propan-2-ol (CHEBI:17824)

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CHEBI:17824 - propan-2-ol

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ChEBI Name	propan-2-ol

ChEBI ID	CHEBI:17824

Definition	A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:8467, CHEBI:43588, CHEBI:14897, CHEBI:26280

Supplier Information	ChemicalBook:CB7300596, ChemicalBook:CB8854102, eMolecules:478530, ZINC000000901159

Download	Molfile XML SDF

more structures >>

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12 11 0 0 0 0 999 V2000

1.2130 -0.2843 0.6625 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0513 -0.4089 -0.2156 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.6843 0.9707 -0.4967 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9912 -1.2608 0.4383 O 0 0 0 0 0 0 0 0 0 0 0 0

1.6551 -1.2652 0.8427 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9603 0.3423 0.1711 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9642 0.1651 1.6264 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2196 -0.8785 -1.1654 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5679 0.8680 -1.1288 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0278 1.6210 -1.0101 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9814 1.4521 0.4377 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7639 -1.3216 -0.1621 H 0 0 0 0 0 0 0 0 0 0 0 0

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3 2 1 0 0 0 0

4 2 1 0 0 0 0

1 5 1 0 0 0 0

1 6 1 0 0 0 0

1 7 1 0 0 0 0

2 8 1 0 0 0 0

3 9 1 0 0 0 0

3 10 1 0 0 0 0

3 11 1 0 0 0 0

4 12 1 0 0 0 0

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Wikipedia	License
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. 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.
Read full article at Wikipedia

Formula

C3H8O

Net Charge

Average Mass

60.09502

Monoisotopic Mass

60.05751

InChI

InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3

InChIKey

KFZMGEQAYNKOFK-UHFFFAOYSA-N

SMILES

CC(C)O

Roles Classification
Chemical Role(s):	protic solvent A polar solvent that is capable of acting as a hydron (proton) donor.

Application(s):	protic solvent A polar solvent that is capable of acting as a hydron (proton) donor.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	propan-2-ol (CHEBI:17824) has role protic solvent (CHEBI:48356) propan-2-ol (CHEBI:17824) is a secondary alcohol (CHEBI:35681) propan-2-ol (CHEBI:17824) is a secondary fatty alcohol (CHEBI:167095)

Incoming	(S)-1-(2,5-xylyloxy)-3-morpholinopropan-2-ol (CHEBI:41617) has functional parent propan-2-ol (CHEBI:17824) 1,1,1,3,3,3-hexafluoropropan-2-ol (CHEBI:63104) has functional parent propan-2-ol (CHEBI:17824) O-propan-2-yl hexanethioate (CHEBI:177491) has functional parent propan-2-ol (CHEBI:17824) isopropyl 3-hydroxybut-2-enoate (CHEBI:38868) has functional parent propan-2-ol (CHEBI:17824) isopropyl ester (CHEBI:35725) has functional parent propan-2-ol (CHEBI:17824) monoisopropyl phthalate (CHEBI:132587) has functional parent propan-2-ol (CHEBI:17824) trimethyl(1-methylethoxy)silane (CHEBI:76336) has functional parent propan-2-ol (CHEBI:17824)

IUPAC Name

propan-2-ol

Synonyms	Sources
1-methylethanol	ChemIDplus
1-methylethyl alcohol	ChemIDplus
2-hydroxypropane	ChemIDplus
2-Propanol	KEGG COMPOUND
i-propanol	NIST Chemistry WebBook
i-Propylalkohol	NIST Chemistry WebBook
IPA	NIST Chemistry WebBook
Isopropanol	KEGG COMPOUND
ISOPROPYL ALCOHOL	PDBeChem
isopropyl alcohol	ChemIDplus
Isopropyl alcohol	KEGG COMPOUND
Isopropylalkohol	ChEBI
Propan-2-ol	KEGG COMPOUND
propan-2-ol	UniProt
sec-propanol	NIST Chemistry WebBook

Manual Xrefs	Databases
4215	DrugCentral
C00048438	KNApSAcK
C01845	KEGG COMPOUND
c0519	UM-BBD
D00137	KEGG DRUG
DB04402	DrugBank
HMDB0000863	HMDB
IPA	PDBeChem
ISO-PROPANOL	MetaCyc
Isopropyl_Alcohol	Wikipedia
YMDB01718	YMDB
View more database links

Registry Numbers	Types	Sources
1464	Gmelin Registry Number	Gmelin
635639	Reaxys Registry Number	Reaxys
67-63-0	CAS Registry Number	KEGG COMPOUND
67-63-0	CAS Registry Number	NIST Chemistry WebBook
67-63-0	CAS Registry Number	ChemIDplus

Citations

Kampf G, Sammann A, Pitten FA, Christiansen B, Heeg P, Nowak N (2014)
Efficacy of two iso-propanol-based skin antiseptics applied to human skin with many sebaceous glands for 2 and 10 minutes.
GMS hygiene and infection control 9, Doc10 [PubMed:24653974]
[show Abstract]

Dub PA, Henson NJ, Martin RL, Gordon JC (2014)
Unravelling the mechanism of the asymmetric hydrogenation of acetophenone by [RuX2(diphosphine)(1,2-diamine)] catalysts.
Journal of the American Chemical Society 136, 3505-3521 [PubMed:24524727]
[show Abstract]
The mechanism of catalytic hydrogenation of acetophenone by the chiral complex trans-[RuCl2{(S)-binap}{(S,S)-dpen}] and KO-t-C4H9 in propan-2-ol is revised on the basis of DFT computations carried out in dielectric continuum and the most recent experimental observations. The results of these collective studies suggest that neither a six-membered pericyclic transition state nor any multibond concerted transition states are involved. Instead, a hydride moiety is transferred in an outer-sphere manner to afford an ion-pair, and the corresponding transition state is both enantio- and rate-determining. Heterolytic dihydrogen cleavage proceeds neither by a (two-bond) concerted, four-membered transition state, nor by a (three-bond) concerted, six-membered transition state mediated by a solvent molecule. Instead, cleavage of the H-H bond is achieved via deprotonation of the η(2)-H2 ligand within a cationic Ru complex by the chiral conjugate base of (R)-1-phenylethanol. Thus, protonation of the generated (R)-1-phenylethoxide anion originates from the η(2)-H2 ligand of the cationic Ru complex and not from NH protons of a neutral Ru trans-dihydride complex, as initially suggested within the framework of a metal-ligand bifunctional mechanism. Detailed computational analysis reveals that the 16e(-) Ru amido complex [RuH{(S)-binap}{(S,S)-HN(CHPh)2NH2}] and the 18e(-) Ru alkoxo complex trans-[RuH{OCH(CH3)(R)}{(S)-binap}{(S,S)-dpen}] (R = CH3 or C6H5) are not intermediates within the catalytic cycle, but rather are off-loop species. The accelerative effect of KO-t-C4H9 is explained by the reversible formation of the potassium amidato complexes trans-[RuH2{(S)-binap}{(S,S)-N(K)H(CHPh)2NH2}] or trans-[RuH2{(S)-binap}{(S,S)-N(K)H(CHPh)2NH(K)}]. The three-dimensional (3D) cavity observed within these molecules results in a chiral pocket stabilized via several different noncovalent interactions, including neutral and ionic hydrogen bonding, cation-π interactions, and π-π stacking interactions. Cooperatively, these interactions modify the catalyst structure, in turn lowering the relative activation barrier of hydride transfer by ~1-2 kcal mol(-1) and the following H-H bond cleavage by ~10 kcal mol(-1), respectively. A combined computational study and analysis of recent experimental data of the reaction pool results in new mechanistic insight into the catalytic cycle for hydrogenation of acetophenone by Noyori's catalyst, in the presence or absence of KO-t-C4H9.

Last Modified

11 May 2023

ChEBI

CHEBI:17824 - propan-2-ol

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