| Identification | More | [Name]
2-AMINO-5-BROMO-3-IODOPYRIDINE | [CAS]
381233-96-1 | [Synonyms]
2-AMINO-5-BROMO-3-IODOPYRIDINE
5-BROMO-3-IODO-PYRIDIN-2-YLAMINE
2-Amino-3-iodo-5-bromopyridine
5-Bromo-3-iodopyridin-2-amine
2-Amine-5-bromo-3-iodopyridine | [Molecular Formula]
C5H4BrIN2 | [MDL Number]
MFCD06659000 | [Molecular Weight]
298.91 | [MOL File]
381233-96-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Brown powder | [Melting point ]
111-112°C | [Boiling point ]
308.2±42.0 °C(Predicted) | [density ]
2.426±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
2.25±0.49(Predicted) | [color ]
White to Yellow to Orange | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C5H4BrIN2/c6-3-1-4(7)5(8)9-2-3/h1-2H,(H2,8,9) | [InChIKey]
XPERZSKJGNUSHI-UHFFFAOYSA-N | [SMILES]
C1(N)=NC=C(Br)C=C1I | [CAS DataBase Reference]
381233-96-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [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 ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37:Wear suitable gloves . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT, LIGHT SENSITIVE | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Brown powder | [Uses]
2-Amino-5-Bromo-3-Iodopyridine is used as an important intermediate of pharmaceuticals and farm chemicals. | [Synthesis]
The general steps for the synthesis of 2-amino-3-iodo-5-bromopyridine from 2-amino-5-bromopyridine are as follows:
Step 1: Iodination reaction
5-Bromo-pyridin-2-ylamine (50 g, 289 mmol) was dissolved in 2 M sulfuric acid (500 mL) and potassium iodate (30.8 g, 144 mmol) was added in batches. The mixture was heated to 100°C and an aqueous solution of potassium iodide (26.5 g, 160 mmol) was added slowly and dropwise (50 mL) over about 1 hour. After 1 hour of reaction, stirring was continued for 30 minutes, followed by cooling to room temperature. The pH of the aqueous phase was adjusted to 8-9 with alkali and then the mixture was extracted with ethyl acetate (3 times). The organic layers were combined and washed sequentially with aqueous sodium thiosulfate, water and brine, dried (Na2SO4) and concentrated to give 2-amino-3-iodo-5-bromopyridine as a brown solid (77.4 g, 90% yield).
NMR data (300 MHz, CDCl3): δ 8.06 (d, J = 2.2 Hz, 1H), 7.96 (d, J = 2.2 Hz, 1H), 4.96 (s, 2H). | [References]
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 10093 - 10096
[2] Angew. Chem., 2013, vol. 52, # 38, p. 10093 - 10096,4
[3] Patent: WO2011/73263, 2011, A1. Location in patent: Page/Page column 78
[4] Patent: WO2012/10538, 2012, A2. Location in patent: Page/Page column 28
[5] Patent: US2012/22258, 2012, A1. Location in patent: Page/Page column 13-14 |
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