Product Name

  • Name

    1-Hexyne

  • EINECS 211-736-9
  • CAS No. 693-02-7
  • Article Data101
  • CAS DataBase
  • Density 0.738 g/cm3
  • Solubility
  • Melting Point -132 °C
  • Formula C6H10
  • Boiling Point 71.424 °C at 760 mmHg
  • Molecular Weight 82.1454
  • Flash Point −6 °F
  • Transport Information UN 3295
  • Appearance colourless liquid
  • Safety 16-26-33-36-62-9
  • Risk Codes 11-36/37/38-65
  • Molecular Structure Molecular Structure of 693-02-7 (1-Hexyne)
  • Hazard Symbols
  • Synonyms Butylacetylene;NSC 9709;n-Butylacetylene;
  • PSA 0.00000
  • LogP 1.80980

Synthetic route

(E)-1,2-dibromohex-1-ene
49677-13-6

(E)-1,2-dibromohex-1-ene

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tri-n-butyl-tin hydride In tetrahydrofuran for 0.5h; Ambient temperature;100%
n-butylethynylmagnesium chloride
58177-69-8

n-butylethynylmagnesium chloride

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With oxygen In tetrahydrofuran at 20℃; for 0.75h;99%
1,2-dibromohexane
624-20-4

1,2-dibromohexane

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h; without <18>krone-6; Yields of byproduct given;96%
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 90℃; for 6h;92%
With potassium hydroxide; 2,5-dimethyl-2,5-hexanediol; tetraoctyl ammonium bromide at 80 - 90℃; for 0.25h;88%
(Z)-1-bromohex-1-ene
13154-12-6

(Z)-1-bromohex-1-ene

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 25℃; for 2h;96%
(E)-1-bromohex-1-ene
13154-13-7

(E)-1-bromohex-1-ene

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h;93%
2-bromohex-1-ene
3017-66-1

2-bromohex-1-ene

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 1h;92%
With sodium amide; xylene at 130℃; und zersetzt das entstandene Produkt mit Eiswasser;
With petroleumfraction of mp: 150-180 degree at 150℃; und zersetzt das entstandene Produkt mit Eiswasser;
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

N-benzylhept-2-yn-1-amine
1379038-80-8

N-benzylhept-2-yn-1-amine

A

N-benzyl-3-cyclohexylprop-2-yn-1-amine

N-benzyl-3-cyclohexylprop-2-yn-1-amine

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 100℃; for 48h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 90%
B n/a
...Expand
1-bromo-butane
109-65-9

1-bromo-butane

sodium acetylide
1066-26-8

sodium acetylide

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
In diethyl ether; ammonia for 2h;80%
32%
With ammonia
Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

N-benzylhept-2-yn-1-amine
1379038-80-8

N-benzylhept-2-yn-1-amine

A

N-benzyl 3-cyclopropyl-prop-2-ynylamine

N-benzyl 3-cyclopropyl-prop-2-ynylamine

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 75%
B n/a
...Expand
C9H18B(1-)*Li(1+)
121826-88-8

C9H18B(1-)*Li(1+)

A

2-Methyl-2-heptanol
625-25-2

2-Methyl-2-heptanol

B

n-pentyl methyl ketone
110-43-0

n-pentyl methyl ketone

C

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodium hydroxide; methanesulfonic acid; dihydrogen peroxide 1.) Et2O, -78 deg C, warming to 25 deg C, 2h; Yield given. Multistep reaction;A 8%
B n/a
C 73%
With sodium hydroxide; methanesulfonic acid; dihydrogen peroxide 1.) Et2O, -78 deg C warming to 25 deg C, 2h; Yield given. Multistep reaction;A 8%
B 9%
C n/a
...Expand
4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

N-benzylhept-2-yn-1-amine
1379038-80-8

N-benzylhept-2-yn-1-amine

A

N-benzyl-5-phenylpent-2-yn-1-amine

N-benzyl-5-phenylpent-2-yn-1-amine

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 70%
B n/a
...Expand
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

dimethyl sulfate
77-78-1

dimethyl sulfate

A

6-methyl-decan-5-one
27649-33-8

6-methyl-decan-5-one

B

3-methylheptan-2-one
2371-19-9

3-methylheptan-2-one

C

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide 1.) THF, -78 deg C, warming to 25 deg C, 2h; Yield given. Multistep reaction;A n/a
B 14%
C 68%
With sodium hydroxide; dihydrogen peroxide 1.) THF, -78 deg C, warming to 25 deg C, 2h; Yield given. Multistep reaction;A 11%
B n/a
C 68%
...Expand
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

A

2-Methyl-2-heptanol
625-25-2

2-Methyl-2-heptanol

B

n-pentyl methyl ketone
110-43-0

n-pentyl methyl ketone

C

5-Methyldecan-5-ol
87258-26-2

5-Methyldecan-5-ol

D

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodium hydroxide; Me2SO3H; dihydrogen peroxide 1.) THF, -78 deg C, warming to 25 deg C, 1h; Yield given. Multistep reaction. Further byproducts given;A 12%
B n/a
C 12%
D 57%
...Expand
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

A

2-Methyl-2-heptanol
625-25-2

2-Methyl-2-heptanol

B

5-Methyldecan-5-ol
87258-26-2

5-Methyldecan-5-ol

C

decan-5-one
820-29-1

decan-5-one

D

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodium hydroxide; methanesulfonic acid; dihydrogen peroxide 1.) THF, -78 deg C, warming to 25 deg C, 2h; Yield given. Multistep reaction. Further byproducts given;A 12%
B 12%
C n/a
D 57%
...Expand
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

N-benzylhept-2-yn-1-amine
1379038-80-8

N-benzylhept-2-yn-1-amine

A

N-benzyl 4,4-dimethyl-pent-2-ynylamine
1610010-33-7

N-benzyl 4,4-dimethyl-pent-2-ynylamine

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 55%
B n/a
...Expand
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

dimethyl sulfate
77-78-1

dimethyl sulfate

A

6-Methylundec-5-ene
859742-90-8

6-Methylundec-5-ene

B

methylheptene
3404-75-9

methylheptene

C

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
Yield given. Multistep reaction;A n/a
B 18%
C 49%
Yield given. Multistep reaction;A 16%
B n/a
C 49%
...Expand
1-(trimethylsilyl)-1-hexyne
3844-94-8

1-(trimethylsilyl)-1-hexyne

n-octyne
629-05-0

n-octyne

A

trimethyl(oct-1-yn-1-yl)silane
15719-55-8

trimethyl(oct-1-yn-1-yl)silane

B

oct-2-yne
2809-67-8

oct-2-yne

C

2-Hexyne
764-35-2

2-Hexyne

D

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; Yb-imine; methyl iodide In tetrahydrofuran for 17h; Ambient temperature;A 25%
B 42%
C 34%
D 10%
...Expand
1,1-dibromo 1-hexene
73383-23-0

1,1-dibromo 1-hexene

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodiumsulfide nonahydrate In dimethyl sulfoxide at 40℃; for 18h;42%
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

A

2-Methyl-2-heptanol
625-25-2

2-Methyl-2-heptanol

B

hept-2-ene
592-77-8

hept-2-ene

C

5-decene
19689-19-1

5-decene

D

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
Yield given. Multistep reaction. Further byproducts given;A 23%
B n/a
C 18%
D 26%
...Expand
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

A

2-Methyl-2-heptanol
625-25-2

2-Methyl-2-heptanol

B

5-decene
19689-19-1

5-decene

C

5-Methyldecan-5-ol
87258-26-2

5-Methyldecan-5-ol

D

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
Yield given. Multistep reaction. Further byproducts given;A n/a
B 18%
C 14%
D 26%
Yield given. Multistep reaction. Further byproducts given;A 23%
B n/a
C 14%
D 26%
Yield given. Multistep reaction. Further byproducts given;A 23%
B 18%
C n/a
D 26%
...Expand
C12H24B(1-)*Li(1+)
121826-81-1

C12H24B(1-)*Li(1+)

A

6-methyl-decan-5-one
27649-33-8

6-methyl-decan-5-one

B

3-methylheptan-2-one
2371-19-9

3-methylheptan-2-one

C

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; dimethyl sulfate 1.) THF, -78 deg C warming to 25 deg C, 2h; Yield given. Multistep reaction;A 11%
B 14%
C n/a
...Expand
1,2-dibromohexane
624-20-4

1,2-dibromohexane

A

2-bromohex-1-ene
3017-66-1

2-bromohex-1-ene

B

(Z)-1-bromohex-1-ene
13154-12-6

(Z)-1-bromohex-1-ene

C

(E)-1-bromohex-1-ene
13154-13-7

(E)-1-bromohex-1-ene

D

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With potassium tert-butylate In Petroleum ether at 80℃; for 6h; Yield given;A n/a
B n/a
C n/a
D 7.8%
With potassium tert-butylate In Petroleum ether at 80℃; for 6h; Yield given;A n/a
B n/a
C n/a
D 7.8%
...Expand
1-iodo-butane
542-69-8

1-iodo-butane

sodium acetylide
1066-26-8

sodium acetylide

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With ammonia
butyl para-toluenesulfonate
778-28-9

butyl para-toluenesulfonate

sodium acetylide
1066-26-8

sodium acetylide

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With diphenylether
1-bromo-2-ethoxyhexane
73694-79-8

1-bromo-2-ethoxyhexane

A

2-ethoxy-1-hexene
54844-02-9

2-ethoxy-1-hexene

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With ammonia; sodium amide
2-bromohex-1-ene
3017-66-1

2-bromohex-1-ene

1-bromohexene
13154-12-6, 13154-13-7, 57855-22-8

1-bromohexene

A

1-hexene
592-41-6

1-hexene

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With sodium; xylene at 25℃;
...Expand
hept-2-ynoic acid
1483-67-6

hept-2-ynoic acid

A

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

B

hex-1-yne
693-02-7

hex-1-yne

7-phenyltrideca-5,8-diyn-7-ol
854638-65-6

7-phenyltrideca-5,8-diyn-7-ol

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
at 230℃; Leiten im Stickstoff-Strom ueber Aluminiumoxyd;
acetylene
74-86-2

acetylene

A

5-decyne
1942-46-7

5-decyne

B

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With diethyl ether; phenylmagnesium bromide Erhitzen des erhaltenen Gemisches aus Acetylenmagnesiumbromid und Acetylen-bis-magnesiumbromid mit Butylbromid auf 80-90grad;
allyl bromide
106-95-6

allyl bromide

hex-1-yne
693-02-7

hex-1-yne

non-1-en-4-yne
31508-12-0

non-1-en-4-yne

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; sodium sulfite; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 30℃; for 4h;100%
With sodium hydroxide; Aliquat 336; copper(l) chloride In dichloromethane; water at 20℃; for 50h;73%
(i) EtMgBr, CuCl, (ii) /BRN= 605308/; Multistep reaction;
With copper(l) iodide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfite In N,N-dimethyl-formamide at 20℃;
hex-1-yne
693-02-7

hex-1-yne

5,7-dodecadiyne
1120-29-2

5,7-dodecadiyne

Conditions
ConditionsYield
With copper diacetate In acetonitrile for 7h; Heating;100%
With copper diacetate; sodium acetate; PEG 6000 at 90℃; for 20h;96%
With N,N,N,N,-tetramethylethylenediamine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; copper(l) chloride at 20℃; for 6h; Glaser oxidative coupling;95%
hex-1-yne
693-02-7

hex-1-yne

7-methylene-5-undecyne
5663-86-5

7-methylene-5-undecyne

Conditions
ConditionsYield
(C5Me5)Ti<ε2-C2(SiMe3)2> In hexane at 30℃; for 120h;100%
With bis(trimethylsilyl)amide yttrium(III); tris(trimethylsilyl)amine In toluene at 100℃; for 17h;99%
With methylaluminoxane In benzene-d6 at 20℃; under 1E-05 Torr; for 24h; Dimerization;99.7%
bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

hex-1-yne
693-02-7

hex-1-yne

4-n-butyldeltacyclen
123186-37-8, 126518-14-7, 128163-06-4, 128163-07-5

4-n-butyldeltacyclen

Conditions
ConditionsYield
With diphosphane; (2S,3S)-(+)-bis(diphenylphosphanyl)bicyclo[2.2.1]hept-5-ene; cobalt(III) acetylacetonate; diethylaluminium chloride In tetrahydrofuran at 35℃; for 4h;100%
formaldehyd
50-00-0

formaldehyd

hex-1-yne
693-02-7

hex-1-yne

hep-2-yn-1-ol
1002-36-4

hep-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;
Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;		100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: formaldehyd In tetrahydrofuran at -78 - 20℃; for 18h;		99%
With n-butyllithium In diethyl ether at 0℃;89%
pentanal
110-62-3

pentanal

hex-1-yne
693-02-7

hex-1-yne

Undec-6-in-5-ol
73252-74-1

Undec-6-in-5-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: pentanal In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;		100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: pentanal In tetrahydrofuran; hexane at 20℃; for 0.5h; Inert atmosphere;		92%
With n-butyllithium In tetrahydrofuran at -78℃; for 2h;87%
PhIO*TfOH

PhIO*TfOH

hex-1-yne
693-02-7

hex-1-yne

<2-<(trifluoromethanesulfonyl)oxy>-1-hexenyl>(phenyl)iodonium trifluoromethanesulfonate

<2-<(trifluoromethanesulfonyl)oxy>-1-hexenyl>(phenyl)iodonium trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane Ambient temperature;100%
PhI(OH)OTs
122220-13-7

PhI(OH)OTs

hex-1-yne
693-02-7

hex-1-yne

<2-<(trifluoromethanesulfonyl)oxy>-1-hexenyl>(phenyl)iodonium trifluoromethanesulfonate

<2-<(trifluoromethanesulfonyl)oxy>-1-hexenyl>(phenyl)iodonium trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;100%
norborn-2-ene
498-66-8

norborn-2-ene

carbon monoxide
201230-82-2

carbon monoxide

hex-1-yne
693-02-7

hex-1-yne

(3aSR,4SR,7RS,7aSR)-2-butyl-3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-1-one
143768-88-1

(3aSR,4SR,7RS,7aSR)-2-butyl-3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-1-one

Conditions
ConditionsYield
dodecacarbonyl tetracobalt In dichloromethane at 150℃; under 7600 Torr; for 22h;100%
Co2Rh2 nanoparticles immobilized on charcoal In tetrahydrofuran at 130℃; under 760 Torr; for 18h; intermolecular Pauson-Khand reaction;60%
...Expand
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

hex-1-yne
693-02-7

hex-1-yne

1-bromo-2-(1-hexynyl)benzene
204334-80-5

1-bromo-2-(1-hexynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 18h; Sonogashira coupling; Inert atmosphere;100%
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 8h; Sonogashira Cross-Coupling; Inert atmosphere;95%
2-iodophenylamine
615-43-0

2-iodophenylamine

hex-1-yne
693-02-7

hex-1-yne

2-(hex-1-ynyl)aniline
116491-50-0

2-(hex-1-ynyl)aniline

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine for 4h; Sonogashira coupling; Reflux;100%
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%
iodobenzene
591-50-4

iodobenzene

hex-1-yne
693-02-7

hex-1-yne

(hex-1-yn-1-yl)benzene
1129-65-3

(hex-1-yn-1-yl)benzene

Conditions
ConditionsYield
Stage #1: iodobenzene; hex-1-yne With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: With copper(l) iodide at 20℃; for 23h; Inert atmosphere;		100%
With copper(I) oxide; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 135℃; for 12h; Inert atmosphere;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 20h; Schlenk technique; Inert atmosphere;99%
hex-1-yne
693-02-7

hex-1-yne

(E)-2-iodoethenyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether
219983-80-9

(E)-2-iodoethenyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether

1E-octen-3-ynyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether
219983-90-1

1E-octen-3-ynyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0)100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); isopropylamine Substitution;455 mg
2-Iodothiophene
3437-95-4

2-Iodothiophene

hex-1-yne
693-02-7

hex-1-yne

2-(hex-1-ynyl)thiophene
19482-59-8

2-(hex-1-ynyl)thiophene

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 50℃;100%
Stage #1: 2-Iodothiophene; hex-1-yne With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere;		93%
With triethylamine; palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) In water at 20℃; for 6h; Sonogashira cross-coupling;89%
benzaldehyde
100-52-7

benzaldehyde

hex-1-yne
693-02-7

hex-1-yne

1-phenylhept-2-yn-1-ol
73922-80-2, 79433-53-7, 143731-62-8, 2108-51-2, 128945-83-5

1-phenylhept-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane		100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.416667h;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at 20℃; for 1h;		96%
With dimethyl zinc(II); (1R,2S)-cis-1-amino-2-indenol-derived oxazolidine In n-heptane; toluene at -4℃; for 48h;96%
Triisopropyl borate
5419-55-6

Triisopropyl borate

hex-1-yne
693-02-7

hex-1-yne

C15H30BO3(1-)*Li(1+)

C15H30BO3(1-)*Li(1+)

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at 20℃; Substitution;100%
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

hex-1-yne
693-02-7

hex-1-yne

1-(hex-1-yn-1-yl)-3-methoxybenzene
112545-96-7

1-(hex-1-yn-1-yl)-3-methoxybenzene

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 50℃;100%
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) at 60℃;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 12h; Schlenk technique;
m-trifluoromethylphenyl iodide
401-81-0

m-trifluoromethylphenyl iodide

hex-1-yne
693-02-7

hex-1-yne

1-(hex-1-yn-1-yl)-3-(trifluoromethyl)benzene
252045-82-2

1-(hex-1-yn-1-yl)-3-(trifluoromethyl)benzene

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 50℃;100%
Sonogashira Cross-Coupling;
N-formyl-2-iodoaniline
10113-39-0

N-formyl-2-iodoaniline

hex-1-yne
693-02-7

hex-1-yne

N-(2-(hex-1-yn-1-yl)phenyl)formamide
302351-88-8

N-(2-(hex-1-yn-1-yl)phenyl)formamide

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran Sonogashira coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

hex-1-yne
693-02-7

hex-1-yne

hex-1-yn-1-yldimethylsilane
79966-86-2

hex-1-yn-1-yldimethylsilane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; pentane at -78 - 20℃;100%
Stage #1: hex-1-yne With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: dimethylmonochlorosilane In tetrahydrofuran; diethyl ether at 0 - 20℃; for 4h; Inert atmosphere;		98%
Stage #1: hex-1-yne With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: dimethylmonochlorosilane In diethyl ether; hexane at -78 - 20℃; Further stages.;		85%
chlorodiisopropylsilane
2227-29-4

chlorodiisopropylsilane

hex-1-yne
693-02-7

hex-1-yne

hex-1-ynyl-diisopropylsilane
321674-10-6

hex-1-ynyl-diisopropylsilane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; pentane at -78 - 20℃;100%
hex-1-yne
693-02-7

hex-1-yne

(E)-1-hexenyldihydroxyborane
42599-18-8

(E)-1-hexenyldihydroxyborane

Conditions
ConditionsYield
With benzo[1,3,2]dioxaborole In tetrahydrofuran Heating;100%
Stage #1: hex-1-yne With dichloroborane dioxane complex In dichloromethane for 4h; Heating;
Stage #2: With water cooling;		61%
Stage #1: hex-1-yne With dimethylsulfide borane complex; (+)-α-pinene In tetrahydrofuran at -40 - 20℃;
Stage #2: With acetaldehyde In tetrahydrofuran at 45℃; for 16h;
Stage #3: With water In tetrahydrofuran at 0℃; for 3h;
hex-1-yne
693-02-7

hex-1-yne

(Z,Z)-5,8-dibromododeca-5,7-diene

(Z,Z)-5,8-dibromododeca-5,7-diene

Conditions
ConditionsYield
With copper(ll) bromide; palladium(II) bromide In acetonitrile; benzene at 20℃; for 6h;100%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

hex-1-yne
693-02-7

hex-1-yne

1-(4-fluorophenyl)hept-2-yn-1-ol
191403-25-5

1-(4-fluorophenyl)hept-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane		100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran; hexane Inert atmosphere;		60%
1-chloro-3-pentyl-7-propyl-pyrrolo[1,2-c]pyrimidine
753470-37-0

1-chloro-3-pentyl-7-propyl-pyrrolo[1,2-c]pyrimidine

hex-1-yne
693-02-7

hex-1-yne

1-hex-1-ynyl-3-pentyl-7-propyl-pyrrolo[1,2-c]pyrimidine
753470-35-8

1-hex-1-ynyl-3-pentyl-7-propyl-pyrrolo[1,2-c]pyrimidine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper at 80℃; Sonogashira coupling;100%
2,4-dibromo-5,6-dimethyl-pyrimidine
753470-32-5

2,4-dibromo-5,6-dimethyl-pyrimidine

5-phenyl-1-pentyne
1823-14-9

5-phenyl-1-pentyne

hex-1-yne
693-02-7

hex-1-yne

2-hex-1-ynyl-4,5-dimethyl-6-(5-phenyl-pent-1-ynyl)-pyrimidine

2-hex-1-ynyl-4,5-dimethyl-6-(5-phenyl-pent-1-ynyl)-pyrimidine

Conditions
ConditionsYield
Stage #1: 2,4-dibromo-5,6-dimethyl-pyrimidine; 5-phenyl-1-pentyne With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20℃; for 12h; Sonogashira coupling;
Stage #2: hex-1-yne In triethylamine at 45℃; for 12h; Sonogashira coupling;		100%
...Expand
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

hex-1-yne
693-02-7

hex-1-yne

1-(pyridin-2-yl)hept-2-yn-1-ol
934399-67-4

1-(pyridin-2-yl)hept-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: pyridine-2-carbaldehyde In tetrahydrofuran at 0℃; for 1h;		100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: pyridine-2-carbaldehyde In tetrahydrofuran at -78℃; Further stages.;
Stage #1: hex-1-yne With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 1h;
Stage #2: pyridine-2-carbaldehyde In tetrahydrofuran at -78 - 20℃; for 1.5h; Further stages.;
C116H92N4O32(2-)*Co(2+)

C116H92N4O32(2-)*Co(2+)

hex-1-yne
693-02-7

hex-1-yne

2-(1-hexenyl)(5,10,15,20-tetrakis[3',5'-bis{3'',5''-bis(3''',5'''-dimethoxybenzoyloxy)benzoyloxy}phenyl]-porphinato)cobalt(III)

2-(1-hexenyl)(5,10,15,20-tetrakis[3',5'-bis{3'',5''-bis(3''',5'''-dimethoxybenzoyloxy)benzoyloxy}phenyl]-porphinato)cobalt(III)

Conditions
ConditionsYield
With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile In chloroform at 20℃; for 5h;100%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

hex-1-yne
693-02-7

hex-1-yne

1-(naphthalen-1-yl)hept-2-yn-1-ol
862776-51-0

1-(naphthalen-1-yl)hept-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: 1-naphthaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane		100%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 1-naphthaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 0.583333h; Inert atmosphere;		80%
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: 1-naphthaldehyde In tetrahydrofuran at -78 - 20℃; Further stages.;

1-Hexyne Chemical Properties

IUPAC Name: hex-1-yne
The MF of 1-Hexyne(693-02-7): C6H10
The MW of 1-Hexyne(693-02-7): 82.14
EINECS: 211-736-9
mp: -132 °C
bp: 71-72 °C(lit.)
density: 0.715 g/mL at 25 °C(lit.)
vapor pressure: 253 mm Hg ( 37.7 °C)
refractive index: n20/D 1.399(lit.)
Fp: -6 °F
storage temp.: 0-6°C
Appearance: colourless liquid
Solubility in water: Slightly soluble
Enthalpy of Vaporization: 29.99 kJ/mol 
Stability: Stable. Incompatible with strong oxidizing agents. Highly flammable - readily forms explosive mixtures with air.
Categories: Miscellaneous;Acetylenes;Acetylenic Hydrocarbons;Alkynes;Organic Building Blocks;Terminal
Synonyms: N-BUTYLACETYLENE;Butylacetylene;C4H9CequivCH;Hex-1-yne;Hexyne;1-HEXYNE;HEXYNE(1-);Butyl acetyne
The Structure of 1-Hexyne(693-02-7):

1-Hexyne Toxicity Data With Reference

1. mouse LD50 intraperitoneal > 100mg/kg (100mg/kg)
   Journal of the American Chemical Society. Vol. 79, Pg. 2311, 1957.
2. mouse LD50 subcutaneous > 400mg/kg (400mg/kg)
   Nature. Vol. 174, Pg. 737, 1954.

1-Hexyne Safety Profile

 Hazard Codes: F,Xn,Xi
Risk Statements: 11-36/37/38-65
11:  Highly Flammable 
36/37/38:  Irritating to eyes, respiratory system and skin 
65:  Harmful: May cause lung damage if swallowed 
Safety Statements: 16-26-36-62-9-33-7/9
16:  Keep away from sources of ignition - No smoking 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
62:  If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label 
9:  Keep container in a well-ventilated place 
33:  Take precautionary measures against static discharges 
7/9:  Keep container tightly closed and in a well-ventilated place 
RIDADR: UN 3295 3/PG 2
WGK Germany: 3
RTECS: MQ9691000
F: 10-23
F 10 Keep under argon.
F 23 Sensitive to air.
Hazard Note: Irritant
HazardClass: 3
PackingGroup: II
HS Code: 29012980

1-Hexyne Specification

1. First Aid Measures
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin:
Get medical aid immediately. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Discard contaminated clothing in a manner which limits further exposure.
Eyes:
Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
2. Handling and Storage
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Refrigerator/flammables.
Handling:
Wash thoroughly after handling. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Do not get in eyes, on skin, or on clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid contact with heat, sparks and flame. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Do not breathe vapors.

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