| Identification | More | [Name]
5-Bromo-2-iodopyrimidine | [CAS]
183438-24-6 | [Synonyms]
5-BROMO-2-IODOPYRIMIDINE
5-Bromo-iodopyrimidine
5-Brmo-2-iodopyrimidine | [EINECS(EC#)]
626-839-8 | [Molecular Formula]
C4H2BrIN2 | [MDL Number]
MFCD01318111 | [Molecular Weight]
284.88 | [MOL File]
183438-24-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
99-103 °C (lit.) | [Boiling point ]
341.0±34.0 °C(Predicted) | [density ]
2.495±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
-2.56±0.22(Predicted) | [color ]
White to tan | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C4H2BrIN2/c5-3-1-7-4(6)8-2-3/h1-2H | [InChIKey]
ZEZKXPQIDURFKA-UHFFFAOYSA-N | [SMILES]
C1(I)=NC=C(Br)C=N1 | [CAS DataBase Reference]
183438-24-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H315-H318 | [Precautionary statements ]
P264-P270-P280-P301+P312-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin .
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 .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT, LIGHT SENSITIVE | [HS Code ]
29335900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
5-Bromo-2-iodopyrimidine can be used to synthesize 5,5′-dibromo-2,2′-bipyrimidine and O,O′-dimethyl hyrtinadine A. | [General Description]
5-Bromo-2-iodopyrimidine can be synthesized by reacting 5-bromo-2-chloropyrimidine with hydroiodic acid. | [Synthesis]
General procedure for the synthesis of 5-bromo-2-iodopyrimidine from 5-bromo-2-chloropyrimidine: 5-bromo-2-chloropyrimidine (5.80 g, 30 mmol) and sodium iodide (7.5 g, 50 mmol) were suspended in chloroform (20 mL), and hydriodic acid (57 wt%, 2.85 g, 25.6 mmol) was slowly added at 0 °C. After cooling was withdrawn, the reaction mixture was stirred at room temperature for 20 hours. Subsequently, the reaction mixture was poured into a mixture of 200 mL of ice water with 30 mL of 10 N sodium hydroxide solution. Chloroform (150 mL) was added and stirred for 10 minutes. The organic phase was separated and the aqueous layer was extracted with chloroform (2 x 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 5-bromo-2-iodopyrimidine as a light yellow solid. Yield: 6.29 g (84%). Mass spectrum (MS): M = 284.8 (ESI+). 1H-NMR (300 MHz, CDCl3): δ 8.54 (s, 2H), 7.56 (d, J = 16.4 Hz, 1H), 7.59-7.66 (m, 4H). | [References]
[1] Angewandte Chemie - International Edition, 1999, vol. 38, # 5, p. 659 - 661
[2] Patent: US2005/222228, 2005, A1. Location in patent: Page/Page column 15-16
[3] Chemical Communications, 1996, # 24, p. 2719 - 2720
[4] Patent: US2012/238751, 2012, A1. Location in patent: Page/Page column 30
[5] Patent: WO2014/43272, 2014, A1. Location in patent: Paragraph 0411; 0412; 0413 |
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