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| | 2-Amino-4,6-dichloropyrimidine Basic information |
| Product Name: | 2-Amino-4,6-dichloropyrimidine | | Synonyms: | Pyrimidine, 2-amino-4,6-dichloro-;2-AMINO-4,6-DICHLOROPYRIMIDINE, TECH. 95%;4,6-Dichloro-2-aminopyrimidine;2-Amino-4,6-dichloropyrimidine,95%,tech.;6-dichloropyriMidine;2-Amino-4,6-dichloropyrimidine,98%;4,6-Dichloropyrimidin-2-amine, 2-Amino-4,6-dichloro-1,3-diazine;2-Amino-4,6-dichL | | CAS: | 56-05-3 | | MF: | C4H3Cl2N3 | | MW: | 163.99 | | EINECS: | 200-253-9 | | Product Categories: | Heterocycle-Pyrimidine series;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrimidinesHeterocyclic Building Blocks;Pyrimidines;Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidine;bc0001 | | Mol File: | 56-05-3.mol |  |
| | 2-Amino-4,6-dichloropyrimidine Chemical Properties |
| Melting point | 219-222 °C (lit.) | | Boiling point | 219-222°C | | density | 1.6662 (rough estimate) | | refractive index | 1.6300 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | pka | 0.14±0.10(Predicted) | | form | Liquid | | color | Clear colorless to light yellow | | Water Solubility | Insoluble in water, soluble in acetone, two monomer (VCM) and thermal toluene. | | BRN | 118454 | | InChI | InChI=1S/C4H3Cl2N3/c5-2-1-3(6)9-4(7)8-2/h1H,(H2,7,8,9) | | InChIKey | JPZOAVGMSDSWSW-UHFFFAOYSA-N | | SMILES | C1(N)=NC(Cl)=CC(Cl)=N1 | | CAS DataBase Reference | 56-05-3(CAS DataBase Reference) | | EPA Substance Registry System | 2-Pyrimidinamine, 4,6-dichloro- (56-05-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-24/25 | | WGK Germany | 3 | | RTECS | UV6260485 | | F | 10 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29335995 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-Amino-4,6-dichloropyrimidine Usage And Synthesis |
| Chemical Properties | LIGHT BROWN CRYSTALLINE POWDER | | Uses | Microwave-assisted synthesis of pyrazolo [3, 4-d] pyrimidines from 2-amino-4, 6-dichloropyrimidine-5-carbaldehyde is under solvent-free conditions. A series of 6-alkynyl-2,4-diaminopyrimidine derivatives bearing various substituents at alkynyl moiety was prepared by the Sonogashira cross-coupling reaction of 2,4-diamino-6-iodopyrimidine using Pd(PPh3)2Cl2 as catalyst. | | Synthesis | The general procedure for the synthesis of 2-amino-4,6-dichloropyrimidine from 2-amino-4,6-dihydroxypyrimidine is as follows: in a four-necked flask equipped with a reflux condenser, 510 g of 2-amino-4,6-dihydroxypyrimidine (98% purity, 4 mol) and 1428 g of phosphorus triclosan (99% purity) were added, heated and stirred. 810 g of triethylamine (99% purity) was slowly added dropwise at 40 to 45 °C through a constant pressure dropping funnel. After the dropwise addition, the reaction temperature was raised to 85 to 90 °C and maintained at this temperature for 2 hours. The progress of the reaction was monitored by high performance liquid chromatography (HPLC) and the reaction was considered complete when the amount of 2-amino-4,6-dihydroxypyrimidine was less than 1%. Subsequently, 3000 g of toluene was added to the reaction mixture, cooled to 0-10°C, and 3000 g of ice-water mixture was added for low temperature hydrolysis. The mixture was then warmed to room temperature and left to stratify. The aqueous layer was extracted twice with 400 g of toluene, and the organic phases were combined and washed sequentially with aqueous sodium carbonate and water until neutral. The organic phase was concentrated and 1800 g of toluene was recovered to give 2668 g of highly concentrated toluene solution. The product was analyzed by HPLC, the purity was 96.8%, the content was 22.58% (external standard method), and the yield of crude product was 92%. | | References | [1] Patent: CN108395409, 2018, A. Location in patent: Paragraph 0046-0047; 0050
[2] Organic Letters, 2009, vol. 11, # 1, p. 61 - 64
[3] Chemical Communications, 2017, vol. 53, # 18, p. 2689 - 2692
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 47, p. 10087 - 10094
[5] Tetrahedron Letters, 2015, vol. 56, # 10, p. 1179 - 1182 |
| | 2-Amino-4,6-dichloropyrimidine Preparation Products And Raw materials |
| Raw materials | Triethylamine-->4,6-Dihydroxypyrimidine-->2-Amino-4,6-dihydroxypyrimidine | | Preparation Products | Bensulfuron methyl-->2-Amino-4,6-dimethoxypyrimidine-->2-AMINO-4-HYDROXY-6-HYDRAZINOPYRIMIDINE-->4-(4,6-Dichloropyrimidin-2-yl)morpholine-->4-chloro-6-(2,3-dichlorophenyl)pyrimidin-2-amine-->6-Chloro-N~4~-ethylpyrimidine-2,4-diamine-->2-AMINO-4-HYDROXY-6-IODOPYRIMIDINE-->5-ETHYLCYCLOHEXANE-1,3-DION-->2-AMINO-4-CHLORO-6-GUANIDINOPYRIMIDINE-->4-Chloro-6-hydrazinylpyrimidin-2-amine-->2-Amino-4,6-dimercaptopyrimidine-->N4,N6-dimethyl-pyrimidine-2,4,6-triamine-->4-CHLORO-6-MORPHOLIN-4-YLPYRIMIDIN-2-AMINE |
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