4,6-Dimethoxy-2-pyrimidinylamine
2-Amino-4,6-dimethoxypyrimidine
CAS: 36315-01-2
Molecular Formula: C6H9N3O2
4,6-Dimethoxy-2-pyrimidinylamine - Names and Identifiers
| Name | 2-Amino-4,6-dimethoxypyrimidine |
| Synonyms | 4,6-dime 2-Amino-4,6-dimethox 6-diMethoxypyriMidine 4,6-dimethoxy-2-pyrimidine 4,6-Dimethoxypyrimidin-2-amine 2-Amino-4,6-dimethoxypyrimidine 4,6-Dimethoxy-2-aminopyrimidine 2-Amino-4,6-dimethoxy pyrimidine 4,6-Dimethoxy-2-pyrimidinylamine |
| CAS | 36315-01-2 |
| EINECS | 252-969-6 |
| InChI | InChI=1/C6H9N3O2/c1-10-4-3-5(11-2)9-6(7)8-4/h3H,1-2H3,(H2,7,8,9) |
4,6-Dimethoxy-2-pyrimidinylamine - Physico-chemical Properties
| Molecular Formula | C6H9N3O2 |
| Molar Mass | 155.15 |
| Density | 1.3092 (rough estimate) |
| Melting Point | 94-96 °C (lit.) |
| Boling Point | 278.95°C (rough estimate) |
| Flash Point | 169.4°C |
| Solubility | Soluble in organic solvents such as methanol, ethanol, benzene, toluene, acetone, etc., have a certain solubility in hot water, and form salt in acid |
| Vapor Presure | 2.92E-05mmHg at 25°C |
| Appearance | White crystal |
| Color | White |
| pKa | 4.02±0.10(Predicted) |
| Storage Condition | 2-8°C(protect from light) |
| Refractive Index | 1.6500 (estimate) |
| MDL | MFCD00038832 |
| Physical and Chemical Properties | melting point 94-96°C |
| Use | For the synthesis of herbicides such as bensulfuron-methyl and pyrisulfuron-methyl |
4,6-Dimethoxy-2-pyrimidinylamine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| TSCA | Yes |
| HS Code | 29335995 |
| Hazard Note | Irritant |
4,6-Dimethoxy-2-pyrimidinylamine - Chemical properties
pure product is white crystal, industrial product is light yellow granular material, m.p.96 ~ 97 ℃, soluble in methanol, ethanol, benzene, toluene, acetone and other organic solvents, have a certain solubility in hot water, acid into salt.
Last Update：2024-04-10 22:29:15
4,6-Dimethoxy-2-pyrimidinylamine - Safety Information
hazard category code 36/37/38
Safety instructions 26-36-37/39
WGK Germany 3
Hazard Note Irritant
Customs Code 29335995
Last Update：2024-04-10 22:29:15
4,6-Dimethoxy-2-pyrimidinylamine - Production method
It is mainly prepared by the reaction of malononitrile, methanol, cyanamide and the like as raw materials, or by the reaction of diethyl malonate with guanidine nitrate and methanol as raw materials, N-dimethylaniline reacts with 2-amino -4, 6-dihydroxypyrimidine and phosphorus oxychloride to form a pale yellow solid 2-amino -4, 6-dichloropyrimidine, which then reacts with sodium methoxide.
There are two main preparation methods
- put methanol and sodium methoxide in the reaction kettle, then add a certain amount of 2-amino -4, 6-dichloropyrimidine, stir, heat reflux reaction for 6H, after sampling and analysis, it is cooled to room temperature, discharged and filtered to obtain the finished product.
- with malononitrile as raw material into the reaction kettle, then add methanol, cooled to 0 ℃, into the dry hydrogen chloride, the reaction exotherm, the temperature gradually increased to 15 ℃, maintain the temperature, after a certain amount of hydrogen chloride was introduced, stirring was continued for 3-4H, and the crystals were cooled and filtered to obtain 1, 3-dimethylpropanediamidine hydrochloride. The 1, 3-dimethylpropanediamidine hydrochloride was added to a sodium bicarbonate solution cooled to 0 °c to adjust pH = 6 to obtain crystalline hydrochloride, which was filtered, and 50% cyanamide solution was added to the filtrate, the mixture was stirred and heated to room temperature and stirred for 2H to give 3-amino-3-methoxy-n-cyano-2-propionamidine as a crystal, which was filtered, washed with water, dried and dissolved in toluene. Toluene was charged in another reaction pot and heated to reflux, and the above-mentioned propiamidine toluene solution was added and stirred for 1H, filtered, concentrated, cooled, and crystallized to give a finished product.
In the above two methods, diethyl malonate is used as a raw material in China to prepare a finished product by methoxylating 2-amino -4, 6-dichloropyrimidine. However, in the preparation of 2-amino -4, 6-dimethoxy pyrimidine by malononitrile method abroad, the purity of the finished product obtained by this method is high.
Last Update：2024-04-10 22:29:15
4,6-Dimethoxy-2-pyrimidinylamine - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Uses | 2-amino -4, 6-dimethoxypyrimidine is an important intermediate of sulfonylurea herbicides, for example, it can prepare bensulfuron-methyl, pyrisulfuron-methyl, nicosulfuron-methyl, sulfuron-methyl, imidazolon-methyl, ethoxuron-methyl, sulfuron-methyl, cyprosulfuron-methyl, imidazuron-methyl, flupyrsulruron, foramsulfuron, mesosulfouron-methyl and trifloxysulfuron-sodium herbicides. This product is an important pesticide intermediate, used for the synthesis of sulfonylurea pesticides, such as bensulfuron-methyl, nicosulfuron-methyl, cyprosulfuron-methyl, ethoxosulfuron-methyl, sulfuron-methyl, sulfuron-methyl, sulfuron-methyl, chlorpyrazosulfuron-methyl, sulfuron-methyl (NC-311), etc. Used to synthesize herbicides bensulfuron-methyl, pyrisulfuron-methyl, etc. |
| production method | is mainly obtained by reacting malononitrile, methanol, cyanamide, etc. as raw materials, or using diethyl malonate, guanidine nitrate and methanol as raw materials. It can also be prepared by reacting N,N-dimethylaniline with 2-amino -4,6-dihydroxypyrimidine and phosphorus oxychloride to form a light yellow solid 2-amino -4, 6-dichloropyrimidine is formed by reacting with sodium methoxide. there are two main preparation methods. (1) Add methanol and sodium methoxide into the reaction kettle, then add a certain amount of 2-amino -4,6-dichloropyrimidine, stir, heat reflux reaction for 6 hours, after sampling and analysis, cool down to room temperature, discharge and filter to obtain the finished product. (2) adding malononitrile as raw material to the reaction kettle, adding methanol, cooling to 0 ℃, adding dry hydrogen chloride, the reaction is exothermic, the temperature gradually rises to 15 ℃, maintaining the temperature, adding a certain amount of hydrogen chloride, then continuing to stir for 3~4 hours, cooling and crystallizing to obtain 1,3-dimethylpropylene diamidine hydrochloride. The 1,3-dimethylpropanediamidine hydrochloride is added to a sodium bicarbonate solution cooled to 0 ℃, pH = 6 is adjusted to obtain crystalline hydrochloride, filtered, 50% cyanamide solution is added to the filtrate, stirred, heated to room temperature, stirred for 2h to obtain 3-amino-3-methoxy-N-cyano-2-propanamidine, filtered, washed with water, dried, and dissolved in toluene. In another reaction pot, toluene is filled and heated to reflux, the above-mentioned propamidine toluene liquid is added, and stirred for 1h, filtered, concentrated, cooled, and crystallized to obtain a finished product. In the above two methods, diethyl malonate is used as raw material in China, and the finished product is prepared by preparing 2-amino -4, 6-dichloropyrimidine for methoxylation. However, 2-amino -4, 6-dimethoxypyrimidine was prepared by malononitrile method abroad, and the finished product obtained by this method has high purity. |
Last Update：2024-04-09 20:49:11
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