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Merck
CN

132195

Trimethyl phosphate

97%

Synonym(s):

TMP, TMPA, TMPO

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About This Item

Linear Formula:
(CH3O)3PO
CAS Number:
512-56-1
Molecular Weight:
140.07
Beilstein:
1071731
EC Number:
208-144-8
MDL number:
MFCD00008348
UNSPSC Code:
12352100
PubChem Substance ID:
24847552
NACRES:
NA.22

Key Documents

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Quality Level

200

Assay

97%

form

liquid

refractive index

n20/D 1.395 (lit.)

bp

197 °C (lit.)

mp

−46 °C (lit.)

density

1.197 g/mL at 25 °C (lit.)

functional group

phosphate

SMILES string

COP(=O)(OC)OC

InChI

1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3

InChI key

WVLBCYQITXONBZ-UHFFFAOYSA-N

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General description

Trimethyl phosphate is an excellent dipolar aprotic solvent that is used as a methylating agent and acid scavenger in many organic transformations.

Application

Trimethyl phosphate can be used as a methylating agent for the:
  • Solvent-free o-methylation of phenolic compounds to synthesize methyl aryl ethers.
  • S-methylation of aryl/alkyl thiols to synthesize S-methylated product in the presence of Ca(OH)2 as a base.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H319,H340,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Muta. 1B - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

302.0 °F - closed cup

Flash Point(C)

150 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6727
MKCZ6726
WXBF3947V
WXBF3386V
MKCS5368

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Hydrolysis of acetyl dimethyl phosphate, a reactive acyl phosphate.
R Kluger et al.
Biochemistry, 11(8), 1544-1546 (1972-04-11)
Yongqing Ma et al.
Analytica chimica acta, 786, 47-53 (2013-06-26)
An analytical method for the determination of 14 organophosphorus flame retardants (OPFRs), including halogenated OPFRs, non-halogenated OPFRs and triphenyl phosphine oxide (TPPO) in biological samples was developed using gas chromatography-mass spectrometry (GC/MS). Biological samples were extracted using microwave-assisted extraction (MAE)
R V Banerjee et al.
Biochemistry, 27(25), 9062-9070 (1988-12-13)
The transfer of 17O and/or 18O from (COOH-17O or -18O) enriched substrates to inorganic phosphate (Pi) has been demonstrated for two enzyme-catalyzed reactions involved in folate biosynthesis and glutamylation. COOH-18O-labeled folate, methotrexate, and dihydropteroate, in addition to [17O]-glutamate, were synthesized
U Schaeppi et al.
Neurobehavioral toxicology and teratology, 6(1), 39-50 (1984-01-01)
Five beagle dogs were treated daily with 1 ml of trimethylphosphate (TMP) for 1 to 4 months. Neurotoxicity was evaluated by observation of behaviour, neurologic examination, neurophysiologic tests and by neuropathology. Neurotoxicity was first detected at the neurologic examination following
Chunhai Ruan et al.
Journal of the American Society for Mass Spectrometry, 19(2), 305-314 (2008-04-15)
Threshold collision-induced dissociation techniques are employed to determine the bond dissociation energies (BDEs) of complexes of alkali metal cations to trimethyl phosphate, TMP. Endothermic loss of the intact TMP ligand is the only dissociation pathway observed for all complexes. Theoretical
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