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| | 4-Amino-3-chlorobenzonitrile Basic information |
| | 4-Amino-3-chlorobenzonitrile Chemical Properties |
| 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) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-20/21/22 | | Safety Statements | 26-36/37-36/37/39 | | 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 |
| | 4-Amino-3-chlorobenzonitrile Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | 4-Amino-3-chlorobenzonitrile is used as a precursor to prepare 3-chloro-4-((6,7-dimethoxyquinazolin-4-yl)amino)benzonitrile by reacting with 4-chloro-6,7-dimethoxyquinazoline in 2-propanol at 80 °C. | | 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 |
| | 4-Amino-3-chlorobenzonitrile Preparation Products And Raw materials |
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