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CAS No.: | 7752-82-1 |
---|---|
Name: | 2-Amino-5-bromopyrimidine |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C4H4BrN3 |
Molecular Weight: | 174 |
Synonyms: | 2-Pyrimidinamine, 5-bromo-;5-Bromo-2-pyrimidinamine;5-bromo-pyrimidin-2-ylamine;5-bromopyrimidin-2-amine;Pyrimidine, 2-amino-5-bromo-;ethyl 6-chloropyridazine-3-carboxylate;5-Bromopyrimidin-2-ylamine;5-Bromo-2-aminopyrimidine;2-Pyrimidinamine, 5-bromo-;5-Brom-2-pyrimidinamin;5-bromopyrimidin-2-amine; |
EINECS: | 629-581-4 |
Density: | 1.844 g/cm3 |
Melting Point: | 241-243 °C(lit.) |
Boiling Point: | 340.743 °C at 760 mmHg |
Flash Point: | 159.876 °C |
Solubility: | insoluble in water |
Appearance: | yellow solid |
Hazard Symbols: | Xi,N,Xn |
Risk Codes: | 22-36-50/53 |
Safety: | 26-60-61 |
Transport Information: | UN 3077 9/PG 3 |
PSA: | 51.80000 |
LogP: | 1.40250 |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.0833333h; | 100% |
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.5h; | 98% |
With N-Bromosuccinimide In acetonitrile at 20℃; Cooling with ice; Darkness; | 97% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 20℃; Darkness; Cooling with ice; | 97% |
2‐aminopyrimidine‐1‐oxide
A
5-bromo-2-aminopyrimidine
B
5-bromo-2-aminopyrimidine 1-oxide
Conditions | Yield |
---|---|
With hydrogen bromide; sodium nitrite | A 26.7% B 30% |
Conditions | Yield |
---|---|
In ethanol at 80℃; Sealed tube; |
5-bromo-2-aminopyrimidine
1,2-bis-(chlorodimethylsilyl)ethane
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at -10 - 0℃; for 1h; Inert atmosphere; | 100% |
5-bromo-2-aminopyrimidine
N,N-dimethylacetamide dimethyl acetal
Conditions | Yield |
---|---|
In ethanol at 120℃; for 18h; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 2h; Suzuki coupling; | 95% |
With potassium phosphate; palladium diacetate In ethylene glycol at 80℃; for 12h; | 50.5% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90℃; for 16h; Inert atmosphere; | 28.5% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 8h; Heating / reflux; |
5-bromo-2-aminopyrimidine
4-fluoroboronic acid
2-amino-5-(4-fluorophenyl)pyrimidine
Conditions | Yield |
---|---|
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 3h; Suzuki coupling; | 95% |
5-bromo-2-aminopyrimidine
di-tert-butyl dicarbonate
2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine
Conditions | Yield |
---|---|
With pyridine at 70℃; | 93% |
With pyridine at 70℃; for 16h; | 93% |
With dmap In tetrahydrofuran at 20℃; Inert atmosphere; | 86% |
5-bromo-2-aminopyrimidine
benzyl bromide
5-bromo-2-dibenzylaminopyrimidine
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-aminopyrimidine With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere; | 92% |
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The 2-Amino-5-bromopyrimidine, with the CAS registry number 7752-82-1, has the systematic name of 5-bromopyrimidin-2-amine. And the molecular formula of this chemical is C4H4BrN3. It is a kind of yellow solid, and belongs to the following product categories: Fine chemical & intermediates; Amines and Anilines; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; Organohalides; Aromatics Compounds; Aromatics; Bases & Related Reagents; Nucleotides; Halides; Pyrazines, Pyrimidines & Pyridazines; Building Blocks; Halogenated Heterocycles. What's more, it should be stored in the refrigerator.
The physical properties of 2-Amino-5-bromopyrimidine are as following: (1)ACD/LogP: 0.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.465; (4)ACD/LogD (pH 7.4): 0.465; (5)ACD/BCF (pH 5.5): 1.328; (6)ACD/BCF (pH 7.4): 1.329; (7)ACD/KOC (pH 5.5): 42.643; (8)ACD/KOC (pH 7.4): 42.655; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 51.8 Å2; (13)Index of Refraction: 1.649; (14)Molar Refractivity: 34.362 cm3; (15)Molar Volume: 94.346 cm3; (16)Polarizability: 13.622×10-24cm3; (17)Surface Tension: 68.982 dyne/cm; (18)Density: 1.844 g/cm3; (19)Flash Point: 159.876 °C; (20)Enthalpy of Vaporization: 58.433 kJ/mol; (21)Boiling Point: 340.743 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Uses of 2-Amino-5-bromopyrimidine: It can react with N-allyl-phthalimide to produce 2-[3-(2-amino-pyrimidin-5-yl)-allyl]-isoindole-1,3-dione. This reaction will need reagents palladium acetate, triethylamine and tri-o-tolylphosphine. The reaction time is 18 hours with temperature of 100°C, and the yield is about 100%.
You should be cautious while dealing with this chemical. It irritates eyes and harmful if swallowed. It is also very toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic. Therefore, you had better take the following instructions: In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; This material and/or its container must be disposed of as hazardous waste; Avoid release to the environment. Refer to special instructions safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: c1c(cnc(n1)N)Br
(2)InChI: InChI=1/C4H4BrN3/c5-3-1-7-4(6)8-2-3/h1-2H,(H2,6,7,8)
(3)InChIKey: UHRHPPKWXSNZLR-UHFFFAOYAH