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
$10.64
Updated
2024/03/01
TCI Chemical
Product number
B2847
Product name
5-Bromo-2-chloropyrimidine
Purity
>97.0%(GC)
Packaging
1g
Price
$18
Updated
2024/03/01
TCI Chemical
Product number
B2847
Product name
5-Bromo-2-chloropyrimidine
Purity
>97.0%(GC)
Packaging
5g
Price
$26
Updated
2024/03/01
Alfa Aesar
Product number
L18360
Product name
5-Bromo-2-chloropyrimidine, 98+%
Packaging
5g
Price
$109.65
Updated
2024/03/01
Alfa Aesar
Product number
L18360
Product name
5-Bromo-2-chloropyrimidine, 98+%
Packaging
1g
Price
$31.6
Updated
2022/04/27
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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].

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

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
Hebei Zhuanglai Chemical Trading Co Ltd
Product
5-Bromo-2-chloropyrimidine 32779-36-5
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 ton
Release date
2024-11-12
Hebei Weibang Biotechnology Co., Ltd
Product
5-Bromo-2-chloropyrimidine 32779-36-5
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-20

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

2-Chloropyrimidine 3-Bromoanisole 5-Bromopyrimidine 5-Bromo-2-iodopyrimidine Chlorobromoisocyanurate 1-Bromo-3-chloro-5,5-dimethylhydantoin 4-BENZYLOXY-5-BROMO-2-CHLOROPYRIMIDINE 4-AMINO-5-BROMO-2-CHLOROPYRIMIDINE, 95+%,4-AMINO-5-BROMO-2-CHLOROPYRIMIDINE 5-Bromo-2,4-dichloropyrimidine 5-Bromo-2,4-dichloro-6-methylpyrimidine 5-BROMO-2-CHLORO-4-METHOXYPYRIMIDINE Bromochloromethane 5-Bromo-2-chloro-4-(dimethylamino)pyrimidine 5-bromo-2-chloro-4-morpholinopyrimidine 5-BROMO-2-CHLORO-4-(1-PIPERIDINYL)PYRIMIDINE 2-Bromo-5-chloropyrimidine 2-Chloro-4-bromopyridine Bromine

  • PYRIMIDINE, 5-BROMO-2-CHLORO-
  • 2-chloro-5-broMopyriMidine(5-broMo-2-chloropyriMidine)
  • 2-chloro -5-broMo - uracil
  • 5 - broMine - 2 - chloro pyriMidine
  • 5-methyl-4,5-dihydrothiazol-2-amine
  • Macitentan Intermediate 5
  • Macitentan Impurity 27
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  • 5-BROMO-2-CHLOROPYRIMIDNE
  • 5-BROMO-2-CHLOROPYRIMIDINE(MINIMUM85%)
  • MAJORIMPURITYIS2,5-DIBROMOPYRIMIDINE
  • 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)
  • Macitentan Impurity 27 CRS
  • 5-Bromo-2-chloropyrimidine2C5BP
  • 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