Trimethyl phosphate

Trimethyl phosphate Basic information
Product Name:Trimethyl phosphate
Synonyms:METHYL PHOSPHATE;PHOSPHORIC ACID TRIMETHYL ESTER;(CH3O)3PO;Methyl phosphate, (MeO)3PO;NCI-C03781;O,O,O-Trimethyl phosphate;o,o,o-trimethylphosphate;Trimethoxyphosphine oxide
CAS:512-56-1
MF:C3H9O4P
MW:140.07
EINECS:208-144-8
Product Categories:organophosphorus compound;Building Blocks;Flame retardants;Chemical Synthesis;Organic Building Blocks;Organic Phosphates/Phosphites;Organics;Functional Materials;Phosphates (Plasticizer);Plasticizer;Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds;Phosphorus Compounds;solvent;512-56-1
Mol File:512-56-1.mol
Trimethyl phosphate Structure
Trimethyl phosphate Chemical Properties
Melting point -46 °C (lit.)
Boiling point 197 °C (lit.)
density 1.197 g/mL at 25 °C (lit.)
vapor pressure 1.133 hPa (25 °C)
refractive index n20/D 1.395(lit.)
Fp 107 °C
storage temp. Store below +30°C.
solubility 1000g/l
form Liquid
color Clear
Specific Gravity1.197
Water Solubility 500 G/L (25 ºC)
Sensitive Moisture Sensitive
BRN 1071731
InChIKeyWVLBCYQITXONBZ-UHFFFAOYSA-N
LogP-0.46 at 25℃
CAS DataBase Reference512-56-1(CAS DataBase Reference)
NIST Chemistry ReferencePhosphoric acid, trimethyl ester(512-56-1)
EPA Substance Registry SystemTrimethyl phosphate (512-56-1)
Safety Information
Hazard Codes T,Xn,Xi
Risk Statements 46-22-40-68-45-20/21/22-38-36
Safety Statements 53-36/37-45-36/37/39-26
RIDADR 2810
WGK Germany 1
RTECS TC8225000
21
Hazard Note Toxic/Moisture Sensitive
TSCA Yes
HS Code 2919 90 00
Hazardous Substances Data512-56-1(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 840 mg/kg LD50 dermal Rabbit 3388 mg/kg
MSDS Information
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SigmaAldrich English
ALFA English
Trimethyl phosphate Usage And Synthesis
Chemical PropertiesTrimethyl phosphate (TMP), the simplest trialkyl ester of phosphoric acid, It is a colourless, nonvolatile liquid. soluble in most organic solvents, low solubility in water. TMP is stable in neutral, acidic or alkaline solutions, and is classified as "not readily biodegradable". Direct photodegradation is not expected because trimethyl phosphate does not absorb UV light.
UsesTrimethyl phosphate is used as an intermediate in organic synthesis. Its industrial applications are much fewer than those of other organic phosphates.Trimethyl phosphate undergoes hydrolysis in contact with water, so it should be stored in a moisture-proof manner. Due to its hydrolysis and release of PO43-, thus becoming a homogeneous precipitant for the formation of insoluble phosphate precipitation, often used as a precipitation reagent for zirconium and hafnium and as a diffusion source for the determination of semiconductors. In addition, trimethyl phosphate is also a phospholipid extractant for the extraction and separation of certain metal ions.
UsesTrimethyl Phosphate is used as an electrolyte additive in the synthesis of lithium ion batteries. for controlling spark plug fouling, surface ignition and rumble in gasoline engines.
Trimethyl phosphate used as a reagent for determination of zirconium, solvent, extractant and gas chromatography stationary phase.
DefinitionChEBI: Trimethyl phosphate is a trialkyl phosphate that is the trimethyl ester of phosphoric acid. It has a role as an insect attractant.
Production MethodsTrimethyl phosphate is prepared by treating phosphorus oxychloride with methanol in the presence of an amine base:
POCl3 + 3 CH3OH + 3 R3N → PO(OCH3)3 + 3 R3NH+Cl
It is a tetrahedral molecule that is a weakly polar solvent.
Synthesis Reference(s)The Journal of Organic Chemistry, 39, p. 3178, 1974 DOI: 10.1021/jo00935a041
Tetrahedron Letters, 28, p. 2981, 1987 DOI: 10.1016/S0040-4039(00)96262-2
General DescriptionTrimethyl phosphate appears as a pale straw colored liquid. Inhalation may irritate respiratory tract. Vapor or liquid may irritate skin or eyes. Ingestion may irritate the mucous membranes of the gastrointestinal tract.
Reactivity ProfileTRIMETHYL PHOSPHATE may explode when heated. Residue from a large scale atmospheric pressure distillation of Trimethyl phosphate has exploded violently. Trimethyl phosphate is incompatible with nitrates. . Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
HazardToxic by ingestion and inhalation, strong irritant to skin and eyes. trimethyl phosphate (TMP) is absorbed rapidly and completely by inhalation of its vapour, through the skin and by ingestion (WHO).
Health HazardTrimethyl phosphate (TMP) is a mutagen, teratogen, and a cancercausing compound. The health hazard from this compound is somewhat different from those of the higher members of the organic phosphate series. While carcinogenicity is observed only for this phosphate, with mutagenicity and the teratogenic effects being more marked, higher alkyl phosphates are more neurotoxic but noncarcinogenic.
TMP is toxic at high dosages.LD50 value,oral(mice):1470 mg/kg(NIOSH 1986)
Laboratory tests on animals indicated clear evidence of its cancer-causing actions, producing uterine and skin tumors. There is so far no report on such carcinogenic actions in humans. The compound tested positive in mutagenic tests and caused fetal deaths and birth defects in mice, rats, and hamsters when given orally or intraperitoneally.
Fire HazardTrimethyl phosphate is nonflammable.
Flammability and ExplosibilityNotclassified
Industrial uses1 Gasoline additive at 0.25 g/gal for controlling surface ignition and spark plug fouling.
2 Methylating agent, chemical intermediate in the production of polymethyl polyphosphates.
3 Flame retardant solvent for paints and polymers.
4 Catalyst in the preparation of polymers and resins.


Safety ProfileSuspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Moderately toxic by ingestion, skin contact, intraperitoneal, and intravenous routes. Experimental reproductive effects. Human mutation data reported. Explodes when heat distilled. When heated to decomposition it emits toxic fumes of POx. See also ESTERS.
MetabolismA system utilizing isolated anterior forearm stratum corneum conjunctum of man to study skin penetrating capacity of a series of organic phosphates was developed. Trimethyl phosphate was tested in the system and had the greatest skin-penetrating capacity of the 8 related compounds tested (Marzulli et al 1965).
Rats treated orally at 100 mg/kg and mice treated i.p. at 1000 mg/kg with [32]P-labeled trimethyl phosphate excreted primarily dimethyl phosphate in the urine. Only traces of the parent compound were detected, and only in the rats at less than 6 h after treatment. S-Methyl cysteine and S-methyl cysteine N-acetate were also isolated. Small amounts of S-methyl glutathione were detected, presumably the initial methylation product in this series of metabolites (Jones 1970). Metabolism of trimethyl phosphate was faster in the mouse than in the rat, but there was no evidence of further conversion to monomethyl phosphate or inorganic phosphate in either species (Jackson and Jones 1968).
Purification MethodsPurify the phosphate by fractionation through an efficient column at high reflux ratio. It is quite soluble in H2O; the solubility is 1:1 at 25o. [Becker J Am Chem Soc 74 2923 1952, IR: Bergmann et al. J Chem Soc 847 1952, McIvor et al. Can J Chem 36 820 1958, Kosolapoff Organophosphorus Compounds, Wiley p 258 1950, and Cherbuliez in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973, Beilstein 1 IV 1259.]
Waste DisposalTMP is mixed with a combustible solvent and destroyed by burning in a chemical incinerator.
Trimethyl orthoacetate Pralmorelin Trimethyl borate Tylosin phosphate Triethyl phosphate AMPHISOL A Diphenolic acid 4-(Diethylamino)salicylaldehyde ROCK PHOSPHATE Trisodium phosphate Trimethoxymethane ADENOSINE 5'-TRIPHOSPHATASE Sodium Phosphate Monobasic Monohydrate 5-Chlorovaleric acid Trimethyl phosphite phosphate Thymidine-5'-monophosphate disodium salt TRIMETHYL CITRATE

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