| Identification | More | [Name]
4-Amino-3-chlorobenzonitrile | [CAS]
21803-75-8 | [Synonyms]
2-CHLORO-4-CYANOANILINE
3-CHLORO-4-AMINBENZONITRILE
3-CHLORO-4-AMINOBENZONITRILE
4-AMINO-3-CHLOROBENZONITRILE
BUTTPARK 29\06-54 | [EINECS(EC#)]
624-402-6 | [Molecular Formula]
C7H5ClN2 | [MDL Number]
MFCD00052917 | [Molecular Weight]
152.58 | [MOL File]
21803-75-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
102-105 °C(lit.)
| [Boiling point ]
277.8±25.0 °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]
-0.22±0.10(Predicted) | [color ]
Light yellow to Brown to Dark green | [BRN ]
1817655 | [InChI]
1S/C7H5ClN2/c8-6-3-5(4-9)1-2-7(6)10/h1-3H,10H2 | [InChIKey]
OREVCMGFYSUYPX-UHFFFAOYSA-N | [SMILES]
Nc1ccc(cc1Cl)C#N | [CAS DataBase Reference]
21803-75-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3276 | [WGK Germany ]
3
| [Hazard Note ]
Harmful/Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Definition]
ChEBI: 4-Amino-3-chlorobenzonitrile is a member of benzenes and a nitrile. | [Synthesis]
Step 1: N-chlorosuccinimide (12.4 g, 93 mmol) was slowly added to a stirred solution of 4-aminobenzonitrile (10.0 g, 84.7 mmol) in acetonitrile (100 mL) at 90 °C. After the addition was completed, the reaction mixture was stirred continuously at 90 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The concentrated residue was dissolved in 500 mL of dichloromethane and washed with 5% aqueous sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-amino-3-chlorobenzonitrile as a brown solid (12.2 g, 95% yield).1H NMR (300 MHz, CDCl3) δ 7.54 (d, J = 1.7 Hz, 1H), 7.35 (dd, J = 1.8,8.4 Hz, 1H), 6.77 (d, J = 8.5 Hz, 1H ), 4.63 (br s, 2H). | [References]
[1] Synlett, 1999, # 12, p. 1984 - 1986
[2] Patent: EP2766359, 2016, B1. Location in patent: Paragraph 0383
[3] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
[4] Organic Letters, 2008, vol. 10, # 1, p. 113 - 116
[5] Synthesis, 1985, # 6/7, p. 669 - 670 |
|
|