Product Name

  • Name

    2-Amino-5-bromopyrimidine

  • EINECS 629-581-4
  • CAS No. 7752-82-1
  • Article Data27
  • CAS DataBase
  • Density 1.844 g/cm3
  • Solubility insoluble in water
  • Melting Point 241-243 °C(lit.)
  • Formula C4H4BrN3
  • Boiling Point 340.743 °C at 760 mmHg
  • Molecular Weight 174
  • Flash Point 159.876 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance yellow solid
  • Safety 26-60-61
  • Risk Codes 22-36-50/53
  • Molecular Structure Molecular Structure of 7752-82-1 (2-Amino-5-bromopyrimidine)
  • Hazard Symbols IrritantXi,DangerousN,HarmfulXn
  • 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;
  • PSA 51.80000
  • LogP 1.40250

Synthetic route

2-aminopyrimidine
109-12-6

2-aminopyrimidine

5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

Conditions
ConditionsYield
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%
2-aminopyridine
504-29-0

2-aminopyridine

5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 20℃; Darkness; Cooling with ice;97%
2‐aminopyrimidine‐1‐oxide
35034-15-2

2‐aminopyrimidine‐1‐oxide

A

5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

B

5-bromo-2-aminopyrimidine 1-oxide
84539-23-1

5-bromo-2-aminopyrimidine 1-oxide

Conditions
ConditionsYield
With hydrogen bromide; sodium nitriteA 26.7%
B 30%
ammonia
7664-41-7

ammonia

5-Bromo-2-chloropyrimidine
32779-36-5

5-Bromo-2-chloropyrimidine

5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

Conditions
ConditionsYield
In ethanol at 80℃; Sealed tube;
5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

1,2-bis-(chlorodimethylsilyl)ethane
13528-93-3

1,2-bis-(chlorodimethylsilyl)ethane

5-bromo-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyrimidine

5-bromo-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyrimidine

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at -10 - 0℃; for 1h; Inert atmosphere;100%
5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

N,N-dimethylacetamide dimethyl acetal
18871-66-4

N,N-dimethylacetamide dimethyl acetal

N'-(5-bromopyrimidin-2-yl)-N,N-dimethylacetamidine

N'-(5-bromopyrimidin-2-yl)-N,N-dimethylacetamidine

Conditions
ConditionsYield
In ethanol at 120℃; for 18h; Sealed tube;98%
5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

phenylboronic acid
98-80-6

phenylboronic acid

5-phenyl-pyrimidin-2-ylamine
31408-23-8

5-phenyl-pyrimidin-2-ylamine

Conditions
ConditionsYield
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
7752-82-1

5-bromo-2-aminopyrimidine

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-amino-5-(4-fluorophenyl)pyrimidine
31408-40-9

2-amino-5-(4-fluorophenyl)pyrimidine

Conditions
ConditionsYield
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 3h; Suzuki coupling;95%
5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine
209959-33-1

2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine

Conditions
ConditionsYield
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
7752-82-1

5-bromo-2-aminopyrimidine

benzyl bromide
100-39-0

benzyl bromide

5-bromo-2-dibenzylaminopyrimidine
886366-28-5

5-bromo-2-dibenzylaminopyrimidine

Conditions
ConditionsYield
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%

2-Amino-5-bromopyrimidine Specification

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%. 

2-Amino-5-bromopyrimidine can react with N-allyl-phthalimide to produce 2-[3-(2-amino-pyrimidin-5-yl)-allyl]-isoindole-1,3-dione

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

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