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Trimethyl phosphate

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Name

Trimethyl phosphate

EINECS 208-144-8
CAS No. 512-56-1 Density 1.154 g/cm3
PSA 54.57000 LogP 1.03370
Solubility 500 G/L (25 ºC) Melting Point -46 °C
Formula C3H9O4P Boiling Point 197.2 °C at 760 mmHg
Molecular Weight 140.076 Flash Point 83.7 °C
Transport Information UN 2810 Appearance clear liquid
Safety 53-36/37-45-36/37/39 Risk Codes 46-40-68-45-20/21/22
Molecular Structure Molecular Structure of 512-56-1 (Trimethyl phosphate) Hazard Symbols HarmfulXn,ToxicT
Synonyms

Methylphosphate, (MeO)3PO (6CI);Trimethoxyphosphineoxide;Trimethyl orthophosphate;Trimethylphosphoric acid;

Article Data 152

Trimethyl phosphate Synthetic route

67-56-1

methanol

512-56-1

trimethyl phosphite

Conditions
ConditionsYield
With sodium hypophosphite; copper dichloride at 24.9℃; for 173h;100%
With phosphorous; phosphoric acid tributyl ester; oxygen; copper dichloride In benzene at 30℃;98.2%
With trichlorophosphate In acetone at 10 - 30℃; under 10 Torr; for 4h;97.5%
121-45-9

phosphorous acid trimethyl ester

512-56-1

trimethyl phosphite

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -95℃;100%
With dihydrogen peroxide In pyridine at -20℃; adding different FeIII compounds; determination of half-lives of reactions;
With naphthalene-1,4-dicarbonitrile; water In water; acetonitrile Irradiation;
121-45-9

phosphorous acid trimethyl ester

A

512-56-1

trimethyl phosphite

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -50℃;A 7%
B 93%
122203-30-9

dimethyl (Z)-α-methoxyiminobenzylphosphonate

A

512-56-1

trimethyl phosphite

B

100-47-0

benzonitrile

Conditions
ConditionsYield
at 140℃; for 0.5h; Product distribution; reflux in 1,2,4-trimethylbenzene, 72 h;A 85%
B 92%
67-56-1

methanol

7357-14-4

p-methoxyphenyl dimethyl phosphate

A

512-56-1

trimethyl phosphite

B

150-76-5

4-methoxy-phenol

Conditions
ConditionsYield
With cesium fluoride at 65℃; for 22h;A 79%
B 88%
67-56-1

methanol

74532-26-6, 74532-27-7

1-decenyl dimethyl phosphate

A

512-56-1

trimethyl phosphite

B

112-31-2

caprinaldehyde

Conditions
ConditionsYield
With cesium fluoride at 65℃; for 22h;A 67%
B 88%
7357-14-4

p-methoxyphenyl dimethyl phosphate

A

512-56-1

trimethyl phosphite

B

150-76-5

4-methoxy-phenol

Conditions
ConditionsYield
With methanol; cesium fluoride at 65℃; for 22h;A 79%
B 88%
74532-26-6, 74532-27-7

1-decenyl dimethyl phosphate

A

512-56-1

trimethyl phosphite

B

112-31-2

caprinaldehyde

Conditions
ConditionsYield
With methanol; cesium fluoride at 65℃; for 22h;A 67%
B 88%
67-56-1

methanol

A

512-56-1

trimethyl phosphite

B

812-00-0

methylphosphate

C

813-78-5

dimethylphosphoric acid

Conditions
ConditionsYield
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis;A 82%
B n/a
C n/a
67-56-1

methanol

10113-28-7

dimethyl phenyl phosphate

A

512-56-1

trimethyl phosphite

B

108-95-2

phenol

Conditions
ConditionsYield
With cesium fluoride at 65℃; for 4h;A 80%
B 65%

Trimethyl phosphate Consensus Reports

 

.

Trimethyl phosphate Specification

The IUPAC name of this chemical is Trimethyl phosphate. With the CAS registry number 512-56-1 and EINECS registry number 208-144-8, it is also named as Phosphoric acid,trimethyl ester. In addition, the molecular formula is C3H9O4P and the molecular weight is 140.07. It is a kind of clear liquid and belongs to the classes of Organics; Functional Materials; Phosphates (Plasticizer); Plasticizer; Organic Building Blocks; Organic Phosphates/Phosphites; Phosphorus Compounds.

Physical properties about this chemical are: (1)ACD/LogP: -0.52; (2)ACD/LogD (pH 5.5): -0.52; (3)ACD/LogD (pH 7.4): -0.52; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 12.46; (7)ACD/KOC (pH 7.4): 12.46; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 54.57 Å2; (11)Index of Refraction: 1.379; (12)Molar Refractivity: 28.05 cm3; (13)Molar Volume: 121.2 cm3; (14)Polarizability: 11.12 ×10-24cm3; (15)Surface Tension: 29.4 dyne/cm; (16)Density: 1.154 g/cm3; (17)Flash Point: 83.7 °C; (18)Enthalpy of Vaporization: 41.57 kJ/mol; (19)Boiling Point: 197.2 °C at 760 mmHg; (20)Vapour Pressure: 0.539 mmHg at 25°C.

Preparation of Trimethyl phosphate: it can be prepared by methanol and trichlorooxyphosphorus in the presence of potassium carbonate. Add methanol and potassium carbonate into reactor at reaction temperature of 5 °C. Then add trichlorooxyphosphorus into the mixture in 2 hours with stirring. The temperature should be controlled below 30 °C. Then add dimethyl sulfate and reflux for 3 hours. At last, you can go through the operation of cooling, filtering by carbon tetrachloride, vacuum distillation and drying to get the products.

Trimethyl phosphate can be prepared by methanol and trichlorooxyphosphorus in the presence of potassium carbonate

Uses of Trimethyl phosphate: this chemical is a mild methylating agent, useful for preparing dimethylation of anilines and related heterocyclic compounds.And it is mianly used as solvent and extractant for medicine and pesticide. Also it can be used as a color inhibitor for fibers, flame retardants and plasticizer. In addition, it can react with pyridine to get 1-methyl-pyridinium; dimethyl phosphate. The reaction time is 5 hours by heating. The yield is about 92%.

Trimethyl phosphate can react with pyridine to get 1-methyl-pyridinium; dimethyl phosphate

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. And it may cause heritable genetic damage and cancer. In addition, it has risk of irreversible effects Possibly. There is limited evidence of a carcinogenic effect. Avoid exposure - obtain special instruction before use. During using it, wear suitable protective clothing, gloves and eye/face protection. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OC)(OC)OC
(2)InChI: InChI=1/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3
(3)InChIKey: WVLBCYQITXONBZ-UHFFFAOYAV

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 1676mg/kg (1676mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1129, 1986.
mouse LD50 intraperitoneal 2250mg/kg (2250mg/kg)   Therapie. Vol. 15, Pg. 237, 1960.
mouse LD50 oral 1470mg/kg (1470mg/kg)   Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
mouse LD50 unreported 540mg/kg (540mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Gigiena Naselennykh Mest. Hygiene in Populated Places. Vol. 17, Pg. 37, 1978.
quail LD50 oral 750mg/kg (750mg/kg)   Journal of Reproduction and Fertility. Vol. 48, Pg. 371, 1976.
rabbit LD50 oral 1275mg/kg (1275mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 338, 1946.
rabbit LD50 skin 2830uL/kg (2.83mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat LD50 oral 840mg/kg (840mg/kg)   Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
rat LD50 unreported 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Gigiena Naselennykh Mest. Hygiene in Populated Places. Vol. 17, Pg. 37, 1978.
rat LDLo intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: OTHER CHANGES
Journal of Pharmacy and Pharmacology. Vol. 11, Pg. 150, 1959.
rat LDLo intravenous 2400mg/kg (2400mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Nature. Vol. 179, Pg. 154, 1957.

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