Product Name

  • Name

    Diethyl cyanomethylphosphonate

  • EINECS 219-806-0
  • CAS No. 2537-48-6
  • Article Data44
  • CAS DataBase
  • Density 1.122 g/cm3
  • Solubility Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.
  • Melting Point
  • Formula C6H12NO3P
  • Boiling Point 305.2 °C at 760 mmHg
  • Molecular Weight 177.14
  • Flash Point 117.3 °C
  • Transport Information UN 1760 8/PG 2
  • Appearance clear colorless to light yellow liquid
  • Safety 26-28-36/37/39-23-45-27
  • Risk Codes 38-36/37/38-20/21/22-34
  • Molecular Structure Molecular Structure of 2537-48-6 (Diethyl cyanomethylphosphonate)
  • Hazard Symbols IrritantXi,HarmfulXn,CorrosiveC
  • Synonyms Cyanomethanephosphonicacid, diethyl ester (6CI);Phosphonic acid, (cyanomethyl)-, diethyl ester(7CI,8CI,9CI);(Cyanomethyl)phosphonicacid diethyl ester;(Diethoxyphosphinyl)acetonitrile;Diethyl (cyanomethyl)phosphonate;NSC 407826;O,O-Diethyl (cyanomethyl)phosphonate;
  • PSA 69.13000
  • LogP 1.77608

Synthetic route

chloroacetonitrile
107-14-2

chloroacetonitrile

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

Conditions
ConditionsYield
at 150℃; for 4h;99%
at 150℃; for 2h;92%
for 3h; Arbusov reaction; Heating;85%
cyanomethyl bromide
590-17-0

cyanomethyl bromide

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

Conditions
ConditionsYield
for 0.0333333h; Michaelis-Arbuzov reaction; microwave irradiation;95%
diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

acetonitrile
75-05-8

acetonitrile

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

Conditions
ConditionsYield
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
107-14-2

chloroacetonitrile

triethyl phosphite
122-52-1

triethyl phosphite

A

chloroethane
75-00-3

chloroethane

B

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

Conditions
ConditionsYield
at 140 - 180℃;A n/a
B 84.5%
methanol
67-56-1

methanol

diazo-cyanomethylphosphonic acid diethyl ester
59463-50-2

diazo-cyanomethylphosphonic acid diethyl ester

A

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

B

diethyl ((cyanomethoxy)methyl)phosphonate
59463-48-8

diethyl ((cyanomethoxy)methyl)phosphonate

Conditions
ConditionsYield
In water for 3h; Irradiation; Sealed tube; Cooling with ice;A 66%
B 11%
diethyl cyanomethylphosphonate potassium salt

diethyl cyanomethylphosphonate potassium salt

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

Conditions
ConditionsYield
With ethyl 4-nitrobenzoate In dimethyl sulfoxide at 24.9℃; Equilibrium constant;
1-cyano-1-(diethoxyphosphoryl)-2-[(6-methylpyrid-2-yl)amino]-2-(trifluoromethyl)ethylene

1-cyano-1-(diethoxyphosphoryl)-2-[(6-methylpyrid-2-yl)amino]-2-(trifluoromethyl)ethylene

A

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

B

2,2,2-trifluoro-N-(6-methyl-2-pyridinyl)acetamide
334711-70-5

2,2,2-trifluoro-N-(6-methyl-2-pyridinyl)acetamide

Conditions
ConditionsYield
With air
2,3-dichloroquinoxaline
2213-63-0

2,3-dichloroquinoxaline

(2-amino-2-thioxoethyl)phosphonic acid diethyl ester
77679-10-8

(2-amino-2-thioxoethyl)phosphonic acid diethyl ester

A

2-chloro-3-[(3-chloro-2-quinoxalinyl)-thio]quinoxaline
1062508-50-2

2-chloro-3-[(3-chloro-2-quinoxalinyl)-thio]quinoxaline

B

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

furfural
98-01-1

furfural

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

(E)-3-(2-furyl)acrylonitrile
6125-63-9

(E)-3-(2-furyl)acrylonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

(7-methoxy-3,4-dihydro-2H-naphthalene-1-ylidene)acetonitrile
127299-26-7

(7-methoxy-3,4-dihydro-2H-naphthalene-1-ylidene)acetonitrile

Conditions
ConditionsYield
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%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

benzaldehyde
100-52-7

benzaldehyde

cinnamic nitrile
1885-38-7

cinnamic nitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

4-(cyanomethylidene)piperidine-1-carboxylic acid tert-butyl ester

4-(cyanomethylidene)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

(4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-4,6-dienal
219130-11-7

(4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-4,6-dienal

(2E,6E,8E)-7-Methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienenitrile

(2E,6E,8E)-7-Methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienenitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran100%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

1-naphthaldehyde
66-77-3

1-naphthaldehyde

3-(1-naphthyl)acrylonitrile
111686-30-7

3-(1-naphthyl)acrylonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

3,3'-difluorobenzophenone
345-70-0

3,3'-difluorobenzophenone

3,3'-bis(3-fluorophenyl)acrylonitrile
170019-08-6

3,3'-bis(3-fluorophenyl)acrylonitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide100%
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
2537-48-6

diethyl 1-cyanomethylphosphonate

N-(4-methoxybenzylidene)-p-toluenesulfonamide
14674-38-5

N-(4-methoxybenzylidene)-p-toluenesulfonamide

diethyl [(E)-1-cyano-2-(4-methoxyphenyl)ethenyl]phosphonate
36315-64-7

diethyl [(E)-1-cyano-2-(4-methoxyphenyl)ethenyl]phosphonate

Conditions
ConditionsYield
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;
3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

4-benzyloxy-3-methoxy-β-cyanostyrene

4-benzyloxy-3-methoxy-β-cyanostyrene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 1.5h;100%
4-methyl-pent-3-en-2-one
141-79-7

4-methyl-pent-3-en-2-one

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

3,5-Dimethyl-2,4-hexadienenitrile
54354-52-8

3,5-Dimethyl-2,4-hexadienenitrile

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃;100%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

3,5-dimethoxybenzaldehdye
7311-34-4

3,5-dimethoxybenzaldehdye

3-(3,5-dimethoxyphenyl)acrylonitrile
153507-02-9

3-(3,5-dimethoxyphenyl)acrylonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

1-[(1-methylcyclopropyl)sulfonyl]azetidin-3-one
1187594-26-8

1-[(1-methylcyclopropyl)sulfonyl]azetidin-3-one

2-(1-((1-methylcyclopropyl)sulfonyl)azetidin-3-ylidene)acetonitrile
1187594-27-9

2-(1-((1-methylcyclopropyl)sulfonyl)azetidin-3-ylidene)acetonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

5,5-dichloro-4-oxo-1-(p-toluenesulfonyl)-4,5,6,7,-tetrahydroindole

5,5-dichloro-4-oxo-1-(p-toluenesulfonyl)-4,5,6,7,-tetrahydroindole

2-(5,5-dichloro-6,7-dihydro-1-tosyl-1H-indol-4(5H)-ylidene)acetonitrile
1236306-10-7

2-(5,5-dichloro-6,7-dihydro-1-tosyl-1H-indol-4(5H)-ylidene)acetonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

tert-butyl 3-formylpyrrolidine-1-carboxylate
59379-02-1

tert-butyl 3-formylpyrrolidine-1-carboxylate

tert-butyl 3-[(E)-2-cyanoethenyl]pyrrolidine-1-carboxylate

tert-butyl 3-[(E)-2-cyanoethenyl]pyrrolidine-1-carboxylate

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

2-cyclopentylacetaldehyde
5623-81-4

2-cyclopentylacetaldehyde

4-cyclopentylbut-2-enenitrile
1269823-36-0

4-cyclopentylbut-2-enenitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

4-N,N-di-n-butylamino-2-methoxybenzaldehyde
103893-16-9

4-N,N-di-n-butylamino-2-methoxybenzaldehyde

3-(4-dibutylamino-2-methoxyphenyl)acrylonitrile
1267604-90-9

3-(4-dibutylamino-2-methoxyphenyl)acrylonitrile

Conditions
ConditionsYield
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%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

C12H16N2O

C12H16N2O

C14H17N3

C14H17N3

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

lithium ethyl cyanomethylphosphonate

lithium ethyl cyanomethylphosphonate

Conditions
ConditionsYield
With lithium bromide at 100℃; for 70h;100%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

7-diethylamino-9,9-dimethylfluorene-2-carbaldehyde
1208005-62-2

7-diethylamino-9,9-dimethylfluorene-2-carbaldehyde

(E)-3-(7-(diethylamino)-9,9-dimethyl-9H-fluoren-2-yl)acrylonitrile

(E)-3-(7-(diethylamino)-9,9-dimethyl-9H-fluoren-2-yl)acrylonitrile

Conditions
ConditionsYield
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%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

C19H34O4Si

C19H34O4Si

C21H35NO3Si

C21H35NO3Si

Conditions
ConditionsYield
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
4746-97-8

cyclohexanedione monoethylene ketal

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

2-<4,4-(ethylenedioxy)cyclohexylidene>acetonitrile
124499-35-0

2-<4,4-(ethylenedioxy)cyclohexylidene>acetonitrile

Conditions
ConditionsYield
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
64872-91-9

2-(1,3-dithian-2-yl)-2-methylpropanal

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

(E)-4-(1,3-dithian-2-yl)-4-methylpent-2-enenitrile
139745-78-1

(E)-4-(1,3-dithian-2-yl)-4-methylpent-2-enenitrile

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran99%
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
2537-48-6

diethyl 1-cyanomethylphosphonate

6,6'-dideuterio-3,3'-dimethylbenzophenone
144617-64-1

6,6'-dideuterio-3,3'-dimethylbenzophenone

C17H13(2)H2N
144617-69-6

C17H13(2)H2N

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane99%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

cyclopentanone
120-92-3

cyclopentanone

cyclopentylideneacetonitrile
5732-88-7

cyclopentylideneacetonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

3-tetrahydropyran-2-yloxy-androst-5-en-17-one
19637-35-5

3-tetrahydropyran-2-yloxy-androst-5-en-17-one

20-carbonitrilopregna-5,17(20)diene 3β-tetrahydropyranyl ether

20-carbonitrilopregna-5,17(20)diene 3β-tetrahydropyranyl ether

Conditions
ConditionsYield
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
5453-80-5, 19926-90-0

5-Norbornene-2-carboxaldehyde

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

(E)-3-Bicyclo[2.2.1]hept-5-en-2-yl-acrylonitrile

(E)-3-Bicyclo[2.2.1]hept-5-en-2-yl-acrylonitrile

Conditions
ConditionsYield
With polymer-anchored quaternary trimethylammonium hydroxide In acetonitrile at 20℃; for 1h; Horner-Emmons olefination;99%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester
1153949-11-1

3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

3-benzyloxy cyclobutanone
30830-27-4

3-benzyloxy cyclobutanone

2-(3-(benzyloxy)cyclobutylidene)acetonitrile
1187595-82-9

2-(3-(benzyloxy)cyclobutylidene)acetonitrile

Conditions
ConditionsYield
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
2537-48-6

diethyl 1-cyanomethylphosphonate

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

(E)-β-[4-(2-nitrobenzenesulfonyloxy)phenyl]acrylonitrile

(E)-β-[4-(2-nitrobenzenesulfonyloxy)phenyl]acrylonitrile

Conditions
ConditionsYield
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%

Diethyl cyanomethylphosphonate Chemical Properties

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

Diethyl cyanomethylphosphonate Safety Profile

Hazard Codes: IrritantXi,HarmfulXn,CorrosiveC
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

Diethyl cyanomethylphosphonate Specification

  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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