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2-Hydroxypyridine

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Name

2-Hydroxypyridine

EINECS 205-520-3
CAS No. 142-08-5 Density 1.111 g/cm3
PSA 33.12000 LogP 0.78720
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 Molecular Structure of 142-08-5 (2-Hydroxypyridine) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

2(1H)-Pyridone;1H-pyridin-2-one;2-Pyridone;2-Pyridinone;2-Pyridinol;2-Hydroxy pyridine;Pyridin-2(1H)-one;

Article Data 196

2-Hydroxypyridine Synthetic route

13161-30-3

2-hydroxy-pyridine N-oxide

142-08-5

2-hydroxypyridin

Conditions
ConditionsYield
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
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 8h; Ambient temperature;A n/a
B 98%
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
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 6h; Ambient temperature;A n/a
B 98%
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
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 4h; Ambient temperature;A n/a
B 98%
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
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 7h; Ambient temperature;A n/a
B 96%
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
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 12h; Ambient temperature;A n/a
B 96%
197958-29-5

pyridin-2-ylboronic acid

142-08-5

2-hydroxypyridin

Conditions
ConditionsYield
With hydrazine hydrate; caesium carbonate In water at 80℃; for 12h;96%
40864-08-2

2-benzyloxypyridine

142-08-5

2-hydroxypyridin

Conditions
ConditionsYield
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
ConditionsYield
With 2,2'-dipyridyl carbonate; dmap In dichloromethane for 1h; Ambient temperature;A 90%
B 95%
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
ConditionsYield
In dichloromethane for 0.166667h; Ambient temperature;A n/a
B 95%

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.

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