| Identification | More | [Name]
Diethyl cyanomethylphosphonate | [CAS]
2537-48-6 | [Synonyms]
CYANOMETHANEPHOSPHONIC ACID DIETHYL ESTER
CYANOMETHYLPHOSPHONIC ACID DIETHYL ESTER
DEPAN
DIETHYL CYANOMETHYLPHOSPHONATE
(DIETHYLPHOSPHONO)ACETONITRILE
LABOTEST-BB LT00233137
(Cyanomethyl)diethoxyphosphine oxide
2-(Diethylphosphonyl)acetonitrile
Diethyl cyanomethanephosphonate
Phosphonic acid, (cyanomethyl)-, diethyl ester
Cyanomethylphosphonic acid diethyl ester~Diethyl phosphonoacetonitrile
Diethylcyanomethylphosphonate,98+%
Diethyl (cyanomethyl)phosphonate 98%
CYANOMETHYL PHOSPHONIC ACID DIETHYL ESTER,(DIETHYL CYANOMETHYLPHOSPHONATE)
(Diethylphosphono)acetonitrile, Cyanomethylphosphonic acid diethyl ester
2-Diethoxyphosphorylacetonitrile
O,O-Diethyl (cyanomethyl)phosphonate
Diethyl cyanomethylphosphonate , 96 %
Diethoxyphosphinylacetonitrile | [EINECS(EC#)]
219-806-0 | [Molecular Formula]
C6H12NO3P | [MDL Number]
MFCD00001893 | [Molecular Weight]
177.14 | [MOL File]
2537-48-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to light yellow liquid | [Boiling point ]
101-102 °C0.4 mm Hg(lit.)
| [density ]
1.095 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.434(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Soluble), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear colorless to light yellow | [Specific Gravity]
1.1261.095 | [Water Solubility ]
Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride. | [BRN ]
1772981 | [InChI]
InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3 | [InChIKey]
KWMBADTWRIGGGG-UHFFFAOYSA-N | [SMILES]
P(CC#N)(=O)(OCC)OCC | [CAS DataBase Reference]
2537-48-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Diethyl cyanomethylphosphonate(2537-48-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn,C | [Risk Statements ]
R38:Irritating to the 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 ]
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 ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
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 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to light yellow liquid | [Uses]
Diethyl cyanomethyl phosphonate is used as an intermediate in Horner-Emmons reaction for the synthesis of substituted nitriles and their amide and heterocyclic derivatives. It is known as a modified Wittig reagent used in the preparation of alpha, beta-unsaturated nitriles from ketones or aldehydes like 3-hydroxy-3-methylbutanal. It reacts with epoxides and nitrones to prepare cyano-substituted cyclopropanes and aziridines respectively. It is actively involved in the synthesis of alpha-arylated alkanenitriles via reaction with aryl iodides in presence of CuI. | [Uses]
Wittig reagent. | [Biological Functions]
Diethyl cyanomethylphosphonate can be used to inhibit and/0r prevent the growth of undesirable algae, bacteria, fungi, yeast, and other microorganisms.
| [General Description]
Diethyl cyanomethylphosphonate is a useful chemical and medical intermediate, which can be used as raw material to synthesize nitrogen-haloamine precursor AEP-ADCT containing triazine-phosphate group | [reaction suitability]
reaction type: C-C Bond Formation | [Synthesis]
The general procedure for the synthesis of diethyl cyanomethylphosphonate from chloroacetonitrile and triethyl phosphite is as follows: 677.5 g (4.0 mol) of triethyl phosphite is heated to 150 °C. At 150 °C, 152.4 g (2.0 mol) of chloroacetonitrile was slowly added dropwise, and the dropwise process lasted for 2 hours (during which the exhaust gas produced was chloroethane). After the dropwise addition was completed, the reaction mixture was continued to be stirred at 150 °C for 2 hours (until the gas escape stopped completely). Upon completion of the reaction, the mixture was distilled under reduced pressure using a small Vigreux fractionation column (height 10 cm). The fraction with a boiling range of 110-139 °C was collected at a reduced pressure of 1 mbar, which was the target product diethyl cyanomethyl phosphate. The product yield was 99% in chloroacetonitrile (based on GC area percentage). | [References]
[1] Patent: WO2005/63780, 2005, A1. Location in patent: Page/Page column 13
[2] Heterocycles, 2014, vol. 89, # 2, p. 375 - 397
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 159, p. 37 - 46
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 433 - 436
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982, p. 25 - 30 |
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