CAS 613-90-1 Phenylglyoxylonitrile (HCID 11953)

Overview

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

Names & identifiers

Preferred name: Phenylglyoxylonitrile
IUPAC: benzoyl cyanide
English name: Benzoyl cyanide
Molecular formula: C8H5NO
Molecular weight: 131.13

Names & synonyms

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

Show more names

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

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 40.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 10
Formal charge: 0
Complexity: 171

Experimental & physicochemical properties

SpringerMaterials PropertiesBoiling point

Physicochemical properties

Melting point: 28 · 28-31 °C(lit.)
Boiling point: 206 °C · 206 °C(lit.)
Density: 1.106 g/mL · 1.106 g/mL at 25 °C(lit.)
refractive index: 1.47 · 1.4700 (estimate)
Flash point: 184 °F · 184 °F
solubility: soluble in Methanol
form: powder to lump to clear liquid
color: White or Colorless to Light yellow
Water Solubility: 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 DataBase Reference: 613 · 613-90-1(CAS DataBase Reference)
FDA UNII: 9 R5O6C18O8 · 9R5O6C18O8
NIST Chemistry Reference: Benzeneacetonitrile, «alpha»-oxo-(613-90-1)
EPA Substance Registry System: Benzeneacetonitrile, .alpha.-oxo- (613-90-1)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 300 · H300
Precautionary statements: 264 · P264-P301+P310
PPE: 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes: T,N
Risk Statements: 25 · 25-50-34-24/25-20
Safety Statements: 36 · 36/37/39-45-61-29-26
RIDADR: 3439 · UN 3439 6.1/PG 2
WGK Germany: 3 · 3
F: 10 · 10
TSCA: TSCA listed
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
HS Code: 29269095 · 29269095
Storage Class: 6.1 B · 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 2 Oral · Acute Tox. 2 Oral
Limited Quantities: 0.5 Kg · 0.5 Kg (solid)
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

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%)

Safety data

F: 10
PPE: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk: 3
tsca: TSCA listed
ridadr: UN 3439 6.1/PG 2
hs_code: 29269095
risk_code: 25-50-34-24/25-20
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T,N
safety_code: 36/37/39-45-61-29-26
hazard_class: 6.1(b)
Storage Class: 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: III
Hazard statements: H300
Limited Quantities: 0.5 Kg (solid)
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Acute Tox. 2 Oral
Precautionary statements: P264-P301+P310

Chemistry & industry

Uses & manufacturing

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

Applications · 2 items

UsesUsing 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.

General DescriptionBenzoyl 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.

Preparation methods · 1 item

PreparationBenzoyl 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%).