2,5-Dibromopyrimidine
- Product Name
- 2,5-Dibromopyrimidine
- CAS No.
- 32779-37-6
- Chemical Name
- 2,5-Dibromopyrimidine
- Synonyms
- 5-Dibromopyrimidine;2,5-dibroMopyriMinde;2,5-dibromopyrimidin;2,5-DIBROMOPYRIMIDINE;Macitentan Impurity 55;2,5-Dibromopyrimidine>Pyrimidine, 2,5-dibromo-;2,5-Dibromopyrimidine, 98%;2,5-DIBROMOPYRIMIDINE, 95+%;2,5-Dibromopyrimidine ISO 9001：2015 REACH
- CBNumber
- CB1449558
- Molecular Formula
- C4H2Br2N2
- Formula Weight
- 237.88
- MOL File
- 32779-37-6.mol
2,5-Dibromopyrimidine Property
- Melting point:
- 83.0 to 87.0 °C
- Boiling point:
- 316.6±34.0 °C(Predicted)
- Density
- 2?+-.0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- soluble in Methanol
- form
- powder to crystal
- pka
- -2.97±0.22(Predicted)
- color
- White to Almost white
- InChI
- InChI=1S/C4H2Br2N2/c5-3-1-7-4(6)8-2-3/h1-2H
- InChIKey
- XAHITOJPIWZJHD-UHFFFAOYSA-N
- SMILES
- C1(Br)=NC=C(Br)C=N1
- CAS DataBase Reference
- 32779-37-6
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-41-36/37/38
- Safety Statements
- 26-39-36/37/39
- WGK Germany
- 3
- HS Code
- 29335990
N-Bromosuccinimide Price
- Product number
- 740381
- Product name
- 2,5-Dibromopyrimidine
- Purity
- 97%
- Packaging
- 1g
- Price
- $104
- Updated
- 2025/07/31
- Product number
- D4225
- Product name
- 2,5-Dibromopyrimidine
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $20
- Updated
- 2025/07/31
- Product number
- D4225
- Product name
- 2,5-Dibromopyrimidine
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $66
- Updated
- 2025/07/31
- Product number
- D426095
- Product name
- 2,5-Dibromopyrimidine
- Packaging
- 250mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- X7051
- Product name
- 2,5-Dibromopyrimidine
- Packaging
- 1g
- Price
- $18
- Updated
- 2021/12/16
2,5-Dibromopyrimidine Chemical Properties,Usage,Production
Chemical Properties
Off-White crystal
Uses
2,5-Dibromopyrimidine is a pyrimidine compound with two reactive groups, bromine atoms, at the 2 and 5 positions. It is used as a raw material for the synthesis of many compounds or pharmaceutical intermediates.
Synthesis
7752-82-1
32779-37-6
General procedure for the synthesis of 2,5-dibromopyrimidines from 2-amino-5-bromopyrimidines: Scheme 1. Preparation of the related pyran(mi)dihalides A-H. The key steps include: (a) Reaction using N-bromosuccinimide (NBS) and ammonium acetate (NH4OAc) in acetonitrile (MeCN) at room temperature for 5 min in 85-90% yield of pyridine (pyr); quantitative yield of pyrimidine (pym); (b) Pyridine: 1-12 h reflux reaction in acetonitrile with aldehyde (RCHO) and sodium cyanoborohydride (Na(CN)BH3) (82% yield, R = C5Hn); pyrimidine: overnight reaction at room temperature in tetrahydrofuran (THF) using sodium hydride (NaH) and alkyl halide (R1) (85% yield, R = Me); (c) Pyridine in 77-83% yield; pyrimidine in 30-40% yield using trimethylbenzylammonium bromide (Me3(Bn)NBr) and tert-butylnitrite (t-BuONO) in dibromomethane (CH2Br2), room temperature reaction overnight; (d) Pyrimidine: 80-85% yield in dichloromethane (CH2Cl2) using hydriodic acid (HI), reacted at 0 °C; (e) i. In water (H2O), using sodium hydroxide (NaOH) and bromine (Br2), reacted at room temperature in 50-60% yield; ii. In phosphorus oxychloride (POCl3) and diethylaniline (PhNEt2), reacted at reflux for 4 hrs in 75-85% yield; iii. In dichloromethane (DCM), using hydriodic acid (HI), reacted at 0°C in 80-85% yield; (f) in alcohol (ROH), using sodium (Na), 1-12 h reaction at room temperature, quantitative yield; (g) Overnight reaction at room temperature using alkyl zinc iodide (RZnI) and dichlorobis(triphenylphosphine)palladium (Cl2Pd(PPh3)2) in N,N-dimethylformamide (DMF)/tetrahydrofuran (THF) in 72% (R = C6H13) yield of pyridine (bromo-substituted) and 81% (R = C6H13) yield of pyrimidine (iodo-substituted); (h) Quantitative yields in acetonitrile using alkynes, cuprous iodide (CuI), dichlorobis(triphenylphosphine)palladium, and triethylamine (Et3N), reacted for 1-12 h at room temperature. Pyrimidinyl bromides were prepared in a similar manner starting from the bromination of 2-aminopyrimidine. N-alkylation could not be achieved by reductive amination (probably due to the reduced nucleophilicity of the amine), but was achieved using sodium hydride and appropriate alkyl halides (B). Non-aqueous diazotization/halogenated deoxidation was used to prepare 5-bromo-2-halogenated pyrimidines, but in reduced yield relative to a similar reaction with 2-aminopyridine (again, possibly due to reduced nucleophilicity of the amine group). Alternatively, the 2-pyrimidinone can be used as a precursor to 5-bromo-2-halogenopyrimidines (Lutz, F.; Kawasaki, T.; Soai, K. Tetrahedron-Asymmetry 2006, 17, 486) or as a substrate for alkylation, yielding 5-bromo-2-alkoxypyrimidines (D) (Kokatla, H.P. Lakshman, M.K. Org. Lett. 2010, 12, 4478). Introduction of an alkynyl substituent at the 2-position (carried out satisfactorily under Sonogashira conditions), but alkylation using Negishi conditions was non-selective. Since bromine was competitively removed upon reduction of 2-alkynylpyrimidinyl bromides (F) to the corresponding 2-alkylpyrimidinyl bromides (H), we turned to 5-bromo-2-iodopyrimidines as precursors for the cross-coupling reaction, with significantly improved selectivity and yield.
References
[1] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6908 - 6916
[2] Patent: WO2012/162818, 2012, A1. Location in patent: Page/Page column 45-46
[3] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
2,5-Dibromopyrimidine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2,5-Dibromopyrimidine manufacturers
- Product
- 2,5-Dibromopyrimidine 32779-37-6
- Price
- US $122.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-01-11
- Product
- 2,5-Dibromopyrimidine 32779-37-6
- Price
- US $0.00/KG
- Min. Order
- 25KG
- Purity
- 99.0%
- Supply Ability
- 5000KG/th
- Release date
- 2023-06-16
- Product
- 2,5-Dibromopyrimidine 32779-37-6
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.00%
- Supply Ability
- 100 Tons Min
- Release date
- 2021-12-01