5-Bromo-2-chloropyrimidine
- Product Name
- 5-Bromo-2-chloropyrimidine
- CAS No.
- 32779-36-5
- Chemical Name
- 5-Bromo-2-chloropyrimidine
- Synonyms
- 2-CHLORO-5-BROMOPYRIMIDINE;2C5BP;5-Bromo-2-chL;Macitentan Impurity 27;Macitentan Intermediate 5;5-BROMO-2-CHLOROPYRIMIDNE;-bromo-2-chloropyrimidine;5-bromo-2-chlorpyrimidine;5-BROMO-2-CHLOROPYRIMIDINE;2-chloro -5-broMo - uracil
- CBNumber
- CB4748175
- Molecular Formula
- C4H2BrClN2
- Formula Weight
- 193.43
- MOL File
- 32779-36-5.mol
5-Bromo-2-chloropyrimidine Property
- Melting point:
- 73-79 °C (lit.)
- Boiling point:
- 95°C 15mm
- Density
- 1.859±0.06 g/cm3(Predicted)
- Flash point:
- 95°C/15mm
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- pka
- -2.84±0.22(Predicted)
- form
- Crystalline Powder
- color
- Off-white to beige
- Water Solubility
- insoluble
- BRN
- 507955
- Stability:
- Hygroscopic
- InChI
- InChI=1S/C4H2BrClN2/c5-3-1-7-4(6)8-2-3/h1-2H
- InChIKey
- XPGIBDJXEVAVTO-UHFFFAOYSA-N
- SMILES
- C1(Cl)=NC=C(Br)C=N1
- CAS DataBase Reference
- 32779-36-5(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/39-37/39-36
- RIDADR
- UN 3335
- WGK Germany
- 3
- HazardClass
- IRRITANT
- HS Code
- 29335990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 596949
- Product name
- 5-Bromo-2-chloropyrimidine
- Purity
- 96%
- Packaging
- 1g
- Price
- $21.84
- Updated
- 2025/07/31
- Product number
- B2847
- Product name
- 5-Bromo-2-chloropyrimidine
- Purity
- >97.0%(GC)
- Packaging
- 1g
- Price
- $20
- Updated
- 2025/07/31
- Product number
- B2847
- Product name
- 5-Bromo-2-chloropyrimidine
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $28
- Updated
- 2025/07/31
- Product number
- 596949
- Product name
- 5-Bromo-2-chloropyrimidine
- Purity
- 96%
- Packaging
- 5g
- Price
- $64.47
- Updated
- 2025/07/31
- Product number
- B2847
- Product name
- 5-Bromo-2-chloropyrimidine
- Purity
- >97.0%(GC)
- Packaging
- 25g
- Price
- $99
- Updated
- 2025/07/31
5-Bromo-2-chloropyrimidine Chemical Properties,Usage,Production
Description
5-Bromo-2-chloropyrimidine is a halogenated pyrimidine analogue containing chloro and bromo substituents at positions 2 and 5 of the benzene ring structure. The compound is used as a pharmaceutical intermediate in the preparation of macitentan, an endothelin receptor antagonist drug for the treatment of pulmonary hypertension.
Chemical Properties
Off-white to beige crystalline powder
Uses
5-Bromo-2-chloropyrimidine is applied as a pharmaceutical intermediate, in the synthesis of pharmaceutical goods such as inhibitors. It is also employed in the cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines.
Uses
5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors.
Preparation
Under nitrogen protection, 35 g (0.2 mol) of 2-hydroxy-5-bromopyrimidine, 61.3 g (0.4 mol) of phosphorus oxychloride, and 200 mL of toluene were added into the reaction flask. At 35 ℃, triethylamine 40.5g was added and then heated up at 80-85 ℃. Stir the reaction for 6 hours, sampling HPLC to detect the raw material (less than 2%), and lower the temperature. After concentrating the mixture under reduced pressure to remove most of the toluene and Phosphorus oxychloride, put the reaction solution into 10°C water, and adjust pH=8-9 with 20% sodium carbonate aqueous solution. Finally, 5-Bromo-2-chloropyrimidine was obtained after purification.
Reactivity Profile
5-Bromo-2-chloropyrimidine, a 2,5-dihalopyrimidine, is a useful organic electrophiles. It could react with tri(3-indolyl)indium reagent through cross-coupling reaction. Other aryl- and heteroarylindium
reagents, such as thiophenyl-, pyridyl-, naphthyl-, and
alkynylindium reagents, also reacted with 5-bromo-2-
chloropyrimidine to afford the corresponding 2-chloro-5-substituted pyrimidines[1].
Synthesis
38353-06-9
32779-36-5
General procedure for the synthesis of 5-bromo-2-chloropyrimidine from 5-bromopyrimidin-2(1H)-one: Phosphoryl chloride (225 mL, 2.4 mol, 1.4 eq.) was slowly added to a reaction flask containing a mixture of 5-bromo-2-hydroxypyrimidine (30 g, 0.17 mol) and dimethylaniline (7.5 mL). The reaction mixture was heated to reflux under nitrogen protection for 4 hours. Upon completion of the reaction, the dark brown reaction mixture was cooled to room temperature and then carefully poured into ice water. The mixture was extracted with ether to separate the organic phase. The organic phase was subsequently washed with sodium bicarbonate solution to remove acidic impurities. The washed organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 5-bromo-2-chloropyrimidine (25 g, 75% yield). [Ref: Goodby, J.W.; Hird, M.; Lewis, R.A.; Toyne, K.J. J. Chem. Soc., Chem. Commun. 1996, 2719.]
References
[1] Mosquera A, et al. Cross-Coupling Reactions of Indium Organometallics with 2,5-Dihalopyrimidines: Synthesis of Hyrtinadine A?. Organic Letters, 2008; 10: 3745–3748.
5-Bromo-2-chloropyrimidine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Bromo-2-chloropyrimidine manufacturers
- Product
- 2-chloro-5-bromopyrimidine 32779-36-5
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1
- Release date
- 2025-08-25
- Product
- 5-Bromo-2-chloropyrimidine 32779-36-5
- Price
- US $100.00-2500.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 2MT per month
- Release date
- 2025-05-19
- Product
- 5-Bromo-2-chloropyrimidine 32779-36-5
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 30tons/month
- Release date
- 2023-02-02