Diethyl phosphorisocyanatidate

HCID 580184

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Basic information

CAS: 20039-33-2
Standard SMILES: CCOP(=O)(N=C=O)OCC
InChIKey: BSCBJDQIQBYMBT-UHFFFAOYSA-N
Molecular formula: C5H10NO4P
Average molar mass: 179.112 g/mol
Monoisotopic mass: 179.03474443

Names & identifiers

Preferred name: Diethyl phosphorisocyanatidate
IUPAC: Diethyl phosphorisocyanatidate
English name: DIETHOXYPHOSPHINYL ISOCYANATE
Molecular formula: C5H10NO4P
Molecular weight: 179.11

Names & synonyms

DIETHYL ISOCYANATOPHOSPHATEdiethoxyphosphorylisocyanateDiethyl isocyanatidophosphateDIETHOXYPHOSPHINYL ISOCYANATEDIETHYL PHOSPHORISOCYANATIDATEdiethoxyphosphorylimino-keto-methanephosphorisocyanatidicacid,diethylester1-(ethoxy-isocyanatophosphoryl)oxyethane1-(ethoxy-isocyanato-phosphoryl)oxyethane

Database identifiers

CAS: 20039-33-2
PubChem CID: 580184
DTXSID: DTXSID20942039
EC Number: 626-051-4
Nikkaji: J526.409J

Properties

Physicochemical properties

Boiling point: 85 · 85-87 °C10 mm Hg(lit.)
Density: 1.165 g/mL · 1.165 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.416(lit.)
Flash point: 119 °F · 119 °F
form: liquid
color: Colourless
InChI: 1S/C5H10NO4P/c1-3-9-11(8,6-5-7)10-4-2/h3-4H2,1-2H3
InChIKey: BSCBJDQIQBYMBT-UHFFFAOYSA-N
SMILES: CCOP(=O)(OCC)N=C=O
UNSPSC Code: 12352100 · 12352100
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Warning
Hazard statements: 226 · H226-H312-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 10 · 10-20/21/22-36/37/38
Safety Statements: 16 · 16-23-26-28-36/37/39
RIDADR: 3080 · UN 3080 6.1/PG 2
WGK Germany: 3 · 3
RTECS: 1250000 · TD1250000
HazardClass: 3.2 · 3.2
PackingGroup: III
HS Code: 2931499090 · 2931499090
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Irrit. 2Flam. Liq. 3Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Toxicity: 50 · mouse,LD50,oral,4080mg/kg (4080mg/kg),Ecotoxicology and Environmental Safety. Vol. 17, Pg. 258, 1989.

Safety & regulation

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
rtecs: TD1250000
ridadr: UN 3080 6.1/PG 2
hs_code: 2931499090
Toxicity: mouse,LD50,oral,4080mg/kg (4080mg/kg),Ecotoxicology and Environmental Safety. Vol. 17, Pg. 258, 1989.
risk_code: 10-20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS02,GHS07
hazard_code: Xn
safety_code: 16-23-26-28-36/37/39
hazard_class: 3.2
Storage Class: 3 - Flammable liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H226-H312-H315-H319-H332-H335
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Irrit. 2Flam. Liq. 3Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Applications

UsesDiethoxyphosphinyl Isocyanate is an intermediate for organic synthesis. Diethoxyphosphinyl Isocyanate is toxic, cytogenetic and embryotoxic to different mice strains.

General DescriptionDiethoxyphosphinyl isocyanate is an isocyanate derivative. It has been investigated for its performance as film forming electrolyte additive in propylene carbonate (PC) and EC/EMC-based electrolytes.

Preparation methods · 1 item

PreparationA solution of diethyl phosphoramidate (30.6 g, 0.2 mol) in tetrachloromethane (50 mL) was slowly added dropwise with stirring and efficient external cooling to a solution of oxalyl chloride (27.9 g, 0.22 mol) in the same solvent (150 mL). The reaction temperature was kept at -5 to 0 °C. After completion of the addition, the temperature of the mixture was slowly increased to 50 °C and this was maintained for 1 h. The mixture was then cooled to room temperature, filtered, and concentrated in vacuo. The residual liquid product was distilled in vacuo (bp 85–87 °C/10 Torr); yield 22.9 g (64%).