Conditions | Yield |
---|---|
With ammonia; N,N-dimethyl-aniline; phosphorus trichloride In 1,2-dichloro-benzene at 10℃; pH=6 - 9; Temperature; pH-value; | 99.71% |
With triethanolamine; phosphorus trichloride In toluene at 15 - 50℃; for 2.7h; Reagent/catalyst; | 96% |
With Tri-n-octylamine; sodium carbonate; triethylamine; phosphorus trichloride In hexane at 5℃; for 2h; Temperature; Reagent/catalyst; | 83.7% |
(2-hydroxyethyl)(methyl)amine
diethyl phosphorylchloridite
A
2-ethoxy-3-methyl-1,3,2-oxazaphospholidine
B
triethyl phosphite
Conditions | Yield |
---|---|
at 10 - 15℃; | A 67% B 92% |
diphosphorous acid tetraethyl ester
orthoformic acid triethyl ester
A
ethyl P-(diethoxymethyl)phosphonite
B
triethyl phosphite
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 20℃; for 3h; argon atmosphere; | A 89% B 69% |
ethanol
diethoxyphosphino ethyl cyclohexylphosphonate
A
ethyl hydrogen cyclohexylphosphonate
B
triethyl phosphite
Conditions | Yield |
---|---|
In benzene for 1h; Heating; argon atmosphere; | A 0.93 g B 87% |
ethanol
S-(2-cyanoethyl) N,N,N',N'-tetraisopropylthiophosphorodiamidite
C
triethyl phosphite
Conditions | Yield |
---|---|
With 1H-tetrazole In acetonitrile at 25℃; for 0.166667h; | A 5% B 85% C 7% |
With 1H-tetrazole In acetonitrile at 25℃; for 0.166667h; | A 22% B 18% C 60% |
diethyl phosphorylchloridite
2-ethoxy-3-methyl-1,3,2-oxazaphospholidine
A
2-chloro-3-methyl-1,3,2-oxazaphospholidine
B
triethyl phosphite
Conditions | Yield |
---|---|
at 100℃; for 1h; | A 83% B 57% |
phosphorodichloridous acid ethyl ester
ethanol
A
diethyl phosphorylchloridite
B
triethyl phosphite
Conditions | Yield |
---|---|
With triethylamine In toluene | A 82% B 18% |
ethanol
O,O-diethyl-N-butyl-N-isobutenyl aminophosphite
A
N-isobutylidenebutylamine
B
triethyl phosphite
Conditions | Yield |
---|---|
at 20℃; for 1440h; | A 72.5% B 81.7% |
O,O-diethyl-N-butyl-N-isobutenyl aminophosphite
A
N-isobutylidenebutylamine
B
triethyl phosphite
Conditions | Yield |
---|---|
With ethanol at 20℃; for 1440h; further reagents; | A 72.5% B 81.7% |
ethanol
2-diethylamido-4-oxo-1,3-dimethyl-1,3,2-diazaphosphorinane
triethyl phosphite
Conditions | Yield |
---|---|
at 70℃; for 3h; | 81% |
diethyl acetyl(trimethylsilyl)phosphoramidite
A
N-Trimethylsilylacetamide
B
triethyl phosphite
Conditions | Yield |
---|---|
With ethanol for 48h; | A 76% B 60% |
O,O-diethyl (triethoxymethyl)phosphonate
A
triethyl phosphite
B
Diethyl carbonate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate under 60 Torr; Heating; | A 75% B n/a |
Conditions | Yield |
---|---|
for 72h; Ambient temperature; | 73% |
at 20℃; for 2h; | 30 % Spectr. |
diethyl phosphorylchloridite
A
2-chloro-1,3-dibutyl-4,5-dimethyl-1,3,2-diazaphospholine
B
triethyl phosphite
Conditions | Yield |
---|---|
With 2-chloro-1,3-dibutyl-4,5-dimethyl-1,3,2-diazaphospholine In benzene at 10℃; for 1h; | A 61.8% B 65.3% |
(4-pentenyl)-phosphonic acid diethyl ester
triethyl phosphite
Conditions | Yield |
---|---|
Stage #1: (4-pentenyl)-phosphonic acid diethyl ester With n-butyllithium; chloro-trimethyl-silane; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Large scale reaction; Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere; | 63% |
diphosphorous acid tetraethyl ester
N,N,N,N-tetraethylammonium tetrafluoroborate
A
fluorophosphoric acid diethyl ester
B
triethyl phosphite
Conditions | Yield |
---|---|
at 200 - 220℃; | A 60% B 55% |
diphosphorous acid tetraethyl ester
A
fluorophosphoric acid diethyl ester
B
triethyl phosphite
Conditions | Yield |
---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate at 200 - 220℃; | A 60% B 55% |
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 15℃; for 12h; | A 60% B n/a C n/a |
2-Bromo-m-xylene
chloromethyl methyl ether
A
2,6-dimethyl-3,5-bis(chloromethyl)bromobenzene
C
triethyl phosphite
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Heating; | A n/a B 57% C n/a |
Conditions | Yield |
---|---|
at 0℃; | 55% |
diethyl phosphorylchloridite
benzene-1,2-diol
A
2-ethoxy-1,3,2-benzodioxaphosphole
B
triethyl phosphite
Conditions | Yield |
---|---|
With triethylamine In benzene at 10 - 15℃; for 10h; | A 50% B 41% |
diethyl phosphorylchloridite
2-amino-benzenethiol
A
triethyl phosphite
B
2-ethoxy-2,3-dihydro-1,3,2-benzothiazaphosphole
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 0 - 5℃; | A 47% B 34% |
diethyl phosphorylchloridite
2-(methylamino)benzenethiol
B
triethyl phosphite
Conditions | Yield |
---|---|
With triethylamine In benzene at 10℃; | A 42% B 44% |
triethyl trithiophosphite
sodium ethanolate
A
Diethyl phosphonate
B
triethyl phosphite
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | A 1.2 g B 42% |
Conditions | Yield |
---|---|
With triethylamine In benzene at 10 - 15℃; | A 42% B n/a C n/a |
diethyl phosphorylchloridite
2-amino-phenol
A
2-ethoxy-2,3-dihydro-1,3,2-benzoxazaphosphole
B
triethyl phosphite
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 5 - 10℃; for 12h; | A 40% B 41% |
With triethylamine In diethyl ether overnight; | A 23% B 29% |
ethanol
2-ethoxy-2,3-dihydro-1,3,2-benzoxazaphosphole
A
2-amino-phenol
B
2',3'-dihydro-3H-2λ5-[2,2']spirobi(benzo[1,3,2]oxazaphosphole)
C
triethyl phosphite
Conditions | Yield |
---|---|
for 3h; Ambient temperature; | A 38% B 25% C 33% |
Conditions | Yield |
---|---|
With triethyl phosphite for 720h; Ambient temperature; | A 3.3 g B 30% |
diethyl phosphorylchloridite
1,2-diamino-benzene
A
triethyl phosphite
B
2-ethoxy-2,3-dihydro-1H-1,3,2-benzodiazaphosphole
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 0 - 5℃; | A 21% B n/a |
diethyl phosphorylchloridite
benzene-1,2-diol
A
2,2-'spirobi(1,3,2-benzodioxaphosphole)
B
2-ethoxy-1,3,2-benzodioxaphosphole
C
phosphonic acid diethyl ester
D
triethyl phosphite
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at -15 - -10℃; | A 9% B 7% C 14% D 18% |
ethyl bromoacetate
triethyl phosphite
diethoxyphosphoryl-acetic acid ethyl ester
Conditions | Yield |
---|---|
at 60 - 80℃; for 0.5h; Arbusov reaction; | 100% |
at 150℃; for 3h; | 99% |
for 0.0333333h; Michaelis-Arbuzov reaction; microwave irradiation; | 98% |
methyl chloroformate
triethyl phosphite
diethyl methoxycarbonylphosphonate
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; | 100% |
at 120℃; | |
for 0.166667h; Arbuzov reaction; |
4-cyanobenzyl bromide
triethyl phosphite
diethyl [(4-cyanophenyl)methyl]phosphonate
Conditions | Yield |
---|---|
at 130℃; Arbuzov reaction; | 100% |
at 120℃; for 8h; | 97% |
at 160 - 170℃; for 8h; | 97% |
1-Chloromethylnaphthalene
triethyl phosphite
diethyl 1-naphthylmethylphosphonate
Conditions | Yield |
---|---|
at 160℃; for 7h; Reflux; | 100% |
at 150℃; |
Conditions | Yield |
---|---|
for 2h; Reflux; | 100% |
at 90℃; for 10h; | 68% |
at 90 - 160℃; |
Ethyl 2-bromohexanoate
triethyl phosphite
ethyl 2-(diethoxyphosphoryl)hexanoate
Conditions | Yield |
---|---|
at 130℃; for 10h; Sealed tube; | 100% |
at 120℃; for 24h; | 98% |
Heating; | 80% |
Methyl 2-bromopropionate
triethyl phosphite
methyl 2-(diethoxyphosphoryl)propanoate
Conditions | Yield |
---|---|
In neat (no solvent) at 110℃; | 100% |
2-hydroxy-5-nitrobenzyl chloride
triethyl phosphite
<(2-hydroxy-5-nitrophenyl)methyl>phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 60℃; for 4h; | 100% |
at 200℃; |
Conditions | Yield |
---|---|
With Triphenylphosphine selenide In chloroform for 0.0833333h; | 100% |
With selenium In benzene for 24h; Ambient temperature; | 92% |
With selenium |
bromoacetic acid methyl ester
triethyl phosphite
Methyl diethylphosphonoacetate
Conditions | Yield |
---|---|
at 50℃; for 2h; | 100% |
for 8h; Inert atmosphere; Heating; | 89% |
at 80 - 130℃; | 88% |
tert-butyl 2-bromopropionate
triethyl phosphite
tert-butyl α-(diethoxyphosphinyl)propionate
Conditions | Yield |
---|---|
at 110℃; for 16h; | 100% |
4-bromo-trans-crotonic acid ethyl ester
triethyl phosphite
ethyl (2E)-4-(diethoxyphosphoryl)crotonate
Conditions | Yield |
---|---|
for 2h; Reflux; | 100% |
at 120 - 130℃; for 1h; | 88% |
In tetrahydrofuran at 100℃; for 4h; | 86.4% |
bromoacetic acid tert-butyl ester
triethyl phosphite
tert-butyl diethylphosphonoacetate
Conditions | Yield |
---|---|
at 65℃; for 2h; Substitution; Michaelis-Arbuzov reaction; | 100% |
at 50℃; for 2h; | 100% |
at 90℃; for 6h; Inert atmosphere; | 97% |
ethyl 2-chloro-2-ethoxyacetate
triethyl phosphite
ethyl 2-ethoxy-2-(diethylphosphono)acetate
Conditions | Yield |
---|---|
at 50℃; for 3h; | 100% |
at 150℃; for 3 - 5h; Product distribution / selectivity; Neat (no solvent); | 100% |
at 150℃; for 5h; | 100% |
methyl 2-chloro-2-methoxyacetate
triethyl phosphite
diethyl (methoxy(methoxycarbonyl)methyl)phosphonate
Conditions | Yield |
---|---|
at 150℃; for 3h; | 100% |
With sodium iodide at 190℃; for 2h; | 55% |
4-bromo-m-xylene
triethyl phosphite
(2,5-dimethylphenyl)diethyl phosphonate
Conditions | Yield |
---|---|
With nickel dibromide at 160℃; for 2h; Inert atmosphere; | 100% |
Irradiation; |
(1R,2S,5R)-menthol bromoacetate
triethyl phosphite
(diethoxy-phosphoryl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
Conditions | Yield |
---|---|
at 100℃; for 3h; Arbuzov Reaction; Inert atmosphere; | 100% |
92% |
2-Chloromethylthiophene
triethyl phosphite
diethyl thien-2-ylmethylphosphonate
Conditions | Yield |
---|---|
at 140℃; for 3h; | 100% |
at 120 - 145℃; for 4.5h; | 99% |
at 160℃; for 7h; Michaelis-Arbuzov condensation; | 97% |
2-bromo-3-(bromomethyl)thiophene
triethyl phosphite
diethyl (2-bromothiophen-3-yl)methylphosphonate
Conditions | Yield |
---|---|
at 140℃; | 100% |
at 160℃; for 4h; | 87% |
at 100℃; for 2h; | 30.4% |
for 5h; Heating; | 12 g |
Conditions | Yield |
---|---|
at 130℃; for 16h; Sealed tube; | 100% |
at 150℃; for 6h; | 98% |
for 0.00833333h; Heating; microwave irradiation; | 97% |
1-(bromomethyl)-4-(1,1-dimethylethyl)benzene
triethyl phosphite
diethyl (4-tert-butyl)benzylphosphonate
Conditions | Yield |
---|---|
at 120℃; for 12h; | 100% |
at 150℃; for 6h; | 83% |
at 140℃; for 1h; Arbuzov Reaction; |
benzalacetophenone
triethyl phosphite
3-(diethoxyphosphoryl)-1,3-diphenylpropan-1-one
Conditions | Yield |
---|---|
With acetic acid | 100% |
2-(bromomethyl)-3-methyl-quinoxaline
triethyl phosphite
Diethyl<(3-methylquinoxaline-2-yl)methyl>phosphonate
Conditions | Yield |
---|---|
at 140℃; for 3h; | 100% |
2-nitrophenylmethyl bromide
triethyl phosphite
diethyl 2-nitrobenzylphosphonate
Conditions | Yield |
---|---|
In toluene for 24h; Inert atmosphere; Reflux; | 100% |
at 110℃; | 97% |
In toluene at 120℃; for 24h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With acetic acid | 100% |
Conditions | Yield |
---|---|
In toluene at 100℃; for 3h; Condensation; | 100% |
In tetrahydrofuran at 20℃; Kinetics; Rate constant; ΔS(excit.); Ea; | |
In diethyl ether at 20℃; | |
In benzene for 2h; Heating; |
1-bromomethyl-3-nitrobenzene
triethyl phosphite
1-(diethoxyphosphorylmethyl)-3-nitro-benzene
Conditions | Yield |
---|---|
at 140℃; for 2h; | 100% |
at 140℃; for 2h; | 100% |
at 150℃; for 16h; | 91% |
4-iodobenzoic acid chloride
triethyl phosphite
diethyl (4-iodobenzoyl)phosphonate
Conditions | Yield |
---|---|
In toluene for 3h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With acetic acid | 100% |
ethyl (1-13C)-bromoacetate
triethyl phosphite
ethyl (diethoxyphosphono)-[1-13C]-acetate
Conditions | Yield |
---|---|
at 180℃; for 0.5h; | 100% |
at 120℃; for 2h; | 98.5% |
at 130 - 140℃; for 3h; | 91% |
Arbusov reaction; | 90% |
at 140℃; for 3h; Inert atmosphere; | 90% |
The Triethyl phosphite is an organic compound with the formula C6H15O3P. The IUPAC name of this chemical is triethyl phosphite. With the CAS registry number 122-52-1, it is also named as Ethyl phosphite. The product's categories are Phosphonate Chemicals; Phosphite Ligands; Catalysis and Inorganic Chemistry; Phosphorus Compounds. Besides, it is a clear colorless liquid, which should be stored in cool and ventilated place.
The Triethyl phosphite is used as a plastic stabilizer and plasticizer, and also used as medicine, pesticide intermediates. It is used to produce analgesic pizotifen, viagra and other pesticides fenitrothion, and also used as plasticizers, stabilizers, lubricants and grease additives.
Physical properties about Triethyl phosphite are: (1)ACD/LogP: 0.67; (2)ACD/LogD (pH 5.5): 0.67; (3)ACD/LogD (pH 7.4): 0.67; (4)ACD/BCF (pH 5.5): 1.89; (5)ACD/BCF (pH 7.4): 1.89; (6)ACD/KOC (pH 5.5): 54.86; (7)ACD/KOC (pH 7.4): 54.86; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 41.28 Å2; (11)Flash Point: 54.1 °C; (12)Enthalpy of Vaporization: 38.01 kJ/mol; (13)Boiling Point: 159.8 °C at 760 mmHg; (14)Vapour Pressure: 3.19 mmHg at 25°C.
Preparation: this chemical can be prepared by ethanol, phosphorus trichloride and ammonia. This reaction will need reagent Xylene.
When you are using this chemical, please be cautious about it as the following:
It is flammable and harmful by inhalation and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and keep away from sources of ignition - No smoking.
You can still convert the following datas into molecular structure:
(1)SMILES: O(P(OCC)OCC)CC
(2)InChI: InChI=1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3
(3)InChIKey: BDZBKCUKTQZUTL-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3
(5)Std. InChIKey: BDZBKCUKTQZUTL-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 6203mg/m3/6H (6203mg/m3) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 218, 1992. |
mouse | LD | intraperitoneal | > 500mg/kg (500mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 5, Pg. 286, 1953. | |
mouse | LD50 | oral | 3720mg/kg (3720mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 218, 1992. |
rabbit | LD50 | skin | 2800mg/kg (2800mg/kg) | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 218, 1992. | |
rat | LC50 | inhalation | 11063mg/m3/6H (11063mg/m3) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 218, 1992. |
rat | LD50 | oral | 1840mg/kg (1840mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 218, 1992. |
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