| Identification | More | [Name]
5-Bromo-2-hydroxypyrimidine | [CAS]
38353-06-9 | [Synonyms]
5-BROMO-2-PYRIMIDINONE
5-BROMOPYRIMIDIN-2(1H)-ONE
5-bromo-2(1h)-pyrimidinon
5-Bromo-2-Hydroxyprimidine
5-BROMO-2-PYRIMIDINONE 96+%
5-Bromo-1H-pyrimidin-2-one
5-Bromo-2-hydroxypyrimidine
5-bromo-2-hydroxypyridmidine
5-Bromo-1,2-dihydropyrimidine-2-one
5-Bromopyrimidine-2(1H)-one
5-Bromo-pyrimidine-2-ol
5-Bromopyrimidine-2-ol | [EINECS(EC#)]
253-896-2 | [Molecular Formula]
C4H3BrN2O | [MDL Number]
MFCD01318956 | [Molecular Weight]
174.98 | [MOL File]
38353-06-9.mol |
| 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 . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29335990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow solid | [Uses]
5-Bromo-2-hydroxypyrimidine is a compound useful in organic synthesis. | [Synthesis]
5-Bromo-2-hydroxypyrimidine is obtained by brominating 2-hydroxypyrimidine, itself prepared from 1,1,3,3-tetramethoxypropane and urea in concentrated HCl in methanol, with bromine in water at room temperature, followed by in vacuo removal of water, precipitation with water and recrystallization from 90% aqueous ethanol[1][2]. Alternatively, 2-hydroxypyrimidine hydrochloride is brominated with Br2 in concentrated aqueous HCl to give 5-bromo-2-hydroxypyrimidine, which is then chlorinated with POCl3 and N,N-dimethylaniline to 5-bromo-2-chloropyrimidine in 65% overall yield[3]. | [References]
[1] Adhikari, A., Kalluraya, B., Sujith, K. V., Gouthamchandra, K., Jairam, R., Mahmood, R., & Sankolli, R. (2012). Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety. European Journal of Medicinal Chemistry, 55, 467–474. https://doi.org/10.1016/j.ejmech.2012.07.002
[2] Vlád, G., & Horváth, I. T. (2002). Improved Synthesis of 2,2'-Bipyrimidine. The Journal of Organic Chemistry, 67(18), 6550–6552. https://doi.org/10.1021/jo0255781
[3] Pérez-Balado, C., Willemsens, A., Ormerod, D., Aelterman, W., & Mertens, N. (2007). Development of a Concise Scaleable Synthesis of 2-Chloro-5-(pyridin-2-yl) Pyrimidine via a Negishi Cross-Coupling. Organic Process Research & Development, 11(2), 237–240. https://doi.org/10.1021/op060241c |
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