Product Name

Synthetic route

1-methoxy-4-(oct-3-yn-1-yloxy)methylbenzene

1-methoxy-4-(oct-3-yn-1-yloxy)methylbenzene

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite at 20℃; for 18h; Green chemistry; chemoselective reaction;93%
2-(3-octyn-1-yloxy)tetrahydro-2H-pyran
85217-50-1

2-(3-octyn-1-yloxy)tetrahydro-2H-pyran

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; water at 23℃; Inert atmosphere;86%
1-hexynyllithium
17689-03-1

1-hexynyllithium

2-chloroetyl vinyl ether
110-75-8

2-chloroetyl vinyl ether

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With iron(III)-acetylacetonate In diethyl ether; ammonia from -30 to 20 deg C, 15 h;65%
1-bromo-butane
109-65-9

1-bromo-butane

1-butyn-4-ol
927-74-2

1-butyn-4-ol

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With lithium; ferric nitrate In tetrahydrofuran; ammonia for 3h;62.2%
Stage #1: 3-Butyn-1-ol With lithium amide; ammonia; ferric nitrate at -50℃; for 1h;
Stage #2: 1-bromo-butane for 2h; Further stages.;
26.6%
With lithium amide In ammonia
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF, hexane, -23 deg C --> r.t., 30 min, 2.) -23 deg C, 4 h; Yield given. Multistep reaction;
With lithium amide; ammonia; ferric nitrate
oxirane
75-21-8

oxirane

hexenylmagnesium bromide
32359-01-6

hexenylmagnesium bromide

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

oxirane
75-21-8

oxirane

sodium butylacetylide
42332-01-4

sodium butylacetylide

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With ammonia
oxirane
75-21-8

oxirane

hex-1-yne
693-02-7

hex-1-yne

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
(i) Na, liq. NH3, Fe(NO3)3, (ii) /BRN= 102378/; Multistep reaction;
Stage #1: hex-1-yne With ethylmagnesium bromide In tetrahydrofuran Reflux;
Stage #2: oxirane In tetrahydrofuran at 20℃;
1-vinyloxy-oct-3-yne
14675-05-9

1-vinyloxy-oct-3-yne

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With hydrogenchloride
oxirane
75-21-8

oxirane

A

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

B

oct-3-yn-2-ol
41746-22-9

oct-3-yn-2-ol

Conditions
ConditionsYield
In benzene 12 h, RT; 4 h, reflux;
oxirane
75-21-8

oxirane

C6H9Hg

C6H9Hg

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With lithium 1) THF, reflux, 2) DMSO, 60 - 65 deg C, 3h; Yield given. Multistep reaction;
ethyl hept-2-ynoate
16930-95-3

ethyl hept-2-ynoate

1,2-dibromomethane
74-95-3

1,2-dibromomethane

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate; n-butyllithium; 2,2,6,6-tetramethylpiperidinyl-lithium; cyclohexa-1,3-diene 1.) THF, hexane, -90 deg, 5 min; 2.) THF, hexane, -90 deg C, then Rt, 30 min; 3.) THF, hexane, reflux, 60 min; 4.) THF, hexane, MeOH, 0 deg C, 30 min; Yield given. Multistep reaction;
oxirane
75-21-8

oxirane

hexyne-(1)-magnesium halide

hexyne-(1)-magnesium halide

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With diethyl ether
With diethyl ether
hex-1-yne
693-02-7

hex-1-yne

tertiary amine

tertiary amine

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Na, liq. NH3
2: aq. HCl
View Scheme
oxirane
75-21-8

oxirane

hexenylmagnesium bromide
32359-01-6

hexenylmagnesium bromide

A

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

B

2-bromoethanol
540-51-2

2-bromoethanol

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

oct-7-yn-1-ol
871-91-0

oct-7-yn-1-ol

Conditions
ConditionsYield
With sodium hydride In ethylenediamine; mineral oil at 45 - 65℃;100%
With potassium hydride; Trimethylenediamine for 18h; Ambient temperature;97%
With potassium tert-butylate; lithium In ethylenediamine at 25℃; for 3h;96%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

oct-3-yn-1-yl methanesulfonate
90515-24-5

oct-3-yn-1-yl methanesulfonate

Conditions
ConditionsYield
Stage #1: oct-3-yn-1-ol With triethylamine In dichloromethane at 0℃; for 1h;
Stage #2: methanesulfonyl chloride In dichloromethane at 0 - 20℃; for 2h;
100%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;
With triethylamine In dichloromethane at -10℃; for 0.5h; Inert atmosphere;
With triethylamine In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere;
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With dmap; palladium(II) tetraphenylporphyrin; hydrogen In pyridine at 25℃; under 760.051 Torr; for 4h; stereoselective reaction;99%
With quinoline; hydrogen; Lindlar's catalyst In various solvent(s) at 20℃; under 760.051 Torr; for 2h;96%
With sodium tetrahydroborate; hydrogen; nickel(II) acetate tetrahydrate In ethanol at 20℃; for 12h;96%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

1-hydroxyoctan-4-one
16378-50-0

1-hydroxyoctan-4-one

Conditions
ConditionsYield
With hexafluoroantimonic acid; AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); water at 120℃; for 24h;99%
With water; mercuric triflate In acetonitrile at 20℃; for 0.0833333h; regioselective reaction;82%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

benzyl bromide
100-39-0

benzyl bromide

C15H20O
1379964-58-5

C15H20O

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 23℃; Inert atmosphere;98%
Bis(triphenylphosphonium)Bromide

Bis(triphenylphosphonium)Bromide

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

1-bromo-oct-3-yne
61685-28-7

1-bromo-oct-3-yne

Conditions
ConditionsYield
In diethyl ether96%
In diethyl ether96%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

oct-3-ynoic acid
57074-96-1

oct-3-ynoic acid

Conditions
ConditionsYield
With Jones reagent In acetone at 0℃; for 0.25h;95.1%
With Jones reagent In acetone at 0℃; for 3h; Inert atmosphere;55%
With chromium(VI) oxide; sulfuric acid; acetone
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

Conditions
ConditionsYield
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran at -36℃; for 2h;95%
With lithium aluminium tetrahydride In tetrahydrofuran; diethylene glycol dimethyl ether Heating;93%
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran at -36℃; for 2h;88%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

oct-3-ynyl 4-methylbenzenesulfonate
100419-71-4

oct-3-ynyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With pyridine 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h;93%
In pyridine at 0℃; for 5h;
With pyridine or Li-salt of the corresponding acetylenic alcohol;
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

octanol
111-87-5

octanol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 5h;93%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

4-methoxy-phenyl-sulphonyl chloride
98-68-0

4-methoxy-phenyl-sulphonyl chloride

oct-3-ynyl 4-methylbenzenesulfonate
100419-71-4

oct-3-ynyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃;93%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-(methoxymethoxy)oct-3-yne
1379964-55-2

1-(methoxymethoxy)oct-3-yne

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; Inert atmosphere;93%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 20h;45%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyldimethyl(oct-3-yn-1-yloxy)silane
1379964-62-1

tert-butyldimethyl(oct-3-yn-1-yloxy)silane

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 23℃; Inert atmosphere;93%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;22%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C10H13F3O2
1379963-92-4

C10H13F3O2

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.25h; Inert atmosphere;93%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

2-diazo-3-oxo-3-phenyl-propionic acid methyl ester
1807-69-8

2-diazo-3-oxo-3-phenyl-propionic acid methyl ester

methyl (E)-2-benzoyl-3-pentylidenetetrahydrofuran-2-carboxylate
1536144-21-4

methyl (E)-2-benzoyl-3-pentylidenetetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; zinc(II) chloride In dichloromethane at 20℃; for 7.5h; Molecular sieve; Reflux; stereoselective reaction;88%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

1-hydroxy-3-octanone
7786-52-9

1-hydroxy-3-octanone

Conditions
ConditionsYield
With AuCl*C33H53OP; C33H53OP*AuCl; water; silver trifluoromethanesulfonate In methanol at 80℃; for 17h;86%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

phenylthiocarbamic acid O-oct-3-ynyl ester

phenylthiocarbamic acid O-oct-3-ynyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃;84%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

C15H17NO4

C15H17NO4

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;83%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

trimethylaluminum
75-24-1

trimethylaluminum

(Z)-4-methyloct-3-en-1-ol
96308-69-9

(Z)-4-methyloct-3-en-1-ol

Conditions
ConditionsYield
Stage #1: oct-3-yn-1-ol; trimethylaluminum In dichloromethane; toluene at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane; toluene at -45℃; for 0.05h; Inert atmosphere; regioselective reaction;
73%
Stage #1: oct-3-yn-1-ol; trimethylaluminum In dichloromethane at 0℃;
Stage #2: With titanium tetrachloride In dichloromethane at -78℃; for 2h;
47%
With titanium tetrachloride In dichloromethane at -45℃; for 0.0166667h;75 % Chromat.
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

1-bromo-oct-3-yne
61685-28-7

1-bromo-oct-3-yne

Conditions
ConditionsYield
With N-Bromosuccinimide; triphenylphosphine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h;71%
With pyridine; diethyl ether; phosphorus tribromide
With triphenyl phosphite; bromine In pyridine; diethyl ether
Multi-step reaction with 2 steps
1: 93 percent / pyridine / 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h
2: 85 percent / LiBr / acetone / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: pyridine / 5 h / 0 °C
2: NaBr / dimethylformamide / 2 h / 75 °C
View Scheme
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

4-nitro-2,6-di-tert-butylphenol
728-40-5

4-nitro-2,6-di-tert-butylphenol

3-octynyl aci-nitronate
75958-89-3

3-octynyl aci-nitronate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 8h;70%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

ethylenediamine
107-15-3

ethylenediamine

oct-7-yn-1-ol
871-91-0

oct-7-yn-1-ol

Conditions
ConditionsYield
Stage #1: ethylenediamine With sodium hydride at 0 - 60℃; for 1h; Inert atmosphere;
Stage #2: oct-3-yn-1-ol at 60℃; for 1h; Inert atmosphere;
58%
ethyl 2-hydroxybutyrate
52089-54-0

ethyl 2-hydroxybutyrate

oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

C12H20O3
1409941-80-5

C12H20O3

Conditions
ConditionsYield
With 1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene In tetrahydrofuran Inert atmosphere; Molecular sieve;52%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl oct-3-yn-1-yl carbonate

ethyl oct-3-yn-1-yl carbonate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 16h;46%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

pivaloyl chloride
3282-30-2

pivaloyl chloride

oct-3-yn-1-yl pivalate

oct-3-yn-1-yl pivalate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;44%
oct-3-yn-1-ol
14916-80-4

oct-3-yn-1-ol

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

1-methoxy-4-(oct-3-yn-1-yloxy)methylbenzene

1-methoxy-4-(oct-3-yn-1-yloxy)methylbenzene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;35%
With sodium hydride

3-OCTYN-1-OL Chemical Properties

IUPAC Name: Oct-3-yn-1-ol
Molecular Formula  C8H14O
Molecular Weight  126.20
Index of Refraction: 1.458
Flash Point: 106 ºC
EINECS: 238-986-1
Density  0.880 g/mL at 25 °C(lit.)}
Refractive index  1.4555-1.4575
Enthalpy of Vaporization: 52.61 kJ/mol 
Boiling Point: 216 °C at 760 mmHg 
Vapour Pressure: 0.031 mmHg at 25°C 
Appearance: Colorless - yellow Liquid
Chemical Stability: Stable under normal temperatures and pressures
Product Categories: Miscellaneous ; Acetylenes ; Acetylenic alcohols & Their derivatives ; Alkynes ; Internal ; Organic building blocks 
Synonyms: 3-Octyne-1-ol ; 3-Octyn-1-ol ; Timtec-bb SBB009106 ; Octynol ; N-butyl-2-hydroxyethylacetylene ; Oct-3-yn-1-ol ; 3-Octyn-1-ol 98% ; 1-Butyl-2-(2-hydroxyethyl)acetylene
Following is the molecular structure of Oct-3-yn-1-ol (14916-80-4):


3-OCTYN-1-OL Safety Profile

Safety Information of Oct-3-yn-1-ol (14916-80-4):
Hazard Codes: Xi
Xi :Irritant
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin 
Safety Statements: 26-36-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36: Wear suitable protective clothing 
37/39: Wear suitable gloves and eye/face protection 
WGK Germany: 3

3-OCTYN-1-OL Specification

Potential Health Effects of Oct-3-yn-1-ol (14916-80-4):
1.Eye: Causes eye irritation. 
2.Skin: Causes skin irritation. May be harmful if absorbed through the skin. 
3.Ingestion: May cause irritation of the digestive tract. May be harmful if swallowed. 
4.Inhalation: Causes respiratory tract irritation. May be harmful if inhaled
First Aid Measures of Oct-3-yn-1-ol (14916-80-4):
1.Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. 
2.Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. 
3.Ingestion: Get medical aid. Wash mouth out with water. 
4.Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. 
5.Notes to Physician: Treat symptomatically and supportively. 
Fire Fighting Measures of Oct-3-yn-1-ol (14916-80-4):
1.General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. 
2.Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.   Accidental Release Measures of Oct-3-yn-1-ol (14916-80-4):
1.General Information: Use proper personal protective equipment as indicated in Section 8. 
2.Spills/Leaks: Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.  
Handling and Storage of Oct-3-yn-1-ol (14916-80-4):
1.Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. 
2.Storage: Store in a cool, dry place. Store in a tightly closed container

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