(3R)-3-methylpent-1-yn-3-ol

Base Information

• Chemical Name: (3R)-3-methylpent-1-yn-3-ol
• CAS No.: 77-75-8
• Molecular Formula: C6H10O
• Molecular Weight: 98.1448
• Hs Code.: 29280090
• NSC Number: 760378
• Nikkaji Number: J1.314.145B
• Mol file: 77-75-8.mol

Synonyms:(3R)-3-methylpent-1-yn-3-ol;MEPARFYLON;(?)-Methylparafynol;Pharmakon1600-01506158;NSC760378;NSC-760378

Chemical Property of (3R)-3-methylpent-1-yn-3-ol

Chemical Property:

• Appearance/Colour: Clear slightly yellow liquid or low melting solid
• Vapor Pressure: 6.5 mm Hg ( 20 °C)
• Melting Point: -30 °C
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 120.5 °C at 760 mmHg
• PKA: 13.34±0.29(Predicted)
• Flash Point: 26.7 °C
• PSA: 20.23000
• Density: 0.901 g/cm³
• LogP: 0.78060
• Storage Temp.: Flammables area
• Solubility.: Cellosolve: miscible
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 98.073164938
• Heavy Atom Count: 7
• Complexity: 98

Purity/Quality:

99.9% ^*data from raw suppliers

3-Methyl-1-pentyn-3-ol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F+
• Hazard Codes: Xn,F+
• Statements: 10-22-51/53-2017/10/22
• Safety Statements: 23-36-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)(C#C)O
• Isomeric SMILES: CC[C@](C)(C#C)O
• Uses: 3-Methylpent-1-yn-3-ol is an inhibitor; used in method for preparing high-insulation solvent-free silicone resin for composite insulator. Stabilizer in chlorinated solvents, viscousreducer, electroplating brightener, intermediate insyntheses of hypnotics and isoprenoid chemicals,solvent for polyamide resins, acid inhibitor, preven-tion of hydrogen embrittlement, medicine (soporificand anesthetic).
• Therapeutic Function: Sedative

Technology Process of (3R)-3-methylpent-1-yn-3-ol

There total 17 articles about (3R)-3-methylpent-1-yn-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

butanone (78-93-3) + acetylene (74-86-2,25067-58-7) → meparfynol (77-75-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.bmcl.2004.09.032

Reference yield: 66.1%

butanone (78-93-3) + lithium acetylide (70277-75-7) → meparfynol (77-75-8)

Guidance literature:

In diethyl ether; at -78 ℃; for 4h;

DOI:10.1016/0957-4166(95)00031-J

Reference yield: 52.0%

butanone (78-93-3) + acetylenemagnesium bromide (4301-14-8) → meparfynol (77-75-8)

Guidance literature:

In tetrahydrofuran; Heating;

upstream raw materials:

3,6-dimethyl-oct-4-yne-3,6-diol

butanone

acetylenemagnesium bromide

sodium acetylide

Downstream raw materials:

propionic acid-(1-ethyl-1-methyl-prop-2-ynyl ester)

3-methylpent-1-yn-3-ol benzoate

3-methylpent-3-en-1-yne

3-acetoxy-3-ethylbutyne

Refernces

Quantitative study of interactions between oxygen lone pair and aromatic rings: Substituent effect and the importance of closeness of contact

10.1021/jo702170j

This research presents a quantitative study examining the interactions between oxygen lone pairs and aromatic rings, with a focus on the substituent effect and the significance of close contact. The purpose of the study was to understand the nature of these interactions, particularly in the context of electron-rich aromatic rings and oxygen lone pairs, and to challenge the current models that describe aromatic rings as polar groups based on their quadrupole moments. The researchers used a triptycene-derived model system to measure the free energies of interactions and equilibrium constants through low-temperature 1H NMR spectroscopy. They also conducted X-ray structure analysis and theoretical calculations at the MP2/aug-cc-pVTZ level to corroborate their experimental findings. The study involved a range of chemicals, including triptycene scaffolds with various substituents (such as NO2, CN, CF3, halogens, CH3, CH3O, and Me2N), methoxymethyl (MOM) groups, and pentafluorophenyl rings. The conclusions drawn from the research indicated that aromatic rings exhibit attractive interactions with oxygen lone pairs even at van der Waals distances, and that these interactions cannot be fully explained by current models, suggesting that dispersion forces and local dipoles should also be considered alongside electrostatic forces.

A photochemical synthesis of benzocyclopropenone

10.1039/C29690000220

The study investigates the photochemical synthesis of benzocyclopropenone (IVa) through the decomposition of lithium 3-p-tolyl sulphonylamino-1,2,3-benzotriazin-4(3H)-one (Ia) and its 6-chloro-analogue (Ib). The precursor compounds are prepared by diazotization of anthranilic acid toluene-sulfonohydrazides and subsequent treatment with lithium hydride or lithium methoxide. Upon UV excitation, Ia decomposes to yield lithium toluene-p-sulphonate, methyl benzoate, and o-methoxybenzoic acid toluene-p-sulphonohydrazide, while Ib gives lithium toluene-p-sulphonate, methyl p-chlorobenzoate, and 5-chloro-2-methoxy-benzoic acid toluene-p-sulphonohydrazide. The formation of p-chlorobenzoate suggests the involvement of a benzocyclopropenone intermediate (IVb) in the reaction mechanism, which undergoes hemiacetal formation and Favorskii ring-opening to produce the ester. The study also explores the thermolysis of Ia in triglyme, which yields triptycene, possibly via decarbonylation of IVa to form benzyne (VIIIa), and the photolysis of Ib in benzene, producing a small amount of p-chlorobenzophenone.