ChemicalBook > CAS DataBase List > 5-Bromo-2-chloropyrimidine

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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
596949
Product name
5-Bromo-2-chloropyrimidine
Purity
96%
Packaging
1g
Price
$21.84
Updated
2025/07/31
TCI Chemical
Product number
B2847
Product name
5-Bromo-2-chloropyrimidine
Purity
>97.0%(GC)
Packaging
1g
Price
$20
Updated
2025/07/31
TCI Chemical
Product number
B2847
Product name
5-Bromo-2-chloropyrimidine
Purity
>97.0%(GC)
Packaging
5g
Price
$28
Updated
2025/07/31
Sigma-Aldrich
Product number
596949
Product name
5-Bromo-2-chloropyrimidine
Purity
96%
Packaging
5g
Price
$64.47
Updated
2025/07/31
TCI Chemical
Product number
B2847
Product name
5-Bromo-2-chloropyrimidine
Purity
>97.0%(GC)
Packaging
25g
Price
$99
Updated
2025/07/31
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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

5-BROMO-2-ETHOXY-PYRIMIDINE 5-Bromopyrimidine-2-carbonitrile 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE 5-BROMOPYRIMIDINE-2-CARBOXYLIC ACID (5-BROMO-PYRIMIDIN-2-YL)-DIETHYL-AMINE 5-BROMO-2-(METHYLAMINO)PYRIMIDINE 5-BROMO-2-(PYRROLIDIN-1-YL)PYRIMIDINE
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View Lastest Price from 5-Bromo-2-chloropyrimidine manufacturers

Jinan Ruitong Biotech Co., Ltd.
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
Anhui Dexinjia Biopharm Co., Ltd
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
WUHAN FORTUNA CHEMICAL CO., LTD
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

32779-36-5, 5-Bromo-2-chloropyrimidineRelated Search:

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  • PYRIMIDINE, 5-BROMO-2-CHLORO-
  • 2-chloro-5-broMopyriMidine(5-broMo-2-chloropyriMidine)
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  • 5-BROMO-2-CHLOROPYRIMIDINE(MINIMUM95%)
  • 5-Bromo-2-chloropyrimidine 85%
  • 2-CHLORO-5-BROMOPYRIMIDINE
  • 2C5BP
  • 5-Bromo-2-chloropyrimidine, 98+%
  • 5-Bromo-2-chloropyrimidine,96%
  • 5-Bromo-2-chloro-1,3-diazine
  • 5-Bromo-2-chL
  • e 5-Bromo-2-chloropyrimidine
  • 5-Bromo-2-chloropyrimidine &gt
  • -bromo-2-chloropyrimidine
  • 5-bromo-2-chlorpyrimidine
  • 5-broMine-2-chChemicalbookloropyriMidine
  • 5-Bromo-2-Chloropyrimidine (Intermediate of Masetitan)
  • 5-Bromo-2-chloropyrimidine2C5BP
  • Macitentan Impurity 27 CRS
  • 32779-36-5
  • 32799-36-5
  • C4H2BrClN2
  • C4H2ClBrN2
  • C4H2BrCIN2
  • C4H2N2BrCl
  • Building Blocks
  • Pyrimidines
  • Heterocyclic Building Blocks
  • Halogenated Heterocycles
  • Pyridines, Pyrimidines, Purines and Pteredines
  • pharmacetical
  • Pyrazines, Pyrimidines & Pyridazines
  • Pyrimidine
  • Pyrimidine Series
  • Halides
  • Heterocycles
  • Pyrazines, Pyrimidines & Pyridazines
  • Building Blocks
  • Halogenated Heterocycles
  • Heterocyclic Building Blocks
  • Pyrimidines
  • PyrimidinesHeterocyclic Building Blocks
  • Variety of halogenated heterocyclic series
  • Halogenated
  • Organohalides
  • Heterocycle-Pyrimidine series
  • Pharmaceutical intermediates
  • Thiophenes
  • Building Blocks
  • C4 to C5