77-75-8

Usage

Uses

Used in High-Insulation Solvent-Free Silicone Resin for Composite Insulators:
3-Methyl-1-pentyn-3-ol is used as an inhibitor in the method for preparing high-insulation solvent-free silicone resin for composite insulators. Its role as an inhibitor helps enhance the insulation properties and overall performance of the silicone resin, making it suitable for use in composite insulators.
Used in Chlorinated Solvents:
In the chlorinated solvents industry, 3-Methyl-1-pentyn-3-ol is utilized as a stabilizer. It helps maintain the stability and longevity of the solvents, ensuring their effectiveness and safety during use.
Used as a Viscosity Reducer:
3-Methyl-1-pentyn-3-ol is employed as a viscosity reducer in various applications, where it helps lower the viscosity of liquids, making them easier to handle and process.
Used as an Electroplating Brightener:
In the electroplating industry, 3-Methyl-1-pentyn-3-ol is used as a brightener to improve the appearance and quality of the electroplated surfaces.
Used as an Intermediate in Synthesis:
3-Methyl-1-pentyn-3-ol serves as an intermediate in the synthesis of hypnotics and isoprenoid chemicals, contributing to the development of pharmaceuticals and other related compounds.
Used as a Solvent for Polyamide Resins:
3-Methyl-1-pentyn-3-ol is also used as a solvent for polyamide resins, which are essential in the production of various plastics and materials with specific properties.
Used as an Acid Inhibitor:
3-Methyl-1-pentyn-3-ol is utilized as an acid inhibitor in different applications, where it helps prevent the formation of acids that could cause corrosion or other undesirable effects.
Used for Prevention of Hydrogen Embrittlement:
In the field of materials science, 3-Methyl-1-pentyn-3-ol is used to prevent hydrogen embrittlement, a phenomenon that can lead to the failure of metals and alloys under stress.
Used in Medicine:
3-Methyl-1-pentyn-3-ol is also used in the medical field, particularly as a soporific (sleep-inducing) and anesthetic agent, thanks to its ability to induce sedation and reduce the sensation of pain.

Originator

Citodorm,Haury

Manufacturing Process

To 5 parts of sodium acetylene in absolute ether 6 parts of dry methyl ethyl ketone was slowly dropwise added with ice cooling and stirring. Than the reaction mixture was poured into excess of acetic acid by ice cooling and extracted with ether. The ether extract was washed with solution of potash for removing the diluted acetic acid and dried over potassium carbonate. The ether was distilled off and residual colorless oil methylpentynol had BP at 120°-121°C. Instead of sodium acetylene the solution of sodium acetylene in liquid ammonia may be successfully used.

Therapeutic Function

Sedative

InChI:InChI=1/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3/t6-/m0/s1

Synthetic route

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

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃;	100%
With tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 5℃; for 1h; Favorskii-Babayan Synthesis;	78%
With sodium amide

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

Conditions	Yield
In diethyl ether at -78℃; for 4h;	66.1%

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

Conditions	Yield
In tetrahydrofuran Heating;	52%
With tetrahydrofuran
Stage #1: butanone; acetylenemagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: With ammonium chloride In tetrahydrofuran; water
In tetrahydrofuran at -10 - 20℃;

3,6-dimethyl-oct-4-yne-3,6-diol (78-66-0) → butanone (78-93-3) + meparfynol (77-75-8)

Conditions	Yield
With potassium carbonate
With potassium carbonate

sodium acetylide (1066-26-8) + butanone (78-93-3) → meparfynol (77-75-8)

Conditions	Yield
With ammonia

3-chloro-3-methylpent-1-yne (14179-94-3) → meparfynol (77-75-8)

Conditions	Yield
With water; calcium carbonate at 80 - 90℃;

ethylamine (75-04-7) + 1-bromo-3-methyl-1,2-pentadiene (10575-70-9) → 3-ethylamino-3-methyl-1-pentyne (14465-45-3) + (E,E)-N-ethyl-4-methyl-1-aza-1,3-hexadiene + meparfynol (77-75-8)

Conditions	Yield
With potassium hydroxide at 25℃; for 120h;	A 91 % Chromat. B n/a C 7 % Chromat.

tert-butylamine (75-64-9) + 1-bromo-3-methyl-1,2-pentadiene (10575-70-9) → 3-t-butylamino-3-methyl-1-pentyne (1185-98-4) + (E,E)-N-t-butyl-4-methyl-1-aza-1,3-hexadiene + meparfynol (77-75-8)

Conditions	Yield
With potassium hydroxide at 100℃; for 5h; Yield given;	A 57 % Chromat. B n/a C 23 % Chromat.

sodium amide + butanone (78-93-3) + acetylene (74-86-2) → meparfynol (77-75-8)

sodium amide + butanone (78-93-3) + acetylene (74-86-2) → 3,6-dimethyl-oct-4-yne-3,6-diol (78-66-0) + meparfynol (77-75-8)

water (7732-18-5) + 3-chloro-3-methylpent-1-yne (14179-94-3) + CaCO3 → meparfynol (77-75-8)

Conditions	Yield
at 80 - 90℃;

butanone (78-93-3) + potassium acetylenide → meparfynol (77-75-8)

3,6-dimethyl-oct-4-yne-3,6-diol (78-66-0) + K2CO3 → butanone (78-93-3) + acetylene (74-86-2) + meparfynol (77-75-8)

Conditions	Yield
at 170℃; mixtures of stereoisomer(ic)/s;
at 170℃; mixtures of stereoisomer(ic)/s;

3-Hydroxy-3-methyl-1-trimethylsilyl-pentin-(1) (17889-43-9) → meparfynol (77-75-8)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 1h; Inert atmosphere;

3,4-dihydro-2H-pyran (110-87-2) + meparfynol (77-75-8) → 2-(3-methylpent-1-yn-3-yloxy)tetrahydro-2H-pyran (28659-16-7)

Conditions	Yield
With lithium hexafluorophosphate In hexane at 10 - 15℃; for 0.25h;	100%
With toluene-4-sulfonic acid In dichloromethane at -20℃; for 1h;	84%
With calcium chloride In dichloromethane at 25℃; for 2h;	80%

acetic anhydride (108-24-7) + meparfynol (77-75-8) → 3-acetoxy-3-ethylbutyne (1185-96-2)

Conditions	Yield
tetrafluoroboric acid; silica gel at 20℃; for 2h;	100%
indium(III) chloride at 20℃; for 0.5h;	100%
With zirconium(IV) chloride at 20℃; for 1h;	100%

meparfynol (77-75-8) → (E)-3-methylpent-3-en-2-one (1567-73-3)

Conditions	Yield
With NH4NO3-exchanged zeolite HSZ-320 In chlorobenzene at 130℃; for 4h;	100%
With sulfuric acid; acetic acid In chloroform for 1h; Heating;	70%
With formic acid oder dessen Acetat;

phenyl isocyanate (103-71-9) + meparfynol (77-75-8) → 3-methylpent-1-yn-3-yl phenylcarbamate (32496-85-8)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 90h;	100%

carbon dioxide (124-38-9) + meparfynol (77-75-8) → 4-ethyl-4-methyl-5-methylene-1,3-dioxolan-2-one (80956-52-1)

Conditions	Yield
With polystyrene-supported N-heterocyclic carbene-silver complex at 40℃; under 37503.8 Torr; for 24h; Autoclave;	99%
With [(triphenylphosphine)2Ag]2CO3 In neat (no solvent) at 25℃; under 750.075 Torr; for 3h; Schlenk technique;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 30℃; under 7500.75 Torr; for 8h; Catalytic behavior; Autoclave; Green chemistry;	98%

benzyl azide (622-79-7) + meparfynol (77-75-8) → C13H17N3O (1354827-07-8)

Conditions	Yield
With (η5-C5Me5)Ru(P(i-Pr)3)Cl In dichloromethane at 20℃; for 0.0166667h;	99%

carbon dioxide (124-38-9) + N-butylamine (109-73-9) + meparfynol (77-75-8) → 3-butyl-5-ethyl-5-methyl-4-methylene-oxazolidin-2-one (91356-08-0)

Conditions	Yield
With copper(l) iodide at 30℃; under 750.075 Torr; for 12h; Schlenk technique; Ionic liquid;	99%
With silver(I) tungstate; triphenylphosphine In neat (no solvent) at 50℃; under 3750.38 Torr; for 12h; Molecular sieve;	89%
With triphenylphosphine In dimethyl sulfoxide at 50℃; under 750.075 Torr; for 12h;	> 99 %Spectr.

5-chloro-2-iodoaniline (6828-35-9) + meparfynol (77-75-8) → 1-(2-amino-4-chlorophenyl)-3-methylpent-1-yn-3-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 30℃; for 4h; Inert atmosphere;	99%

carbon dioxide (124-38-9) + meparfynol (77-75-8) → C13H20O4

Conditions	Yield
With C9H16N2*C5H5NO at 50℃; under 3750.38 Torr; for 18h;	99%

meparfynol (77-75-8) → 3-hydroxy-3-methyl-1-pentene (918-85-4)

Conditions	Yield
With quinoline; hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr;	98%
With potassium hydroxide; hydrogen; Lindlar's catalyst In pentane for 4h;	88%
With hydrogen; palladium on barium sulfate In pyridine for 2h; reduced pressure;	67.3%

bis(triphenylphosphine)palladium(II) dichloride + 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (372080-84-7) + meparfynol (77-75-8) → 3-cyclopentyl-2-[4-(3-hydroxy-3-methyl-pent-1-ynyl)-phenyl]-propionic acid methyl ester

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide	98%

2-Methoxypropene (116-11-0) + meparfynol (77-75-8) → 6-methyl-octa-4,5-dien-2-one (1043584-53-7)

Conditions	Yield
With sulfonic acid resin T239 at 90℃; for 5h; Autoclave; Inert atmosphere;	98%
sulfuric acid In methanol at 95 - 105℃; for 1.91667 - 20h; Product distribution / selectivity;	95%

carbon dioxide (124-38-9) + benzyl alcohol (100-51-6) + meparfynol (77-75-8) → benzyl (3-methyl-2-oxopentan-3-yl) carbonate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In acetonitrile at 80℃; under 7500.75 Torr; for 24h; Autoclave; Sealed tube; chemoselective reaction;	98%
With tetrabutylammomium bromide; silver sulfadiazine at 80℃; under 750.075 Torr; for 18h; Schlenk technique;	98%
With triphenylphosphine; silver carbonate In acetonitrile at 80℃; under 7500.75 Torr; for 18h; Autoclave;	93%
With DBN In N,N-dimethyl-formamide at 50℃; under 7500.75 Torr; for 6h;	90 %Spectr.

meparfynol (77-75-8) → rac-3-hydroxy-3-methylpentanenitrile (14368-30-0)

Conditions	Yield
With C24H20N2O4Ru; hydrazine hydrate In toluene at 150℃; Inert atmosphere; Microwave irradiation;	98%

t-butyldimethylsiyl triflate (69739-34-0) + meparfynol (77-75-8) → tert-butyldimethyl((3-methylpent-1-yn-3-yl)oxy)silane (128176-27-2)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 2h; Inert atmosphere;	98%

meparfynol (77-75-8) → 3-hydroxy-3-methyl-1-pentene (918-85-4) + 3-methylpentan-3-ol (77-74-7)

Conditions	Yield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr; for 0.0666667h; Product distribution; Kinetics; Further Variations:; Catalysts; reaction time;	A 97% B 3%
With sodium hydroxide; copper bei der elektrolytischen Reduktion;
With quinoline; hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr; Kinetics; Product distribution; Further Variations:; Catalysts; Solvents;
With sodium bromate; acetic acid; hydrazine In water at 20 - 60℃; for 5h;
With hydrogen In toluene at 139.84℃; under 67506.8 Torr; Reagent/catalyst; Flow reactor;

Phenylselenyl chloride (5707-04-0) + meparfynol (77-75-8) → E-1-phenylseleno-2-chloro-3-methyl-1-penten-3-ol (77955-92-1)

Conditions	Yield
In dichloromethane Ambient temperature;	97%

pyrrolidine (123-75-1) + carbon dioxide (124-38-9) + meparfynol (77-75-8) → 3-methyl-2-oxopentan-3-yl pyrrolidine-1-carboxylate

Conditions	Yield
With silver(I) tungstate; triphenylphosphine In neat (no solvent) at 50℃; under 3750.38 Torr; for 12h;	97%
With [2,2]bipyridinyl; copper at 100℃; under 28880 Torr; for 24h;	90 % Chromat.
With silver(I) bromide In neat (no solvent) at 50℃; under 11251.1 Torr; for 5h; Schlenk technique;	92 %Chromat.
With laccase and 2,2,6,6-tetra-methylpiperidine-1oxyl immobilized onto glycidyloxypropyl functionalized fibrous phosphosilicate nanoparticles In water at 50℃; under 1125.11 Torr; Schlenk technique; Green chemistry;	94 %Chromat.

(2-iodo-9-isopropyl-9H-purin-6-yl)(4-methoxybenzyl)amine (267885-16-5) + meparfynol (77-75-8) → OL 567

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-butylamine In N,N-dimethyl-formamide at 80℃; Substitution;	97%

2,5-diphenyl-3-iodoselenophene (950894-38-9) + meparfynol (77-75-8) → 1-(2,5-diphenylselenophen-3-yl)-2-methylpent-1-yn-3-ol (1032198-08-5)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 12h; Sonogashira coupling;	97%

meparfynol (77-75-8) → 1-bromo-3-methyl-pent-1-yn-3-ol (2028-52-6)

Conditions	Yield
With potassium hydroxide; potassium hypobromite In pentane for 0.5h; Ambient temperature;	96%
With potassium hypobromite
With sodium hypobromide

phenyl isocyanate (103-71-9) + meparfynol (77-75-8) → 5-ethyl-5-methyl-4-methylene-3-phenyloxazolidin-2-one (74470-78-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 40℃; for 12h; Inert atmosphere;	96%
With sodium methylate In cyclohexane

piperidine (110-89-4) + carbon dioxide (124-38-9) + meparfynol (77-75-8) → Piperidine-1-carboxylic acid 1-ethyl-1-methyl-2-oxo-propyl ester

Conditions	Yield
With triphenylphosphine; silver carbonate In acetonitrile at 30℃; for 16h; Schlenk technique;	96%
With [2,2]bipyridinyl; copper at 100℃; under 28880 Torr; for 24h;	94 % Chromat.
With silver(I) bromide In neat (no solvent) at 50℃; under 11251.1 Torr; for 5h; Schlenk technique;	88 %Chromat.

(2-iodo-9-isopropyl-9H-purin-6-yl)(3,4-dimethoxybenzyl)amine + meparfynol (77-75-8) → 1-[6-(3,4-dimethoxy-benzylamino)-9-isopropyl-9H-purin-2-yl]-3-methyl-pent-1-yn-3-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-butylamine In N,N-dimethyl-formamide at 80℃; Substitution;	96%

6-iodo-1-(triisopropylsilyl)indoline + meparfynol (77-75-8) → 3-methyl-1-(1-(triisopropylsilyl)indolin-6-yl)pent-1-yn-3-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 40℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere;	96%

methanol (67-56-1) + carbon monoxide (201230-82-2) + meparfynol (77-75-8) → Methyl 4-hydroxy-4-methylhex-2-ynoate (90199-69-2)

Conditions	Yield
With sodium acetate; copper dichloride; palladium dichloride at 12 - 13℃; for 1.5h;	95.6%
With sodium acetate; copper dichloride; palladium dichloride	38%

(2-iodo-9-isopropyl-9H-purin-6-yl)(phenyl)amine (267885-23-4) + meparfynol (77-75-8) → 1-(9-isopropyl-6-phenylamino-9H-purin-2-yl)-3-methyl-pent-1-yn-3-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-butylamine In N,N-dimethyl-formamide at 80℃; Substitution;	95%

(2-iodo-9-isopropyl-9H-purin-6-yl)(4-methoxyphenyl)amine + meparfynol (77-75-8) → 1-[9-isopropyl-6-(4-methoxy-phenylamino)-9H-purin-2-yl]-3-methyl-pent-1-yn-3-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-butylamine In N,N-dimethyl-formamide at 80℃; Substitution;	95%

1-iodo-1-hexyne (1119-67-1) + meparfynol (77-75-8) → 3-methyl-undeca-4,6-diyn-3-ol (333753-95-0)

Conditions	Yield
With pyrrolidine; copper(l) iodide	95%

Upstream product

• 78-66-0 3,6-dimethyl-oct-4-yne-3,6-diol 
• 78-93-3 butanone 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-26-8 sodium acetylide 
• 74-86-2 acetylene 
• 14179-94-3 3-chloro-3-methylpent-1-yne 
• 75-04-7 ethylamine 
• 10575-70-9 1-bromo-3-methyl-1,2-pentadiene 
• 70277-75-7 lithium acetylide 
• 7732-18-5 water 
• 17889-43-9 3-Hydroxy-3-methyl-1-trimethylsilyl-pentin-⁽¹⁾ 
• 75-64-9 tert-butylamine 

Downstream Products

• 131-67-9 3-methyl-1-pentyn-3-ol hydrogen phthalate 
• 100144-74-9 propionic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 1185-96-2 3-acetoxy-3-ethylbutyne 
• 108999-92-4 3-methylpent-1-yn-3-ol benzoate 
• 1574-33-0 3-methylpent-3-en-1-yne 
• 33243-76-4 2,2,2-trichloro-1-(1-ethyl-1-methyl-prop-2-ynyloxy)-ethanol 
• 98426-10-9 methyl-carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 99180-92-4 (+/-)-Buttersaeure-<1-ethyl-1-methyl-prop-2-inylester> 
• 302-66-9 carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 100883-62-3 phenoxy-acetic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 3592-23-2 3-methyl-pent-3t-en-2-one-(2,4-dinitro-phenylhydrazone) 
• 22802-35-3 3-methoxy-3-methyl-pent-1-yne 
• 99062-84-7 ethyl-carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 100400-48-4 butyl-carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 

Relevant academic research and scientific papers

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Regio- and stereoselective palladium-catalyzed reactions of allene-substituted 1,3-dienes 1 in acetic acid at room temperature lead to cyclization with formation of a carbon-carbon bond between the middle carbon of the allene and the terminal carbon of the 1,3-diene. Two different types of reactions, both that constitute 1,4-carboacetoxylations of the 1,3-diene, have been developed. In one of the reactions, Pd(II) catalyzes the oxidation of 1 to bicyclic compounds 2, and in the other, Pd(0) catalyzes the transformation of 1 to bicyclic compounds 3. The products 2 are useful for further synthetic tr0nsformations and undergo Diels-Alder reactions with dienophiles to give polycyclic ring systems.

REACTIONS OF NITROGEN NUCLEOPHILES WITH 1-BROMOALLENES: REGIOSELECTIVE SYNTHESIS OF PROPARGYLAMINES

The results of a study on the reactivity of 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes 2 towards nitrogen nucleophiles, such as aqueous ammonia, lithium amide, aliphatic and aromatic amines allowed us to propose new methods for the synthesis of propargylamines, 1, with an available acetylenic hydrogen.The regio- and the stereoselectivity of these reactions are examined and possible mechanisms are discussed.

The reaction of some propargyl alcohols with benzeneselenenyl chloride

The reaction of benzeneselenenyl chloride with twenty-two propargyl alcohols in methylene chloride solution is reported.Products of both Markownikoff and anti-Markownikoff regiochemistry are formed in an anti stereospecific manner.The regioselectivity or specificity is found to be very dependent upon the nature of the substituents geminal to the alcoholic moiety.In general the presence of bulky substituents geminal to the alcoholic moiety tend to favour formation of the anti-Markownikoff adduct under conditions of kinetic control.The Markownikoff adducts are found to be favoured thermodynamically.