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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

122-52-1 Well-known Company Product Price

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  • Alfa Aesar

  • (L00339)  Triethyl phosphite, 98%   

  • 122-52-1

  • 100ml

  • 108.0CNY

  • Detail
  • Alfa Aesar

  • (L00339)  Triethyl phosphite, 98%   

  • 122-52-1

  • 500ml

  • 225.0CNY

  • Detail

122-52-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Triethyl phosphite

1.2 Other means of identification

Product number -
Other names ethyl phosphite

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122-52-1 SDS

122-52-1Synthetic route

ethanol
64-17-5

ethanol

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
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
109-83-1

(2-hydroxyethyl)(methyl)amine

diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

A

2-ethoxy-3-methyl-1,3,2-oxazaphospholidine
7077-42-1

2-ethoxy-3-methyl-1,3,2-oxazaphospholidine

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
at 10 - 15℃;A 67%
B 92%
diphosphorous acid tetraethyl ester
21646-99-1

diphosphorous acid tetraethyl ester

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

A

ethyl P-(diethoxymethyl)phosphonite
65600-72-8

ethyl P-(diethoxymethyl)phosphonite

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 20℃; for 3h; argon atmosphere;A 89%
B 69%
ethanol
64-17-5

ethanol

diethoxyphosphino ethyl cyclohexylphosphonate
96529-96-3

diethoxyphosphino ethyl cyclohexylphosphonate

A

ethyl hydrogen cyclohexylphosphonate
4546-15-0

ethyl hydrogen cyclohexylphosphonate

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
In benzene for 1h; Heating; argon atmosphere;A 0.93 g
B 87%
ethanol
64-17-5

ethanol

S-(2-cyanoethyl) N,N,N',N'-tetraisopropylthiophosphorodiamidite
127088-86-2

S-(2-cyanoethyl) N,N,N',N'-tetraisopropylthiophosphorodiamidite

A

Thiophosphorous acid S-(2-cyano-ethyl) ester O,O'-diethyl ester

Thiophosphorous acid S-(2-cyano-ethyl) ester O,O'-diethyl ester

B

C11H23N2OPS

C11H23N2OPS

C

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
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
589-57-1

diethyl phosphorylchloridite

2-ethoxy-3-methyl-1,3,2-oxazaphospholidine
7077-42-1

2-ethoxy-3-methyl-1,3,2-oxazaphospholidine

A

2-chloro-3-methyl-1,3,2-oxazaphospholidine
22082-71-9

2-chloro-3-methyl-1,3,2-oxazaphospholidine

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
at 100℃; for 1h;A 83%
B 57%
phosphorodichloridous acid ethyl ester
1498-42-6

phosphorodichloridous acid ethyl ester

ethanol
64-17-5

ethanol

A

diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With triethylamine In tolueneA 82%
B 18%
ethanol
64-17-5

ethanol

O,O-diethyl-N-butyl-N-isobutenyl aminophosphite
79948-06-4

O,O-diethyl-N-butyl-N-isobutenyl aminophosphite

A

N-isobutylidenebutylamine
6898-75-5

N-isobutylidenebutylamine

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
at 20℃; for 1440h;A 72.5%
B 81.7%
O,O-diethyl-N-butyl-N-isobutenyl aminophosphite
79948-06-4

O,O-diethyl-N-butyl-N-isobutenyl aminophosphite

A

N-isobutylidenebutylamine
6898-75-5

N-isobutylidenebutylamine

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With ethanol at 20℃; for 1440h; further reagents;A 72.5%
B 81.7%
ethanol
64-17-5

ethanol

2-diethylamido-4-oxo-1,3-dimethyl-1,3,2-diazaphosphorinane
73868-59-4

2-diethylamido-4-oxo-1,3-dimethyl-1,3,2-diazaphosphorinane

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
at 70℃; for 3h;81%
diethyl acetyl(trimethylsilyl)phosphoramidite
58068-57-8

diethyl acetyl(trimethylsilyl)phosphoramidite

A

N-Trimethylsilylacetamide
13435-12-6

N-Trimethylsilylacetamide

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With ethanol for 48h;A 76%
B 60%
O,O-diethyl (triethoxymethyl)phosphonate
17507-52-7

O,O-diethyl (triethoxymethyl)phosphonate

A

triethyl phosphite
122-52-1

triethyl phosphite

B

Diethyl carbonate
105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate under 60 Torr; Heating;A 75%
B n/a
ethanol
64-17-5

ethanol

2-ethoxy-1,3,2-benzodioxaphosphole
10072-02-3

2-ethoxy-1,3,2-benzodioxaphosphole

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
for 72h; Ambient temperature;73%
at 20℃; for 2h;30 % Spectr.
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

A

2-chloro-1,3-dibutyl-4,5-dimethyl-1,3,2-diazaphospholine
141968-99-2

2-chloro-1,3-dibutyl-4,5-dimethyl-1,3,2-diazaphospholine

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
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
77697-54-2

(4-pentenyl)-phosphonic acid diethyl ester

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
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
21646-99-1

diphosphorous acid tetraethyl ester

N,N,N,N-tetraethylammonium tetrafluoroborate
429-06-1

N,N,N,N-tetraethylammonium tetrafluoroborate

A

fluorophosphoric acid diethyl ester
371-22-2

fluorophosphoric acid diethyl ester

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
at 200 - 220℃;A 60%
B 55%
diphosphorous acid tetraethyl ester
21646-99-1

diphosphorous acid tetraethyl ester

A

fluorophosphoric acid diethyl ester
371-22-2

fluorophosphoric acid diethyl ester

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With N,N,N,N-tetraethylammonium tetrafluoroborate at 200 - 220℃;A 60%
B 55%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

1,2-Bis-[(E)-methylimino]-cyclohexane

1,2-Bis-[(E)-methylimino]-cyclohexane

A

1,3-dimethyl-2-ethoxy-5,6-dihydro-1,3,2-diazaphosphindane

1,3-dimethyl-2-ethoxy-5,6-dihydro-1,3,2-diazaphosphindane

B

triethyl phosphite
122-52-1

triethyl phosphite

C

triethylamine hydrochloride

triethylamine hydrochloride

Conditions
ConditionsYield
With triethylamine In diethyl ether at 15℃; for 12h;A 60%
B n/a
C n/a
2-Bromo-m-xylene
576-22-7

2-Bromo-m-xylene

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

A

2,6-dimethyl-3,5-bis(chloromethyl)bromobenzene
79539-15-4

2,6-dimethyl-3,5-bis(chloromethyl)bromobenzene

B

bis(3-bromo-5-chloromethyl-2,4-dimethylphenyl)methane

bis(3-bromo-5-chloromethyl-2,4-dimethylphenyl)methane

C

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With sulfuric acid for 3h; Heating;A n/a
B 57%
C n/a
ethanol
64-17-5

ethanol

S-acetyl O,O-diethyl phosphorothioite
121883-63-4

S-acetyl O,O-diethyl phosphorothioite

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
at 0℃;55%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

benzene-1,2-diol
120-80-9

benzene-1,2-diol

A

2-ethoxy-1,3,2-benzodioxaphosphole
10072-02-3

2-ethoxy-1,3,2-benzodioxaphosphole

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With triethylamine In benzene at 10 - 15℃; for 10h;A 50%
B 41%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

triethyl phosphite
122-52-1

triethyl phosphite

B

2-ethoxy-2,3-dihydro-1,3,2-benzothiazaphosphole
62290-28-2

2-ethoxy-2,3-dihydro-1,3,2-benzothiazaphosphole

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 5℃;A 47%
B 34%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

2-(methylamino)benzenethiol
21749-63-3

2-(methylamino)benzenethiol

A

2-ethoxy-2,3-dihydro-3-methyl-1,3,2-benzothiazaphosphole

2-ethoxy-2,3-dihydro-3-methyl-1,3,2-benzothiazaphosphole

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With triethylamine In benzene at 10℃;A 42%
B 44%
triethyl trithiophosphite
688-62-0

triethyl trithiophosphite

sodium ethanolate
141-52-6

sodium ethanolate

A

Diethyl phosphonate
762-04-9, 123-22-8

Diethyl phosphonate

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
In ethanol for 2h; Heating;A 1.2 g
B 42%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

1,2-Bis-[(E)-butylimino]-cyclohexane

1,2-Bis-[(E)-butylimino]-cyclohexane

A

1,3-dibutyl-2-ethoxy-5,6-dihydro-1,3,2-diazaphosphindane

1,3-dibutyl-2-ethoxy-5,6-dihydro-1,3,2-diazaphosphindane

B

triethyl phosphite
122-52-1

triethyl phosphite

C

triethylamine hydrochloride

triethylamine hydrochloride

Conditions
ConditionsYield
With triethylamine In benzene at 10 - 15℃;A 42%
B n/a
C n/a
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

2-amino-phenol
95-55-6

2-amino-phenol

A

2-ethoxy-2,3-dihydro-1,3,2-benzoxazaphosphole
7051-22-1

2-ethoxy-2,3-dihydro-1,3,2-benzoxazaphosphole

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
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
64-17-5

ethanol

2-ethoxy-2,3-dihydro-1,3,2-benzoxazaphosphole
7051-22-1

2-ethoxy-2,3-dihydro-1,3,2-benzoxazaphosphole

A

2-amino-phenol
95-55-6

2-amino-phenol

B

2',3'-dihydro-3H-2λ5-[2,2']spirobi(benzo[1,3,2]oxazaphosphole)
67528-50-1, 16841-91-1

2',3'-dihydro-3H-2λ5-[2,2']spirobi(benzo[1,3,2]oxazaphosphole)

C

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
for 3h; Ambient temperature;A 38%
B 25%
C 33%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

propan-2-one azine
627-70-3

propan-2-one azine

A

diethyl [1-methyl-1-(isopropylidenehydrazino)ethyl]phosphonate

diethyl [1-methyl-1-(isopropylidenehydrazino)ethyl]phosphonate

B

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With triethyl phosphite for 720h; Ambient temperature;A 3.3 g
B 30%
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

triethyl phosphite
122-52-1

triethyl phosphite

B

2-ethoxy-2,3-dihydro-1H-1,3,2-benzodiazaphosphole
58825-45-9

2-ethoxy-2,3-dihydro-1H-1,3,2-benzodiazaphosphole

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 5℃;A 21%
B n/a
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

benzene-1,2-diol
120-80-9

benzene-1,2-diol

A

2,2-'spirobi(1,3,2-benzodioxaphosphole)
181-85-1

2,2-'spirobi(1,3,2-benzodioxaphosphole)

B

2-ethoxy-1,3,2-benzodioxaphosphole
10072-02-3

2-ethoxy-1,3,2-benzodioxaphosphole

C

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

D

triethyl phosphite
122-52-1

triethyl phosphite

Conditions
ConditionsYield
With triethylamine In diethyl ether at -15 - -10℃;A 9%
B 7%
C 14%
D 18%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

triethyl phosphite
122-52-1

triethyl phosphite

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
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
79-22-1

methyl chloroformate

triethyl phosphite
122-52-1

triethyl phosphite

diethyl methoxycarbonylphosphonate
41760-84-3

diethyl methoxycarbonylphosphonate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;100%
at 120℃;
for 0.166667h; Arbuzov reaction;
4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

triethyl phosphite
122-52-1

triethyl phosphite

diethyl [(4-cyanophenyl)methyl]phosphonate
1552-41-6

diethyl [(4-cyanophenyl)methyl]phosphonate

Conditions
ConditionsYield
at 130℃; Arbuzov reaction;100%
at 120℃; for 8h;97%
at 160 - 170℃; for 8h;97%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 1-naphthylmethylphosphonate
53575-08-9

diethyl 1-naphthylmethylphosphonate

Conditions
ConditionsYield
at 160℃; for 7h; Reflux;100%
at 150℃;
1-bromoacetone
598-31-2

1-bromoacetone

triethyl phosphite
122-52-1

triethyl phosphite

Diethyl (2-oxopropyl)phosphonate
1067-71-6

Diethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
for 2h; Reflux;100%
at 90℃; for 10h;68%
at 90 - 160℃;
Ethyl 2-bromohexanoate
615-96-3

Ethyl 2-bromohexanoate

triethyl phosphite
122-52-1

triethyl phosphite

ethyl 2-(diethoxyphosphoryl)hexanoate
4134-14-9

ethyl 2-(diethoxyphosphoryl)hexanoate

Conditions
ConditionsYield
at 130℃; for 10h; Sealed tube;100%
at 120℃; for 24h;98%
Heating;80%
Methyl 2-bromopropionate
5445-17-0

Methyl 2-bromopropionate

triethyl phosphite
122-52-1

triethyl phosphite

methyl 2-(diethoxyphosphoryl)propanoate
29668-62-0

methyl 2-(diethoxyphosphoryl)propanoate

Conditions
ConditionsYield
In neat (no solvent) at 110℃;100%
2-hydroxy-5-nitrobenzyl chloride
2973-19-5

2-hydroxy-5-nitrobenzyl chloride

triethyl phosphite
122-52-1

triethyl phosphite

<(2-hydroxy-5-nitrophenyl)methyl>phosphonic acid diethyl ester
51917-76-1

<(2-hydroxy-5-nitrophenyl)methyl>phosphonic acid diethyl ester

Conditions
ConditionsYield
at 60℃; for 4h;100%
at 200℃;
triethyl phosphite
122-52-1

triethyl phosphite

O,O,O-triethylselenophosphate
2651-89-0

O,O,O-triethylselenophosphate

Conditions
ConditionsYield
With Triphenylphosphine selenide In chloroform for 0.0833333h;100%
With selenium In benzene for 24h; Ambient temperature;92%
With selenium
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

triethyl phosphite
122-52-1

triethyl phosphite

Methyl diethylphosphonoacetate
1067-74-9

Methyl diethylphosphonoacetate

Conditions
ConditionsYield
at 50℃; for 2h;100%
for 8h; Inert atmosphere; Heating;89%
at 80 - 130℃;88%
triethyl phosphite
122-52-1

triethyl phosphite

tert-butyl α-(diethoxyphosphinyl)propionate
31460-03-4

tert-butyl α-(diethoxyphosphinyl)propionate

Conditions
ConditionsYield
at 110℃; for 16h;100%
4-bromo-trans-crotonic acid ethyl ester
37746-78-4

4-bromo-trans-crotonic acid ethyl ester

triethyl phosphite
122-52-1

triethyl phosphite

ethyl (2E)-4-(diethoxyphosphoryl)crotonate
42516-28-9

ethyl (2E)-4-(diethoxyphosphoryl)crotonate

Conditions
ConditionsYield
for 2h; Reflux;100%
at 120 - 130℃; for 1h;88%
In tetrahydrofuran at 100℃; for 4h;86.4%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

triethyl phosphite
122-52-1

triethyl phosphite

tert-butyl diethylphosphonoacetate
27784-76-5

tert-butyl diethylphosphonoacetate

Conditions
ConditionsYield
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
34006-60-5

ethyl 2-chloro-2-ethoxyacetate

triethyl phosphite
122-52-1

triethyl phosphite

ethyl 2-ethoxy-2-(diethylphosphono)acetate
13676-06-7

ethyl 2-ethoxy-2-(diethylphosphono)acetate

Conditions
ConditionsYield
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
13157-96-5

methyl 2-chloro-2-methoxyacetate

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (methoxy(methoxycarbonyl)methyl)phosphonate
16141-79-0

diethyl (methoxy(methoxycarbonyl)methyl)phosphonate

Conditions
ConditionsYield
at 150℃; for 3h;100%
With sodium iodide at 190℃; for 2h;55%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

triethyl phosphite
122-52-1

triethyl phosphite

(2,5-dimethylphenyl)diethyl phosphonate
58983-18-9

(2,5-dimethylphenyl)diethyl phosphonate

Conditions
ConditionsYield
With nickel dibromide at 160℃; for 2h; Inert atmosphere;100%
Irradiation;
(1R,2S,5R)-menthol bromoacetate
16832-20-5, 32815-12-6, 55284-67-8

(1R,2S,5R)-menthol bromoacetate

triethyl phosphite
122-52-1

triethyl phosphite

(diethoxy-phosphoryl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
141540-20-7

(diethoxy-phosphoryl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions
ConditionsYield
at 100℃; for 3h; Arbuzov Reaction; Inert atmosphere;100%
92%
2-Chloromethylthiophene
765-50-4

2-Chloromethylthiophene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl thien-2-ylmethylphosphonate
2026-42-8

diethyl thien-2-ylmethylphosphonate

Conditions
ConditionsYield
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
40032-76-6

2-bromo-3-(bromomethyl)thiophene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (2-bromothiophen-3-yl)methylphosphonate
40033-08-7

diethyl (2-bromothiophen-3-yl)methylphosphonate

Conditions
ConditionsYield
at 140℃;100%
at 160℃; for 4h;87%
at 100℃; for 2h;30.4%
for 5h; Heating;12 g
benzyl bromide
100-39-0

benzyl bromide

triethyl phosphite
122-52-1

triethyl phosphite

O,O-diethyl benzylphosphonate
1080-32-6

O,O-diethyl benzylphosphonate

Conditions
ConditionsYield
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
18880-00-7

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (4-tert-butyl)benzylphosphonate
118578-89-5

diethyl (4-tert-butyl)benzylphosphonate

Conditions
ConditionsYield
at 120℃; for 12h;100%
at 150℃; for 6h;83%
at 140℃; for 1h; Arbuzov Reaction;
benzalacetophenone
94-41-7

benzalacetophenone

triethyl phosphite
122-52-1

triethyl phosphite

3-(diethoxyphosphoryl)-1,3-diphenylpropan-1-one
195324-59-5

3-(diethoxyphosphoryl)-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
With acetic acid100%
2-(bromomethyl)-3-methyl-quinoxaline
5320-95-6

2-(bromomethyl)-3-methyl-quinoxaline

triethyl phosphite
122-52-1

triethyl phosphite

Diethyl<(3-methylquinoxaline-2-yl)methyl>phosphonate
5559-64-8

Diethyl<(3-methylquinoxaline-2-yl)methyl>phosphonate

Conditions
ConditionsYield
at 140℃; for 3h;100%
2-nitrophenylmethyl bromide
3958-60-9

2-nitrophenylmethyl bromide

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 2-nitrobenzylphosphonate
4914-12-9

diethyl 2-nitrobenzylphosphonate

Conditions
ConditionsYield
In toluene for 24h; Inert atmosphere; Reflux;100%
at 110℃;97%
In toluene at 120℃; for 24h; Inert atmosphere;97%
4'-chlorochalcone
956-02-5

4'-chlorochalcone

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 3-(4-chlorophenyl)-3-oxo-1-phenylpropylphosphonate

diethyl 3-(4-chlorophenyl)-3-oxo-1-phenylpropylphosphonate

Conditions
ConditionsYield
With acetic acid100%
Phenyl azide
622-37-7

Phenyl azide

triethyl phosphite
122-52-1

triethyl phosphite

triethyl N-phenylphosphorimidate
2397-47-9

triethyl N-phenylphosphorimidate

Conditions
ConditionsYield
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
3958-57-4

1-bromomethyl-3-nitrobenzene

triethyl phosphite
122-52-1

triethyl phosphite

1-(diethoxyphosphorylmethyl)-3-nitro-benzene
104097-04-3

1-(diethoxyphosphorylmethyl)-3-nitro-benzene

Conditions
ConditionsYield
at 140℃; for 2h;100%
at 140℃; for 2h;100%
at 150℃; for 16h;91%
4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (4-iodobenzoyl)phosphonate
156017-40-2

diethyl (4-iodobenzoyl)phosphonate

Conditions
ConditionsYield
In toluene for 3h; Ambient temperature;100%
3-(4-chlorophenyl)-1-phenylprop-2-en-1-one
956-04-7

3-(4-chlorophenyl)-1-phenylprop-2-en-1-one

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)phosphonate

diethyl (1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)phosphonate

Conditions
ConditionsYield
With acetic acid100%
ethyl (1-13C)-bromoacetate
61203-71-2

ethyl (1-13C)-bromoacetate

triethyl phosphite
122-52-1

triethyl phosphite

ethyl (diethoxyphosphono)-[1-13C]-acetate
61203-67-6

ethyl (diethoxyphosphono)-[1-13C]-acetate

Conditions
ConditionsYield
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%

122-52-1Related news

Nucleophilic addition of Triethyl phosphite (cas 122-52-1) to acetates of the baylis-hillman adducts: Stereoselective synthesis of (E)- and (Z)-allylphosphonates09/25/2019

Nucleophilic addition of triethyl phosphite to 3-acetoxy-2-methylenealkanenitriles and methyl 3-acetoxy-2-methylenealkanoates provides (2E)-2-(diethoxyphosphorylmethyl)alk-2- enenitriles and methyl (2Z)-2-(diethoxy-phosphorylmethyl)alk-2-enoates respectively with good stereoselectivity.detailed

The arbuzov reaction of Triethyl phosphite (cas 122-52-1) with elemental iodine09/24/2019

Triethyl phosphite and elemental iodine in solution give transient iodotriethyl-phosphonium iodide which eliminates ethyl iodide to form diethyl phosphoroiodidate. An examination of the 31P NMR and IR spectra over the temperature range −100° − 0°C fails to disclose any evidence for triethoxydi...detailed

Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) Triethyl phosphite (cas 122-52-1) complex09/10/2019

(E)-Alkenyl halides were transformed into (E)-alkenyl sulfides by the nickel(0) triethyl phosphite complex-catalyzed reaction with thiols, whereas (Z)-alkenyl halides gave alkynes under the same reaction conditions. Aryl halides were also transformed into aryl sulfides using the same reagent system.detailed

Cerium(IV) oxide as a neutral catalyst for aldehyde-induced decarboxylative coupling of l-proline with Triethyl phosphite (cas 122-52-1) and nitromethane09/08/2019

The application of cerium(IV) oxide (CeO2) as a neutral and heterogeneous catalyst for aldehyde-induced decarboxylative coupling of l-proline with triethyl phosphite and nitromethane is described. In addition, a [3+2] cycloaddition reaction of the in situ generated 1,3-dipolar intermediate with ...detailed

Reaction of benzolactams with Triethyl phosphite (cas 122-52-1) prompted by phosphoryl chloride affords benzoannulated monophosphonates instead of expected bisphoshonates09/07/2019

In contrast to aliphatic lactams, which gave cyclic aminomethylene-gem-bisphosphonates in reaction with triethyl phosphite and phosphoryl chloride, the corresponding benzoannulated lactams usually provide monophosphonates of variable structures, which depend on size of the substrate aliphatic ri...detailed

122-52-1Relevant articles and documents

Janczak

, (1926)

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)

-

-

Jamzak

, p. 784 ()

-

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)

-

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

-

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.

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