5-(4-Bromophenyl)-4,6-dichloropyrimidine
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5-(4-Bromophenyl)-4,6-dichloropyrimidine
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CAS No:
146533-41-7
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Formula:
C10H5BrCl2N2
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Chemical Name:
5-(4-Bromophenyl)-4,6-dichloropyrimidine
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Synonyms:
Pyrimidine,5-(4-bromophenyl)-4,6-dichloro-;5-(4-Bromophenyl)-4,6-dichloropyrimidine;4,6-Dichloro-5-(4-bromophenyl)pyrimidine
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CAS No:
Safety Information
|Warning|H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 5 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-(4-Bromophenyl)-4,6-dichloropyrimidine Use and Manufacturing
A stirred solution of 100 g 5-(4-bromophenyl)pyrimidine-4, 6–diol (11, 0.374 mol) was added to 300 cm3 phosphorousoxy chloride. The reaction mass was heated to 90 Cand maintained until completion (monitored by HPLC).After completion of the reaction, the reaction mass wascooled to 10–15 C and quenched over water below 15 C.The obtained solid was filtered and washed with water until the pH of the filtrate became 6.5–7.0. The material was dried under reduced pressure at 65 C to obtain the crudesolid. The crude solid was further recrystallized in methanol and the obtained solid was filtered and dried toprovide 2. Yield: 90 g (79percent); purity by HPLC: 99.7percent;m.p.: 100–103 C. The spectral data of compound 2 werefound to agree with the reported data [8].Triethyl amine (130 mL) was added to a mixture of 5-(4-bromophenyl)-pyrimidine-4, 6-diol (100 g), phosphoryl chloride (400 mL) and acetonitrile (600 mL) at 25-35°C under nitrogen atmosphere for a period of 60 mins. The reaction mass was heated to 80-85°C and stirred for 4 hrs. The reaction mass was distilled off under vacuum at below 75°C followed by stripped off with acetonitrile. The reaction mass was cooled to 10-15°C, water (500 mL) was added and stirred for 30 mins. Aqueous hydrochloric acid (2N, 500 ml) was added to the reaction mass at 10-15°C and stirred for 30 mins. The solid obtained was filtered, washed with water and dried under vacuum at 40-45°C for 6 hrs to get the title compound. Yield: 100 g; purity by HPLC: 99.0percent
Computed Properties
Molecular Weight:303.97
XLogP3:4.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:301.90132
Monoisotopic Mass:301.90132
Topological Polar Surface Area:25.8
Heavy Atom Count:15
Complexity:200
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-(4-Bromophenyl)-4,6-dichloropyrimidine
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