Basic information
- CAS
140-53-4- Standard SMILES
N#CCc1ccc(Cl)cc1- InChIKey
IVYMIRMKXZAHRV-UHFFFAOYSA-N- Molecular formula
- C8H6ClN
- Average molar mass
- 151.59 g/mol
- Monoisotopic mass
- 151.01887687
Overview
4-chlorophenylacetonitrile is a nitrile that is acetonitrile in which one of the hydrogens has been replaced by a p-chlorophenyl group. It is a nitrile and a member of monochlorobenzenes. It is functionally related to an acetonitrile.
Names & identifiers
- Preferred name
- 4-Chlorobenzyl cyanide
- IUPAC
- 2-(4-chlorophenyl)acetonitrile
- English name
- 4-Chlorobenzyl cyanide
- Molecular formula
- C8H6ClN
- Molecular weight
- 151.59
Names & synonyms
4-Chlorobenzyl cyanide140-53-4(4-Chlorophenyl)acetonitrile4-Chlorophenylacetonitrile2-(4-Chlorophenyl)acetonitrileBenzeneacetonitrile, 4-chloro-p-Chlorobenzyl cyanide4-Chlorobenzeneacetonitrile(p-Chlorophenyl)acetonitrileAcetonitrile, (p-chlorophenyl)-p-ChlorophenylacetonitrileMFCD00001918
Show more names
Para chloro benzyl cyanidePCCNPyrimethamine EP Impurity C4-Chlorobenzyl cyanide/4-ChlorophenylacetonitrilePCNN
4-Chlor-benzyl-cyanidNSC 49108DTXSID8051708K2K7AKZ2Z72-(4-chlorophenyl)-acetonitrileNSC-491084-Chlorobenzylcyanide2-(4-chlorophenyl)ethanenitrile
Database identifiers
- CAS
140-53-4- PubChem CID
- 241582
- DTXSID
DTXSID8051708- ChEBI
CHEBI:17346- UNII
- K2K7AKZ2Z7
- EC Number
- 205-418-9
- Nikkaji
- J38.178K
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 23.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 139
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP2.47
Vapor Pressure0.01 [mmHg]
Physical DescriptionWhite to light yellow solid with a pungent odor; mp = 28-31 deg C; [Alfa Aesar MSDS]
Collision Cross Section130.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8051708]
Physicochemical properties
- Melting point
- 25 · 25-28 °C(lit.)
- Boiling point
- 265 · 265-267 °C(lit.)
- Density
- 1.19 g/mL · 1.19 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.543
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 0.3 g/l · 0.3g/l
- form
- Liquid After Melting
- color
- Clear colorless to yellow
- BRN
- 971171 · 971171
- Exposure limits
- 25 mg/m3 · NIOSH: IDLH 25 mg/m3
- InChI
- 1S/C8H6ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2
- InChIKey
- IVYMIRMKXZAHRV-UHFFFAOYSA-N
- SMILES
- Clc1ccc(CC#N)cc1
- CAS DataBase Reference
- 140 · 140-53-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 K7AKZ2Z7 · K2K7AKZ2Z7
- NIST Chemistry Reference
- 4 · Benzeneacetonitrile, 4-chloro-(140-53-4)
- EPA Substance Registry System
- 4 · Benzeneacetonitrile, 4-chloro- (140-53-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300-H315-H319-H335
- Precautionary statements
- 301 · P301+P310+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T,Xi
- Risk Statements
- 23 · 23/24/25-36/37/38
- Safety Statements
- 26 · 26-36/37/39-45-28B
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 8250000 · AL8250000
- Hazard Note
- Irritant/Toxic
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29269095 · 29269095
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 OralEye · Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (20%): Fatal if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzeneacetonitrile, 4-chloro-
4-Chlorobenzyl cyanide: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes convulsions and dyspnea in dermal lethal-dose studies of rabbits; Causes ataxia, dyspnea, and decreased body temperature in oral lethal-dose studies of rats; [RTECS] A skin, respiratory tract, and strong eye irritant; Highly toxic by ingestion; Toxic by inhalation and skin absorption; [Alfa Aesar MSDS] See 2-Chlorobenzonitrile.
Hazard Classes and CategoriesAcute Tox. 2 (20%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AL8250000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29269095
- risk_code
- 23/24/25-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T,Xi
- hazard_note
- Irritant/Toxic
- safety_code
- 26-36/37/39-45-28B
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H300-H315-H319-H335
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P301+P310+P330-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzeneacetonitrile, 4-chloro-: INACTIVE
Applications
Uses4-Chlorobenzyl cyanide is an intermediate for the preparation of 3-methyl-2-(4-chlorophenyl)butyric acid, which can be used to prepare pyrethroid insecticides such as fenvalerate and deltamethrin, and can be used in medicine Industrial preparation of pyrimethamine.
Preparation methods
Preparation4-Chlorobenzyl cyanide is obtained by the reaction of 4-Chlorobenzyl chloride with sodium cyanide. Add 4-Chlorobenzyl chloride and Benzyldodecyldimethylammonium bromide into the reaction pot, heat to 100°C, slowly add sodium cyanide aqueous solution, and react at 100-104°C for 5h (add sodium cyanide for 3h, keep warm for 2h). Then add water to dissolve sodium chloride, and separate the water layer to obtain the crude benzyl chloride cyanide, which is distilled under reduced pressure to collect 160 (2.66kPa) fractions to obtain the finished product of 4-Chlorobenzyl cyanide. The yield is above 81%.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
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Additional notes
DefinitionChEBI: 4-Chlorobenzyl cyanide is a nitrile that is acetonitrile in which one of the hydrogens has been replaced by a p-chlorophenyl group. It is a member of monochlorobenzenes and a nitrile. It derives from an acetonitrile.
Related reactions
181 records
Compound notes
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