Conditions | Yield |
---|---|
In 1,2-dichloro-ethane for 24h; Ambient temperature; molar ratio 1:1; | 98% |
Conditions | Yield |
---|---|
With sodium carbonate at 120℃; under 760.051 Torr; Reflux; Inert atmosphere; | 94.5% |
With titanium(IV) isopropylate at 40℃; for 18h; | 62% |
propylamine
diethyl benzoylphosphonate
A
diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate
B
N-(n-propyl)benzamide
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In diethyl ether for 20h; Product distribution; Ambient temperature; variation of time, different solvents, reaction with several amines; | A 55% B 94% C 33% |
In diethyl ether for 20h; Ambient temperature; | A 55% B 94% C 33% |
Conditions | Yield |
---|---|
With potassium naphthalenide In tetrahydrofuran at -78℃; for 1h; | 94% |
With samarium diiodide In tetrahydrofuran for 3h; Heating; | 10% |
ethanol
phosphorus trichloride
A
chloroethane
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 85℃; under 30.003 Torr; Addition of ca.3% diethyl phosphite (triethyl phosphite or ethyl chloride are also possible); | A n/a B 94% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; water at 25℃; Sealed tube; | 93% |
With water In tetrahydrofuran at 20℃; Inert atmosphere; | 87% |
With lithium chloride at 200℃; das Lithium-Verbindung (Lithium-diaethyl-phophit) ensteht; |
Conditions | Yield |
---|---|
With phosphorus trichloride at 5℃; | 90% |
With phosphorus trichloride | 90% |
With phosphorus trichloride In chloroform at 5 - 20℃; for 3.16667h; | 84.5% |
Conditions | Yield |
---|---|
With N,N-diethyl-1,1,1-trimethylsilanamine at 110℃; for 0.5h; Inert atmosphere; | 86% |
ethanol
1,2,3-trihydrotetrafluoropropyl dichlorophosphite
A
phosphonic acid bis-(2,2,3,3-tetrafluoro-propyl) ester
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
Ambient temperature; | A n/a B n/a C 85% |
propionaldehyde
triethyl phosphite
A
diethyl (1-hydroxypropyl)phosphonate
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at -10℃; for 1h; | A 84% B n/a |
isobutyraldehyde
triethyl phosphite
A
diethyl (1-hydroxy-2-methylpropyl)phosphonate
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at -10℃; for 1h; | A 83% B n/a |
diethyl benzoylphosphonate
benzylamine
A
diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate
B
N-benzylbenzamide
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In diethyl ether for 3h; Ambient temperature; | A 12% B 82% C 45% |
triethyl phosphite
2-(methylamino)benzenethiol
A
2-methylaminophenyl ethyl sulphide
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 150℃; for 10h; | A 70% B 82% |
ethanol
S,S-diethyl O-(trimethylsilyl) phosphorodithioite
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
81.8% |
O,O,O-triethyl phosphorothioate
A
Diethyl phosphate
B
ethylphosphonic acid diethyl ester
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With magnesium monoperoxyphthalate hexahydrate In water at 25℃; for 24h; | A 10% B 81% C 9% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether 0 deg C, 0.5 h then 20 deg C, 2 h; | A 63% B 81% |
3-nitro-benzaldehyde
triethyl phosphite
A
diethyl 1-hydroxy-1-(3-nitrophenyl)methylphosphonate
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at -10℃; for 1h; | A 80% B n/a |
4-methoxy-benzaldehyde
triethyl phosphite
A
diethyl (hydroxy(4-methoxyphenyl)methyl)phosphonate
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at -10℃; for 1h; | A 80% B n/a |
cyclohexanone
triethyl phosphite
A
diethyl (1-hydroxycyclohexyl)phosphonate
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at -10℃; for 1h; | A 80% B n/a |
ethanol
A
triethyl phosphate
B
ethylphosphonic acid diethyl ester
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With phosphorous; CuCl2bpy3 In N,N-dimethyl-formamide at 50℃; Electrolysis; | A 79.3% B 5.4% C 15.3% |
With phosphorous; CuCl2bpy3 In acetonitrile at 50℃; Electrolysis; | A 55% B 15.5% C 29.5% |
With phosphorous; CuCl2bpy3 at 50℃; Electrolysis; | A 28.5% B 17.5% C 16% |
diethyl benzoylphosphonate
phenethylamine
A
diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate
B
N-phenethylbenzamide
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In diethyl ether for 1h; Ambient temperature; | A 20% B 79% C 43% |
diethyl benzoylphosphonate
N-butylamine
A
diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate
B
N-butylbenzamide
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In diethyl ether for 0.333333h; Ambient temperature; | A 18% B 79% C 42% |
Acetic formic anhydride
triethyl phosphite
A
(diethoxyphosphinyl)methyl diethyl phosphate
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 20℃; for 20h; | A 79% B 12% |
3-phenyl-propenal
triethyl phosphite
A
(1-hydroxy-3-phenyl-allyl)-phosphonic acid diethyl ester
B
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at -10℃; for 1h; | A 79% B n/a |
diisopropyl benzoylphosphonate
ethanolamine
A
N-(2-hydroxyethyl)-benzamide
B
2-benzamidoethyl benzoate
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran for 72h; Ambient temperature; | A 78% B 9% C 3% |
diethyl benzoylphosphonate
isobutylamine
A
diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate
B
N-isobutyl-benzamide
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In diethyl ether for 1h; Ambient temperature; | A 22% B 77% C 40% |
triethyl phosphite
A
triethyl phosphate
B
O,O-diethyl benzylphosphonate
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 130℃; for 0.5h; Inert atmosphere; | A n/a B 76% C n/a |
toluene-4-sulfonic acid
triethyl phosphite
A
phosphonic acid diethyl ester
B
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
In toluene for 24h; Product distribution; Heating; investigate effect of molar ratio, solvent and temperature; | A n/a B 75% |
furfural
phosphonic acid diethyl ester
diethyl (hydroxy(furan-2-yl)methyl)phosphonate
Conditions | Yield |
---|---|
With triethylamine In neat (no solvent) at 20℃; Pudovik Reaction; Inert atmosphere; | 100% |
With triethylamine at 50℃; Pudovik Reaction; Inert atmosphere; Sealed tube; | 100% |
With 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene In neat (no solvent) at 30℃; for 3h; Pudovik Reaction; Green chemistry; | 99% |
4-nitrobenzaldehdye
phosphonic acid diethyl ester
diethyl (hydroxy(4-nitrophenyl)methyl)phosphonate
Conditions | Yield |
---|---|
With magnesium oxide for 0.17h; | 100% |
With {(μ-η5:η1):η1-2-[(2,6-Me2C6H3)NCH2](C4H3N)SmN(SiMe3)2}2 In toluene at 20℃; for 0.166667h; Inert atmosphere; | 99% |
With [(μ-η5:η1):η1:η1-3-(2-C4H3NCH=NCH2CH2)C8H5N]Yb3(μ3-O)-(μ2-Cl)2(THF)2[N(SiMe3)2] In neat (no solvent) at 20℃; for 0.166667h; Inert atmosphere; | 99% |
benzaldehyde
phosphonic acid diethyl ester
diethyl [hydroxy(phenyl)methyl]phosphonate
Conditions | Yield |
---|---|
100% | |
With {(μ-η5:η1):η1-2-[(2,6-Me2C6H3)NCH2](C4H3N)SmN(SiMe3)2}2 at 20℃; for 0.0833333h; Inert atmosphere; neat (no solvent); | 99% |
With C42H74LiN6Si4Yb at 20℃; for 0.333333h; Neat (no solvent); Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium hydrogencarbonate; tetrabutylammomium bromide In tetrachloromethane at 15 - 20℃; for 4h; | 100% |
With iodine In neat (no solvent) at 20℃; for 0.5h; Solvent; | 86% |
With copper(l) iodide; oxygen In acetonitrile at 55℃; under 760.051 Torr; for 24h; | 84% |
phosphonic acid diethyl ester
2-nitro-benzaldehyde
diethyl (hydroxy)(2-nitrophenyl)methylphosphonate
Conditions | Yield |
---|---|
With triethylamine In neat (no solvent) at 20℃; for 24h; Pudovik Reaction; Inert atmosphere; | 100% |
With triethylamine at 50℃; Pudovik Reaction; Inert atmosphere; Sealed tube; | 100% |
With C42H74LiN6Si4Yb at 20℃; for 0.333333h; Neat (no solvent); Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With tert-butylhypochlorite In dichloromethane at 20℃; Inert atmosphere; | 100% |
With trichloroisocyanuric acid In acetonitrile at 20℃; | 98% |
With 1,3-dichloro-5,5-dimethylhydantoin In tetrachloromethane; acetonitrile at 20℃; for 0.166667h; | 97% |
4-tolyl iodide
phosphonic acid diethyl ester
diethyl 4-methylphenylphosphonate
Conditions | Yield |
---|---|
With Pd(PPh2)(m-C6H4SO3Na)*(H2O)4; triethylamine In water; acetonitrile for 1.5h; Ambient temperature; | 100% |
With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; triethylamine In toluene for 0.183333h; Irradiation; | 91% |
With water extract of rice straw ash (WERSA) In water at 90℃; for 4h; | 90% |
benzyl-(4-isopropyl-benzyliden)-amine
phosphonic acid diethyl ester
[Benzylamino-(4-isopropyl-phenyl)-methyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 14h; | 100% |
phosphonic acid diethyl ester
[Benzylamino-(3-isopropyl-phenyl)-methyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 14h; | 100% |
phosphonic acid diethyl ester
[1-Benzylamino-1-(4-isopropyl-phenyl)-ethyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 14h; | 100% |
(2S,3S)-3-benzyloxy-1,2-epoxybutane
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran; hexane 1.) -78 deg C, 15 min, 2.) -78 deg C, 2 h; | 100% |
(2S,3R,4R)-2,4-Dimethyl-2-phenyl-3,4-dihydro-2H-pyrrole-3-carboxylic acid ethyl ester; compound with picric acid
phosphonic acid diethyl ester
(2R,3R,4S,5R)-5-(Diethoxy-phosphoryl)-2,4-dimethyl-2-phenyl-pyrrolidine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
at 130℃; for 3h; | 100% |
(3S,4S)-3-Phenyl-2-aza-spiro[4.5]dec-1-ene-4-carboxylic acid ethyl ester
phosphonic acid diethyl ester
(1R,3S,4R)-1-(Diethoxy-phosphoryl)-3-phenyl-2-aza-spiro[4.5]decane-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
at 130℃; for 3h; | 100% |
(2R,3S)-3-(benzyloxy)-1,2-epoxybutane
phosphonic acid diethyl ester
Diethyl (2R,3S)-3-(benzyloxy)-2-hydroxybutanephosphonate
Conditions | Yield |
---|---|
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran; hexane 1.) -78 deg C, 15 min, 2.) -78 deg C, 2 h; | 100% |
phosphonic acid diethyl ester
(2S,3S)-3-Methyl-2-phenyl-3,4-dihydro-2H-pyrrole-3-carboxylic acid ethyl ester
(2S,3R,5R)-5-(Diethoxy-phosphoryl)-3-methyl-2-phenyl-pyrrolidine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
at 130℃; for 3h; | 100% |
phosphonic acid diethyl ester
(2R,3R)-4,4-Dimethyl-2-phenyl-3,4-dihydro-2H-pyrrole-3-carboxylic acid ethyl ester
(2S,3R,5R)-5-(Diethoxy-phosphoryl)-4,4-dimethyl-2-phenyl-pyrrolidine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
at 130℃; for 3h; | 100% |
4-ethoxybenzaldehyde
phosphonic acid diethyl ester
diethyl ((4-ethoxyphenyl)(hydroxy)methyl)phosphonate
Conditions | Yield |
---|---|
With aluminum oxide for 48h; Ambient temperature; | 100% |
With cholin hydroxide In neat (no solvent) at 20℃; for 0.1h; Green chemistry; | 96% |
phosphonic acid diethyl ester
propynoic acid ethyl ester
ethyl β,β-bis(diethoxyphosphoryl)propionate
Conditions | Yield |
---|---|
With aluminum oxide; potassium hydroxide In dichloromethane at 20℃; for 0.0833333h; | 100% |
With sodium hexamethyldisilazane 1) THF, -50 deg C, 15 min; 2) THF, -50 deg C, 10 min; Yield given. Multistep reaction; | |
With aluminum oxide; potassium hydroxide at 20℃; for 0.0833333h; Yield given; |
phosphonic acid diethyl ester
2,3,4-trimethoxybenzaldehyde
[Hydroxy-(2,3,4-trimethoxy-phenyl)-methyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With aluminum oxide for 48h; Ambient temperature; | 100% |
1-naphthaldehyde
phosphonic acid diethyl ester
diethyl hydroxy(naphth-1-yl)methylphosphonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 20℃; for 17h; | 100% |
With N-ethyl-N,N-diisopropylamine at 20℃; for 18h; | 100% |
With (2,6-iPr2PhNH)5SmLi2(THF)2 In hexane at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; | 99% |
2,4-dichlorobenzaldeyhde
phosphonic acid diethyl ester
diethyl [(2-4-dichlorophenyl)(hydroxy)methyl]phosphonate
Conditions | Yield |
---|---|
With magnesium oxide for 0.17h; | 100% |
With C42H74LiN6Si4Yb at 20℃; for 0.333333h; Neat (no solvent); Inert atmosphere; | 99% |
With [(μ-η5:η1):η1:η1-3-(2-C4H3NCH=NCH2CH2)C8H5N]Yb3(μ3-O)-(μ2-Cl)2(THF)2[N(SiMe3)2] In neat (no solvent) at 20℃; for 0.166667h; Inert atmosphere; | 98% |
Reported in EPA TSCA Inventory.
The Diethyl phosphite, with the CAS registry number 762-04-9 and EINECS registry number 212-091-6, is also called phosphonic acid, diethyl ester. And the molecular formula of this chemical is C4H11O3P. It is a kind of colorless liquid, and belongs to the following product categories: Pharmaceutical Intermediates; Organic Building Blocks; Organic Phosphates/Phosphites; Catalysis and Inorganic Chemistry; Phosphorus Compounds; Phosphorus Precursors.
The physical properties of Diethyl phosphite are as following: (1)ACD/LogP: -0.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 18; (8)ACD/KOC (pH 7.4): 18; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 59 Å2.
Preparation of Diethyl phosphite: It can be prepared by absolute ethyl alcohol and phosphorus trichloride. The reaction will need the solvent carbon tetrachloride. The raction time is 1 hour with the temperature of 70°C. And the solvent can be removed by pressure reduction.
3C2H5OH+PCl3→(C2H5O)2PHO+C2H5Cl+2HCl↑
Uses of Diethyl phosphite: It can be used as intermediate of extraction agent and phosphoric acid esters. It is also used as solvent and acid acceptor in the synthesis of polypeptide. What's more, it is also used in the synthetic reaction, such as reduction of phenol.
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and may also cause sensitization by skin contact. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Take off immediately all contaminated clothing; After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OCC)OCC
(2)InChI: InChI=1/C4H11O3P/c1-3-6-8(5)7-4-2/h8H,3-4H2,1-2H3
(3)InChIKey: MJUJXFBTEFXVKU-UHFFFAOYAQ
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | 2020uL/kg (2.02mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LD50 | oral | 3900mg/kg (3900mg/kg) | Albright & Wilson Inc. Vol. #OPB-3, Pg. 1984, |
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