6777
BCCN0699
BCCM4081

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P-Arylation: Arynes to Aryl-Phosphonates,-Phosphinates, and-Phosphine Oxides.
Dhokale RA & Mhaske SB.
Organic Letters, 15(9), 2218-2221 (2013)
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)
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)
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)
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)
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