122-52-1 Usage
Chemical Properties
Triethyl phosphite is a clear colorless liquid with a strong foul odor. Insoluble in water; soluble in alcohol and ether. Combustible.Vapors heavier than air.
Uses
Different sources of media describe the Uses of 122-52-1 differently. You can refer to the following data:
1. Synthesis, plasticizers, stabilizers, lubricant and
grease additives.
2. Triethyl phosphite is an organophosphorus compound. It is used as a reducing agent; can react with electrophiles to form phosphonates or phosphates; forms a stable complex with copper(I) iodide.
Triethyl phosphite is a very good nucleophile. The carbon adjacent to the bromine is the most electrophilic position, and phosphorus is the only nucleophile. Triethyl phosphite displaces the bromine in an SN2-like process, and back attack by the bromide which is released generates a phosphonate product, in which the α-protons are strongly acidic.
3. Triethyl phosphite is used as a ligand in organometallic chemistry and as a reagent in organic synthesis. It is used as reference to phosphoric acid standard in 31P NMR spectroscopy. It acts as a reducing agent to prepare 2-phenylindazole from o-nitrobenzylidineaniline as well as reacts with electrophiles to get phosphonates. It forms a stable complex with copper(I) iodide. It finds application in a modified Staudinger reaction for the alkyl bromide to an amine through the azide. Further, it is also used in the preparation of 3-phenyl-2-substituted indoles by reacting with beta-nitro styrenes.
Preparation
Triethyl phosphite is produced in a closed system by reaction of phosphorous trichlorid and ethanol in the presence of an inorganic or organic base. The product is purified by distillation (Bayer AG, 2002a).
Triethyl phosphite is exclusively used as an intermediate for the manufacturing of different products: flame retardants (about 60 %), optical brighteners (about 15 %), pesticides (about 15 %), antioxidants (about 5 %), and pharmaceuticals (about 5 %).
Reactions
This reaction is currently used for the preparation of synthetically useful phosphonate reagents employed in modified retinal studies. Thus, diethyl 3-alkoxycarbonyl-2-propenylphosphonates are prepared in 72-91% yields by the reaction of methyl or ethyl 4-bromocrotonates with triethyl phosphite at 150-160°C. Similarly, diethyl 3-(ethoxycarbonyl)-2 methyl-2-propenylphosphonate is prepared in 81% yield from triethyl phosphite and ethyl 3-methyl-4-chlorocrotonate by heating at 180- 200°C.The diethyl (E)- and (Z)-3-ethoxycarbonyl-3 fluoro-2 -methyl-2-propenylphosphonates are respectively obtained from triethyl phosphite and (E)- or (Z)-4-bromo-2-fuoro-3-methyl-2-butenoates at 140°C.
Reactivity Profile
Triethyl phosphite is colorless, moderately toxic liquid, combustible. Flammable when exposed to heat or flame. When heated to decomposition Triethyl phosphite emits toxic fumes of oxides of phosphorus [Lewis, 3rd ed., 1993, p. 1271].
Health Hazard
Exposure to high concentrations may cause headache, nausea, and dizziness due to reduced chlolinesterase activity.
Fire Hazard
Special Hazards of Combustion Products: May form hazardous decomposition products.
Flammability and Explosibility
Flammable
Safety Profile
Moderately toxic by
ingestion. A skin and eye irritant. Flammable
liquid when exposed to heat, sparks, or
flame. When heated to decomposition it
emits toxic fumes of POx.
Toxicity evaluation
The acute toxicity after oral, dermal, and inhalation exposure is relatively low. The oral LD50s in rats ranged between 1840 mg/kg bw (females) and 2470 mg/kg bw (males). Symptoms of rapid breathing and tremors were observed prior to death. In mice LD50 values above 3700 mg/kg bw were recorded. The 6-hour inhalation LC50 with an aerosol of 1.6-3.5 μm MMAD in rats was between 11,100 mg/m3 (females) and 11,600 mg/m3 (males). Clinical signs included eye and upper respiratory irritation, salivation and rapid, shallow breathing. The dermal LD50 in rabbits was between 2800 mg/kg bw (males) and > 3000 mg/kg bw (females).
Check Digit Verification of cas no
The CAS Registry Mumber 122-52-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 122-52:
(5*1)+(4*2)+(3*2)+(2*5)+(1*2)=31
31 % 10 = 1
So 122-52-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3
122-52-1Relevant articles and documents
ACID AND ALKALINE CATALYSIS IN EXCHANGE REACTIONS OF PHOSPHOROUS THIOESTERS
Sinyashin, O. G.,Batyeva, E. S.,Pudovik, A. N.,Ofitserov, E. N.
, p. 1752 - 1753 (1981)
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A simple and efficient synthesis of [2H10]deuterated bromfenvinphos by the Perkow reaction
Huras, Bogumiaa,Konopski, Leszek,Zakrzewski, Jerzy
, p. 399 - 400 (2011)
(E,Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl bis[ethyl-2H 5] phosphate ([2H10]bromfenvinphos), a regiospecifically deuterium-labelled pesticide, was synthesized in two steps starting from [2H6]ethanol, phosphorus trichloride and 2,4-dichlorophenacylidene bromide, and fully characterized. The deuterated biologically active bromfenvinphos is an important compound for the advancement of environmental degradation testing and some mass spectrometric studies.
ALCOHOLYSIS OF AMIDOPHOSPHITES
Kibardin, A. M.,Gryaznov, P. I.,Gazizov, T. Kh.,Pudovik, A. N.
, p. 1693 - 1695 (1987)
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Silver-Catalyzed Regioselective Phosphorylation of para-Quinone Methides with P(III)-Nucleophiles
Liu, Yu,Tang, Ke-Wen,Wong, Wai-Yeung,Xie, Jun,Xiong, Biquan,Xu, Shipan,Xu, Weifeng
, p. 14983 - 15003 (2021/11/12)
A simple and efficient method for the silver-catalyzed regioselective phosphorylation of para-quinone methides (p-QMs) with P(III)-nucleophiles (P(OR)3, ArP(OR)2, Ar2P-OR) has been established via Michaelis-Arbuzov-type reaction. A broad range of P(III)-nucleophiles and para-quinone methides are well tolerated under the mild conditions, giving the expected diarylmethyl-substituted organophosphorus compounds with good to excellent yields. Moreover, a series of corresponding enantiomers can be obtained by employing dialkyl arylphosphonite (ArP(OR)2) as substrates. The control experiments and 31P NMR tracking experiments were also performed to gain insights for the plausible reaction mechanism. This protocol may have significant implications for the formation of C(sp3)-P bonds in Michaelis-Arbuzov-type reactions.
Synthesis process of antioxidant 618
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Paragraph 0027; 0028-0041; 0047-0051; 0047-0051, (2019/08/06)
The invention belongs to the synthesis technology of phosphite antioxidants, in particular to a synthesis technology of antioxidant 618. Triethyl phosphite is synthesized through a microreactor, pentaerythritol diphosphite is synthesized, and the antioxidant 618 is finally synthesized. The synthesis process of the antioxidant 618 has the advantages of good sealing performance, easy control of reaction conditions, reflux utilization of solvents and products, and cost saving.