2-Amino-3-hydroxypyridine supplier

Name
2-Amino-3-hydroxypyridine
EINECS 240-886-8
CAS No. 16867-03-1
Article Data26
CAS DataBase
Density 1.32 g/cm³
Solubility
Melting Point 168-172 °C(lit.)
Formula C₅H₆N₂O
Boiling Point 385.187 °C at 760 mmHg
Molecular Weight 110.115
Flash Point 186.755 °C
Transport Information UN 2811
Appearance white to light yellow crystal powder
Safety 26-45-37/39-28-36-22
Risk Codes 36/37/38-25-40
Molecular Structure
Hazard Symbols Xi,T,Xn
Synonyms 3-Hydroxy-2-aminopyridine;3-Pyridinol, 2-amino;2-Aminopyridin-3-ol;3-Hydroxy-2-pyridinamine;
PSA 59.14000
LogP 0.95060

Synthetic route

: 6332-56-5
2-hydroxy-3-nitropyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
palladium-carbon In methanol	89%

: 2-amino-3-hydroxypyridinesulfonic acid salt

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
In water at 35 - 90℃; for 1.5h; Time;	79%

: 16867-02-0
2-imino-3-hydroxypyridinesulfonic acid

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
In water at 95℃; for 1h; Temperature; Large scale;	77.1%

: 15128-82-2
3-hydroxy-2-nitropyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: 3-hydroxy-2-nitropyridine With hydrogenchloride; 1,1,1,3',3',3'-hexafluoro-propanol; iron In water at 20℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In water chemoselective reaction;	70%
With methanol; palladium on activated charcoal Hydrogenation;
With hydrogenchloride; tin(ll) chloride

: 40263-57-8
2-iodo-3-hydroxypyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With ammonium hydroxide; copper(II) sulfate

: 933-90-4
3-hydroxypyridine-2-carboxamide

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With sodium hypobromide

: 10006-74-3
2-Amino-3-(ethoxy)pyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With acetic acid hydrobromide at 130℃;

: 93596-90-8
2-(p-nitrophenylazo)-3-hydroxypyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With sodium dithionite

ammonium salt of 2-nitro-pyridin-3-ol: ammonium salt of 2-nitro-pyridin-3-ol

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With sodium dithionite; ammonia

sulfuric acid mono-<2-amino-<3>pyridyl ester: sulfuric acid mono-<2-amino-<3>pyridyl ester

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With hydrogenchloride

: 24016-03-3
2-amino-3-benzyloxypyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With trimethylammonium heptachlorodialuminate In dichloromethane Heating;

: 109-00-2
3-HYDROXYPYRIDINE

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 20 - 30 °C 2: SnCl2; concentrated aqueous HCl View Scheme

: 14773-50-3
3-ethoxypyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid; fuming nitric acid / -15 °C / und folgenden 1-stdg.Erwaermen auf dem Wasserbad 2: tin (II)-chloride; concentrated hydrochloric acid 3: hydrogen bromide-glacial acetic acid / 130 °C View Scheme

: 74037-50-6
3-ethoxy-2-nitropyridine

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin (II)-chloride; concentrated hydrochloric acid 2: hydrogen bromide-glacial acetic acid / 130 °C View Scheme

: 874-24-8
3-hydroxypyridine-2-carboxylic acid

: 16867-03-1
2-amino-3-hydroxypyridine

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 611-13-2
2-furoic acid methyl ester

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With ammonium bromide; ammonia

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 609-38-1
furan-2-carboxylic acid amide

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With ammonium chloride; ammonia

phosphoric acid-tris-(dimethylamide) (hexametapol): phosphoric acid-tris-(dimethylamide) (hexametapol)

: 614-99-3
Ethyl 2-furoate

: 16867-03-1
2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With ammonium chloride; ammonia

: 16867-03-1
2-amino-3-hydroxypyridine

: C13H12N2O3

: C13H12N2O3*C5H6N2O

Conditions

Conditions	Yield
In chloroform Solvent; Milling;	100%

: 16867-03-1
2-amino-3-hydroxypyridine

: 619-58-9
4-iodobenzoic acid

: C12H7IN2O

Conditions

Conditions	Yield
With polyphosphoric acid trimethylsilyl ester at 180℃; for 4h;	99.78%
With trichlorophosphate at 90℃; for 12h;	73.5%
With trichlorophosphate at 90℃; for 12h;	73.5%
With trichlorophosphate at 0 - 90℃; for 12h;	73.5%

: 16867-03-1
2-amino-3-hydroxypyridine

: 122-51-0
orthoformic acid triethyl ester

: 273-97-2
oxazolo<4,5-b>pyridine

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 85℃; for 0.333333h;	98%
Reflux;	90%
With toluene-4-sulfonic acid at 160℃; Inert atmosphere;	68%

: 16867-03-1
2-amino-3-hydroxypyridine

: 115-80-0
Triethyl orthopropionate

: 52333-88-7
2-ethyloxazolo<4,5-b>pyridine

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 85℃; for 0.166667h;	98%
With bismuth(lll) trifluoromethanesulfonate at 85℃; for 0.1h;	85%
With toluene-4-sulfonic acid at 140 - 180℃;	30%
With toluene-4-sulfonic acid at 20 - 180℃;	30%

: 16867-03-1
2-amino-3-hydroxypyridine

: 15781-70-1
malonic acid bis-(2,4,6-trichloro-phenyl) ester

: 36866-05-4
2,9-dihydroxypyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
In various solvent(s) for 3h; Heating;	98%
In brombenzane for 3h; Heating / reflux;	98%

: 16867-03-1
2-amino-3-hydroxypyridine

: 762-42-5
dimethyl acetylenedicarboxylate

: (Z)-3-methoxycarbonylmethylene-3,4-dihydro-2H-5-aza-1,4-benzoxazin-2-one

Conditions

Conditions	Yield
at 20℃; for 0.0666667h; Michael addition;	98%
In methanol at 20℃; for 1h; Inert atmosphere;	45%

: 16867-03-1
2-amino-3-hydroxypyridine

: 600-00-0
ethyl 2-bromoisobutyrate

: 20348-21-4
2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Conditions

Conditions	Yield
With potassium carbonate In acetone at 70℃; for 16h;	97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-octyl-3-methylimidazolium tetrafluoroborate at 20℃; for 2h; chemoselective reaction;	94%
(i) NaOMe, DMSO, (ii) /BRN= 1098947/; Multistep reaction;

: 16867-03-1
2-amino-3-hydroxypyridine

: 78-39-7
Triethyl orthoacetate

: 86467-39-2
2-methyloxazolo<4,5-b>pyridine

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 85℃; for 0.116667h;	97%
at 100℃; for 7h;	86%
With bismuth(lll) trifluoromethanesulfonate at 85℃; for 0.133333h;	85%

: 16867-03-1
2-amino-3-hydroxypyridine

: 372-48-5
2-fluoropyridine

: 960299-93-8
3-(pyridin-2-yloxy)pyridin-2-amine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;	97%

: 16867-03-1
2-amino-3-hydroxypyridine

: 762-21-0
acetylenedicarboxylic acid diethyl ester

: 1349803-08-2
(Z)-3-ethoxycarbonylmethylene-3,4-dihydro-2H-5-aza-1,4-benzoxazin-2-one

Conditions

Conditions	Yield
at 20℃; for 0.0833333h; Michael addition;	97%

: 16867-03-1
2-amino-3-hydroxypyridine

: 105-45-3
acetoacetic acid methyl ester

: 40966-84-5
2-methyl-9-hydroxy-4H-pyrido<1,2-a>pyrimidin-4-one

Conditions

Conditions	Yield
With bismuth(III) chloride at 100℃; for 3h; Green chemistry;	97%

: 16867-03-1
2-amino-3-hydroxypyridine

: 394-47-8
2-fluorobenzonitrile

: benzo[f]pyrido[3,2-b][1,4]oxazepin-10-amine

Conditions

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 6h;	97%

: 16867-03-1
2-amino-3-hydroxypyridine

: C10H6N4O2

Conditions

Conditions	Yield
With CotA-laccase In aq. phosphate buffer at 20℃; for 2h; pH=6; Enzymatic reaction;	97%
With eosin y In methanol; aq. phosphate buffer at 20℃; for 12h; pH=7.2; Irradiation;	83%

: 16867-03-1
2-amino-3-hydroxypyridine

: 3222-47-7
6-methylnicotinic acid

: 120623-52-1
2-(6-Methyl-pyridin-3-yl)-oxazolo[4,5-b]pyridine

Conditions

Conditions	Yield
With PPA at 210℃; for 2h;	96%

: 16867-03-1
2-amino-3-hydroxypyridine

: 638-07-3
ethyl (2-chloroaceto)acetate

: 162469-86-5
2-chloromethyl-8-hydroxy-4H-pyrido<1,2-a>pyrimidin-4-one

Conditions

Conditions	Yield
With PPA at 110℃; for 2h;	96%
With phosphoric acid at 110℃; for 2h;	49%

: 16867-03-1
2-amino-3-hydroxypyridine

: 22408-61-3
4-chloro-2-oxo-2H-[1]benzopyran-3-carbonitrile

: 11-hydroxy-7-imino-7H-7a,12-diazabenzo[a]anthracen-6-one

Conditions

Conditions	Yield
With triethylamine In acetonitrile Heating;	96%

: 16867-03-1
2-amino-3-hydroxypyridine

: 99-94-5
p-Toluic acid

: 52333-87-6
2-(4-methylphenyl)[1,3]oxazolo[4,5-b]pyridine

Conditions

Conditions	Yield
With silica-supported perchloric acid nanoparticles In methanol at 20℃; Green chemistry;	96%
With silica nanoparticles-supported perchloric acid In methanol at 20℃;	96%
at 170℃; for 0.0333333h; microwave irradiation;	82%

: 1121-60-4
pyridine-2-carbaldehyde

: 16867-03-1
2-amino-3-hydroxypyridine

: ammonium hexafluorophosphate

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: [(η6-p-cymene)RuCl(κ2-N,N-2-[(pyridin-2-ylmethylene)amino]pyridin-3-ol)]·PF6

Conditions

Conditions	Yield
Stage #1: pyridine-2-carbaldehyde; 2-amino-3-hydroxypyridine; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol at 20℃; for 24h; Stage #2: ammonium hexafluorophosphate In methanol	96%

...Expand

: 16867-03-1
2-amino-3-hydroxypyridine

: 1514-09-6
4-(trifluoromethyl)benzothioic S-acid

: N-(3-hydroxy-2-pyridyl)-4-trifluoromethylthiobenzamide

Conditions

Conditions	Yield
Stage #1: 4-(trifluoromethyl)benzothioic S-acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: 2-amino-3-hydroxypyridine In dichloromethane at 20℃; for 12h;	96%

: 16867-03-1
2-amino-3-hydroxypyridine

: 140-89-6
potassium ethyl xanthogenate

: 53052-06-5
oxazolo<4,5-b>pyridine-2(3H)-thione

Conditions

Conditions	Yield
In ethanol for 18h; Heating / reflux;	95%
In ethanol; water for 3h; Condensation; cyclization; Heating;	40%

: 16867-03-1
2-amino-3-hydroxypyridine

: 24424-99-5
di-tert-butyl dicarbonate

: 902835-93-2
N-(tert-butoxycarbonyl)-2-amino-3-hydroxypyridine

Conditions

Conditions	Yield
With guanidine hydrochloride In ethanol at 35 - 40℃; for 2.5h;	95%
With amberlyst-15 In ethanol at 20℃; for 2.5h; chemoselective reaction;	93%

: 16867-03-1
2-amino-3-hydroxypyridine

: 93-99-2
benzoic acid phenyl ester

: 69634-16-8
N1-(3-hydroxy-2-pyridyl)benzamide

Conditions

Conditions	Yield
With allylchloro-[1,3-bis(diisopropylphenyl)-imidazole-2-ylidene]palladium(II); water; potassium carbonate In toluene at 110℃; for 16h; Inert atmosphere;	95%

: 16867-03-1
2-amino-3-hydroxypyridine

: 24424-99-5
di-tert-butyl dicarbonate

: C15H22N2O5

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 12h; Solvent; Inert atmosphere;	95%

: 16867-03-1
2-amino-3-hydroxypyridine

: 485-47-2
indan-1,2,3-trione hydrate

: 5a-Hydroxyindeno[2,1-b]pyrido[2,3-e][1,4]oxazin-6(5aH)-one

Conditions

Conditions	Yield
In water at 30℃; for 0.0138889h; Irradiation; Sonication; Green chemistry;	95%

: 16867-03-1
2-amino-3-hydroxypyridine

: 459-57-4
4-fluorobenzaldehyde

: 52333-47-8
2-(4-fluorophenyl)oxazolo[4,5-b]pyridine

Conditions

Conditions	Yield
Stage #1: 2-amino-3-hydroxypyridine; 4-fluorobenzaldehyde In acetonitrile at 90℃; for 3h; Stage #2: With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(l) chloride In acetonitrile Reflux;	94.2%

: 16867-03-1
2-amino-3-hydroxypyridine

: 100-09-4
4-methoxybenzoic acid

: 52333-46-7
2-(4-methoxyphenyl)[1,3]oxazolo[4,5-b]pyridine

Conditions

Conditions	Yield
With silica-supported perchloric acid nanoparticles In methanol at 20℃; Green chemistry;	94%
With silica nanoparticles-supported perchloric acid In methanol at 20℃;	94%
boric acid at 170℃; for 0.133333h; microwave irradiation;	44%
With PPA Heating;
With PPA at 100℃; for 2.5h;

: 16867-03-1
2-amino-3-hydroxypyridine

: 99-05-8
meta-aminobenzoic acid

: 52333-90-1
3-(oxazolo[4,5-b]pyridin-2-yl)aniline

Conditions

Conditions	Yield
With PPA at 220℃;	93%
With PPA at 180℃;	80%
With polyphosphoric acid at 200℃; for 6h;	47%
With polyphosphoric acid at 220℃; for 4h;	35%

: 16867-03-1
2-amino-3-hydroxypyridine

: 492-88-6
3-ethoxysalicylaldehyde

: (Z)-2-ethoxy-6-(((3-hydroxypyridin-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one

Conditions

Conditions	Yield
In ethanol at 20℃; for 0.0833333h; Sonication;	93%

: 16867-03-1
2-amino-3-hydroxypyridine

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 151055-11-7
C16H12N2O2

Conditions

Conditions	Yield
With acetic acid In ethanol at 85℃; for 4h;	92.5%

: 16867-03-1
2-amino-3-hydroxypyridine

: 100-52-7
benzaldehyde

: 52333-44-5
2-phenyl[1,3]oxazolo[4,5-b]pyridine

Conditions

Conditions	Yield
Stage #1: 2-amino-3-hydroxypyridine; benzaldehyde at 80℃; for 3h; Stage #2: With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(l) chloride Reflux;	92.2%

2-Amino-3-hydroxypyridine Specification

The 2-Amino-3-hydroxypyridine, with the CAS registry number 16867-03-1, is also known as 2-Amino-3-pyridinol. It belongs to the product categories of Pyridines, Pyrimidines, Purines and Pteredines; Pharmacetical; Pyridine; Pyridines Derivates; Chemical Amines; Pyridines; Amines; Aromatics. Its EINECS registry number is 240-886-8. This chemical's molecular formula is C₅H₆N₂O and molecular weight is 110.11. What's more, its IUPAC name is called 2-Aminopyridin-3-ol. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 2-Amino-3-hydroxypyridine are: (1)ACD/LogP: -0.258; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.64; (4)ACD/LogD (pH 7.4): -0.44; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 7.18; (8)ACD/KOC (pH 7.4): 11.46; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 59.14 Å²; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 30.462 cm³; (15)Molar Volume: 83.367 cm³; (16)Polarizability: 12.076×10^-24cm³; (17)Surface Tension: 71.319 dyne/cm; (18)Density: 1.321 g/cm³; (19)Flash Point: 186.755 °C; (20)Enthalpy of Vaporization: 65.876 kJ/mol; (21)Boiling Point: 385.187 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of 2-Amino-3-hydroxypyridine: (1) it is used as an intermediate for agrochemicals, pharmaceutical and dyes; (2) it is used to produce other chemicals. For example, it can react with carbonochloridic acid ethyl ester to get (3-hydroxy-[2]pyridyl)-carbamic acid ethyl ester. This reaction needs reagent triethylamine and solvent CH₂Cl₂ at temperature of 20 °C. The reaction time is 4 hours. The yield is 39 %.

2-Amino-3-hydroxypyridine can react with carbonochloridic acid ethyl ester to get (3-hydroxy-[2]pyridyl)-carbamic acid ethyl ester.

When you are dealing with this chemical, you should be very careful. This chemical is toxic by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. Therefore, you could take off immediately all contaminated clothing. And you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: c1cc(c(nc1)N)O
(2) InChI: InChI=1S/C5H6N2O/c6-5-4(8)2-1-3-7-5/h1-3,8H,(H2,6,7)
(3) InChIKey: BMTSZVZQNMNPCT-UHFFFAOYSA-N

Product Name

2-Amino-3-hydroxypyridine

Synthetic route

2-Amino-3-hydroxypyridine Specification

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