Trichlorfon

Base Information

• Chemical Name: Trichlorfon
• CAS No.: 52-68-6
• Deprecated CAS: 37333-09-8,50924-44-2,66758-31-4,56042-25-2,56042-25-2,66758-31-4
• Molecular Formula: C4H8Cl3O4P
• Molecular Weight: 257.438
• Hs Code.: 29319090
• European Community (EC) Number: 200-149-3
• ICSC Number: 0585
• NSC Number: 759241,8923
• UN Number: 2783
• UNII: 1MVY4KU98F,DBF2DG4G2K,37VCQ9C0OG
• DSSTox Substance ID: DTXSID0021389
• Nikkaji Number: J2.309D
• Wikipedia: Metrifonate
• Wikidata: Q422991
• NCI Thesaurus Code: C84225
• Metabolomics Workbench ID: 53295
• ChEMBL ID: CHEMBL167150
• Mol file: 52-68-6.mol

Synonyms:Bilarcil;Chlorofos;Chlorophos;Dipterex;Dylox;Foschlor;Metrifonate;Metriphonate;Neguvon;Ricifon;Trichlorfon;Trichlorphon

Chemical Property of Trichlorfon

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 0.00097mmHg at 25°C
• Melting Point: 77-81 °C
• Refractive Index: 1.3439
• Boiling Point: 269.3 °C at 760 mmHg
• PKA: 6 (est.)
• Flash Point: 116.7 °C
• PSA: 65.57000
• Density: 1.574 g/cm³
• LogP: 2.16090
• Storage Temp.: 2-8°C
• Solubility.: Freely soluble in water, very soluble in methylene chloride, freely soluble in acetone and in ethanol (96 per cent).
• Water Solubility.: Slightly soluble. 1-5 g/100 mL at 21 ºC
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 255.922579
• Heavy Atom Count: 12
• Complexity: 183
• Transport DOT Label: Poison

Purity/Quality:

98%TC 80%WP 80%SP ^*data from raw suppliers

Trichlorfon ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn,N
• Statements: 22-43-50/53
• Safety Statements: 24-37-60-61-2

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: COP(=O)(C(C(Cl)(Cl)Cl)O)OC
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system by a cholinesterase inhibiting effect. This may result in convulsions, respiratory failure and death. Cholinesterase inhibition. Exposure at high levels could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the nervous system. Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.
• Indications: For the treatment of Schistosoma haematobium infections. During mass treatment programmes, when cost is a major factor, metrifonate may be preferred over praziquantel. When radical treatment is desired and cost is not a problem, praziquantel is the first drug of choice, i.e. in places where re-infection is not expected. Metrifonate is an organophosphorous compound that is effective only in the treatment of S. haematobium. The active metabolite, dichlorvos, inactivates acetylcholinesterase and potentiates inhibitory cholinergic effects. The schistosomes are swept away from the bladder to the lungs and are trapped. Therapeutic doses produce no untoward side effects except for mild cholinergic symptoms. It is contraindicated in pregnancy, previous insecticide exposure, or with depolarizing neuromuscular blockers. Metrifonate is not available in the United States.
• Description: Trichlorfon is a colorless crystalline powder. It is soluble in water (120 g/L) and most organic solvents, except aliphatic hydrocarbons. Log Kow = 0.43. Trichlorfon is rapidly converted to dichlorvos by alkalis (2) and then hydrolyzed; DT50 (22 ?C) values at pH 4, 7, and 9 are 510 d, 46 h, and <30 min, respectively.
• Uses: Insecticide used to control ?ies and roaches. One of the biologically active forms of nicotinic acid. Differs from NAD by an additional phosphate group at the 2?position of the adenosine moiety. Serves as a coenzyme of hydrogenases and dehydrogenases. Present in living cells primarily in the r anticholinergic, urinary incontenance therapy Trichlorfon is an irreversible organophosophate acetylcholinesterase inhibitor and the prodrug of Dichlorvos (D435950). Trichlorfon have also shown potential actions to be utilized as an effective org anophosphorus pesticide. Trichlorfon is used to control a wide range of insects in many crops and to control household pests, flies in animal houses and ectoparasites in domestic animals.
• Clinical Use: Urinary schistosomiasis (especially mass chemotherapy control programs)

Technology Process of Trichlorfon

There total 8 articles about Trichlorfon which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

chloral hydrate (302-17-0) + phosphorous acid trimethyl ester (121-45-9) → Dichlorvos (62-73-7) + trichlorfon (52-68-6,66758-31-4) + dichlorovinylmethyl phosphoric acid (13445-62-0)

Guidance literature:

In hexane; for 10h; Heating;

Reference yield:

chloral hydrate (302-17-0) + phosphorous acid trimethyl ester (121-45-9) → Dichlorvos (62-73-7) + trichlorfon (52-68-6,66758-31-4)

Guidance literature:

In hexane; for 1h; Product distribution; Mechanism;

Reference yield:

chloral (75-87-6) + Dimethyl phosphite (868-85-9) → trichlorfon (52-68-6,66758-31-4)

Guidance literature:

With aluminum oxide; potassium fluoride; at 20 ℃; for 0.5h;

DOI:10.1080/10426500600614253

upstream raw materials:

methyl phosphite

chloral

diazomethane

(2,2,2-trichloro-1-hydroxy-ethyl)-phosphonic acid monomethyl ester

Downstream raw materials:

Dichlorvos

(1-Acetoxy-2,2,2-trichlor-aethyl)-phosphonsaeure-dimethylester

(1-butyryloxy-2,2,2-trichloro-ethyl)-phosphonic acid dimethyl ester

O,O-dimethyl 1-(3-chloro-4-fluorophenoxyacetoxy)-2,2,2-trichloroethylphosphonate

Refernces

• 1、 Barthel et al.. "-". . p. 4186. Retrieved 1954.
• 2、 -. "RESIST UNDERLAYER FILM-FORMING COMPOSITION, PRODUCTION METHOD OF SEMICONDUCTOR DEVICE USING THE SAME, AND ADDITIVE FOR RESIST UNDERLAYER FILM-FORMING COMPOSITION". . . Retrieved 2010/08/22.
• 3、 Wang, Tao,Lei, Da You,Huang, Ying,Ao, Li Hua. "Synthesis and biological activity of O,O-Dimethyl-2,6-Pyridinyl diformyloxy alkyl phosphonates". scheme or table. p. 2777 - 2785. Retrieved 2010/04/03.