Conditions | Yield |
---|---|
at 150℃; for 4h; | 99% |
at 150℃; for 2h; | 92% |
for 3h; Arbusov reaction; Heating; | 85% |
Conditions | Yield |
---|---|
for 0.0333333h; Michaelis-Arbuzov reaction; microwave irradiation; | 95% |
Conditions | Yield |
---|---|
Stage #1: acetonitrile With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78℃; for 0.5h; Metallation; Stage #2: diethyl chlorophosphate In tetrahydrofuran at -78 - 0℃; for 0.25h; Substitution; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Hydrolysis; Further stages.; | 88% |
With lithium diisopropyl amide 1.) THF, -30 deg C, 0.5 h, 2.) -30 deg C, 5 h; Yield given. Multistep reaction; | |
With lithium diisopropyl amide 1.) THF, -80 deg C, 15 min, 2.) THF, from -80 deg C to 0 deg C, 1 h; Multistep reaction; |
chloroacetonitrile
triethyl phosphite
A
chloroethane
B
diethyl 1-cyanomethylphosphonate
Conditions | Yield |
---|---|
at 140 - 180℃; | A n/a B 84.5% |
methanol
diazo-cyanomethylphosphonic acid diethyl ester
A
diethyl 1-cyanomethylphosphonate
B
diethyl ((cyanomethoxy)methyl)phosphonate
Conditions | Yield |
---|---|
In water for 3h; Irradiation; Sealed tube; Cooling with ice; | A 66% B 11% |
diethyl 1-cyanomethylphosphonate
Conditions | Yield |
---|---|
With ethyl 4-nitrobenzoate In dimethyl sulfoxide at 24.9℃; Equilibrium constant; |
A
diethyl 1-cyanomethylphosphonate
B
2,2,2-trifluoro-N-(6-methyl-2-pyridinyl)acetamide
Conditions | Yield |
---|---|
With air |
2,3-dichloroquinoxaline
(2-amino-2-thioxoethyl)phosphonic acid diethyl ester
A
2-chloro-3-[(3-chloro-2-quinoxalinyl)-thio]quinoxaline
B
diethyl 1-cyanomethylphosphonate
Conditions | Yield |
---|---|
With water; barium dihydroxide In 1,4-dioxane at 70℃; for 0.666667h; | 100% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: furfural In tetrahydrofuran at 28℃; | |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: furfural In tetrahydrofuran; mineral oil at 0 - 25℃; for 2h; |
diethyl 1-cyanomethylphosphonate
7-Methoxy-1-tetralone
(7-methoxy-3,4-dihydro-2H-naphthalene-1-ylidene)acetonitrile
Conditions | Yield |
---|---|
With sodium methylate In methanol at -20 - -10℃; for 24h; Reagent/catalyst; Wittig Rearrangement; | 100% |
Stage #1: diethyl 1-cyanomethylphosphonate With potassium hydroxide In dimethyl sulfoxide at 15 - 25℃; for 1h; Industry scale; Stage #2: 7-Methoxy-1-tetralone In tetrahydrofuran; dimethyl sulfoxide at 15 - 25℃; for 2.5h; Product distribution / selectivity; | 95% |
Stage #1: 7-Methoxy-1-tetralone With sodium hydride In 1,2-dimethoxyethane at 15℃; for 0.5h; Stage #2: diethyl 1-cyanomethylphosphonate In monoethylene glycol diethyl ether at 10 - 15℃; | 89% |
Conditions | Yield |
---|---|
With caesium carbonate at 20℃; for 24h; Horner reaction; | 100% |
With sodium hydride 1.) THF, RT, 20 min, 2.) THF, RT, 72 h; Multistep reaction; | |
In tetrahydrofuran at 0℃; for 3h; Yield given; |
diethyl 1-cyanomethylphosphonate
N-tert-butyloxycarbonylpiperidin-4-one
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.666667h; Inert atmosphere; | 100% |
With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.666667h; Inert atmosphere; | 100% |
With lithium bromide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 100% |
diethyl 1-cyanomethylphosphonate
(4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-4,6-dienal
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran | 100% |
diethyl 1-cyanomethylphosphonate
1-naphthaldehyde
3-(1-naphthyl)acrylonitrile
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Wadsworth-Emmons reaction; | 100% |
With potassium carbonate for 0.25h; Ambient temperature; |
diethyl 1-cyanomethylphosphonate
3,3'-difluorobenzophenone
3,3'-bis(3-fluorophenyl)acrylonitrile
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 100% |
With sodium hydride In N,N-dimethyl-formamide Horner-Emmons coupling; | 100% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.416667h; Stage #2: 3,3'-difluorobenzophenone In tetrahydrofuran; mineral oil at 80℃; Cooling with ice; |
diethyl 1-cyanomethylphosphonate
N-(4-methoxybenzylidene)-p-toluenesulfonamide
diethyl [(E)-1-cyano-2-(4-methoxyphenyl)ethenyl]phosphonate
Conditions | Yield |
---|---|
With dimethyl sulfoxide at 20℃; for 1h; Knoevenagel condensation; Inert atmosphere; Molecular sieve; optical yield given as %de; stereoselective reaction; | 100% |
With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.0333333h; Condensation; | 81% |
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In dimethyl sulfoxide Knoevenagel type condensation; Stage #2: N-(4-methoxybenzylidene)-p-toluenesulfonamide In dimethyl sulfoxide at 20℃; Kinetics; |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; for 1.5h; | 100% |
4-methyl-pent-3-en-2-one
diethyl 1-cyanomethylphosphonate
3,5-Dimethyl-2,4-hexadienenitrile
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; | 100% |
diethyl 1-cyanomethylphosphonate
3,5-dimethoxybenzaldehdye
3-(3,5-dimethoxyphenyl)acrylonitrile
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 20℃; for 17h; | 100% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 28℃; |
diethyl 1-cyanomethylphosphonate
1-[(1-methylcyclopropyl)sulfonyl]azetidin-3-one
2-(1-((1-methylcyclopropyl)sulfonyl)azetidin-3-ylidene)acetonitrile
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: 1-[(1-methylcyclopropyl)sulfonyl]azetidin-3-one In tetrahydrofuran; mineral oil at 20℃; for 16h; | 100% |
diethyl 1-cyanomethylphosphonate
2-(5,5-dichloro-6,7-dihydro-1-tosyl-1H-indol-4(5H)-ylidene)acetonitrile
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 5,5-dichloro-4-oxo-1-(p-toluenesulfonyl)-4,5,6,7,-tetrahydroindole In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; | 100% |
diethyl 1-cyanomethylphosphonate
tert-butyl 3-formylpyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: tert-butyl 3-formylpyrrolidine-1-carboxylate In tetrahydrofuran at 0 - 20℃; for 16h; | 100% |
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 12h; | 86.1% |
diethyl 1-cyanomethylphosphonate
2-cyclopentylacetaldehyde
4-cyclopentylbut-2-enenitrile
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: 2-cyclopentylacetaldehyde In tetrahydrofuran; mineral oil at 20℃; | 100% |
diethyl 1-cyanomethylphosphonate
4-N,N-di-n-butylamino-2-methoxybenzaldehyde
3-(4-dibutylamino-2-methoxyphenyl)acrylonitrile
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran for 0.416667h; Cooling with ice; Stage #2: 4-N,N-di-n-butylamino-2-methoxybenzaldehyde In tetrahydrofuran for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 5 - 20℃; for 1h; Inert atmosphere; Stage #2: C12H16N2O In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
diethyl 1-cyanomethylphosphonate
Conditions | Yield |
---|---|
With lithium bromide at 100℃; for 70h; | 100% |
diethyl 1-cyanomethylphosphonate
7-diethylamino-9,9-dimethylfluorene-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 7-diethylamino-9,9-dimethylfluorene-2-carbaldehyde In tetrahydrofuran at 20℃; for 4h; | 100% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 7-diethylamino-9,9-dimethylfluorene-2-carbaldehyde In tetrahydrofuran; mineral oil at 20℃; for 4h; | 100% |
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: C19H34O4Si In tetrahydrofuran; hexane at 0 - 20℃; Wittig-Horner Reaction; | 100% |
cyclohexanedione monoethylene ketal
diethyl 1-cyanomethylphosphonate
2-<4,4-(ethylenedioxy)cyclohexylidene>acetonitrile
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride In tetrahydrofuran; paraffin for 12h; | 99% |
Stage #1: diethyl 1-cyanomethylphosphonate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride In tetrahydrofuran for 0.416667h; Inert atmosphere; Stage #2: cyclohexanedione monoethylene ketal at 20℃; for 3h; | 96% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran Stage #2: cyclohexanedione monoethylene ketal With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran | 95% |
2-(1,3-dithian-2-yl)-2-methylpropanal
diethyl 1-cyanomethylphosphonate
(E)-4-(1,3-dithian-2-yl)-4-methylpent-2-enenitrile
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran | 99% |
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 45 min; 2.) -78 deg C, 2 h; RT, 2 h; | 99% |
diethyl 1-cyanomethylphosphonate
6,6'-dideuterio-3,3'-dimethylbenzophenone
C17H13(2)H2N
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane | 99% |
diethyl 1-cyanomethylphosphonate
cyclopentanone
cyclopentylideneacetonitrile
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether at 20℃; Cooling with ice; | 99% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: cyclopentanone In N,N-dimethyl-formamide at 0 - 20℃; | 89% |
With potassium carbonate In water at 80℃; for 2.5h; | 88% |
diethyl 1-cyanomethylphosphonate
3-tetrahydropyran-2-yloxy-androst-5-en-17-one
Conditions | Yield |
---|---|
With sodium hydride Wittig-Horner reaction; | 99% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In 1,2-dimethoxyethane for 0.166667h; Heating; Stage #2: 3-tetrahydropyran-2-yloxy-androst-5-en-17-one In 1,2-dimethoxyethane for 5h; Wittig-Horner reaction; Heating; Further stages.; | 99% |
5-Norbornene-2-carboxaldehyde
diethyl 1-cyanomethylphosphonate
Conditions | Yield |
---|---|
With polymer-anchored quaternary trimethylammonium hydroxide In acetonitrile at 20℃; for 1h; Horner-Emmons olefination; | 99% |
tert-butyl 3-oxoazetidine-1-carboxylate
diethyl 1-cyanomethylphosphonate
3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran; mineral oil Product distribution / selectivity; | 99% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0℃; Stage #3: With water In tetrahydrofuran | 98% |
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0 - 30℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0 - 30℃; | 95% |
diethyl 1-cyanomethylphosphonate
3-benzyloxy cyclobutanone
2-(3-(benzyloxy)cyclobutylidene)acetonitrile
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With triethylamine; lithium bromide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 3-benzyloxy cyclobutanone at 20℃; for 20h; Concentration; | 99% |
Stage #1: diethyl 1-cyanomethylphosphonate With triethylamine; lithium bromide In tetrahydrofuran at 10℃; for 1.5h; Inert atmosphere; Stage #2: 3-benzyloxy cyclobutanone In tetrahydrofuran at 10℃; for 20h; Inert atmosphere; | 91% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 3-benzyloxy cyclobutanone In tetrahydrofuran at 20℃; | 80% |
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 3-benzyloxy cyclobutanone In tetrahydrofuran at 20℃; Inert atmosphere; | 80% |
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; Stage #2: 3-benzyloxy cyclobutanone In tetrahydrofuran at 0 - 20℃; |
diethyl 1-cyanomethylphosphonate
4-hydroxy-benzaldehyde
2-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-benzaldehyde; 2-Nitrobenzenesulfonyl chloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1.5h; Stage #2: diethyl 1-cyanomethylphosphonate With lithium chloride at 20℃; for 24h; Inert atmosphere; | 99% |
IUPAC Name: 2-diethoxyphosphorylacetonitrile
Empirical Formula: C6H12NO3P
Molecular Weight: 177.1381
EINECS: 219-806-0
Structure of Phosphonicacid, P-(cyanomethyl)-, diethyl ester (CAS NO.2537-48-6):
Index of Refraction: 1.422
Molar Refractivity: 40.12 cm3
Molar Volume: 157.8 cm3
Polarizability: 15.9×10-24cm3
Surface Tension: 37.5 dyne/cm
Density: 1.122 g/cm3
Flash Point: 117.3 °C
Enthalpy of Vaporization: 54.57 kJ/mol
Boiling Point: 305.2 °C at 760 mmHg
Vapour Pressure: 0.000831 mmHg at 25°C
Product Categories: Phosphorus compounds;Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction
Hazard Codes: Xi,Xn,C
Risk Statements: 38-36/37/38-20/21/22-34
R38:Irritating to skin.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R34:Causes burns.
Safety Statements: 26-28-36/37/39-23-45-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S23:Do not breathe vapour.
S25:Avoid contact with eyes.
S27:Take off immediately all contaminated clothing.
RIDADR: UN 1760 8/PG 2
WGK Germany: 3
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
HS Code: 29310095
Phosphonicacid, P-(cyanomethyl)-, diethyl ester , its cas register number is 2537-48-6. It also can be called (Cyanomethyl)diethoxyphosphine oxide ; Diethyl (cyanomethyl)phosphonate ; Diethyl cyanomethanephosphonate ; Diethyl-(cyanmethyl)phosphonat ; Phosphonic acid, (cyanomethyl)-, diethyl ester ; (Diethylphosphono)acetonitrile ; 2-(Diethylphosphonyl)acetonitrile . Phosphonicacid, P-(cyanomethyl)-, diethyl ester (CAS NO.2537-48-6) is a clear colorless to light yellow liquid.
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