2-Hydroxypyridine supplier

Name
2-Hydroxypyridine
EINECS 205-520-3
CAS No. 142-08-5
Article Data196
CAS DataBase
Density 1.111 g/cm³
Solubility Soluble in water 450 g/L @ 20°C and ethanol, slightly soluble in benzene and ether.
Melting Point 105-107 °C(lit.)
Formula C₅H₅NO
Boiling Point 323.7 °C at 760 mmHg
Molecular Weight 95.1008
Flash Point 181.1 °C
Transport Information UN 2811
Appearance white to light yellow crystal
Safety 26-36-37/39-22
Risk Codes 36/37/38-40
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 2(1H)-Pyridone;1H-pyridin-2-one;2-Pyridone;2-Pyridinone;2-Pyridinol;2-Hydroxy pyridine;Pyridin-2(1H)-one;
PSA 33.12000
LogP 0.78720

Synthetic route

: 13161-30-3
2-hydroxy-pyridine N-oxide

: 142-08-5
2-hydroxypyridin

Conditions

Conditions	Yield
With triphenylphosphine; N-fused tetraphenylporphyrin rhenium(VII) trioxide In dichloromethane at 23℃; for 3h;	99%
With carbon dioxide; water; iron at 100℃; for 10h; Autoclave; Green chemistry; chemoselective reaction;	99%
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction;	91%

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

: L-threonine, dicyclohexylammonium salt

A: 142-08-5
2-hydroxypyridin

B: 2592-18-9
Boc-Thr-OH

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 8h; Ambient temperature;	A n/a B 98%

...Expand

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

: 147-85-3
L-proline

A: 142-08-5
2-hydroxypyridin

B: 15761-39-4
1-(tert-butoxycarbonyl)-L-proline

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 6h; Ambient temperature;	A n/a B 98%

...Expand

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

: 73-22-3
L-Tryptophan

A: 142-08-5
2-hydroxypyridin

B: 13139-14-5
Boc-Trp-OH

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 4h; Ambient temperature;	A n/a B 98%

...Expand

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

: L-methionine, dicyclohexylammonium salt

A: 142-08-5
2-hydroxypyridin

B: 2488-15-5
N-tert-butoxycarbonyl-L-methionine

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 7h; Ambient temperature;	A n/a B 96%

...Expand

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

: L-phenylalanine, dicyclohexylammonium salt

A: 142-08-5
2-hydroxypyridin

B: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 12h; Ambient temperature;	A n/a B 96%

...Expand

: 197958-29-5
pyridin-2-ylboronic acid

: 142-08-5
2-hydroxypyridin

Conditions

Conditions	Yield
With hydrazine hydrate; caesium carbonate In water at 80℃; for 12h;	96%

: 40864-08-2
2-benzyloxypyridine

: 142-08-5
2-hydroxypyridin

Conditions

Conditions	Yield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 1h;	96%
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 3h; Schlenk technique; Irradiation; Inert atmosphere; chemoselective reaction;	95%

: 67-56-1
methanol

: 117-34-0
2,2-diphenylacetic acid

A: 142-08-5
2-hydroxypyridin

B: 3469-00-9
methyl 2,2-diphenylacetate

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 1h; Ambient temperature;	A 90% B 95%

...Expand

: 134-32-7
1-amino-naphthalene

: 96989-50-3
di-2-pyridyl thionocarbonate

A: 142-08-5
2-hydroxypyridin

B: 551-06-4
1-isothiocyanatonaphthalene

Conditions

Conditions	Yield
In dichloromethane for 0.166667h; Ambient temperature;	A n/a B 95%

...Expand

: 96989-50-3
di-2-pyridyl thionocarbonate

: 106-49-0
p-toluidine

A: 142-08-5
2-hydroxypyridin

B: 622-59-3
1-isothiocyanato-4-methylbenzene

Conditions

Conditions	Yield
In dichloromethane for 0.0833333h; Ambient temperature;	A n/a B 95%

...Expand

: 108-98-5
thiophenol

: 621-82-9
Cinnamic acid

A: 142-08-5
2-hydroxypyridin

B: 70030-52-3
(E)-S-phenyl 3-phenylprop-2-enethioate

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 6h; Ambient temperature;	A 90% B 95%

...Expand

: 61-90-5
L-leucine

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

A: 142-08-5
2-hydroxypyridin

B: 13139-15-6
N-tert-butoxycarbonyl-L-leucine

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 4h; Ambient temperature;	A n/a B 94%

...Expand

: 96989-50-3
di-2-pyridyl thionocarbonate

: 109-73-9
N-butylamine

A: 142-08-5
2-hydroxypyridin

B: 592-82-5
butyl isothiocyanate

Conditions

Conditions	Yield
In dichloromethane for 0.0833333h; Ambient temperature;	A n/a B 94%

...Expand

: 124-07-2
Octanoic acid

: 100-51-6
benzyl alcohol

A: 142-08-5
2-hydroxypyridin

B: 10276-85-4
benzyl caprylate

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 2h; Ambient temperature;	A 89% B 94%

...Expand

: 67-56-1
methanol

: 621-82-9
Cinnamic acid

A: 142-08-5
2-hydroxypyridin

B: 103-26-4
methyl cinnamate

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 2h; Ambient temperature;	A 90% B 93%

...Expand

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

: L-serine, dicyclohexylammonium salt

A: 142-08-5
2-hydroxypyridin

B: 3262-72-4
(S)-N-(tert-butoxycarbonyl)serine

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 7h; Ambient temperature;	A n/a B 93%

...Expand

: 120-57-0
piperonal

: 1219454-89-3
2-((difluoromethyl)sulfinyl)pyridine

A: 142-08-5
2-hydroxypyridin

B: 253266-72-7
5-(2,2-difluorovinyl)benzo[d][1,3]dioxole

Conditions

Conditions	Yield
Stage #1: piperonal; 2-((difluoromethyl)sulfonyl)pyridine With potassium tert-butylate In N,N-dimethyl-formamide at -50 - -40℃; for 0.25h; Julia-Kocienski type gem-difluoroolefination; Inert atmosphere; Stage #2: With hydrogenchloride; water; ammonium chloride In N,N-dimethyl-formamide at -40 - 20℃; Inert atmosphere;	A n/a B 93%

...Expand

: 72-18-4
L-valine

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

A: 142-08-5
2-hydroxypyridin

B: 13734-41-3
t-Boc-L-valine

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 9h; Ambient temperature;	A n/a B 92%

...Expand

: 4041-95-6
N,N-di-tert-butylthiourea

A: 142-08-5
2-hydroxypyridin

B: 691-24-7
1,3-di-tert-butylcarbodiimide

Conditions

Conditions	Yield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile for 6h; Ambient temperature;	A n/a B 92%

: 79-31-2
isobutyric Acid

: 108-95-2
phenol

A: 142-08-5
2-hydroxypyridin

B: 20279-29-2
phenyl isobutyrate

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 1h; Ambient temperature;	A 90% B 92%

...Expand

: 1219454-89-3
2-((difluoromethyl)sulfinyl)pyridine

: 66-99-9
β-naphthaldehyde

A: 142-08-5
2-hydroxypyridin

B: 131581-40-3
1,1-difluoro-2-(2-naphthyl)ethene

Conditions

Conditions	Yield
Stage #1: 2-((difluoromethyl)sulfonyl)pyridine; β-naphthaldehyde With potassium tert-butylate In N,N-dimethyl-formamide at -50 - -40℃; for 0.25h; Julia-Kocienski type gem-difluoroolefination; Inert atmosphere; Stage #2: With hydrogenchloride; water; ammonium chloride In N,N-dimethyl-formamide at -40 - 20℃; Inert atmosphere;	A n/a B 92%

...Expand

: 115-20-8
1,1,1-trichloroethanol

: 124-07-2
Octanoic acid

A: 142-08-5
2-hydroxypyridin

B: 84443-53-8
n-heptanoic acid 2,2,2-trichloroethylester

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 0.5h; Ambient temperature;	A 90% B 91%

...Expand

: 6336-01-2
3-n-butyl-1-phenylthiourea

A: 142-08-5
2-hydroxypyridin

B: 21848-95-3
N-phenyl-N'-(n-butyl)carbodiimide

Conditions

Conditions	Yield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile for 1h; Ambient temperature;	A n/a B 91%

: 1219454-89-3
2-((difluoromethyl)sulfinyl)pyridine

: 100-10-7
4-dimethylamino-benzaldehyde

A: 142-08-5
2-hydroxypyridin

B: 38935-94-3
4-dimethylamino-β,β-difluorostyrene

Conditions

Conditions	Yield
Stage #1: 2-((difluoromethyl)sulfonyl)pyridine; 4-dimethylamino-benzaldehyde With potassium tert-butylate In N,N-dimethyl-formamide at -50 - -40℃; for 0.25h; Julia-Kocienski type gem-difluoroolefination; Inert atmosphere; Stage #2: With hydrogenchloride; water; ammonium chloride In N,N-dimethyl-formamide at -40 - 20℃; Inert atmosphere;	A n/a B 91%

...Expand

: 67-56-1
methanol

: 103-82-2
phenylacetic acid

A: 142-08-5
2-hydroxypyridin

B: 101-41-7
benzeneacetic acid methyl ester

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 1h; Ambient temperature;	A 90% B 89%

...Expand

: 103-82-2
phenylacetic acid

: 109-79-5
1-butanethiol

A: 142-08-5
2-hydroxypyridin

B: 54829-39-9
S-butyl 2-phenylethanethioate

Conditions

Conditions	Yield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 1h; Ambient temperature;	A 90% B 82%

...Expand

: 56-41-7
L-alanin

: 89985-91-1
tert-butyl pyridin-2-yl carbonate

A: 142-08-5
2-hydroxypyridin

B: 15761-38-3
L-N-Boc-Ala

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 8h; Ambient temperature;	A n/a B 90%

...Expand

: 34780-32-0
N-cyclohexyl-N'-(t-butyl)thiourea

A: 142-08-5
2-hydroxypyridin

B: 1202-53-5
t-butylcyclohexylcarbodiimide

Conditions

Conditions	Yield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile for 12h; Ambient temperature;	A n/a B 90%

: 14327-04-9
N-tert-butyl-N'-phenylthiourea

A: 142-08-5
2-hydroxypyridin

B: 2219-34-3
N-((tert-butylimino)methylene)aniline

Conditions

Conditions	Yield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile for 1h; Ambient temperature;	A n/a B 90%

: 142-08-5
2-hydroxypyridin

: 675-20-7
piperidin-2-one

Conditions

Conditions	Yield
Stage #1: 2-hydroxypyridin With palladium 10% on activated carbon; hydrogen; acetic acid at 24 - 28℃; for 15h; Stage #2: In methanol	100%
With palladium on activated charcoal; hydrogen; acetic acid at 20℃; under 760.051 Torr; for 15h; Time;	100%
With nickel-copper at 200 - 235℃; under 29420.3 Torr; Hydrogenation;

: 142-08-5
2-hydroxypyridin

: 1067910-16-0
C17H12BrCl2NO3S

: 1067910-17-1
C22H16Cl2N2O4S

Conditions

Conditions	Yield
With sodium hydride; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl-formamide	100%

: 142-08-5
2-hydroxypyridin

: 110-52-1
1,4-dibromo-butane

: 82791-51-3
C14H16N2O2

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 5.5h;	100%

: 142-08-5
2-hydroxypyridin

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: C9H16N2*C5H5NO

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	100%
at 25 - 30℃; for 24h;

: 142-08-5
2-hydroxypyridin

: 80-70-6
N,N,N',N'-tetramethylguanidine

: C5H5NO*C5H13N3

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	100%
at 25 - 30℃;

: 142-08-5
2-hydroxypyridin

: 62-49-7
choline

: C5H14NO(1+)*C5H4NO(1-)

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 24h;	100%

: 142-08-5
2-hydroxypyridin

: 23329-69-3, 454677-87-3
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)

: 1758-54-9, 79462-42-3, 81563-77-1
1-pyridin-2-yl-ethanone oxime

: 2-acetylpyridineoximato-2-pyridineato-bis(8-quinolinato)titanium(IV)

Conditions

Conditions	Yield
In toluene at 100 - 120℃;	98.1%

...Expand

: 142-08-5
2-hydroxypyridin

: 591-50-4
iodobenzene

: 13131-02-7
1-phenyl-1H-pyridin-2-one

Conditions

Conditions	Yield
With caesium carbonate; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine In acetonitrile at 82℃; for 24h; Conversion of starting material; activated 3 A molecular sieve (KnNa12,-n[(AlO2)12(SiO2)12]);	98%
With potassium phosphate; copper(l) iodide; N-(2-fluorophenyl)picolinamide at 150℃; for 24h; Green chemistry;	98%
With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine In toluene for 18h; Heating;	84%
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 6h;	72%

: 142-08-5
2-hydroxypyridin

: trimethylgallium etherate

: [MeGa(O(C5H4N))2]

Conditions

Conditions	Yield
In benzene byproducts: CH4, Et2O; under N2; a soln. of a ligand in benzene was added to a benzene soln. ofGa-contg. compd. and stirred for 4 h; the solvent was removed under reduced pressure; elem. anal.;	98%

: 142-08-5
2-hydroxypyridin

: 102-71-6
triethanolamine

: 1-(2-pyridyloxy)silatrane

Conditions

Conditions	Yield
With potassium hydroxide; tetraethoxy orthosilicate In o-xylene Heating;	98%

: 142-08-5
2-hydroxypyridin

: 488151-80-0
3-(p-methoxyphenyl)-2-propen-1-yl methyl carbonate

: C15H15NO2

Conditions

Conditions	Yield
With propylamine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; [O,O’-((S)-1,1´-dinaphthyl-2,2´-diyl)-N,N´-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite]; caesium carbonate In tetrahydrofuran at 50℃; for 1.5h; Schlenk technique; Inert atmosphere; enantioselective reaction;	98%

: 142-08-5
2-hydroxypyridin

: 3153-26-2
bis(acetylacetonate)oxovanadium

: [VO(acetylacetonate)2(pyrid-2-one)]

Conditions

Conditions	Yield
In methanol at 20℃; for 2h;	98%

: 142-08-5
2-hydroxypyridin

: 110-80-5
2-ethoxy-ethanol

: 23329-69-3, 454677-87-3
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)

: 2-ethoxyethanolato-2-pyridineato-bis(8-quinolinato)titanium(IV)

Conditions

Conditions	Yield
In toluene at 100 - 120℃; Reflux;	97.9%

...Expand

: 142-08-5
2-hydroxypyridin

: 23329-69-3, 454677-87-3
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)

: 5007-50-1
1-(2-furyl)ethanone oxime

: 2-acetylfuranoximato-2-pyridineato-bis(8-quinolinato)titanium(IV)

Conditions

Conditions	Yield
In toluene at 100 - 120℃;	97.8%

...Expand

: 142-08-5
2-hydroxypyridin

: 14049-60-6
tetra-n-butylammonium octabromodirhenate(III)

: 104647-37-2
Re2(2-hydroxypyridinate)4Br2

Conditions

Conditions	Yield
In pentan-1-ol the soln. of Re complex and ligand was refluxed for 15 h under N2; ppt. was filtered off, washed with n-pentanol, ether, dried in vac., elem. anal.;	97%

: 142-08-5
2-hydroxypyridin

: 313683-65-7
C5(CH3)5Fe(CO)Si(CH3)2Si(CH3)2OC5H4N

: 375388-38-8
η5-C5Me5(CO)Fe(H)-(SiMe2O(2-C5H4N))2

Conditions

Conditions	Yield
In toluene at room temp.; elem. anal.;	97%

: 142-08-5
2-hydroxypyridin

: 31121-29-6
triethylgallium diethyl ether adduct

: [Et2Ga(O(C5H4N))]

Conditions

Conditions	Yield
In benzene byproducts: C2H6, Et2O; under N2; a soln. of a ligand in benzene was added to a benzene soln. ofGa-contg. compd. and stirred for 4 h; the solvent was removed under reduced pressure; elem. anal.;	97%

: 142-08-5
2-hydroxypyridin

: 31121-29-6
triethylgallium diethyl ether adduct

: [EtGa(O(C5H4N))2]

Conditions

Conditions	Yield
In benzene byproducts: C2H6, Et2O; under N2; a soln. of a ligand in benzene was added to a benzene soln. ofGa-contg. compd. and stirred for 4 h; the solvent was removed under reduced pressure; elem. anal.;	97%

2-Hydroxypyridine Consensus Reports

Reported in EPA TSCA Inventory.

2-Hydroxypyridine Specification

The 2-Oxopyridine with CAS registry number of 142-08-5 is also called 2-Hydroxypyridine. The IUPAC name is 1H-pyridin-2-one. Its EINECS registry number is 205-520-3. In addition, the molecular formula is C₅H₅NO and the molecular weight is 95.10. It is a kind of white to light yellow crystal and belongs to the classes of Pyridines; Pyridine; Pyridines derivates; (intermediate of benzoxazole); Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides. And it should be stored in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: -0.58; (2)ACD/LogD (pH 5.5): -0.58; (3)ACD/LogD (pH 7.4): -0.58; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 11.52; (7)ACD/KOC (pH 7.4): 11.52; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Polar Surface Area: 20.31 Å²; (11)Index of Refraction: 1.513; (12)Molar Refractivity: 25.74 cm³; (13)Molar Volume: 85.5 cm³; (14)Polarizability: 10.2 ×10^-24cm³; (15)Surface Tension: 35.7 dyne/cm; (16)Density: 1.111 g/cm³; (17)Flash Point: 181.1 °C; (18)Enthalpy of Vaporization: 56.57 kJ/mol; (19)Boiling Point: 323.7 °C at 760 mmHg; (20)Vapour Pressure: 0.000257 mmHg at 25°C.

Preparation of 2-Oxopyridine: it can be prepared by pyridine 1-oxide. There are some other products, such as pyridin-2-yl-acetonitrile, [2,2']bipyridinyl, pyrrole and pyridine. The yield of this reaction is about 31% at reaction temperature of 750-850 °C.

2-Oxopyridine can be prepared by pyridine 1-oxide

Uses of 2-Oxopyridine: it can be used to get 2-chloro-pyridine. This reaction will need reagents N-chloruccinimide and PPh₃ and solvent dioxane. The reaction time is 4 hours by heating . The yield is about 43%.

2-Oxopyridine can be used to get 2-chloro-pyridine

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. There is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing, gloves and eye/face protection and do not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc[nH]c(=O)c1
(2)InChI: InChI=1/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)
(3)InChIKey: UBQKCCHYAOITMY-UHFFFAOYAK

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	410mg/kg (410mg/kg)		Toxicon. Vol. 23, Pg. 815, 1985.
mouse	LD50	intravenous	750mg/kg (750mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 93, Pg. 143, 1953.

Product Name

2-Hydroxypyridine

Synthetic route

2-Hydroxypyridine Consensus Reports

2-Hydroxypyridine Specification

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