1-Pentanol

Last updated: March 19, 2023

1-Pentanol is an organic compound with formula C₅H₁₁OH.

Table of contents

Names

List of substance names

Nomenclature

Name

Typical name: 1-Pentanol

Substitutive nomenclature: Pentan-1-ol
★Preferred IUPAC name; 1-Pentanol

Functional class nomenclature: Pentyl alcohol

Other names: n-Pentanol; n-Pentyl alcohol; n-Amyl alcohol

Formulae and structures

List of formulae

Formula name

Formula

Typical formula: C₅H₁₁OH

Molecular formula: C₅H₁₁OH

Empirical formula: C₅H₁₂O

Condensed formula: CH₃(CH₂)₃CH₂OH

Structural formula

Structural formula with no C–H bond

Skeletal formula

Skeletal formula with terminal carbon

Lewis structure

Colored Lewis structure

Properties

List of substance properties

Item

Value

Name: 1-Pentanol

Formula: C₅H₁₁OH

Appearance: Colorless liquid

Odor: Characteristic odor^[1]; Stench odor^[2]

Molar mass: 88.150 g/mol

Density: 0.8146 g/cm³^[3]
Liquid, 20°C; 0.8144 g/cm³^[4]
Liquid, 20°C

Melting point: −79 °C^[3]; −77.58 °C^[4]

Boiling point: 137.5 °C^[3]; 137.6 °C^[4]

Flash point: 33 °C^[3]

Refractive index: 1.4100^[3]
20°C; 1.4101^[4]
20°C

Constituents

Constituent atoms

Atom	Name	Oxidation state	Number
C	Carbon	−3	1
C	Carbon	−2	3
C	Carbon	−1	1
H	Hydrogen	+1	12
O	Oxygen	−2	1

Ratio of atoms

Atom	Atomic weight	Number	Atomic ratio	Weight ratio
C	12.011	5	27.78%	68.13%
H	1.008	12	66.67%	13.72%
O	15.999	1	5.56%	18.15%

Thermodynamic properties

Phase transition properties

Item

Value

Enthalpy of fusion: 9.83 kJ · mol⁻¹^[3]
at −79°C; 10.50 kJ · mol⁻¹^[4]
at -77.58°C

Enthalpy of vaporization: 44.4 kJ · mol⁻¹^[3]
at 137.5°C; 44.36 kJ · mol⁻¹^[4]
at 137.6°C

Enthalpy of vaporization at 25°C: 57.0 kJ · mol⁻¹^[3]; 57.02 kJ · mol⁻¹^[4]

Enthalpy of other transition: –

Solubility

Qualitative solubility

Reactive

Miscible: C₂H₅OH^[3][4]Ethanol
C₂H₅OC₂H₅^[3][4]Diethyl ether

Very soluble

Soluble: H₂OWater
CH₃COCH₃^[4]Acetone
CHCl₃^[4]Trichloromethane

Slightly soluble

Very slightly soluble

Insoluble

Solubility in water (g/100 g)^[3]

22°C
2.7

Solubility curve (g/100 g)

Hazards

GHS label^[5]

Item

Value

Hazard pictograms: GHS02: Flame; GHS07: Exclamation mark; GHS08: Health hazard

Signal word: Warning

Hazard statements: H226: Flammable liquid and vapor; H315: Causes skin irritation; H319: Causes serious eye irritation; H371: May cause damage to organs; H371: May cause damage to central nervous system; H335: May cause respiratory irritation; H402: Harmful to aquatic life

Physical hazards^[5]

Classification	Category	Label	Hazard statement
Explosives	Not applicable
Flammable gases	Not applicable
Aerosols	Not applicable
Oxidizing gases	Not applicable
Gases under pressure	Not applicable
Flammable liquids	Category 3	Warning	H226: Flammable liquid and vapor
Flammable solids	Not applicable
Self reactive substances and mixtures	Not applicable
Pyrophoric liquids	Not classified
Pyrophoric solids	Not applicable
Self heating substances and mixtures	Classification not possible
Substances and mixtures which in contact with water emit flammable gases	Not applicable
Oxidizing liquids	Not applicable
Oxidizing solids	Not applicable
Organic peroxides	Not applicable
Substances and mixtures corrosive to metals	Classification not possible
Desensitized explosives	No data

Health hazards^[5]

Classification	Category	Label	Hazard statement
Acute oral toxicity	Not classified
Acute dermal toxicity	Not classified
Acute inhalation toxicity by gas	Not applicable
Acute inhalation toxicity by vapor	Classification not possible
Acute inhalation toxicity by dust or mist	Not classified
Skin corrosion irritation	Category 2	Warning	H315: Causes skin irritation
Serious eye damage eye irritation	Category 2A	Warning	H319: Causes serious eye irritation
Respiratory sensitization	Classification not possible
Skin sensitization	Classification not possible
Germ cell mutagenicity	Classification not possible
Carcinogenicity	Classification not possible
Reproductive toxicity	Classification not possible
Specific target organ toxicity single exposure	Category 2 (Central nervous system)	Warning	H371: May cause damage to organs H371: May cause damage to central nervous system
Specific target organ toxicity single exposure	Category 3 (Respiratory tract irritation)	Warning	H335: May cause respiratory irritation
Specific target organ toxicity repeated exposure	Classification not possible
Aspiration hazard	Classification not possible

Environmental hazards^[5]

Classification	Category	Hazard statement
Hazardous to the aquatic environment short term	Category 3	H402: Harmful to aquatic life
Hazardous to the aquatic environment long term	Not classified
Hazardous to the ozone layer	No data

Preparations

Reaction of aldehyde and hydrogen

The reaction of pentanal and hydrogen yields 1-Pentanol.

Reaction of pentanal and hydrogen: C₄H₉CHOPentanal + H₂Hydrogen
Ni|Pd|Pt
⟶

C₅H₁₁OH1-Pentanol

Reaction of alkyl halide and hydroxide ion

The reaction of 1-Chloropentane and hydroxide ion yields 1-Pentanol and chloride ion.

Reaction of 1-Chloropentane and hydroxide ion: C₅H₁₁Cl1-Chloropentane + OH⁻Hydroxide ion
⟶
C₅H₁₁OH1-Pentanol + Cl⁻Chloride ion

Reaction of carboxylic acid, tetrahydridoaluminate, and hydrogen ion

The reaction of pentanoic acid, lithium tetrahydridoaluminate, and hydrogen ion yields 1-Pentanol, lithium ion, aluminium ion, and water.

Reaction of pentanoic acid, lithium tetrahydridoaluminate, and hydrogen ion: 2C₄H₉COOHPentanoic acid + Li[AlH₄]Lithium tetrahydridoaluminate + 4H⁺Hydrogen ion
① Li[AlH₄]
⟶
② H⁺
2C₅H₁₁OH1-Pentanol + Li⁺Lithium ion + Al³⁺Aluminium ion + 2H₂OWater

Reaction of aldehyde, tetrahydridoaluminate, and hydrogen ion

The reaction of pentanal, lithium tetrahydridoaluminate, and hydrogen ion yields 1-Pentanol, lithium ion, and aluminium ion.

Reaction of pentanal, lithium tetrahydridoaluminate, and hydrogen ion: 4C₄H₉CHOPentanal + Li[AlH₄]Lithium tetrahydridoaluminate + 4H⁺Hydrogen ion
⟶
4C₅H₁₁OH1-Pentanol + Li⁺Lithium ion + Al³⁺Aluminium ion

Chemical reactions

Reaction with halogenide ion and hydrogen ion

The reaction of 1-Pentanol, chloride ion, and hydrogen ion yields 1-Chloropentane and water.

Reaction of 1-Pentanol, chloride ion, and hydrogen ion: C₅H₁₁OH1-Pentanol + Cl⁻Chloride ion + H⁺Hydrogen ion
⟶
C₅H₁₁Cl1-Chloropentane + H₂OWater

Dehydration of 1-Pentanol

The reaction of 1-Pentanol yields 1-Pentene and water.

Dehydration of 1-Pentanol: C₅H₁₁OH1-Pentanol
H₂SO₄, 🔥
⟶

C₅H₁₀1-Pentene + H₂OWater

References

List of references

1
Maryadele J O'Neil, Patricia E. Heckelman, Peter H. Dobbelaar, Cristin J. Roman, Catherine M. Kenny, Linda S. Karaffa (2013)
The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Edition
https://pubs.rsc.org/en/content/ebook/978-1-84973-670-1
Royal Society of Chemistry
- Amazon
Citation list
- ^ Odor, Characteristic odor - p.1324
2
Fisher Scientific
Fisher Scientific: Lab Equipment and Lab Supplies
https://www.fishersci.com/us/en/home.html
Thermo Fisher Scientific
Citation list
- ^ Odor, Stench odor [Reference page]
3
James G. Speight (2017)
Lange's Handbook of Chemistry, 17th edition
https://www.accessengineeringlibrary.com/content/book/9781259586095
McGraw Hill Education
- Amazon
Citation list
- ^ Density, 0.8146 g/cm³ - p.652
- ^ Melting point, −79 °C - p.652
- ^ Boiling point, 137.5 °C - p.652
- ^ Flash point, 33°C - p.652
- ^ Refractive index, 1.4100 (20°C) - p.652
- ^ Enthalpy of fusion, 9.83 kJ · mol⁻¹ - p.1015
- ^ Enthalpy of vaporization, 44.4 kJ · mol⁻¹ - p.1015
- ^ Enthalpy of vaporization at 25°C, 57.0 kJ · mol⁻¹ - p.1015
- ^ Qualitative solubility, Miscible with ethanol - p.652
- ^ Qualitative solubility, Miscible with diethyl ether - p.652
- ^ Solubility in Water (g/100 g), See the table - p.652
4
John R. Rumble Jr, David R. Lide, Thomas J. Bruno (2019)
CRC Handbook of Chemistry and Physics 100th Edition
https://www.routledge.com/CRC-Handbook-of-Chemistry-and-Physics/book-series/CRCHANCHEPHY
CRC Press
- Amazon
Citation list
- ^ Density, 0.8144 g/cm³ - p.3-44
- ^ Melting point, −77.58 °C - p.3-44
- ^ Boiling point, 137.6 °C - p.3-44
- ^ Refractive index, 1.4101 (20°C) - p.3-44
- ^ Enthalpy of fusion, 10.50 kJ · mol⁻¹ - p.6-159
- ^ Enthalpy of vaporization, 44.36 kJ · mol⁻¹ - p.6-149
- ^ Enthalpy of vaporization at 25°C, 57.02 kJ · mol⁻¹ - p.6-149
- ^ Qualitative solubility, Miscible with ethanol - p.3-44
- ^ Qualitative solubility, Miscible with diethyl ether - p.3-44
- ^ Qualitative solubility, Soluble in acetone - p.3-44
- ^ Qualitative solubility, Soluble in trichloromethane - p.3-44
5
Chemical Management Center
GHS Classification Results
https://www.nite.go.jp/chem/english/ghs/all_fy_e.html
National Institute of Technology and Evaluation
Citation list

1-Pentanol

Names

List of substance names

Formulae and structures

List of formulae

Properties

List of substance properties

Constituents

Constituent atoms

Ratio of atoms

Thermodynamic properties

Phase transition properties

Solubility

Qualitative solubility

Solubility in water (g/100 g)[3]

Solubility curve (g/100 g)

Hazards

GHS label[5]

Physical hazards[5]

Health hazards[5]

Environmental hazards[5]

Preparations

Reaction of aldehyde and hydrogen

Reaction of alkyl halide and hydroxide ion

Reaction of carboxylic acid, tetrahydridoaluminate, and hydrogen ion

Reaction of aldehyde, tetrahydridoaluminate, and hydrogen ion

Chemical reactions

Reaction with halogenide ion and hydrogen ion

Dehydration of 1-Pentanol

References

List of references

Related substances

Aliphatic alcohol

Primary alcohol

Related categories

Solubility in water (g/100 g)^[3]

GHS label^[5]

Physical hazards^[5]

Health hazards^[5]

Environmental hazards^[5]