Basic information
- CAS
61593-47-3- Standard SMILES
N#Cc1ccccc1Cl- InChIKey
NHWQMJMIYICNBP-UHFFFAOYSA-N- Molecular formula
- C7H4ClN
- Average molar mass
- 137.56 g/mol
- Monoisotopic mass
- 137.00322681
Overview
structure in first source
Names & identifiers
- Preferred name
- 2-Chlorobenzonitrile
- IUPAC
- 2-chlorobenzonitrile
- English name
- 2-Chlorobenzonitrile
- Molecular formula
- C7H4ClN
- Molecular weight
- 137.57
Names & synonyms
2-Chlorobenzonitrile873-32-5Benzonitrile, 2-chloro-DTXSID5052593NSC-8438C8Z5NE7QXJDTXCID2031166RefChem:470388212-836-5O-CHLOROBENZONITRILEo-Chlorocyanobenzeneo-Cyanochlorobenzene
Show more names
2-Cl-PhCN2-ChlorobenzonorobenzonitriLO-chloronitrileISOLEUCINE, L-(P)2-Chlorbenzonitrilo-Chlorotolunitrile
Benzonitrile, o-chloro-o-Chlorbenzonitril2-chloro-benzonitrileChlorobenzonitrileOCBNNitril kyseliny o-chlorbenzooveMFCD000017792-chlorobenzenecarbonitrile
Database identifiers
- CAS
61593-47-3、873-32-5- PubChem CID
- 13391
- DTXSID
DTXSID5052593- ChEMBL
CHEMBL3248211- UNII
- C8Z5NE7QXJ
- EC Number
- 212-836-5
- Nikkaji
- J42.016F
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 23.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 135
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials PropertiesDensity
Physical DescriptionWhite crystalline powder; Slightly soluble in water; [MSDSonline]
Physicochemical properties
- Melting point
- 43 · 43-46 °C(lit.)
- Boiling point
- 232 °C · 232 °C(lit.)
- Density
- 1 · 1,18 g/cm3
- refractive index
- 1.453 · 1.4530 (estimate)
- Flash point
- 227 °F · 227 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1 g/l · 1g/l
- form
- Crystalline Solid
- color
- White to very slightly yellow
- BRN
- 1363916 · 1363916
- Exposure limits
- 25 mg/m3 · NIOSH: IDLH 25 mg/m3
- InChI
- 1S/C7H4ClN/c8-7-4-2-1-3-6(7)5-9/h1-4H
- InChIKey
- NHWQMJMIYICNBP-UHFFFAOYSA-N
- SMILES
- Clc1ccccc1C#N
- CAS DataBase Reference
- 873 · 873-32-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-2
- NIST Chemistry Reference
- 2 · 2-Chlorobenzoic acid nitrile(873-32-5)
- EPA Substance Registry System
- 2 · Benzonitrile, 2-chloro- (873-32-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302-H311-H319-H412
- Precautionary statements
- 264 · P264-P273-P280-P301+P312-P302+P352+P312-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 21 · 21/22-36-21/22/23
- Safety Statements
- 23 · 23
- RIDADR
- 3439 · 3439
- WGK Germany
- 2 · 2
- RTECS
- 2625000 · DI2625000
- Hazard Note
- Harmful/Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29269095 · 29269095
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P321, P330, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P317, P321, P330, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: Benzonitrile, 2-chloro-
Commission Regulation No 844/2012
Status: Active Update: 09-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13245
2-Chlorobenzonitrile: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn eye irritant; [eChemPortal: ERMA] An irritant; [MSDSonline] See NITRILES.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute Tox. 4 *
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DI2625000
- ridadr
- 3439
- hs_code
- 29269095
- risk_code
- 21/22-36-21/22/23
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,Xi
- hazard_note
- Harmful/Irritant
- safety_code
- 23
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H302-H311-H319-H412
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2
- Precautionary statements
- P264-P273-P280-P301+P312-P302+P352+P312-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesUsed as an intermediate in the production of azo dyes; [Ullmann]
General Manufacturing InformationBenzonitrile, 2-chloro-: ACTIVE
Applications
UsesIntermediate for the synthesis of agrochemicals, pharmaceuticals and chemical intermediates. 2-Chlorobenzonitrile is mainly used in the synthesis of dye intermediates 2-cyano-4-nitroaniline, and in the pharmaceutical industry for the synthesis of new anti-malarial drugs such as nitroquine.
Uses2-Chlorobenzonitrile is an activated aryl chloride that is commonly used in reactions that involve the Palladium-catalyzed direct arylation of heteroaromatics (e.g. 3-aminopicolinic acid [A627800]). 2-Chlorobenzonitrile and its substituted derivatives (e.g. 2,3-dichloro-6-nitrobenzonitrile [2112-22-3]) also have potential anti-inflammatory properties.
Preparation methods
Preparation2-chlorobenzonitrile is obtained by the reaction of o-chlorobenzoic acid and urea: o-chlorobenzoic acid, sulfamic acid and urea are mixed and heated to about 140℃ and melted, then reacted vigorously under stirring, and a large amount of gas is released, and the temperature automatically rises to 220-230℃ for 2h. Then it is cooled to below 15℃, filtered, and the solids obtained are washed with 3% ammonia and water to neutral, then dried and the finished products are obtained.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
127 records
Compound notes
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