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Merck

240907

Trimethyl phosphite

≥99%, liquid

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
NACRES:
NA.22
PubChem Substance ID:
24854442
UNSPSC Code:
12352108
EC Number:
204-471-5
MDL number:
MFCD00008350
Beilstein/REAXYS Number:
956570

Key Documents

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Product Name

Trimethyl phosphite, ≥99%

InChI key

CYTQBVOFDCPGCX-UHFFFAOYSA-N

InChI

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

SMILES string

COP(OC)OC

vapor density

4.3 (vs air)

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.)

Quality Level

200

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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.

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - 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
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)
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.
M A Mehlman et al.
Toxicology and applied pharmacology, 72(1), 119-123 (1984-01-01)
Trimethyl phosphite (TMP) is an organophosphorus alkylating agent used primarily in the synthesis of organophosphate compounds. To evaluate teratogenic potential, TMP was administered by gavage to pregnant rats at rates of 16, 49, or 164 mg/kg/day, on gestation Days 6
D Vaughan Griffiths et al.
Organic & biomolecular chemistry, 6(3), 577-585 (2008-01-26)
Dialkyl heteroaroylphosphonates based on thiophene, pyrrole or furan have been prepared and their reactions with trimethyl phosphite investigated. Deoxygenation of the carbonyl groups in these heteroaroylphosphonates occurs to give carbene intermediates, which then undergo further reaction. In the case of
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