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Propargyl alcohol

CAS No.:
107-19-7
Catalog Number:
AG003TYY
Molecular Formula:
C3H4O
Molecular Weight:
56.0633
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Purity
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Product Description
Catalog Number:
AG003TYY
Chemical Name:
Propargyl alcohol
CAS Number:
107-19-7
Molecular Formula:
C3H4O
Molecular Weight:
56.0633
MDL Number:
MFCD00002912
IUPAC Name:
prop-2-yn-1-ol
InChI:
InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2
InChI Key:
TVDSBUOJIPERQY-UHFFFAOYSA-N
SMILES:
OCC#C
EC Number:
203-471-2
UNII:
E920VF499L
NSC Number:
8804
RTECS Number:
UK5075000
Properties
Complexity:
38.5  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
56.026g/mol
Formal Charge:
0
Heavy Atom Count:
4  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
56.064g/mol
Monoisotopic Mass:
56.026g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
20.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.4  
Literature
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A highly efficient preparative method of alpha-ylidene-beta-diketones via Au(III)-catalyzed acyl migration of propargylic esters. Journal of the American Chemical Society 20060705
Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: novel methylenepyrrolidine and methylenetetrahydrofuran syntheses. The Journal of organic chemistry 20060428
Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups. The Journal of organic chemistry 20060414
Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. Bioorganic & medicinal chemistry letters 20060315
[1,3]-Transfer of chirality during the Nicholas reaction in gamma-benzyloxy propargylic alcohols. Chemistry (Weinheim an der Bergstrasse, Germany) 20060308
Synthesis of a NO-releasing prodrug of rofecoxib. The Journal of organic chemistry 20060120
Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition. Journal of the American Chemical Society 20051221
Carbon 1s excitation spectroscopy of propyne, trifluoropropyne, and propargyl alcohol. The journal of physical chemistry. A 20051215
O-Directed free-radical hydrostannations of propargyl ethers, acetals, and alcohols with Ph3SnH and Et3B. Organic letters 20051124
Electron inventory, kinetic assignment (E(n)), structure, and bonding of nitrogenase turnover intermediates with C2H2 and CO. Journal of the American Chemical Society 20051116
Concise and practical synthesis of C-glycosyl ketones from sugar benzothiazoles and their transformation into chiral tertiary alcohols. The Journal of organic chemistry 20051111
Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols. Journal of the American Chemical Society 20051019
Reactivity of alkynes containing alpha-hydrogen atoms with a triruthenium hydrido carbonyl cluster: alkenyl versus allyl cluster derivatives. Chemistry (Weinheim an der Bergstrasse, Germany) 20051007
Synergistic dimetallic effects in propargylic substitution reaction catalyzed by thiolate-bridged diruthenium complex. Journal of the American Chemical Society 20050706
Highly stereoselective one-pot procedure to prepare bis- and tris-chalcogenide alkenes via addition of disulfides and diselenides to terminal alkynes. The Journal of organic chemistry 20050624
Generation of N-heterocyclic carbenes by metal-mediated coupling of propargylamine and isocyanides. Journal of the American Chemical Society 20050622
Flexible synthesis of enantiomerically pure 2,8-dialkyl-1,7-dioxaspiro[5.5]undecanes and 2,7-dialkyl-1,6-dioxaspiro[4.5]decanes from propargylic and homopropargylic alcohols. The Journal of organic chemistry 20050415
Ruthenium-catalyzed cycloisomerizations of diynols. Journal of the American Chemical Society 20050406
Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines. The Journal of organic chemistry 20050318
Synthesis of diindeno-fused 4H-cyclopenta[def]phenanthren-4-ones and related compounds via benzannulated enediynyl propargylic alcohols. The Journal of organic chemistry 20050318
Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers. Bioorganic & medicinal chemistry 20050315
Aryl annulation of cyclic ketones via a magnesium carbometalation-6-pi- electrocyclization protocol. Organic letters 20050303
Substrate interactions with the nitrogenase active site. Accounts of chemical research 20050301
Ruthenium-catalyzed propargylic substitution reactions of propargylic alcohols with oxygen-, nitrogen-, and phosphorus-centered nucleophiles. Chemistry (Weinheim an der Bergstrasse, Germany) 20050218
Ruthenium-catalyzed synthesis of alkylidenecyclobutenes via head-to-head dimerization of propargylic alcohols and cyclobutadiene-ruthenium intermediates. Chemistry (Weinheim an der Bergstrasse, Germany) 20050204
Highly regioselective coupling reactions of allylic and propargylic alcohol derivatives with gamma,gamma-dialkoxyallylic zirconium species via Zr-to-Cu transmetalation. The Journal of organic chemistry 20050121
Phototransformation of clodinafop-propargyl. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20050101
Substrate interaction at an iron-sulfur face of the FeMo-cofactor during nitrogenase catalysis. The Journal of biological chemistry 20041217
Ruthenium- and platinum-catalyzed sequential reactions: selective synthesis of fused polycyclic compounds from propargylic alcohols and alkenes. Journal of the American Chemical Society 20041215
Meerwein-Ponndorf-Verley alkynylation of aldehydes: essential modification of aluminium alkoxides for rate acceleration and asymmetric synthesis. Organic & biomolecular chemistry 20041121
Regioselectivity control in a ruthenium-catalyzed cycloisomerization of diyne-ols. Organic letters 20041111
Silicon-assisted propargylic transfer to aldehydes. Chemical communications (Cambridge, England) 20041107
The mechanism of nitrogenase. Computed details of the site and geometry of binding of alkyne and alkene substrates and intermediates. Journal of the American Chemical Society 20040929
New strategy for the construction of a monotetrahydrofuran ring in Annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of Solamin. The Journal of organic chemistry 20040820
An organometallic intermediate during alkyne reduction by nitrogenase. Journal of the American Chemical Society 20040811
B(C6F5)3-catalyzed allylation of propargyl acetates with allylsilanes. Organic letters 20040610
Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: a one-pot synthesis of methylenetetrahydrofurans. Organic letters 20040610
Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by a camphorsulfonamide ligand. Organic letters 20040415
Rhenium-catalyzed aromatic propargylation. Organic letters 20040415
Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the gypsy moth, Lymantria dispar. Lipids 20040401
Ru(II)-catalyzed chemo- and regioselective cyclotrimerization of three unsymmetrical alkynes through boron temporary tether. One-pot four-component coupling via cyclotrimerization/Suzuki-Miyaura coupling. Journal of the American Chemical Society 20040331
Convenient and efficient synthesis of functionalized oligopyridine ligands bearing accessory pyrromethene-BF2 fluorophores. The Journal of organic chemistry 20040319
Construction of azacycles based on endo-mode cyclization of allenes. The Journal of organic chemistry 20040319
Phosphorylated 1,6-diphenyl-1,3,5-hexatriene. Bioorganic & medicinal chemistry letters 20040308
Investigations on the effects of cobalt-alkyne complexes on leukemia and lymphoma cells: cytotoxicity and cellular uptake. Journal of inorganic biochemistry 20040301
Screening of modified DNA aptamers that recognize DNA secondary structure. Nucleic acids symposium series (2004) 20040101
Rhenium-catalyzed coupling of propargyl alcohols and allyl silanes. Journal of the American Chemical Society 20031224
Facile one-pot synthesis of photochromic pyrans. Organic letters 20031030
A mechanistic dichotomy in ruthenium-catalyzed propargyl alcohol reactivity: a novel hydrative diyne cyclization. Journal of the American Chemical Society 20030924
Total synthesis and structure confirmation of leptofuranin D. The Journal of organic chemistry 20030919
Localization of a substrate binding site on the FeMo-cofactor in nitrogenase: trapping propargyl alcohol with an alpha-70-substituted MoFe protein. Biochemistry 20030805
A Rh(I)-catalyzed cycloisomerization of homo- and bis-homopropargylic alcohols. Journal of the American Chemical Society 20030625
Synthesis, molecular structure, and C-C coupling reactions of carbeneruthenium(II) complexes with C5H5Ru(=CRR') and C5Me5Ru(=CRR') as molecular units. Chemistry (Weinheim an der Bergstrasse, Germany) 20030606
Clotrimazole, ketoconazole, and clodinafop-propargyl as potent growth inhibitors of equine Babesia parasites during in vitro culture. The Journal of parasitology 20030601
A mild C-O bond formation catalyzed by a rhenium-oxo complex. Journal of the American Chemical Society 20030521
Ruthenium-catalyzed alkyne-propargyl alcohol addition. An asymmetric total synthesis of (+)-alpha-kainic acid. Organic letters 20030501
A mechanism for the formation of bis-glutathione conjugates of propargyl alcohol. Pest management science 20030301
Application of selectively acylated glycosides for the alpha-galactosidase-catalyzed synthesis of disaccharides. Folia microbiologica 20030101
Coupling-isomerization-coupling sequences switched on by propargyl alcohol-enone-isomerization. Molecular diversity 20030101
Dehydration reaction of hydroxyl substituted alkenes and alkynes on the Ru(2)S(2) complex. Journal of the American Chemical Society 20021106
A silica gel-supported ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide. The Journal of organic chemistry 20021101
Total synthesis of rhizoxin D, a potent antimitotic agent from the fungus Rhizopus chinensis. The Journal of organic chemistry 20021101
Characterization of propargyl bromide transformation in soil. Pest management science 20021001
Steric control of organic transformation by a dendrimer cage: organocobalt dendrimer porphyrins as novel coenzyme B(12) mimics. Journal of the American Chemical Society 20020925
Asymmetric synthesis of anti-homopropargylic alcohols from aldehydes and chiral sulfonimidoyl substituted bis(allyl)titanium complexes through generation and elimination of novel chiral alkylidenecarbene (dimethylamino)sulfoxonium ylides. Journal of the American Chemical Society 20020904
Asymmetric total synthesis of 11-deoxytetrodotoxin, a naturally occurring congener. Journal of the American Chemical Society 20020703
An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols. Journal of the American Chemical Society 20020424
Propargyloxycarbonyl (Poc) amino acid chlorides as efficient coupling reagents for the synthesis of 100% diastereopure peptides and resin bound tetrathiomolybdate as an effective deblocking agent for the Poc group. Chemical communications (Cambridge, England) 20020421
A Ru catalyzed divergence: oxidative cyclization vs cycloisomerization of bis-homopropargylic alcohols. Journal of the American Chemical Society 20020320
A Highly diastereoselective synthesis of (1R)-(+)-camphor-based chiral allenes and their asymmetric hydroboration-oxidation reactions. The Journal of organic chemistry 20020222
Ruthenium-catalyzed two-component addition to form 1,3-dienes: optimization, scope, applications, and mechanism. Journal of the American Chemical Society 20011219
Coupling of alkynylTMS derivatives with vinylic iodides. An efficient route to 1,3-enynes and dienes. Organic letters 20011213
A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence. Organic letters 20011018
Lipase-mediated resolution of 4-TMS-3-butyn-2-ol and use of the mesylate derivatives as a precursor to a highly stereoselective chiral allenylindium reagent. Organic letters 20011018
Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using alpha-alkoxypropargylstannanes. Organic letters 20010920
Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D. Journal of the American Chemical Society 20010613
Disposition of propargyl alcohol in rat and mouse after intravenous, oral, dermal and inhalation exposure. Xenobiotica; the fate of foreign compounds in biological systems 20010601
Atom economy: aldol-type products by vanadium-catalyzed additions of propargyl alcohols and aldehydes. Journal of the American Chemical Society 20010214
Cytochrome P450 2E1 metabolically activates propargyl alcohol: propiolaldehyde-induced hepatocyte cytotoxicity. Chemico-biological interactions 20010130
Reactions of first-row transition metal ions with propargyl alcohol in the gas phase. Rapid communications in mass spectrometry : RCM 20010101
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