| Identification | More | [Name]
2-AMINO-5-IODOPYRIMIDINE | [CAS]
1445-39-2 | [Synonyms]
2-AMINO-5-IODOPYRIMIDINE
5-Iodo-2-pyrimidinamine | [EINECS(EC#)]
625-750-1 | [Molecular Formula]
C4H4IN3 | [MDL Number]
MFCD01075666 | [Molecular Weight]
221 | [MOL File]
1445-39-2.mol |
| Chemical Properties | Back Directory | [Appearance]
cream to brown crystalline powder | [Melting point ]
219 °C | [Boiling point ]
364.9±34.0 °C(Predicted) | [density ]
2.204±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder | [pka]
2.08±0.10(Predicted) | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C4H4IN3/c5-3-1-7-4(6)8-2-3/h1-2H,(H2,6,7,8) | [InChIKey]
HAFKCGZQRIIADX-UHFFFAOYSA-N | [SMILES]
C1(N)=NC=C(I)C=N1 | [CAS DataBase Reference]
1445-39-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HS Code ]
2933599590 |
| Hazard Information | Back Directory | [Chemical Properties]
cream to brown crystalline powder | [Uses]
2-Amino-5-iodopyrimidine is used as a reactant in the synthesis of aminopyrimidine and cyclic guanidine amino acids. | [Synthesis]
General procedure for the synthesis of 2-amino-5-iodopyrimidine from 2-aminopyrimidine: a mixture of 2-aminopyrimidine (2.4 g, 25 mmol, 1.0 eq.) and elemental iodine (2.7 g, 10.7 mmol, 0.43 eq.) was dissolved in 60 mL of glacial acetic acid, followed by the addition of periodate (0.86 g, 3.76 mmol, 0.15 eq.) and 0.5 mL of concentrated sulfuric acid dissolved in 3 mL of water. The reaction mixture was heated to 80 °C and maintained for 24 h under nitrogen protection. Upon completion of the reaction, the reaction mixture was poured into saturated aqueous sodium thiosulfate solution until the solution was clarified (200 mL each time for 3 times) and then extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography afforded 2-amino-5-iodopyrimidine (1.4 g, 22.2% yield) as a white solid. | [References]
[1] Heterocycles, 1984, vol. 22, # 5, p. 1195 - 1210
[2] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7468 - 7474
[3] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
[4] Synthesis, 1984, # 3, p. 252 - 254
[5] Patent: CN105622638, 2016, A. Location in patent: Paragraph 0362 |
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