Isopropyl alcohol

Isopropyl alcohol
Skeletal formula of isopropyl alcohol	Ball-and-stick model of isopropyl alcohol
Names
	Preferred IUPAC name Propan-2-ol
	Other names 2-Propanol; Isopropanol; Rubbing alcohol; sec-Propyl alcohol; 2-Hydroxypropane; i-PrOH; Dimethyl carbinol; IPA
Identifiers
CAS Number	67-63-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	635639
ChEBI	CHEBI:17824 ;
ChEMBL	ChEMBL582 ;
ChemSpider	3644 ;
ECHA InfoCard	100.000.601
Gmelin Reference	1464
KEGG	D00137 ;
PubChem CID	3776;
RTECS number	NT8050000;
UNII	ND2M416302 ;
UN number	1219
CompTox Dashboard (EPA)	DTXSID7020762 ;
	InChI InChI=1S/C3H7OH/c1-3(2)4/h3-4H,1-2H3 Key: KFZMGEQAYNKOFK-UHFFFAOYSA-N ;
	SMILES CC(O)C;
Properties
Chemical formula	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)
Solubility in water	Miscible with water
Solubility	Miscible with benzene, chloroform, ethanol, diethyl ether, glycerol; soluble in acetone
log P	−0.16
Acidity (pKa)	16.5
Magnetic susceptibility (χ)	−45.794·10−6 cm3/mol
Refractive index (nD)	1.3776
Viscosity	2.86 cP at 15 °C; 1.96 cP at 25 °C; 1.77 cP at 30 °C
Dipole moment	1.66 D (gas)
Pharmacology
ATC code	D08AX05 (WHO)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable, mildly toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H319, H336
Precautionary statements	P210, P261, P305+P351+P338
NFPA 704 (fire diamond)	1 3 0
Flash point	Open cup: 11.7 °C (53.1 °F; 284.8 K) ; Closed cup: 13 °C (55 °F)
Autoignition; temperature	399 °C (750 °F; 672 K)
Explosive limits	2–12.7%
Threshold limit value (TLV)	980 mg/m3 (TWA), 1225 mg/m3 (STEL)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	12800 mg/kg (dermal, rabbit); 3600 mg/kg (oral, mouse); 5000 mg/kg (oral, rat); 2364 mg/kg (oral, rabbit);
LC50 (median concentration)	53,000 mg/m3 (inhalation, mouse)[citation needed]; 12,000 ppm (rat, 8 h);
LCLo (lowest published)	16,000 ppm (rat, 4 h); 12,800 ppm (mouse, 3 h);
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 400 ppm (980 mg/m3)
REL (Recommended)	TWA 400 ppm (980 mg/m3), ST 500 ppm (1225 mg/m3)
IDLH (Immediate danger)	2000 ppm
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). verify (what is ?) Infobox references

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.

^ "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.
^ 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.
^ "Isopropanol_msds". chemsrc.com. Archived from the original on 10 March 2020. Retrieved 4 May 2018.
^ 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.
^ ^a ^b Yaws, C.L. (1999). Chemical Properties Handbook. McGraw-Hill. ISBN 978-0-07-073401-2.
^ Isopropyl alcohol toxicity
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0359". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c ^d "Isopropyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "Isopropanol". PubChem. Archived from the original on 12 February 2019. Retrieved 10 February 2019.

[iupac1979-1] "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.

[iupac2013-2] 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.

[chemsrc-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.

[yaws-5] Yaws, C.L. (1999). Chemical Properties Handbook. McGraw-Hill. ISBN 978-0-07-073401-2.

[6] Isopropyl alcohol toxicity

[PGCH-7] NIOSH Pocket Guide to Chemical Hazards. "#0359". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-8] "Isopropyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[PubChem-9] "Isopropanol". PubChem. Archived from the original on 12 February 2019. Retrieved 10 February 2019.

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