629-05-0

Basic information

• Product Name: 1-Octyne
• Synonyms: 1-0ctyne;Hexylacetylene;oct-1-yne;Octyne-1;1-OCTYNE;1-Octyne (6CI, 8CI, 9CI);1-Octyne,98+%;n-hexylacetylene
• CAS NO: 629-05-0
• Molecular Formula: C₈H₁₄
• Molecular Weight: 110.2
• EINECS: 211-069-3
• Product Categories: Miscellaneous;Acetylenes;Acetylenic Hydrocarbons;Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 629-05-0.mol
• Article Data: 29

Chemical Properties

• Melting Point: -80 °C
• Boiling Point: 127-128 °C(lit.)
• Flash Point: 64 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.747 g/mL at 25 °C(lit.)
• Vapor Pressure: 37.7 mm Hg ( 37.7 °C)
• Refractive Index: n20/D 1.416(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.024g/l
• Explosive Limit: 0.8%(V)
• Water Solubility: Miscible with alcohol, ether and other organic solvents. Immiscible with water.
• BRN: 1734494
• CAS DataBase Reference: 1-Octyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Octyne(629-05-0)
• EPA Substance Registry System: 1-Octyne(629-05-0)

Safety Data

• Hazard Codes: F,Xn,Xi
• Statements: 11-65-36/37/38
• Safety Statements: 16-62-33-26
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• RTECS: RI2655000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 629-05-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO YELLOW LIQUID

Uses

1-Octyne is widely used in organic reactions such as halogenation, hydration, oxidative cleavage, hydrogenation, hydrohalogenation, nitrile formation, polymerization and substitution reactions. It is used a precursor for the preparation of monohalogen substituted akenes or dihalogen substituted alkanes on treated with hydrogen halides.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

Distil I-octyne from NaBH4 to remove peroxides. Fractionate it through a 10inch Widmer column (p 11) at 125-126o/759mm [Sletzinger & Dawson J Org Chem 14 853 1949.] [Beilstein 1 III 1005, 1 IV 1034.]

InChI:InChI=1/C8H14/c1-3-5-7-8-6-4-2/h1H,4-8H2,2H3

Synthetic route

oct-1-yn-3-yl benzoate (196302-07-5) → n-octyne (629-05-0) + benzoic acid (65-85-0)

Conditions	Yield
tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;	A 55% B 97%

1,2-dibromooctane (152212-49-2, 152212-73-2) → n-octyne (629-05-0)

Conditions	Yield
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 90℃; for 6h;	95%
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h; without <18>krone-6;	92%
With tetrabutylammomium bromide; potassium hydroxide In water at 150℃; for 10h;	90%

(Z)-1-bromo-1-octene (42843-49-2) → n-octyne (629-05-0)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 25℃; for 2h;	92%

2-bromo-1-octene (13249-60-0) → n-octyne (629-05-0)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 1h;	90%
With 1,2,4-Trimethylbenzene; sodium amide at 150℃;
With ammonia; sodium amide

(E)-1-bromo-1-octene (51751-87-2) → n-octyne (629-05-0)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h;	90%

1,2-dichlorooctane (21948-46-9, 72778-28-0) → n-octyne (629-05-0)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 80℃; for 8h;	84%

1-phenyl-1-octyne (16967-02-5) + phenylacetylene (536-74-3) → n-octyne (629-05-0)

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 8h; Sonogashira Cross-Coupling;	80%

2,2-dichloro-octane (73642-95-2) → oct-2-yne (2809-67-8) + n-octyne (629-05-0) + octa-1,2-diene (1072-19-1)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 80℃; for 12h; Title compound not separated from byproducts;	A 15% B 62% C 7%

(E)-1,2-Bis(phenyltelluro)-1-octene (139517-41-2) → n-octyne (629-05-0) + diphenyl ditelluride (32294-60-3)

Conditions	Yield
In chloroform-d1 at 40℃; for 6h; Irradiation; other ditelluroalkenes;	A 60% B n/a

8-bromo-1-octyne (81216-13-9) → hexadeca-1,15-diyne (39750-95-3) + n-octyne (629-05-0)

Conditions	Yield
With hydrogenchloride; sodium peroxide; magnesium 1.) 22 deg C, 30 min, diethyl ether; Yield given. Multistep reaction;	A 28% B n/a
With hydrogenchloride; sodium peroxide; magnesium 1.) 22 deg C, 30 min, diethyl ether; Yield given. Multistep reaction;

oct-1-ene (111-66-0) → n-octyne (629-05-0)

Conditions	Yield
In methyl cyclohexane; pentane at 15℃; Irradiation;	18%
In methyl cyclohexane; pentane at 15℃; Rate constant; Product distribution; Mechanism; Irradiation;	18%
Multi-step reaction with 3 steps 1: hydrogen bromide; dihydrogen peroxide / ethanol; water / 80 °C 2: potassium phosphate / ethanol / 0.17 h / 80 °C 3: potassium phosphate / ethanol / 80 °C View Scheme

1,2-dibromooctane (152212-49-2, 152212-73-2) → n-octyne (629-05-0) + 2-bromo-1-octene (13249-60-0) + (Z)-1-bromo-1-octene (42843-49-2) + (E)-1-bromo-1-octene (51751-87-2)

Conditions	Yield
With potassium tert-butylate In Petroleum ether at 80℃; for 6h; Yield given;	A 6% B n/a C n/a D n/a
With potassium hydroxide; 1,8-Octanediol; tetraoctylammonium chloride 1.) petroleum ether, 75 degC; 2.) petroleum ether, 75 degC; Yield given. Multistep reaction;
With potassium tert-butylate In Petroleum ether Mechanism; Product distribution; temperature and time was variabled;

oct-2-yne (2809-67-8) → n-octyne (629-05-0)

Conditions	Yield
With sodium
With 1,2,4-Trimethylbenzene; sodium amide at 150℃;

1-bromo-hexane (111-25-1) + acetylenemagnesium bromide (4301-14-8) → n-octyne (629-05-0)

1-bromo-hexane (111-25-1) + sodium acetylide (1066-26-8) → n-octyne (629-05-0)

Conditions	Yield
With tetrahydrofuran; N,N-dimethyl-formamide
With tetrahydrofuran; 1-methyl-pyrrolidin-2-one
In ammonia at -60℃;
With ammonia

oct-3-yne (15232-76-5) → n-octyne (629-05-0)

Conditions	Yield
With petroleum; sodium amide at 170℃;

2-methylheptanal (16630-91-4) → n-octyne (629-05-0)

Conditions	Yield
With phosphorus pentachloride ueber mehrere Stufen;

1-bromo-oct-1-ene (42843-49-2, 51751-87-2, 1119-88-6) → n-octyne (629-05-0)

Conditions	Yield
With potassium hydroxide; mineral oil at 175℃;
With potassium phosphate In ethanol at 80℃;

non-2-ynoic acid (1846-70-4) → n-octyne (629-05-0)

Conditions	Yield
at 200℃;

n-pentylmagnesium bromide (693-25-4) + propargyl bromide (106-96-7) → n-octyne (629-05-0) + octa-1,2-diene (1072-19-1)

Conditions	Yield
With diethyl ether at -15℃;

1,1-dibromo-1-octene (73383-25-2) → n-octyne (629-05-0)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In benzene for 0.166667h; Ambient temperature;	90 % Chromat.
With n-butyllithium In hexane at -78 - 20℃; for 5h;

1,1-dibromo-1-octene (73383-25-2) → n-octyne (629-05-0) + oct-1-ene (111-66-0)

Conditions	Yield
With 1,1-Dibromoethane; magnesium In tetrahydrofuran for 4h; Heating; Yield given. Yields of byproduct given;

1-bromo-octane (111-83-1) + 8-bromo-1-octyne (81216-13-9) → octane (111-65-9) + hexadeca-1,15-diyne (39750-95-3) + n-octyne (629-05-0) + Hexadecane (544-76-3)

Conditions	Yield
With hydrogenchloride; sodium peroxide; magnesium 1.) 22 deg C, 30 min, diethyl ether; Multistep reaction. Further byproducts given;

1-bromo-octane (111-83-1) + 8-bromo-1-octyne (81216-13-9) → hexadeca-1,15-diyne (39750-95-3) + hexadec-1-yne (629-74-3) + n-octyne (629-05-0) + Hexadecane (544-76-3)

Conditions	Yield
With hydrogenchloride; sodium peroxide; magnesium 1.) 22 deg C, 30 min, diethyl ether; Multistep reaction. Further byproducts given;
With hydrogenchloride; sodium peroxide; magnesium 1.) 22 deg C, 30 min, diethyl ether; Yield given. Multistep reaction. Further byproducts given;
With hydrogenchloride; sodium peroxide; magnesium 1.) 22 deg C, 30 min, diethyl ether; Multistep reaction. Further byproducts given;

oct-1-ene (111-66-0) → octane (111-65-9) + decane (124-18-5) + cis-2-octene (7642-04-8) + trans-2-Octene (13389-42-9) + n-octyne (629-05-0)

Conditions	Yield
In pentane for 3h; Quantum yield; Mechanism; Product distribution; Irradiation; various wavelengths;	A 1.8 % Chromat. B 22 % Chromat. C 18 % Chromat. D 15 % Chromat. E 27 % Chromat.

oct-1-ene (111-66-0) → octane (111-65-9) + cis-2-octene (7642-04-8) + trans-2-Octene (13389-42-9) + n-octyne (629-05-0)

Conditions	Yield
With oxygen In pentane for 3h; Irradiation; Further byproducts given. Title compound not separated from byproducts;	A 0.1 % Chromat. B 20 % Chromat. C 10 % Chromat. D 20 % Chromat.

oct-1-ene (111-66-0) → decane (124-18-5) + cis-2-octene (7642-04-8) + trans-2-Octene (13389-42-9) + n-octyne (629-05-0)

Conditions	Yield
In pentane for 3h; Irradiation; Further byproducts given. Title compound not separated from byproducts;	A 22 % Chromat. B 18 % Chromat. C 15 % Chromat. D 27 % Chromat.

oct-1-ene (111-66-0) → n-octyne (629-05-0) + hexyl-methyl-ketone (111-13-7)

Conditions	Yield
With perchloric acid; air; Pd(OAc)2-OPTA In 1,4-dioxane; water at 70℃; for 6h;	A 10 % Chromat. B 90 % Chromat.
With perchloric acid; air; Pd(OAc)2-OPTA In ethanol at 70℃; for 3.66667h;	A 90 % Chromat. B 8 % Chromat.

1,2-dichlorooctane (21948-46-9, 72778-28-0) → n-octyne (629-05-0) + 2-chloro-oct-1-ene (31283-43-9) + (E)-1-chlorooct-1-ene (59871-24-8) + 1c-chloro-oct-1-ene (64531-23-3)

Conditions	Yield
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 75℃; Product distribution; Quantum yield; comparative studies of the conversion with or without pinacol as cocatalyst;

1,2-dichlorooctane (21948-46-9, 72778-28-0) → n-octyne (629-05-0) + 2-bromo-1-octene (13249-60-0) + (Z)-1-bromo-1-octene (42843-49-2) + (E)-1-bromo-1-octene (51751-87-2)

Conditions	Yield
With potassium hydroxide; 2,3-dimethyl-2,3-butane diol; tetraoctyl ammonium bromide 1.) petroleum ether, 75 degC; 2.) petroleum ether, 75 degC; Multistep reaction;

n-octyne (629-05-0) → oct-1-ene (111-66-0)

Conditions	Yield
With zirconocene dichloride; tert-butylmagnesium chloride; water Product distribution; multistep reaction; other hydrozirconation agents; other substrates;	100%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 2.5h;	95%
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In neat (no solvent) at -78 - 40℃; for 1h;	95%

formaldehyd (50-00-0) + n-octyne (629-05-0) → 2-nonyn-1-ol (5921-73-3)

Conditions	Yield
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere;	100%
Stage #1: n-octyne With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: formaldehyd In diethyl ether; hexane at 20℃;	98%
Stage #1: n-octyne With n-butyllithium In diethyl ether; hexane at -78℃; Inert atmosphere; Stage #2: formaldehyd In diethyl ether; hexane at -78 - 20℃; for 14.5h; Inert atmosphere;	88%

n-octyne (629-05-0) + PhIO*TfOH → <2-<(trifluoromethanesulfonyl)oxy>-1-octenyl>(phenyl)iodonium trifluoromethanesulfonate

Conditions	Yield
In dichloromethane Ambient temperature;	100%

n-octyne (629-05-0) + PhI(OH)OTs (122220-13-7) → <2-<(trifluoromethanesulfonyl)oxy>-1-octenyl>(phenyl)iodonium trifluoromethanesulfonate

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	100%

n-octyne (629-05-0) → octane (111-65-9)

Conditions	Yield
With hydrogen In neat (no solvent) at 30℃; for 5h; Catalytic behavior; Flow reactor;	100%
With iron(III) chloride hexahydrate; hydrazine hydrate In ethanol at 20℃; for 24h;	99%
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In neat (no solvent) at -78 - 40℃; for 2h;	95%

n-octyne (629-05-0) → 1-chloro-1-octyne (64531-26-6)

Conditions	Yield
With N-chloro-succinimide; silver(I) acetate In acetone Inert atmosphere; Reflux;	100%
With N-chloro-succinimide; potassium carbonate; silver carbonate In propan-1-ol at 50℃; for 20h; Sealed tube; Inert atmosphere; Green chemistry;	86%
With N-chloro-succinimide; n-butyllithium In tetrahydrofuran -25 deg C, 2 h -> -10 deg C, 30 min -> room temperature;	78%
With N-chloro-succinimide; potassium carbonate; silver carbonate In propan-1-ol at 50℃; for 5h; Inert atmosphere;	75%
With n-butyllithium; benzenesulfonyl chloride In tetrahydrofuran; hexane at 35℃; for 1h;	68%

n-octyne (629-05-0) → 1-bromo-1-octyne (38761-67-0)

Conditions	Yield
With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 3h; Inert atmosphere;	100%
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With bromine In tetrahydrofuran at -78℃; for 0.25h; Reagent/catalyst;	96%
With N-Bromosuccinimide; silver nitrate In acetone at 20℃; Inert atmosphere;	88%

n-octyne (629-05-0) + para-iodoanisole (696-62-8) → 1-methoxy-4-(oct-1-ynyl)benzene (144493-14-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 4h; Sonogashira-Linstrumelle coupling; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃;	99%
With tetra(n-butyl)ammonium hydroxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 6h; Sonogashira-Hagihara coupling;	98%

n-octyne (629-05-0) + di(p-tolyl) disulfide (103-19-5) → (Z)-1,2-bis[(4-methylphenyl)thio]oct-1-ene (137540-56-8)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; rhodium hydrido (PEt3)3 complex; trifluorormethanesulfonic acid In 1,2-dichloro-ethane for 3h; Heating;	100%
With MCM-41-supported bidentate phosphine palladium(0) complex In toluene at 140℃; for 2h; Inert atmosphere; Sealed tube; stereoselective reaction;	92%

n-octyne (629-05-0) + poly(methylhydrosiloxane) → Poly[methyl(1-octen-1-yl)siloxane]

Conditions	Yield
bis(tetrabutylammonium) hexachloroplatinate(IV) at 60℃; for 24h;	100%

n-octyne (629-05-0) + o-nitroiodobenzene (609-73-4) → 1-nitro-2-(oct-1-yn-1-yl)benzene

Conditions	Yield
With copper(l) iodide; C27H34Cl2N4Pd; potassium carbonate; triphenylphosphine In ethanol at 60℃; for 13h; Solvent; Reagent/catalyst; Time; Sonogashira Cross-Coupling;	100%
With triethylamine; zinc dibromide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 23℃;	89%
Stage #1: o-nitroiodobenzene With bis(triphenylphosphine)palladium(II) chloride; triethylamine at 20℃; for 0.166667h; Stage #2: n-octyne With copper(l) iodide at 20℃; for 6h;

n-octyne (629-05-0) + Diphenylphosphine oxide (4559-70-0) → [(E)-1-octen-1-yl]diphenylphosphine oxide (178943-30-1)

Conditions	Yield
tris(triphenylphosphine)rhodium(I) iodide In toluene at 20℃; for 1h;	100%
With triethylamine; rhodium(III) chloride In ethanol; toluene at 80℃; for 3h;	97%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane; water for 8h;	96%

n-octyne (629-05-0) + bis(2-phenylethyl)phosphane sulfide → oct-1-enyl(diphenethyl)phosphine sulfide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In 1,4-dioxane at 60 - 65℃;	100%

n-octyne (629-05-0) + 2-iodophenylamine (615-43-0) → 2-(oct-1-yn-1-yl)aniline (157869-10-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 5h; Inert atmosphere;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; for 2h; Sonogashira coupling reaction;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;	99%

latter phosphonate + methyl phosphite (96-36-6, 868-85-9) + n-octyne (629-05-0) + dimethyl 1-octen-2-yl-phosphonate (174781-89-6) → dimethyl (E)-octenylphosphonate

Conditions	Yield
palladium diacetate	100%

cis-PdMe2(PPhMe2)2were + n-octyne (629-05-0) + diphenyl-phosphinic acid (1707-03-5) + Diphenylphosphine oxide (4559-70-0) → [(E)-1-octen-1-yl]diphenylphosphine oxide (178943-30-1) + 2-(diphenylphosphinyl)-1-octene

Conditions	Yield
In benzene	A 100% B n/a

n-octyne (629-05-0) + trans-[Pt(C6H4Me-p)(SC6H4OCH3-p)(PPh3)2] (876621-18-0) + 4-tolyl iodide (624-31-7) → trans-PtI(PPh3)2C6H4Me-p (67254-06-2, 53424-02-5)

Conditions	Yield
With triphenylphosphine In (2)H8-toluene byproducts: p-CH3C6H4CHC(n-C6H13)SC6H4OCH3-p, p-CH3C6H4SC6H4OCH3-p; P(C6H5)3, toluene-d8, 110°C, 10 h; detected by NMR spectra;	100%

n-octyne (629-05-0) + ethyl phosphinate (14684-32-3) → (E)-oct-1-enylphosphinic acid ethyl ester (853411-40-2)

Conditions	Yield
Pd2(dba)3/xanthphos In acetonitrile for 12h; Heating;	100%

n-octyne (629-05-0) + 4-fluoro-1-iodobenzene (352-34-1) → 1-(4-fluorophenyl)-2-hexylacetylene (201735-31-1)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In diisopropylamine; toluene at 40℃; for 7h;	100%
With copper(l) iodide; iron; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 20h; Sonogashira coupling; Inert atmosphere;	84%
Stage #1: 4-fluoro-1-iodobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 0.166667h; Inert atmosphere; Stage #2: n-octyne at 25℃; Inert atmosphere;	52%

n-octyne (629-05-0) + 2,4,6-trimethylaniline (88-05-1) → 2,4,6-trimethyl-N-(octan-2-ylidene)aniline (914388-61-7)

Conditions	Yield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 2h; Inert atmosphere; regioselective reaction;	100%
With C33H49Cl2N2PPd; silver trifluoromethanesulfonate In acetonitrile at 80℃; for 25h; Inert atmosphere; Schlenk technique;	59%
With silver hexafluoroantimonate; C25H28Au2Br2N4 In neat (no solvent) at 40℃; for 4h; Inert atmosphere; Schlenk technique;	76 %Spectr.
With (η1,η5)bis(pentamethylcyclopentadienyl)zinc; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In benzene-d6 at 20℃; for 4h; Inert atmosphere; regioselective reaction;

n-octyne (629-05-0) + 6-methyl-1H-benzo[d][1,2,3]triazol-1-ol (26198-26-5) → 6-methyl-1-(oct-1-en-2-yloxy)-1H-benzo[d][1,2,3]triazole (1422198-30-8)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; regioselective reaction;	100%

n-octyne (629-05-0) + isobutyraldehyde (78-84-2) + benzylamine (100-46-9) → benzyl(2-methylundec-4-yn-3-yl)amine (1355023-06-1)

Conditions	Yield
With copper(I) bromide dimethylsulfide complex In toluene at 150℃; for 0.416667h; Inert atmosphere; Microwave irradiation;	100%

n-octyne (629-05-0) + N-(benzenesulfonyl)-4-bromo-1,2-dihydroquinoline → N-(benzenesulfonyl)-4-(1-octynyl)-1,2-dihydroquinoline

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere;	100%

n-octyne (629-05-0) + [(pentamethylcyclopentadienyl)Ir(2-phenylpyridine(-1H))(CH3CN)]PF6 (1147996-79-9) → C31H40IrN2(1+)*F6P(1-)

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h;	100%

n-octyne (629-05-0) + trimethylsilyl cyanide (7677-24-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-hexyl-1-methyl-1H-pyrrole-2-carbonitrile

Conditions	Yield
With ammonium iodide at 100℃; for 3h; Reagent/catalyst; Temperature;	100%
With iodine In neat (no solvent) at 80℃; for 2h; Schlenk technique; Green chemistry;	83%

n-octyne (629-05-0) → hexyl-methyl-ketone (111-13-7)

Conditions	Yield
With methyl(triphenylphosphine)gold(I); trifluorormethanesulfonic acid In methanol; water at 70℃; for 1h;	99%
With carbon monoxide; water; methyl(triphenylphosphine)gold(I); sulfuric acid In methanol at 70℃; under 760.051 Torr; for 1h; Product distribution / selectivity;	99%
With 1,3-bis{2,6-bis[bis(4-tert-butylphenyl)methyl]-4-methylphenyl}-1H-imidazol-2-ylidenegold(I) chloride; water; silver(I) triflimide In methanol at 80℃; for 1.5h; Temperature;	98%

n-octyne (629-05-0) → 1-iodooct-1-yne (81438-46-2)

Conditions	Yield
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.333333h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;	99%
With iodine; potassium carbonate; copper(l) iodide; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide Ambient temperature; overnight;	98%
With copper(l) iodide; tetrabutylammomium bromide; iodine; triethylamine In water at 20℃; for 24h;	95%

n-octyne (629-05-0) → (E)-1-iodo-1-octene (42599-17-7)

Conditions	Yield
Stage #1: n-octyne With diisobutylaluminium hydride In hexane at 50℃; for 3h; Stage #2: With iodine In tetrahydrofuran at -50 - 20℃;	99%
Stage #1: n-octyne With diisobutylaluminium hydride In hexane at 20 - 50℃; for 3h; Stage #2: With iodine In tetrahydrofuran at -50 - 20℃;	96%
Stage #1: n-octyne With diisobutylaluminium hydride In hexane at 50℃; for 4h; Stage #2: With iodine In tetrahydrofuran at -50 - 20℃;	95%

Chloro(chloromethyl)dimethylsilane (1719-57-9) + n-octyne (629-05-0) → 1-(chloromethyl)dimethylsilyl-1-octyne (91898-67-8)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃;	99%

n-octyne (629-05-0) + carbon dioxide (124-38-9) → non-2-ynoic acid (1846-70-4)

Conditions	Yield
With 3-(1-mesityl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate; caesium carbonate; potassium iodide; silver(l) oxide In N,N-dimethyl-formamide at 35℃; under 750.075 Torr; for 24h; Darkness;	99%
With (4,7-diphenyl-1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; caesium carbonate In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 16h;	97%
With (4,7-diphenyl-1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; caesium carbonate In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Temperature;	95%

Upstream product

• 15232-76-5 oct-3-yne 
• 693-25-4 n-pentylmagnesium bromide 
• 106-96-7 propargyl bromide 
• 64531-26-6 1-chloro-1-octyne 
• 42843-49-2 (Z)-1-bromo-1-octene 
• 51751-87-2 (E)-1-bromo-1-octene 
• 101354-46-5 N-(2-hydroxy-octyl)-N-nitroso-benzamide 
• 111-83-1 1-bromo-octane 
• 81216-13-9 8-bromooct-1-yne 
• 73383-25-2 1,1-dibromo-1-octene 
• 13249-60-0 2-bromo-1-octene 
• 152212-49-2 1,2-dibromooctane 
• 111-25-1 1-bromo-hexane 
• 1066-26-8 sodium acetylide 

Downstream Products

• 1070-27-5 1,1,1,3-tetrachlorononane 
• 64183-49-9 octadec-7-yne 
• 79496-57-4 Non-2-yn-1-al diethyl acetal 
• 69668-93-5 (+/)-dec-3-yn-2-ol 
• 818-72-4 1-Octyn-3-ol 
• 2809-67-8 oct-2-yne 
• 111-66-0 oct-1-ene 
• 407-89-6 2,2-Difluor-octan 
• 40586-08-1 3-(pentadec-8-ynyl)anisole 
• 111-13-7 hexyl-methyl-ketone 
• 64955-00-6 (E)-3-(1-octen-1-yl)cyclopentanone 
• 55976-13-1 (E)-undeca-1,4-diene 
• 51916-54-2 (E)-3-Hexyl-1-phenyl-dec-3-en-1-one 
• 51916-49-5 1-Phenyl-4-n-hexyldecan-1,4-dion 

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