3-Chlorphenylacetonitril

Bezeichnung:3-Chlorphenylacetonitril

Englisch Name:3-Chlorobenzyl cyanide

CBNumberCB5115138

SummenformelC8H6ClN

Molgewicht151.59

Synonyma

3-Chlorphenylacetonitril

3-Chlorphenylacetonitril physikalisch-chemischer Eigenschaften

Schmelzpunkt	11-13 °C(lit.)
Siedepunkt	134-136 °C10 mm Hg(lit.)
Dichte	1.283 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.544(lit.)
Flammpunkt	>230 °F
storage temp.	Store at room temperature
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	clear liquid
Farbe	Colorless to Light yellow to Light orange
Wichte	1.280～1.282
BRN	2042965
Expositionsgrenzwerte	NIOSH: IDLH 25 mg/m3
Stabilität	Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents.
InChI	1S/C8H6ClN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4H2
InChIKey	GTIKLPYCSAMPNG-UHFFFAOYSA-N
SMILES	Clc1cccc(CC#N)c1
CAS Datenbank	1529-41-5(CAS DataBase Reference)
NIST chemische Informationen	Benzeneacetonitrile, 3-chloro-(1529-41-5)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	23/24/25-36/37/38
S-Sätze:	36/37/39-45-28B
RIDADR	UN 3276 6.1/PG 1
WGK Germany	3
RTECS-Nr.	AL8240000
HazardClass	6.1
PackingGroup	II
HS Code	29269090
Speicherklasse	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral
Toxizität	mouse,LD50,intraperitoneal,38mg/kg (38mg/kg),PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGEBEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD,Pesticide Biochemistry and Physiology. Vol. 2, Pg. 95, 1972.

Gefahreninformationscode (GHS)

R-Sätze Betriebsanweisung:
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Chemische Eigenschaften
colourless liquid
Verwenden
3-Chlorobenzyl Cyanide is a useful synthetic intermediate. It was used to design EGFR Tyrosine Kinase Inhibitors. It can also be used to synthesize imidoyl thioureas as non-nucleoside reverse transcriptase inhibitors.
Synthese

773837-37-9

620-20-2

1529-41-5

GENERAL METHOD: 3-chlorobenzyl chloride (1.0 mmol) and sodium cyanide (2 mmol) were dissolved in water (5 mL) and polyethylene glycol modified diisocyanate (PEG-MDIL, 0.2 g) was added. The reaction suspension was magnetically stirred under reflux conditions for the reaction time shown in Table 2. After completion of the reaction, the mixture was extracted with ether (2 × 10 mL). The organic extracts were combined and dried with anhydrous calcium chloride and subsequently concentrated under reduced pressure. By this method, the target product 3-chlorobenzeneacetonitrile was obtained in good to excellent yields (Scheme 3).
Einzelnachweise
[1] Journal of Molecular Liquids, 2015, vol. 202, p. 34 - 39

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