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2537-48-6 molecular structure
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diethyl (cyanomethyl)phosphonate

ChemBase ID: 91244
Molecular Formular: C6H12NO3P
Molecular Mass: 177.138141
Monoisotopic Mass: 177.05547988
SMILES and InChIs

SMILES:
P(=O)(CC#N)(OCC)OCC
Canonical SMILES:
CCOP(=O)(CC#N)OCC
InChI:
InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3
InChIKey:
KWMBADTWRIGGGG-UHFFFAOYSA-N

Cite this record

CBID:91244 http://www.chembase.cn/molecule-91244.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
diethyl (cyanomethyl)phosphonate
IUPAC Traditional name
diethyl cyanomethylphosphonate
Synonyms
(Diethylphosphono)acetonitrile
(Diethoxyphosphoryl)acetonitrile
Diethyl (cyanomethyl)phosphonate 98%
DIETHYL CYANOMETHYL PHOSPHATE
diethyl (cyanomethyl)phosphonate
Cyanomethylphosphonic acid diethyl ester
Diethyl cyanomethylphosphonate
(Diethylphosphono)acetonitrile
P-(Cyanomethyl)phosphonic Acid Diethyl Ester
(Cyanomethyl)diethoxyphosphine Oxide
(Diethoxyphosphinyl)acetonitrile
Diethyl Cyanomethanephosphonate
O,O-Diethyl (Cyanomethyl)phosphonate
NSC 407826
Diethyl Cyanomethylphosphonate
Diethyl phosphonoacetonitrile
二乙基氰甲基磷酸酯
氰甲基膦酸二乙酯
二乙基氰甲基磷酸酯
氰甲基膦酸二乙酯
氰甲基磷酸二乙酯
CAS Number
2537-48-6
EC Number
219-806-0
MDL Number
MFCD00001893
Beilstein Number
1772981
PubChem SID
24894272
162077948
PubChem CID
75676

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.055647  H Acceptors
H Donor LogD (pH = 5.5) 0.17517574 
LogD (pH = 7.4) 0.17516631  Log P 0.17517588 
Molar Refractivity 41.0751 cm3 Polarizability 16.410683 Å3
Polar Surface Area 59.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Ethyl Acetate expand Show data source
Tetrahydrofuran expand Show data source
Apperance
Clear Oil expand Show data source
Boiling Point
101-102 °C/0.4 mmHg(lit.) expand Show data source
101-102°C/0.4mm expand Show data source
132-135°C/1.2mm expand Show data source
Flash Point
>110°C(230°F) expand Show data source
113 °C expand Show data source
113°C expand Show data source
235.4 °F expand Show data source
Density
1.094 expand Show data source
1.095 expand Show data source
1.095 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4330 expand Show data source
n20/D 1.434 expand Show data source
n20/D 1.434(lit.) expand Show data source
Storage Warning
Corrosive/Irritant expand Show data source
European Hazard Symbols
X expand Show data source
Irritant Irritant (Xi) expand Show data source
UN Number
1760 expand Show data source
UN3278 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
8 expand Show data source
Packing Group
2 expand Show data source
III expand Show data source
Risk Statements
20/21/22-36/38 expand Show data source
38 expand Show data source
Safety Statements
26-28 expand Show data source
9-23-26-36/37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315 expand Show data source
H331-H302-H312-H315-H319 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1760 8/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (GC) expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Linear Formula
NCCH2PO(OC2H5)2 expand Show data source

DETAILS

DETAILS

TRC TRC MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05206945 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - D91705 external link
Packaging
10, 50 g in glass bottle
Sigma Aldrich - 28503 external link
Other Notes
Horner-Wittig reagent1

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Laine, D., et al.: J. Med. Chem., 52, 5241 (2009)
  • • Nakao, A., et al.: Bioorg. Med. Chem. Lett., 19, 4607 (2009)
  • • Arakawa, Y., et al.: Chem. Pharm. Bull., 57, 167 (2009)
  • • Horner-Wadsworth-Emmons olefination converts carbonyl compounds to substituted acrylonitriles: J. Am. Chem. Soc., 83, 1733 (1961); J. Org. Chem., 30, 505 (1965). LiOH has been found to be an effective base for this reaction: Tetrahedron Lett., 44, 1333 (2003). See Appendix 1. See also 3-Coumaranone, A10202.
  • • The active methylene group can be monoalkylated under phase transfer conditions with alkyl iodides or allylic or benzylic bromides: Synthesis, 516 (1975). Use of alumina as base leads predominantly to the Knoevenagel product rather than the Wadsworth-Emmons: Tetrahedron, 41, 1259 (1985).
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PATENTS

PATENTS

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INTERNET

INTERNET

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