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CAS No.: | 109-12-6 |
---|---|
Name: | 2-Aminopyrimidine |
Article Data: | 71 |
Molecular Structure: | |
Formula: | C4H5N3 |
Molecular Weight: | 95.1038 |
Synonyms: | pyrimidin-2-amine;2-Pyrimidiylamine;Pyrimidine, 2-amino-;2-Pyrimidinamine;2-Amino-pyrimidine;pyrimidin-2-ylamine; |
EINECS: | 203-648-4 |
Density: | 1.216 g/cm3 |
Melting Point: | 122-126 °C(lit.) |
Boiling Point: | 275.1 °C at 760 mmHg |
Flash Point: | 144.5 °C |
Solubility: | soluble in water |
Appearance: | white to light yellow powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36-37/39 |
Transport Information: | UN 2811 |
PSA: | 51.80000 |
LogP: | 0.64000 |
Conditions | Yield |
---|---|
97% |
Conditions | Yield |
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With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere; | 94% |
nitro-pyrimidine
2-aminopyrimidine
Conditions | Yield |
---|---|
With triethylamine In water at 80℃; for 8h; Inert atmosphere; Green chemistry; chemoselective reaction; | 90% |
With sodium tetrahydroborate In methanol; water at 40℃; for 0.5h; Green chemistry; |
2-chloropyrimidine
O-potassio-2,4-dimethyl-3-pentanone
A
2-aminopyrimidine
B
2,4-Dimethyl-2-pyrimidin-2-yl-pentan-3-one
C
2-(2-chloropyrimidin-4-yl)-2,4-dimethyl-3-pentanone
Conditions | Yield |
---|---|
With ammonia In diethyl ether for 0.25h; Product distribution; Mechanism; Irradiation; effect of inhibitor (di-tert-butyl-nitroxide) and exclusion of light; | A 4% B 88% C n/a |
Conditions | Yield |
---|---|
With potassium amide In diethyl ether; ammonia for 0.25h; exclusion of light; | 88% |
With ammonia at 20℃; Kinetics; | |
With ammonia at 80℃; under 67506.8 Torr; Kinetics; Temperature; |
Conditions | Yield |
---|---|
for 3h; Heating; | 74% |
tetrazolo[1,5-a]pyrimidine
benzene
A
2-aminopyrimidine
B
phenyl-pyrimidin-2-yl-amine
C
biphenyl
Conditions | Yield |
---|---|
With trifluoroacetic acid at 25℃; for 8h; Irradiation; | A 11% B 66% C n/a |
With trifluoroacetic acid at 25℃; for 8h; Product distribution; with/without heavy-atom solvent (CH2CCl2, CH2Br2); other solvent; other reag; other temp.; | A 11% B 66% C n/a |
2-chloropyrimidine
potassium enolate of acetone
A
2-aminopyrimidine
B
1-(2-pyrimidinyl)-2-propanone
Conditions | Yield |
---|---|
With ammonia In diethyl ether for 0.25h; Mechanism; Product distribution; Irradiation; effect of inhibitor (di-tert-butyl-nitroxide) and exclusion of light; | A 4% B 61% |
Conditions | Yield |
---|---|
With Rhodococcus erythropolis DSM 6138 In ethanol for 16h; | A n/a B n/a C 58% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -75℃; for 22h; hetero-Diels-Alder reaction; | A n/a B 14% C 51% |
The 2-Aminopyrimidine, with the CAS registry number 109-12-6 and EINECS registry number 203-648-4, has the systematic name of pyrimidin-2-amine. And the molecular formula of this chemical is C4H5N3. It is a kind of white to light yellow powder, and belongs to the following product categories: Pyrimidine; Fine chemical & intermediates; APIs & Intermediate; Amines; Nucleic acids.
Physical properties about 2-Aminopyrimidine are: (1)ACD/LogP: -0.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.23; (4)ACD/LogD (pH 7.4): -0.22; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 17.68; (8)ACD/KOC (pH 7.4): 18.08; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 29.02 Å2; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 26.67 cm3; (15)Molar Volume: 78.1 cm3; (16)Polarizability: 10.57×10-24cm3; (17)Surface Tension: 64.3 dyne/cm; (18)Density: 1.216 g/cm3; (19)Flash Point: 144.5 °C; (20)Enthalpy of Vaporization: 51.35 kJ/mol; (21)Boiling Point: 275.1 °C at 760 mmHg; (22)Vapour Pressure: 0.00521 mmHg at 25°C.
Preparation and uses of 2-Aminopyrimidine: It can be prepared by from Mucochloric acid and guanidine nitrate via cyclization, decarboxylation and dechlorination. What's more, it is often used in the biochemical study and organic systhesis.
Chemical reaction: It is used in the synthesis of other chemicals. For example, it can react with hexane-2,5-dione to produce 2-(2,5-dimethyl-pyrrol-1-yl)-pyrimidine. The reaction time is 24 hours with temperature of 100°C, and the yield is about 36%.
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: c1cnc(nc1)N
(2)InChI: InChI=1/C4H5N3/c5-4-6-2-1-3-7-4/h1-3H,(H2,5,6,7)
(3)InChIKey: LJXQPZWIHJMPQQ-UHFFFAOYAJ
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intravenous | 790mg/kg (790mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950. |