2-Amino-5-bromopyrimidine
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2-Amino-5-bromopyrimidine
structure -
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CAS No:
7752-82-1
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Formula:
C4H4BrN3
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Chemical Name:
2-Amino-5-bromopyrimidine
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Synonyms:
2-Pyrimidinamine,5-bromo-;Pyrimidine,2-amino-5-bromo-;5-Bromo-2-pyrimidinamine;2-Amino-5-bromopyrimidine;5-Bromopyrimidin-2-ylamine;NSC 27269;5-Bromo-2-aminopyrimidine
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CAS No:
Characteristics
51.8
0.5
White to light beige Crystalline Powder, Crystals or Flakes
1.8±0.1 g/cm3
237-238 °C
340.743ºC at 760 mmHg
159.9±25.7 °C
1.649
Insoluble
Refrigerator (+4°C)
Safety Information
III
IRRITANT, IRRITANT-HARMFUL
UN 3077 9/PG 3
3
22-36-50/53
26-60-61
Xn,N,Xi
Harmful
P273-P305 + P351 + P338
H302-H319-H400
|Warning|H302 (81.63%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 49 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Amino-5-bromopyrimidine Use and Manufacturing
The 2-aminopyrimidine (2.5g, 26.29mmol) was dissolved in acetonitrile (25mL) was added N- bromosuccinimide (4.6g, 27.9mmol) under ice-cooling, stirred in the dark overnight at room temperature. Recovery of the solvent under reduced pressure, washed with water (100 mL) was washed, filtered off with suction, and dried in vacuo to give a white solid. Yield: 97percentA 1 L flask was charged with 40 g (0.42 mol) of 2-aminopyrimidine and 840 mL of acetonitrile / 84 mL of DCM was added, and 78.6 g (0.44 mol) of NBS (N-bromosuccinimide) was added thereto at a temperature of 5 ° C for 4 times. The temperature was gradually raised to room temperature and stirred for 24 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, 1000 mL of water and 1000 mL of DCM were added, and the mixture was stirred for 2 hours. The separated organic layer was washed with 500 mL of brine, dried over anhydrous Na2SO4, and concentrated. The concentrate was recrystallized under DCM / Hexane conditions to give 67.5 g (yield: 92.4percent) of a compound as a white solid (Intermediate (19)).5-Thiophen-3-yl-pyrimidin-2-ylamine (A1 ); 2-amino-pyrimidine (1.9 g, 20 mmol) was suspended in 40 mL of dichloromethane and 40 mL of acetonitrile. N-Bromosuccinimide (5.34 g, 30 mmol) was added with stirring. The mixture was stirred for 72 hours at room temperature. The mixture was washed with sodium bisulfite solution, water and chloroform. The precipitate was collected by vacuum filtration and washed with acetone. The solids were dried under vacuum to give 3.2 g (91 percent yield) of 2-amino-5-bromo-pyrimidine as a white solid. 'H-NMR (dimethylsulfoxide-d6) No. 8.28 (s, 2H, aromatic), 6.87 (s, 2H, NH2). MS (m/z) 174 [M+1].A 5 L three-necked round bottom flask was charged with 2-aminopyrimidine (285.30 g, 3 mol), N-bromosuccinimide (1.17 kg, 6.6 mol), acetonitrile 2 L and methanol 1 L. The mixture in the reaction flask was stirred at 70 ° C for 6 hours. TLC and HPLC confirmed the reaction was complete. After the reaction was completed, the solvent was removed by rotary evaporation to give the crude product. The crude product was concentrated by evaporation and recrystallized to give the pure product 2-amino-5-bromopyrimidine. After drying, the yield was 90.48percent and the purity was 99.05percent (HPLC).Preparation
Computed Properties
Molecular Weight:174.00
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:172.95886
Monoisotopic Mass:172.95886
Topological Polar Surface Area:51.8
Heavy Atom Count:8
Complexity:69.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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