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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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847552
EC Number:
208-144-8
Beilstein/REAXYS Number:
1071731
MDL number:
MFCD00008348
Assay:
97%
Form:
liquid

Key Documents

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InChI key

WVLBCYQITXONBZ-UHFFFAOYSA-N

InChI

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

SMILES string

COP(=O)(OC)OC

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

Quality Level

200

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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

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8178V
MKCZ6727
MKCZ6726
WXBF3947V
WXBF3386V

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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)
Miguel Machuqueiro et al.
Journal of inorganic biochemistry, 94(1-2), 193-196 (2003-03-07)
The methyl transfer from trimethyl phosphate to alkyl thiols was investigated in the presence of zinc ions and in the absence of strong base. The chelating thiol N-(2-mercaptoethyl)picolylamine (MEPAH) was methylated by trimethyl phosphate, in MeOH, in the presence of
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
Guilherme Menegon Arantes et al.
The journal of physical chemistry. A, 109(25), 5625-5635 (2006-07-13)
Phosphate esters are important compounds in living systems. Their biological reactions with alcohol and thiol nucleophiles are catalyzed by a large superfamily of phosphatase enzymes. However, very little is known about the intrinsic reactivity of these nucleophiles with phosphorus centers.
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