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693-02-7

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693-02-7 Usage

General Description

1-Hexyne is a colorless, flammable liquid chemical compound belonging to the alkyne group, with the chemical formula C6H10. It is a highly reactive and volatile compound, classified as a terminal alkyne due to the triple bond present at the terminal carbon. 1-Hexyne is commonly used as a building block in the synthesis of various organic compounds and pharmaceuticals. It is also used in the production of specialty chemicals, polymers, and as a solvent in certain industrial processes. However, it is important to handle 1-Hexyne with caution as it is toxic if ingested or inhaled, and may cause irritations upon skin contact. Additionally, it poses a high risk of combustion and should be stored and handled in a well-ventilated area with appropriate safety measures in place.

Check Digit Verification of cas no

The CAS Registry Mumber 693-02-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 3 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 693-02:
(5*6)+(4*9)+(3*3)+(2*0)+(1*2)=77
77 % 10 = 7
So 693-02-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H10/c1-3-5-6-4-2/h1H,4-6H2,2H3

693-02-7 Well-known Company Product Price

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  • TCI America

  • (H0140)  1-Hexyne  >97.0%(GC)

  • 693-02-7

  • 25mL

  • 350.00CNY

  • Detail
  • TCI America

  • (H0140)  1-Hexyne  >97.0%(GC)

  • 693-02-7

  • 250mL

  • 1,980.00CNY

  • Detail
  • Alfa Aesar

  • (A13156)  1-Hexyne, 98+%   

  • 693-02-7

  • 10g

  • 229.0CNY

  • Detail
  • Alfa Aesar

  • (A13156)  1-Hexyne, 98+%   

  • 693-02-7

  • 50g

  • 756.0CNY

  • Detail
  • Alfa Aesar

  • (A13156)  1-Hexyne, 98+%   

  • 693-02-7

  • 250g

  • 3272.0CNY

  • Detail
  • Aldrich

  • (244422)  1-Hexyne  97%

  • 693-02-7

  • 244422-25ML

  • 400.14CNY

  • Detail
  • Aldrich

  • (244422)  1-Hexyne  97%

  • 693-02-7

  • 244422-100ML

  • 1,279.98CNY

  • Detail

693-02-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Hexyne

1.2 Other means of identification

Product number -
Other names Hexyne

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:693-02-7 SDS

693-02-7Synthetic 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
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
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
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
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%
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%
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%
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
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%
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%
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%
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%
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
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%
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

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℃;
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

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%
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%
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%
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.;

693-02-7Relevant articles and documents

-

Smith et al.

, p. 3560,3562 (1960)

-

Relative Migratory Aptitudes of Alkyl Groups in the Iodination of Lithium Ethynyltrialkylborates

Slayden, Suzanne W.

, p. 2311 - 2314 (1981)

Relative migratory aptitudes of various alkyl groups have been determined in the iodine-induced rearrangement of lithium ethynyltrialkylborates.Trialkylboranes of types R3-nBR'n and thexyl-BRR' were complexed with lithium acetylide-ethylenediamine.Iodination, followed by deiodoboration of the rearranged intermediates, produced 1-alkynes in amounts which depend, after statistical correction, on the relative rates of alkyl group migration in an intramolecular competition.In some cases, the migratory aptitude was found to depend on the alkyl substitution pattern in the organoborate.The overall migratory aptitude order is bicyclooctyl > n-butyl > cyclohexyl, isobutyl, sec-butyl > thexyl.When the secondary and primary migrating carbon series are considered separately, the order is consistently bicyclooctyl > cyclohexyl > sec-butyl, and n-butyl > isobutyl.

Method for synthesizing terminal alkyne by utilizing 1, 2-dihaloalkane

-

Paragraph 0022-0024, (2020/04/29)

The invention discloses a method for synthesizing terminal alkyne by utilizing 1, 2-dihaloalkane. According to the method, 1, 3-dihaloalkane is used as a raw material and terminal alkyne is synthesized under the action of alkali and a catalyst, wherein the molar ratio of the alkali to the 1, 2-dihaloalkane is 2: 1-5: 1, the use amount of the catalyst is 2%-10% of the mass of the 1, 2-dihaloalkane,the reaction temperature is 100-150 DEG C and the reaction time is 3-10 h. The method has the advantages of environmental protection, high selectivity, high yield and the like.

Na2S-mediated synthesis of terminal alkynes from: Gem -dibromoalkenes

Singh, Radhey M.,Nandini, Durgesh,Bharadwaj, Kishor Chandra,Gupta, Tanu,Singh, Raj Pal

, p. 9979 - 9982 (2017/12/26)

The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed. Various precursors derived from heteroaromatic/aromatic/aliphatic aldehydes were found compatible. The reaction is proposed to proceed through the Fritsch-Buttenberg-Wiechell (FBW) rearrangement involving the corresponding vinyl carbene. Using mild reaction conditions with inexpensive Na2S·9H2O under air atmosphere has significant advantages over earlier routes.

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