| Identification | More | [Name]
3-AMINO-4-CHLOROBENZONITRILE | [CAS]
53312-79-1 | [Synonyms]
2-CHLORO-5-CYANO-ANILINE
3-AMINO-4-CHLOROBENZONITRILE
3-Amino-4-chlorobenzonitrile 96% | [EINECS(EC#)]
258-471-5 | [Molecular Formula]
C7H5ClN2 | [MDL Number]
MFCD00017089 | [Molecular Weight]
152.58 | [MOL File]
53312-79-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
87-91 °C | [Boiling point ]
292.0±20.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
0.85±0.10(Predicted) | [color ]
Light yellow to Yellow to Orange | [InChI]
1S/C7H5ClN2/c8-6-2-1-5(4-9)3-7(6)10/h1-3H,10H2 | [InChIKey]
KRBRYJLBILJHAS-UHFFFAOYSA-N | [SMILES]
Nc1cc(ccc1Cl)C#N | [CAS DataBase Reference]
53312-79-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3439 | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
2926907090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| Questions And Answer | Back Directory | [Application]
3-Amino-4-chlorobenzonitrile is a pharmaceutical intermediate. Literature reports that 3-amino-4-chlorobenzonitrile can be used to prepare 2-amino-4-cyano-3',4'-difluoro-1,1'-biphenyl. Fluorinated benzidines are an important class of intermediates widely used in the industrial production of pesticides, pharmaceuticals and other fields. |
| Hazard Information | Back Directory | [Synthesis Reference(s)]
Tetrahedron Letters, 36, p. 9305, 1995 DOI: 10.1016/0040-4039(95)02003-8 | [Synthesis]
General procedure for the synthesis of 3-amino-4-chlorobenzonitrile from 4-chloro-3-nitrobenzonitrile:
Example 1: Preparation of N-(1-(5-cyano-2-(3,5-dichlorophenoxy)benzenesulfonyl)piperidin-4-yl)-3-fluorobenzenesulfonamide (25)
1. Commercially available 4-chloro-3-nitrobenzonitrile was dissolved in tetrahydrofuran (THF) with solvent dosage of 4 times the volume of the raw material.
2. Sodium hydrosulfide (3 equiv.) was added to the reaction system and the reaction mixture was stirred at 45 °C overnight.
3. The progress of the reaction was monitored using thin layer chromatography (TLC) with the unfolding agent being a hexane solution of 25% ethyl acetate to confirm the completion of the reaction.
4. Upon completion of the reaction, the THF solvent was removed by rotary evaporator under reduced pressure to precipitate the product.
5. The white solid product was collected by vacuum filtration and washed with water to remove impurities. 6.
6. The product was placed in a vacuum oven and dried under mild heating conditions to obtain the target compound in 97.0% yield. | [References]
[1] Patent: US2011/230487, 2011, A1. Location in patent: Page/Page column 35
[2] Synlett, 2010, # 20, p. 3019 - 3022
[3] Patent: US2012/196824, 2012, A1
[4] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 369
[5] Chem.Abstr., 1948, vol. 42, p. 148 |
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Energy Chemical
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