14916-80-4

Basic information

• Product Name: 3-Octyn-1-ol
• 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
• CAS NO: 14916-80-4
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 238-986-1
• Product Categories: Miscellaneous;Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Internal;Organic Building Blocks
• Mol File: 14916-80-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: -39°C (estimate)
• Boiling Point: 86-88 °C (9 mmHg)
• Flash Point: >230 °F
• Appearance: clear to yellowish oily liquid
• Density: 0.880 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.031mmHg at 25°C
• Refractive Index: n20/D 1.4569(lit.)
• PKA: 14.34±0.10(Predicted)
• Water Solubility: It is soluble in water.
• BRN: 1739950
• CAS DataBase Reference: 3-Octyn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Octyn-1-ol(14916-80-4)
• EPA Substance Registry System: 3-Octyn-1-ol(14916-80-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: 238-986-1
• TSCA: Yes
• Hazardous Substances Data: 14916-80-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

Different sources of media describe the Uses of 14916-80-4 differently. You can refer to the following data:
1. 3-Octyn-1-ol, is used for a study of the reduction of acetylenic compounds, including this alcohol, to (E)-alkenes by alkali metals in liquid ammonia. Some other applications includes as corrosion inhibitor formulation, metal complex solution, solvent stabilizer, biodegradable chemical intermediate to make pharmaceuticals, chemical compound synthesis and reagents
2. 3-Octyn-1-ol may be used in the preparation of:(3Z)-octen-1-ol7-octyn-1-ol3-cis-octenoic acid

General Description

3-Octyn-1-ol is a homopropargylic alcohol that can be prepared from 3-butyn-1-ol and 1-bromobutane.

InChI:InChI=1/C8H14O/c1-2-3-4-5-6-7-8-9/h9H,2-4,7-8H2,1H3

Synthetic route

1-methoxy-4-(oct-3-yn-1-yloxy)methylbenzene → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
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) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
With toluene-4-sulfonic acid In methanol; water at 23℃; Inert atmosphere;	86%

1-hexynyllithium (17689-03-1) + 2-chloroetyl vinyl ether (110-75-8) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
With iron(III)-acetylacetonate In diethyl ether; ammonia from -30 to 20 deg C, 15 h;	65%

1-bromo-butane (109-65-9) + 1-butyn-4-ol (927-74-2) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
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) + hexenylmagnesium bromide (32359-01-6) → oct-3-yn-1-ol (14916-80-4)

oxirane (75-21-8) + sodium butylacetylide (42332-01-4) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
With ammonia

oxirane (75-21-8) + hex-1-yne (693-02-7) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
(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) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
With hydrogenchloride

oxirane (75-21-8) + C4H7BrMg (38203-73-5, 38203-81-5, 106872-21-3) → oct-3-yn-1-ol (14916-80-4) + oct-3-yn-2-ol (41746-22-9)

Conditions	Yield
In benzene 12 h, RT; 4 h, reflux;

oxirane (75-21-8) + C6H9Hg → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
With lithium 1) THF, reflux, 2) DMSO, 60 - 65 deg C, 3h; Yield given. Multistep reaction;

ethyl hept-2-ynoate (16930-95-3) + 1,2-dibromomethane (74-95-3) → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
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) + hexyne-(1)-magnesium halide → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
With diethyl ether
With diethyl ether

hex-1-yne (693-02-7) + tertiary amine → oct-3-yn-1-ol (14916-80-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na, liq. NH3 2: aq. HCl View Scheme

oxirane (75-21-8) + hexenylmagnesium bromide (32359-01-6) → oct-3-yn-1-ol (14916-80-4) + 2-bromoethanol (540-51-2)

oct-3-yn-1-ol (14916-80-4) → oct-7-yn-1-ol (871-91-0)

Conditions	Yield
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) + methanesulfonyl chloride (124-63-0) → oct-3-yn-1-yl methanesulfonate (90515-24-5)

Conditions	Yield
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) → cis-3-octen-1-ol (18185-81-4, 20125-84-2, 20125-85-3)

Conditions	Yield
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) → 1-hydroxyoctan-4-one (16378-50-0)

Conditions	Yield
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) + benzyl bromide (100-39-0) → C15H20O (1379964-58-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 23℃; Inert atmosphere;	98%

Bis(triphenylphosphonium)Bromide + oct-3-yn-1-ol (14916-80-4) → 1-bromo-oct-3-yne (61685-28-7)

Conditions	Yield
In diethyl ether	96%
In diethyl ether	96%

oct-3-yn-1-ol (14916-80-4) → oct-3-ynoic acid (57074-96-1)

Conditions	Yield
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) → (E)-oct-3-en-1-ol (18185-81-4, 20125-84-2, 20125-85-3)

Conditions	Yield
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) + p-toluenesulfonyl chloride (98-59-9) → oct-3-ynyl 4-methylbenzenesulfonate (100419-71-4)

Conditions	Yield
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) → octanol (111-87-5)

Conditions	Yield
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) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → oct-3-ynyl 4-methylbenzenesulfonate (100419-71-4)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	93%

oct-3-yn-1-ol (14916-80-4) + chloromethyl methyl ether (107-30-2) → 1-(methoxymethoxy)oct-3-yne (1379964-55-2)

Conditions	Yield
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) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethyl(oct-3-yn-1-yloxy)silane (1379964-62-1)

Conditions	Yield
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) + trifluoroacetic anhydride (407-25-0) → C10H13F3O2 (1379963-92-4)

Conditions	Yield
In dichloromethane at 0℃; for 0.25h; Inert atmosphere;	93%

oct-3-yn-1-ol (14916-80-4) + 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester (1807-69-8) → methyl (E)-2-benzoyl-3-pentylidenetetrahydrofuran-2-carboxylate (1536144-21-4)

Conditions	Yield
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) → 1-hydroxy-3-octanone (7786-52-9)

Conditions	Yield
With AuCl*C33H53OP; C33H53OP*AuCl; water; silver trifluoromethanesulfonate In methanol at 80℃; for 17h;	86%

oct-3-yn-1-ol (14916-80-4) + phenyl isothiocyanate (103-72-0) → phenylthiocarbamic acid O-oct-3-ynyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃;	84%

oct-3-yn-1-ol (14916-80-4) + 4-nitro-benzoyl chloride (122-04-3) → C15H17NO4

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	83%

oct-3-yn-1-ol (14916-80-4) + trimethylaluminum (75-24-1) → (Z)-4-methyloct-3-en-1-ol (96308-69-9)

Conditions	Yield
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) → 1-bromo-oct-3-yne (61685-28-7)

Conditions	Yield
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) + 4-nitro-2,6-di-tert-butylphenol (728-40-5) → 3-octynyl aci-nitronate (75958-89-3)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 8h;	70%

oct-3-yn-1-ol (14916-80-4) + ethylenediamine (107-15-3) → oct-7-yn-1-ol (871-91-0)

Conditions	Yield
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) + oct-3-yn-1-ol (14916-80-4) → C12H20O3 (1409941-80-5)

Conditions	Yield
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) + chloroformic acid ethyl ester (541-41-3) → ethyl oct-3-yn-1-yl carbonate

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 16h;	46%

oct-3-yn-1-ol (14916-80-4) + pivaloyl chloride (3282-30-2) → oct-3-yn-1-yl pivalate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;	44%

oct-3-yn-1-ol (14916-80-4) + p-methoxybenzyl chloride (824-94-2) → 1-methoxy-4-(oct-3-yn-1-yloxy)methylbenzene

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

Upstream product

• 75-21-8 oxirane 
• 42332-01-4 sodium butylacetylide 
• 109-65-9 1-bromo-butane 
• 927-74-2 3-Butyn-1-ol 
• 38203-73-5 C₄H₇BrMg 
• 17689-03-1 1-hexynyllithium 
• 110-75-8 2-chloroetyl vinyl ether 
• 85217-50-1 2-(3-octyn-1-yloxy)tetrahydro-2H-pyran 
• 16930-95-3 ethyl hept-2-ynoate 
• 74-95-3 1,1-dibromomethane 
• 14675-05-9 1-vinyloxy-oct-3-yne 
• 693-02-7 hex-1-yne 
• 32359-01-6 hexenylmagnesium bromide 

Downstream Products

• 18185-81-4 cis-3-octen-1-ol 
• 18185-81-4 (E)-oct-3-en-1-ol 
• 57074-96-1 oct-3-ynoic acid 
• 100419-71-4 oct-3-ynyl 4-methylbenzenesulfonate 
• 111-87-5 octanol 
• 81216-13-9 8-bromooct-1-yne 
• 1205551-39-8 N-benzyloct-3-yn-1-amine 
• 1310563-84-8 1-benzyl-2-n-butylpyrrolidine-2-carbonitrile 
• 1310563-90-6 1-benzyl-2-butyl-2-(trifluoromethyl)pyrrolidine 
• 5163-67-7 (E)-oct-3-enoic acid 
• 1379964-60-9 C₂₁H₃₆OSi 
• 1379964-61-0 C₂₁H₃₆OSi 
• 1379964-58-5 C₁₅H₂₀O 
• 38421-90-8 (E)-5-decen-1-yl acetate 

Relevant articles and documents

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A procedure for the selective deprotection of p-methoxybenzyl ethers using catalytic amounts of DDQ and of sodium nitrite, with oxygen as the terminal oxidant, is reported.

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