Isopropyl alcohol

Isopropyl alcohol
Skeletal formula of isopropyl alcohol
Skeletal formula of isopropyl alcohol
Ball-and-stick model of isopropyl alcohol
Ball-and-stick model of isopropyl alcohol
Names
Preferred IUPAC name
Propan-2-ol[2]
Other names
2-Propanol
Isopropanol[1]
Rubbing alcohol
sec-Propyl alcohol
2-Hydroxypropane
i-PrOH
Dimethyl carbinol
IPA
Identifiers
3D model (JSmol)
635639
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.601 Edit this at Wikidata
1464
KEGG
RTECS number
  • NT8050000
UNII
UN number 1219
  • InChI=1S/C3H7OH/c1-3(2)4/h3-4H,1-2H3 checkY
    Key: KFZMGEQAYNKOFK-UHFFFAOYSA-N checkY
  • CC(O)C
Properties
C3H8O
Molar mass 60.096 g/mol
Appearance Colorless liquid
Odor Pungent alcoholic odor
Density 0.786 g/cm3 (20 °C)
Melting point −89 °C (−128 °F; 184 K)
Boiling point 82.6 °C (180.7 °F; 355.8 K)
Miscible with water
Solubility Miscible with benzene, chloroform, ethanol, diethyl ether, glycerol; soluble in acetone
log P −0.16[3]
Acidity (pKa) 16.5[4]
−45.794·10−6 cm3/mol
1.3776
Viscosity 2.86 cP at 15 °C
1.96 cP at 25 °C[5]
1.77 cP at 30 °C[5]
1.66 D (gas)
Pharmacology
D08AX05 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, mildly toxic[6]
GHS labelling:
GHS07: Exclamation mark GHS02: Flammable
Danger
H225, H302, H319, H336
P210, P261, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point Open cup: 11.7 °C (53.1 °F; 284.8 K)
Closed cup: 13 °C (55 °F)
399 °C (750 °F; 672 K)
Explosive limits 2–12.7%
980 mg/m3 (TWA), 1225 mg/m3 (STEL)
Lethal dose or concentration (LD, LC):
  • 12800 mg/kg (dermal, rabbit)[8]
  • 3600 mg/kg (oral, mouse)
  • 5000 mg/kg (oral, rat)[8]
  • 2364 mg/kg (oral, rabbit)
  • 16,000 ppm (rat, 4 h)
  • 12,800 ppm (mouse, 3 h)[8]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 400 ppm (980 mg/m3)[7]
REL (Recommended)
TWA 400 ppm (980 mg/m3), ST 500 ppm (1225 mg/m3)[7]
IDLH (Immediate danger)
2000 ppm[7]
Safety data sheet (SDS) [1]
Related compounds
Related alcohols
1-Propanol, ethanol, 2-butanol
Supplementary data page
Isopropyl alcohol (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor.[9]

Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, and chloroform, demonstrating its ability to dissolve a wide range of substances including ethyl cellulose, polyvinyl butyral, oils, alkaloids, and natural resins. Notably, it is not miscible with salt solutions and can be separated by adding sodium chloride in a process known as salting out. It forms an azeotrope with water, resulting in a boiling point of 80.37 °C and is characterized by its slightly bitter taste. Isopropyl alcohol becomes viscous at lower temperatures, freezing at −89.5 °C, and has significant ultraviolet-visible absorbance at 205 nm. Chemically, it can be oxidized to acetone or undergo various reactions to form compounds like isopropoxides or aluminium isopropoxide. As an isopropyl group linked to a hydroxyl group (chemical formula (CH3)2CHOH) it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether. They all have the formula C3H8O.

It was first synthesized in 1853 by Alexander William Williamson and later produced for cordite preparation. It is produced through hydration of propene or hydrogenation of acetone, with modern processes achieving anhydrous alcohol through azeotropic distillation. Beyond its production, isopropyl alcohol serves in medical settings as a rubbing alcohol and hand sanitizer, and in industrial and household applications as a solvent. It is a common ingredient in products such as antiseptics, disinfectants and detergents. More than a million tonnes are produced worldwide annually. Despite its utility, isopropyl alcohol poses safety risks due to its flammability and potential for peroxide formation. Its ingestion or absorption leads to toxic effects including central nervous system depression and coma, primarily treated through supportive measures.

  1. ^ "Alcohols Rule C-201.1". Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H. Oxford: Pergamon Press. 1979. Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because there are no hydrocarbons isopropane, sec-butane, and tert-butane to which the suffix "-ol" can be added; such names should be abandoned. Isopropyl alcohol, sec-butyl alcohol, and tert-butyl alcohol are, however, permissible (see Rule C-201.3) because the radicals isopropyl, sec-butyl, and tert-butyl do exist.
  2. ^ Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 631. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ "Isopropanol_msds". chemsrc.com. Archived from the original on 10 March 2020. Retrieved 4 May 2018.
  4. ^ Reeve, W.; Erikson, C. M.; Aluotto, P. F. (1979). "A new method for the determination of the relative acidities of alcohols in alcoholic solutions. The nucleophilicities and competitive reactivities of alkoxides and phenoxides". Can. J. Chem. 57 (20): 2747–2754. doi:10.1139/v79-444.
  5. ^ a b Yaws, C.L. (1999). Chemical Properties Handbook. McGraw-Hill. ISBN 978-0-07-073401-2.
  6. ^ Isopropyl alcohol toxicity
  7. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0359". National Institute for Occupational Safety and Health (NIOSH).
  8. ^ a b c d "Isopropyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  9. ^ "Isopropanol". PubChem. Archived from the original on 12 February 2019. Retrieved 10 February 2019.