Phenylglyoxylonitrile (HCID 11953)

Überblick

Benzoyl cyanide is an alpha-ketonitrile and an aromatic ketone. It is functionally related to a benzoic acid.

Namen und Bezeichner

Bevorzugter Name: Phenylglyoxylonitrile
IUPAC: benzoyl cyanide
Lokaler Name: Benzoylcyanid
Englischer Name: Benzoyl cyanide
Summenformel: C8H5NO
Molmasse: 131.13

Namen und Synonyme

BENZOYL CYANIDE613-90-1PhenylglyoxylonitrileBenzoyl nitrileOxo(phenyl)acetonitrileGlyoxylonitrile, phenyl-alpha-OxobenzeneacetonitrileBenzeneacetonitrile, .alpha.-oxo-alpha-oxo-alpha-tolunitrile.alpha.-Oxobenzeneacetonitrilealpha-Tolunitrile, alpha-oxo-Benzeneacetonitrile, alpha-oxo-

Weitere Namen anzeigen

Benzoylcyanide98%Benzoylcyanide 98%PhenylglyoxynitrilePhenylglyoxonitrileα-oxo-α-tolunitrileBenzoyl cyanide,95%Ritalin Impurity 11Benzoyl Cyanide >

9R5O6C18O8EINECS 210-359-7PHENYL GLYOXONITRILENSC 401920NSC-401920AI3-13150DTXSID2060626CHEBI:51853

Datenbank-Bezeichner

CAS: 613-90-1
PubChem CID: 11953
DTXSID: DTXSID2060626
ChEBI: CHEBI:51853
UNII: 9R5O6C18O8
EC Number: 210-359-7
Nikkaji: J7.025D

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,9
Polarare Oberfläche (TPSA): 40,9 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 10
Formalladung: 0
Komplexität: 171

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesBoiling point

Physikochemische Eigenschaften

Schmelzpunkt: 28 · 28-31 °C(lit.)
Siedepunkt: 206 °C · 206 °C(lit.)
Dichte: 1.106 g/mL · 1.106 g/mL at 25 °C(lit.)
Brechungsindex: 1.47 · 1.4700 (estimate)
Flammpunkt: 184 °F · 184 °F
Löslichkeit: soluble in Methanol
Aggregatzustand: powder to lump to clear liquid
Farbe: White or Colorless to Light yellow
Wasserlöslichkeit: slihtly soluble, decomposes
BRN: 1072101 · 1072101
InChI: InChI=1S/C8H5NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H
InChIKey: GJQBHOAJJGIPRH-UHFFFAOYSA-N
SMILES: C(C1C=CC=CC=1)(=O)C#N
CAS Datenbank: 613 · 613-90-1(CAS DataBase Reference)
NIST chemische Informationen: Benzeneacetonitrile, «alpha»-oxo-(613-90-1)
EPA chemische Informationen: Benzeneacetonitrile, .alpha.-oxo- (613-90-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationBenzeneacetonitrile, .alpha.-oxo-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Sicherheitsdaten

F: 10
wgk: 3
tsca: TSCA listed
ridadr: UN 3439 6.1/PG 2
hs_code: 29269095
risk_code: 25-50-34-24/25-20
hazard_code: T,N
safety_code: 36/37/39-45-61-29-26
hazard_class: 6.1(b)
packing_group: III
Speicherklasse: 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: Acute Tox. 2 Oral

Chemie und Industrie

Verwendung und Herstellung

General Manufacturing InformationBenzeneacetonitrile, .alpha.-oxo-: ACTIVE

Anwendungen · 1 Eintrag

VerwendenUsing benzoyl cyanide as an electrophile also gives selective acylation of the 3-position, as does levulinic acid in the presence of DCC. Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by Rhodococcus sp. CCZU10-1 to form benzoylformic acid. Reagent for selective acylation of amino compounds.

Darstellung · 1 Eintrag

synthetischeBenzoyl cyanide is prepared by treatment of benzoyl chloride with sodium cyanide under phase-transfer catalytic conditions. This process is also used to convert 4-methyl, 4-methoxy, and 4-chlorobenzoyl chlorides into the corresponding benzoyl cyanides, and similarly cinnamoyl chloride into cinnamoyl cyanide (98%).