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132195

Sigma-Aldrich

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

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

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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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)
H Tezuka et al.
Mutation research, 157(2-3), 205-213 (1985-08-01)
Dominant lethal and heritable translocation studies were performed in male mice receiving a single intraperitoneal injection of trimethyl phosphate (TMP). The germ cell stage investigated was the spermatid. Methyl methanesulfonate (MMS) was used as a positive control in the latter
Antifertility activity of trimethylphosphate in male rats.
P J Hanna et al.
Experientia, 37(9), 999-1001 (1981-01-01)
K Aflatooni et al.
The Journal of chemical physics, 125(5), 054301-054301 (2006-09-01)
Total cross sections for the dissociative electron attachment process are presented for the DNA bases thymine, cytosine, and adenine and for three compounds used as surrogates for the ribose and phosphate groups, tetrahydrofuran, 3-hydroxytetrahydrofuran, and trimethylphosphate, respectively. Cross section magnitudes
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