77-75-8

Basic information

• Product Name: 3-Methyl-1-pentyn-3-ol
• Synonyms: 3-methyl-1-pentyn-3-o;3-Methyl-1-pentynol;3-Methylpent-1-yn-3-ol;3-Methyl-pentin-(1)-ol-(3);3-Methylpentin-3-ol;3-Methylpentyn-3-ol;3-Metil-pentin-3-ol;Allotropal
• CAS NO: 77-75-8
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• EINECS: 201-055-5
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Chemistry
• Mol File: 77-75-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 121-122 °C(lit.)
• Flash Point: 80 °F
• Appearance: Clear slightly yellow liquid or low melting solid
• Density: 0.866 g/mL at 25 °C(lit.)
• Vapor Density: 3 (vs air)
• Vapor Pressure: 6.5 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: Flammables area
• Solubility: Cellosolve: miscible
• PKA: 13.34±0.29(Predicted)
• Explosive Limit: 1.8-16.0%(V)
• Merck: 13,5870
• BRN: 969340
• CAS DataBase Reference: 3-Methyl-1-pentyn-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-1-pentyn-3-ol(77-75-8)
• EPA Substance Registry System: 3-Methyl-1-pentyn-3-ol(77-75-8)

Safety Data

• Hazard Codes: Xn,F+
• Statements: 10-22-51/53-2017/10/22
• Safety Statements: 23-36-61
• RIDADR: UN 1986 3/PG 3
• WGK Germany: 1
• RTECS: SC4900000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 77-75-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear slightly yellow liquid or low melting solid

Originator

Citodorm,Haury

Uses

Different sources of media describe the Uses of 77-75-8 differently. You can refer to the following data:
1. 3-Methylpent-1-yn-3-ol is an inhibitor; used in method for preparing high-insulation solvent-free silicone resin for composite insulator.
2. 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).

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

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

Downstream Products

• 131-67-9 3-methyl-1-pentyn-3-ol hydrogen phthalate 
• 108999-92-4 3-methylpent-1-yn-3-ol benzoate 
• 1574-33-0 3-methylpent-3-en-1-yne 
• 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) 
• 22802-35-3 3-methoxy-3-methyl-pent-1-yne 
• 100883-28-1 phenyl-acetic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 98491-15-7 trichloro-acetic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 98426-10-9 methyl-carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 99189-01-2 propyl-carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 77967-00-1 allophanic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 100400-50-8 isobutyl-carbamic acid-(1-ethyl-1-methyl-prop-2-ynyl ester) 
• 918-85-4 3-hydroxy-3-methyl-1-pentene 

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