60010-51-7

Basic information

• Product Name: 2,2,2-TRICHLOROETHYL PHOSPHORODICHLORIDITE
• Synonyms: 2,2,2-TRICHLOROETHYL DICHLOROPHOSPHITE;2,2,2-TRICHLOROETHYL PHOSPHORODICHLORIDITE;Phosphorodichloridous acid, 2,2,2-trichloroethyl ester;Dichloridophosphorous acid 2,2,2-trichloroethyl ester;Einecs 262-021-3
• CAS NO: 60010-51-7
• Molecular Formula: C₂H₂Cl₅OP
• Molecular Weight: 250.28
• EINECS: 262-021-3
• Mol File: 60010-51-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 42 °C/0.1 mmHg(lit.)
• Flash Point: 87.6°C
• Appearance: /
• Density: 1.606 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0298mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• CAS DataBase Reference: 2,2,2-TRICHLOROETHYL PHOSPHORODICHLORIDITE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRICHLOROETHYL PHOSPHORODICHLORIDITE(60010-51-7)
• EPA Substance Registry System: 2,2,2-TRICHLOROETHYL PHOSPHORODICHLORIDITE(60010-51-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: 1760
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 60010-51-7(Hazardous Substances Data)

Usage

Description

2,2,2-Trichloroethyl phosphorodichloridite is a chemical compound characterized by its phosphorus atom bonded to two chlorine atoms and one oxygen atom, along with a trichloroethyl group. It is a highly reactive phosphorodichloridite used in the synthesis of various phosphorus-containing compounds, including organophosphates, which are extensively utilized as pesticides in agriculture.

Uses

Used in Agricultural Chemicals Production:
2,2,2-Trichloroethyl phosphorodichloridite is used as a key intermediate in the production of insecticides and herbicides for agricultural applications. Its reactivity allows for the synthesis of organophosphates, which are effective in controlling pests and weeds, thereby enhancing crop yields and protecting plants from damage.
Used in Synthesis of Phosphorus-Containing Compounds:
In the chemical industry, 2,2,2-trichloroethyl phosphorodichloridite is used as a versatile building block for the synthesis of other phosphorus-containing compounds. Its unique structure enables the creation of a wide range of organophosphorus compounds with diverse applications, such as flame retardants, plasticizers, and pharmaceuticals.
Used in Pesticide Formulation:
2,2,2-Trichloroethyl phosphorodichloridite is used as a precursor in the formulation of various pesticides. Its reactivity allows for the development of new and improved pesticides with enhanced efficacy and selectivity, contributing to more sustainable and efficient agricultural practices.
Safety Considerations:
Due to its high reactivity and potential health hazards, 2,2,2-trichloroethyl phosphorodichloridite must be handled with extreme care. Strict safety protocols, including proper personal protective equipment, containment measures, and emergency response plans, should be followed to minimize the risk of exposure and ensure the safe use of this chemical compound in various applications.

InChI:InChI=1/C2H2Cl5OP/c3-2(4,5)1-8-9(6)7/h1H2

Upstream product

• 115-20-8 1,1,1-trichloroethanol 
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Downstream Products

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• 96016-69-2 Phosphorochloridous acid 2,2,2-trichloro-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 77259-47-3 C₉₁H₁₂₆Cl₉N₈O₃₀P₃Si₄ 
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• 69504-17-2 2,2,2-trichloroethyl 3'-[2'-O-(tert-butyldimethylsilyl)-5'-O-(p-methoxyphenyldiphenylmethyl)uridyl]-5'-[2',3'-O-(bis-tert-butyldimethylsilyl)uridyl] phosphate 
• 77244-98-5 C₅₇H₇₄Cl₃N₄O₁₆PSi₂ 
• 73496-64-7 C₆₂H₆₄Cl₆N₆O₂₀P₂ 
• 72599-85-0 C₆₆H₈₈Cl₃N₈O₁₃PSi₃ 

Relevant articles and documents

New approach to the synthesis of phosphorodichloridites, phosphorochloridites, and trialkyl phosphites

Different trivalent organophosphorus esters such as phosphorodichloridites, phosphorochloridites, and mixed trialkyl phosphites have been easily synthesized in good yields using a HCl-catalyzed reaction of the corresponding chlorophosphine and alkoxytrimethylsilane by mutual exchange of the alkoxy and chlorine ligand pIIICl/ROSiR′3; exchange reaction). Chemoselectivity of the exchange reaction with primary and secondary alkoxytrimethylsilanes, as well as with alkoxytrimethylsilanes and thioalkoxytrimethylsilanes, respectively, has also been examined. It has been also found that the substitution reaction of chlorophosphines with secondary amine occurs more rapidly than the exchange reaction with ROSiR′ 3.

Bis(2,2,2-trichloroethyl) Phosphorochloridite as a Reagent for the Phosphorylation of Oligonucleotides: Preparation of 5'-Phosphorylated 2',5'-Oligoadenylates

Bis(2,2,2-trichloroethyl) phosphorochloridite was found to be a useful reagent for the phosphorylation of protected nucleosides and oligonucleotides especially when the phosphate blocking group was 2,2,2-trichloroethyl and the hydroxyl protecting group was tert-butyldimethylsilyl.Thus compounds 2a-c,f,g could be phosphorylated to the corresponding 5'-phosphotriesters 4a-c,f,g in yields of 75-99percent.Removal of the protecting groups (to give the 5'-monophosphates 6a-c,f,g) was achieved by zinc-copper couple/2,4-pentanedione/DMF treatment to remove the 2,2,2-trichloroethyl group and tetrabutylammonium fluoride/THF treatment to remove the tert-butyldimethylsilyl groups.A method was found that permits preparation of reproducibly active zinc-copper couple.As a hydroxyl protecting group, the isopropylidene moiety was somewhat less useful in conjunction with the use of bis(2,2,2-trichloroethyl) phosphorochloridite.Thus, upon phosphorylation of 2d and 2e, the phosphotriesters 4d and 4e were obtained in yields of 83percent and 61percent, respectively.Deblocking of the isopropylidene groups was accomplished with formic acid at room temperature to give 6a and 6b in yields of 74percent and 70percent, respectively.The 5'-phosphorylated 2'-5'-linked oligonucleotides 6f and 6g were converted to the corresponding 5'-triphosphates to give compounds 1a and 1b which are found in extracts of interferon-treated cells upon incubation with double-stranded RNA.