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

General Description

2,2,2-Trichloroethyl phosphorodichloridite is a chemical compound used in the production of insecticides, herbicides, and other agricultural chemicals. It is a phosphorodichloridite, meaning it contains a phosphorus atom bonded to two chlorine atoms and one oxygen atom, as well as a trichloroethyl group. 2,2,2-TRICHLOROETHYL PHOSPHORODICHLORIDITE is highly reactive and can be toxic if not handled properly. It is also used in the synthesis of other phosphorus-containing compounds, such as organophosphates, which are widely used as pesticides. Due to its reactivity and potential health hazards, 2,2,2-trichloroethyl phosphorodichloridite must be handled with great care and in accordance with strict safety protocols.

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

Upstream product

• 115-20-8 1,1,1-trichloroethanol 
• 41262-38-8 trimethyl(2,2,2-trichloroethoxy)silane 

Downstream Products

• 72599-85-0 C₆₆H₈₈Cl₃N₈O₁₃PSi₃ 
• 77244-98-5 C₅₇H₇₄Cl₃N₄O₁₆PSi₂ 
• 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 
• 77259-47-3 C₉₁H₁₂₆Cl₉N₈O₃₀P₃Si₄ 
• 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 
• 84554-06-3 Phosphorochloridous acid 2,2,2-trichloro-ethyl ester (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 73496-64-7 C₆₂H₆₄Cl₆N₆O₂₀P₂ 
• 73496-62-5 trichloroethyl 5'-O-(phenoxyacetyl)thymidine-3' 3'-O-(mono-p-methoxytrityl)thymidine-5' phosphite 

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.