58833
Diethyl isocyanomethylphosphonate
purum, ≥97.0% (GC)
Synonym(s):
Isocyanomethylphosphonic acid diethyl ester
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About This Item
Linear Formula:
CNCH2P(O)(OC2H5)2
CAS Number:
Molecular Weight:
177.14
PubChem Substance ID:
UNSPSC Code:
12352108
Beilstein/REAXYS Number:
4674920
MDL number:
grade
purum
assay
≥97.0% (GC)
reaction suitability
reaction type: C-C Bond Formation
refractive index
n20/D 1.433 (lit.)
bp
84-87 °C/0.1 mmHg (lit.)
density
1.105 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
CCOP(=O)(C[N+]#[C-])OCC
InChI
1S/C6H12NO3P/c1-4-9-11(8,6-7-3)10-5-2/h4-6H2,1-2H3
InChI key
ICURVXBGGDVHDT-UHFFFAOYSA-N
Application
Reactant for:
- Copper-catalyzed cycloaddition reactions
- Preparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase
- Synthesis of sterol analogs as antifungal agents against plant pathogens
- Asymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactions
- The Passerini reaction
Other Notes
Prep. of phosphonic acid analogs of amino acids; Synthesis of aldehydes from carbonyl compounds
signalword
Warning
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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J. Stoelwinder et al
The Journal of Organic Chemistry, 57, 2249-2249 (1992)
U. Schollkopf et al.
Synthesis, 1033-1033 (1984)
B. Kohler et al.
Liebigs Ann. Chem., 267-267 (1987)