3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide

Basic Information

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CAS Number

475271-62-6

Molecular Formula

C16H14Cl2N2O3

Molecular Weight

353.21 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Agricultural Chemicals Pesticides Herbicides

Basic Physical Properties

Boiling Point

448.6±45.0°C at 760 mmHg

Solubility

Insuluble (7.1E-3 g/L) (25 ºC),

SMILES

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c1cc(c(cc1C(=O)Nc2c(cncc2Cl)Cl)OCC3CC3)O

InChI

InChI=1S/C16H14Cl2N2O3/c17-11-6-19-7-12(18)15(11)20-16(22)10-3-4-13(21)14(5-10)23-8-9-1-2-9/h3-7,9,21H,1-2,8H2,(H,19,20,22)

InChIKey

IJTMJUHUWQHBEA-UHFFFAOYSA-N

LogP

4.135100000000002

Topological Polar Surface Area

71.45 Å²

Hydrogen Bond Donor/Acceptor

2 / 5

Complexity

412

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H332 Harmful if inhaled
Acute toxicity, inhalation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

3-(Cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-hydroxybenzamide
4-O-Des(difluoromethyl) Roflumilast
RofluMilast related substance
AK122862
AX8247040
N-(3,5-dichloropyrid-4-yl)-3-cyclopropylmethoxy-4-hydroxybenzamide
3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide
N-(3,5-Dichloro-4-pyridyl)-3-(cyclopropylmethoxy)-4-hydroxybenzamide
Roflumilast Impurity B
BCP21143
4-O-Des(difluoromethyl) Roflumilast;3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide

MDL Number

MFCD23703091

FAQ

What are the physical and chemical properties of 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide (CAS: 475271-62-6)?

This compound is a crystalline solid with a molecular weight of approximately 394.12 g/mol. It has a low solubility in water (0.1 g/100 mL at 25°C) but is more soluble in organic solvents like methanol and dimethylformamide. It shows moderate reactivity towards nucleophiles and exhibits good stability under neutral to slightly acidic conditions. The compound is a white or off-white powder with a melting point range of 155-158°C.

How is 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide (CAS: 475271-62-6) typically synthesized?

The compound is typically synthesized via a multi-step reaction involving protection of a hydroxyl group, subsequent alkylation, and the formation of a pyridyl derivative. Key reagents include cyclopropylmethanol, dichloropyridine, and a suitable coupling agent. The reaction is carried out under mild conditions and requires careful control of pH and temperature to achieve high selectivity and yield. Common catalysts include triphenylphosphine and various base systems.

What industries use 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide (CAS: 475271-62-6)?

This compound is primarily used in the pharmaceutical industry for its potential as an intermediate in drug synthesis. It is also explored in the sensor technology sector for its reactivity and electronic properties. Additionally, it may have applications in the polymer industry as a functional monomer or additive. Its use in semiconductors is limited but could be relevant for specific applications requiring precise molecular structure control.

What precautions should be taken when handling 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-hydroxybenzamide (CAS: 475271-62-6)?

Proper handling requires the use of personal protective equipment (PPE) such as gloves, goggles, and a lab coat. This compound should be handled in a well-ventilated area or a fume hood due to its potential for respiratory irritation. Spills should be cleaned up immediately with appropriate absorbent materials and disposed of according to local hazardous waste regulations. Always refer to the Safety Data Sheet (SDS) for comprehensive handling recommendations and emergency procedures. Storage should be in a cool, dry place away from direct sunlight and incompatible materials.