1-Methyl-aminomethyl naphthalene CAS 14489-75-9
1-Methyl-aminomethyl naphthalene Basic information
| Product Name: | 1-Methyl-aminomethyl naphthalene |
| Synonyms: | N-METHYL-1-NAPHTHALENEMETHYLAMINE;N-METHYL-1-NAPHTHYLMETHYLAMINE;N-METHYLNAPHTHALENE-1-METHYLAMINE;N-METHYL NAPHTHYLMETHYLAMINE;TIMTEC-BB SBB005765;CL134;N-Methyl-C-(naphthalen-1-yl)methanamine HC;AURORA KA-7760 |
| CAS: | 14489-75-9 |
| MF: | C12H13N |
| MW: | 171.24 |
| EINECS: | 238-497-3 |
| Product Categories: | Chemical intermediate for Terbinafine;Anilines, Aromatic Amines and Nitro Compounds;Terbinafine;Amines;Aromatics;Naphthalene series;14489-75-9 |
| Mol File: | 14489-75-9.mol |
1-Methyl-aminomethyl naphthalene Chemical Properties
| Melting point | 189.5-190 °C |
| Boiling point | 104 °C |
| density | 1,05 g/cm3 |
| refractive index | 1.6160-1.6190 |
| storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| pka | 9.38±0.10(Predicted) |
| form | clear liquid |
| color | Colorless to Orange to Green |
| PH | 10.71 at 24℃ and 10g/L |
| InChI | InChI=1S/C12H13N/c1-13-9-11-7-4-6-10-5-2-3-8-12(10)11/h2-8,13H,9H2,1H3 |
| InChIKey | MQRIUFVBEVFILS-UHFFFAOYSA-N |
| SMILES | C1(CNC)=C2C(C=CC=C2)=CC=C1 |
| CAS DataBase Reference | 14489-75-9(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36/37/39 |
| HS Code | 2921.49.5000 |
| HazardClass | IRRITANT |
| Uses | 1-Methyl-aminomethyl naphthalene has been used as reagent for the determination of isocyanates in air by UV or fluorescence detection. 1-Methyl-aminomethyl naphthalene has been used in the preparation of key intermediate required for the synthesis of terbinafine. |
| Chemical Properties | Yellow Oil |
| Uses | Terbinafine EP Impurity A. Terbinafine BP Impurity A. Terbinafine USP Related Compound A |
| Synthesis | 1498015-90-9 14489-75-9 The crude product N-methyl-N-(1-naphthylmethyl)formamide prepared according to step (a) was suspended in 300 mL of 20% aqueous sodium hydroxide solution and the reaction was heated at 60-70°C for 7 hours. Upon completion of the reaction, the mixture was cooled to 25 °C and subsequently extracted with toluene (2 x 200 mL). The toluene extracts were combined and back-extracted with 3N hydrochloric acid (2 x 300 mL). The aqueous phase was decolorized with activated carbon and the pH was adjusted with 20% aqueous sodium hydroxide to 10.0. The released free base was extracted with toluene, and the toluene layers were combined and distilled to remove the solvent to give 86 g of crude product. Finally, 82 g (85% yield) of pure N-methyl-1-naphthalenemethylamine was obtained by high vacuum distillation purification. |
| References | [1] Patent: WO2004/80945, 2004, A1. Location in patent: Page 8 [2] Patent: WO2004/80945, 2004, A1. Location in patent: Page 9-10 |
1-Methyl-aminomethyl naphthalene Preparation Products And Raw materials
| Raw materials | Methanol, (methylamino)--->1-NAPHTHALENEMETHYLAMINE-->N-Methylnaphthalene-1-carboxamide-->Formamide, N-methyl-N-(2-naphthalenylmethyl)--->Methylamine-->1-Chloromethyl naphthalene-->Sodium hydroxide-->Water |
| Preparation Products | Terbinafine-->Butenafine hydrochloride-->3-[Methyl(1-naphthalenylmethyl)amino]-1-phenyl-1-Propanone-->1-Naphthalenemethanamine, N-(2-fluoroethyl)-N-methyl--->Terbinafine Hydrochloride |
