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4-Hydroxypyridine

4-Hydroxypyridine structure

CAS No:
626-64-2
Formula:
C5H5NO
Chemical Name:
4-Hydroxypyridine
Synonyms:
4-Pyridinol;4-Pyridol;4-Hydroxypyridine;γ-Hydroxypyridine;NSC 5080;811801-35-1
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Beige crystalline powder

4-pyridone is the simplest member of the class of pyridin-4-ones, that is 1,4-dihydropyridine in which the hydrogens at position 4 have been replaced by an oxo group. It is a tautomer of a 4-hydroxypyridine.

4-Hydroxypyridine Basic Attributes

Molecular Weight：

95.1

Exact Mass：

95.10

BRN：

105800

EC Number：

210-958-3

UNII：

3P2MV07G53

NSC Number：

146174|5080

DSSTox ID：

DTXSID2052310

HScode：

2933399090

Characteristics

PSA：

29.1

XLogP3：

-1.3

Appearance：

Beige to light brown Powder or Chunks

Density：

1.2±0.1 g/cm3

Melting Point：

149.8 °C

Boiling Point：

257 °C

Flash Point：

221 °C

Refractive Index：

1.560

Water Solubility：

H2O: soluble

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-41-37/38-22

safety instructions：

26-36-37/39-39

RTECS Number：

UU7701450

Marks：

Xi,Xn

Hazard note：

Harmful/Irritant

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P280-P305 + P351 + P338

Hazard Statements：

H302-H315-H318-H335

GHS Classification：

|Danger|H302 (85.71%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 49 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4(1H)-pyridinone

4-Hydroxypyridine Use and Manufacturing

Methods of Manufacturing

General procedure: In a typical reaction, 10 molpercent CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 molpercent EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 °C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.General procedure: To a solution of [2-(phenoxy)-ethyl]-trimethyl-silane (Table-3, entry-1) (195mg, 1.0 mmol) in dry DMF (2 ml) was added cesium fluoride (576 mg, 3.0 mmol) and heated at 60°C for 1 h. Reaction mass was diluted with water and extracted with ethyl acetate (3 x 20 ml). The combined organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduce pressure to give phenol 92mg (93percent yield). Phenols of Table-3 are commercially available from Aldrich and its identity was confirmed by comparison of 1H NMR data with authentic sample.General procedure: In a typical experiment, benzyl 4-methoxyphenyl carbamate (1a, 1 mmol) and 10 cm

Uses

Used in the synthesis of diuretic drug torasemide or other drug intermediates

Manufacturing Info：

4(1H)-Pyridinone: ACTIVE|4-Pyridinol: ACTIVE

Computed Properties

Molecular Weight:95.10
XLogP3:-1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:95.037113783
Monoisotopic Mass:95.037113783
Topological Polar Surface Area:29.1
Heavy Atom Count:7
Complexity:121
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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4-Hydroxypyridine

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