| Identification | More | [Name]
2-Amino-4,6-dichloropyrimidine | [CAS]
56-05-3 | [Synonyms]
2-AMINO-4,6-DICHLOROPYRIMIDINE
2-PYRIMIDINAMINE, 4,6-DICHLORO-
4,6-dichloro-2-pyrimidinamine
4,6-DICHLOROPYRIMIDIN-2-AMINE
4,6-DICHLORO-PYRIMIDIN-2-YLAMINE
ADCP
AKOS 90013
LABOTEST-BB LT00080771
TIMTEC-BB SBB003919
2-amino-4,6-dichloro-pyrimidin
4,6-dichloro-2-pyrimidinamin
py11
2-AMINO-4-6-DICHLOROPYRIMIDINECRYSTALLIN E
2-amino-4,6-dichoropyrimidine
2-AMINO-4,6-DICHLOROPYRIMIDINE 95+%
2-AMINO-4,6-DICHLOROPYRIMIDINE 97+%
Pyrimidine, 2-amino-4,6-dichloro-
2-AMINO-4,6-DICHLOROPYRIMIDINE, TECH. 95%
4,6-Dichloro-2-aminopyrimidine | [EINECS(EC#)]
200-253-9 | [Molecular Formula]
C4H3Cl2N3 | [MDL Number]
MFCD00006090 | [Molecular Weight]
163.99 | [MOL File]
56-05-3.mol |
| Chemical Properties | Back Directory | [Appearance]
LIGHT BROWN CRYSTALLINE POWDER | [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 | [form ]
Liquid | [pka]
0.14±0.10(Predicted) | [color ]
Clear colorless to light yellow | [Water Solubility ]
Insoluble in water, soluble in acetone, two monomer (VCM) and thermal toluene. | [Detection Methods]
HPLC,NMR | [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]
56-05-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
UV6260485
| [F ]
10 | [TSCA ]
T | [HazardClass ]
IRRITANT | [HS Code ]
29335995 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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