5-(4-Bromophenyl)-4,6-dichloropyrimidine
Uses- Product Name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- CAS No.
- 146533-41-7
- Chemical Name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- Synonyms
- macitentan INT;5-(4-broMophenyl)-4;MacitentanImpurity44;Macitentan Impurity 26;Macitentan Intermediate 1;Macitentan Impurity 26 CRS;potassiuM (N-propylsulfaMoyl)aMide;(4-broMophenyl)-4,6-dichloroPyriMidine;5-(4-Bromophenyl)-4,6-dichloro-Pyrimidin;5-(4-broMophenyl)-4,6-dichloropyriMidine
- CBNumber
- CB42624288
- Molecular Formula
- C10H5BrCl2N2
- Formula Weight
- 303.97
- MOL File
- 146533-41-7.mol
5-(4-Bromophenyl)-4,6-dichloropyrimidine Property
- Melting point:
- 98.0 to 102.0 °C
- Boiling point:
- 368.7±42.0 °C(Predicted)
- Density
- 1.677±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly)
- form
- Solid
- pka
- -4.92±0.26(Predicted)
- color
- Off-White
- InChI
- InChI=1S/C10H5BrCl2N2/c11-7-3-1-6(2-4-7)8-9(12)14-5-15-10(8)13/h1-5H
- InChIKey
- WEEFLZORZXLIJE-UHFFFAOYSA-N
- SMILES
- C1=NC(Cl)=C(C2=CC=C(Br)C=C2)C(Cl)=N1
Safety
- HS Code
- 2933599590
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
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.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- B4950
- Product name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $124
- Updated
- 2024/03/01
- Product number
- B687865
- Product name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- Packaging
- 2.5g
- Price
- $130
- Updated
- 2021/12/16
- Product number
- B687865
- Product name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- Packaging
- 500mg
- Price
- $50
- Updated
- 2021/12/16
- Product number
- B687865
- Product name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- Packaging
- 25g
- Price
- $645
- Updated
- 2021/12/16
- Product number
- 3H32-D-72
- Product name
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine
- Purity
- 97%
- Packaging
- 5G
- Price
- $240
- Updated
- 2021/12/16
5-(4-Bromophenyl)-4,6-dichloropyrimidine Chemical Properties,Usage,Production
Uses
5-(4-Bromophenyl)-4,6-dichloropyrimidine is a reactant used in the synthesis of Macitentan, an orally active dual endothelin receptor antagonist.
Description
5 - (4-Bromophenyl)-4, 6- dichloropyrimidine is a key intermediate and has a wide range of applications in the pharmaceutical and chemical fields.
Uses
5-(4-Bromophenyl)-4,6-dichloropyrimidine is a reactant used in the synthesis of Macitentan, an orally active dual endothelin receptor antagonist.
Synthesis
Dimethyl 2-(4-bromophenyl) malonate (6)
A solution of methyl 2-(4-bromophenyl)acetate (5) (206.8 g, 0.9 mol) in THF (400mL), then it
was added drop-wise to a suspension of sodium hydride (65.0 g,2.71 mol) in THF solution(1000mL)
at room temperature, control the drip rate and the temperature was kept 25 ~ 27 , when dropping ??
was completed, keep the temperature for 1h, then dimethyl carbonate (DMC) (325.1 g, 3.6 mol) was
added, keep the reaction for 14 h. After cooling to -10 , the s ?? olution is adjusted to pH 6~7 using
hydrochloric acid (36%) then removed THF under reduced pressure, ethyl acetate (1600mL) was
added to the solution, the organic phase was washed with hydrochloric acid solution (1 mol/L, 36%)
saturated brine and was dried by magnesium sulfate, then it was distilled under reduced pressure to
afford yellow oil. The yellow oil was solidified by cyclohexane, after mixture was filtered and
driedto obtain yellow solid, then re-crystallized with ethanol- acetone (5:2) to obtain 6 as white
solid (192.9 g).yield: 72.3%. M.p.77-79 , ?? MS; 308.8 [M + Na] +
, 596.7[2M+Na]+
.
5-(4-Bromophenyl) pyrimidine-4, 6-diol (7)
Sodium (46.9g, 2.0mol) was slowly added into methanol (600mL) at 0 . Dimethyl ?? ¨C 2 - ( 4
¨Cbromophenyl ) malonate(192.9g,0.67mol) was dissolved in methanol (380mL) added into the
solution of sodium methoxide, after dropping, keep the reaction for 1h at roo was added, heated to
40 for 3.5 h. After cooling to room temperature, methanol was ?? distilled off under reduced
pressure, the solution of citric acid was added into the residue and stirred for 1 hours. The
precipitated solid was suction filtered, and the solid w m temperature, then formamidineas washed
with water, then dried to give a yellow solid. The crude product was added into cyclohexane
(900mL) was stirred for 3h at room temperature, then the precipitated solid was suction filtered, the
solid was washed with cyclohexane and dried to obtain7 as light yellow solid (149.1 g ,84.4%).
M.p.178-180 ??; MS; 269.0[M+H] +
, 288.9[M + Na] +
.
5-(4-Bromophenyl)-4, 6-dichloropyrimidine (1)
5-(4-Bromophenyl) pyrimidine-4, 6-diol (53.4g, 0.2mol) was slowly added into POCl3 (427mL),
refluxed for 8h. POCl3 was distilled off under reduced pressure, then the black viscous residue was
poured into ice water (1000mL), The solution was adjusted to pH9~10 using potassium carbonate.
The product was filtered off, washed with water and dried under reduced pressure to afford
5-(4-bromophenyl)-4, 6-dichloropyrimidine (1) as white solid (52.6 g, 86.5%). M. P. 101 -102 , ??
MS: 302 [M+H] +
; 1 H -NMR (300 MHz, DMSO-d 6 ) |? 8.96(s, 1H,Ar-H), 7.72(d, J = 8.5 Hz, 2H,
Ar-H), 7.39(d, J = 8.5Hz, 2H, Ar-H).
5-(4-Bromophenyl)-4,6-dichloropyrimidine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-(4-Bromophenyl)-4,6-dichloropyrimidine manufacturers
- Product
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine 146533-41-7
- Price
- US $5.00-0.10/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-09
- Product
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine 146533-41-7
- Price
- US $26.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000 tons
- Release date
- 2023-03-22
- Product
- 5-(4-Bromophenyl)-4,6-dichloropyrimidine 146533-41-7
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10tons
- Release date
- 2020-07-17