Product Name

  • Name

    1-Propyne

  • EINECS 200-828-4
  • CAS No. 74-99-7
  • Article Data295
  • CAS DataBase
  • Density 0.648 g/cm3
  • Solubility
  • Melting Point -102.7 °C(lit.)
  • Formula C3H4
  • Boiling Point -23.2 °C(lit.)
  • Molecular Weight 40.0648
  • Flash Point -51 °C
  • Transport Information UN 1954
  • Appearance
  • Safety 16-36-38
  • Risk Codes 11-37
  • Molecular Structure Molecular Structure of 74-99-7 (1-Propyne)
  • Hazard Symbols FlammableF,IrritantXi
  • Synonyms Propyne(8CI);Allylene;Methylacetylene;1-Propyne;
  • PSA 0.00000
  • LogP 0.63950

Synthetic route

4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

A

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

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

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 95%
B n/a
...Expand
acetaldehyde
75-07-0

acetaldehyde

C8H21N4PSi
145397-30-4

C8H21N4PSi

A

α-trimethylsilyloxyethyl-N,N,N',N'-tetramethylphosphondiamide

α-trimethylsilyloxyethyl-N,N,N',N'-tetramethylphosphondiamide

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
In pentane at 20℃;A 91%
B n/a
...Expand
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

A

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

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

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 90%
B n/a
...Expand
benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

A

N-benzyl-3-(4-methylphenyl)-2-propynylamine
1273578-50-9

N-benzyl-3-(4-methylphenyl)-2-propynylamine

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 87%
B n/a
...Expand
4-methylpentyne
7154-75-8

4-methylpentyne

benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

A

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

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

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 87%
B n/a
...Expand
benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

hex-1-yne
693-02-7

hex-1-yne

A

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

N-benzylhept-2-yn-1-amine

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 120℃; for 12h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 87%
B n/a
...Expand
Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

A

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

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

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 86%
B n/a
...Expand
benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

phenylacetylene
536-74-3

phenylacetylene

A

N-(3-phenylprop-2-ynyl)benzenemethanamine
40032-57-3

N-(3-phenylprop-2-ynyl)benzenemethanamine

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 85%
B n/a
...Expand
sodium acetylide
1066-26-8

sodium acetylide

methyl iodide
74-88-4

methyl iodide

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
In ammonia84%
With ammonia
1-ethynyl-4-fluorobenzene
766-98-3

1-ethynyl-4-fluorobenzene

benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

A

N-benzyl-3-(4-fluorophenyl)prop-2-yn-1-amine

N-benzyl-3-(4-fluorophenyl)prop-2-yn-1-amine

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 80%
B n/a
...Expand
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

benzyl(but-2-yn-1-yl)amine
4626-58-8

benzyl(but-2-yn-1-yl)amine

A

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

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

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A 80%
B n/a
...Expand
1-(4-methoxyphenyl)-4-(triphenylphosphoranylidene)hexane-1,5-dione

1-(4-methoxyphenyl)-4-(triphenylphosphoranylidene)hexane-1,5-dione

A

1-(4-methoxyphenyl)prop-2-en-1-one
7448-86-4

1-(4-methoxyphenyl)prop-2-en-1-one

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at 650℃; under 0.01 - 0.1 Torr; for 2h;A 79%
B n/a
triphenylprop-2-ynylarsonium bromide
5903-83-3

triphenylprop-2-ynylarsonium bromide

A

1,2-propanediene
463-49-0

1,2-propanediene

B

triphenylarsineoxide
1153-05-5, 856568-31-5

triphenylarsineoxide

C

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 25℃; for 1h;A n/a
B 71.51%
C n/a
...Expand
tributyl(2-bromo-2-propenyl)phosphonium bromide

tributyl(2-bromo-2-propenyl)phosphonium bromide

A

Tributylphosphine oxide
814-29-9

Tributylphosphine oxide

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With potassium hydroxide In water for 1h; Hydrolysis; Heating;A 66%
B 70%
protoanemonin
108-28-1

protoanemonin

A

1,2-propanediene
463-49-0

1,2-propanediene

B

maleic anhydride
930-60-9

maleic anhydride

C

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at 1100℃;A 10%
B 60%
C 25%
...Expand
3-(triphenylphosphoranylidene)octane-2,6-dione
163495-05-4

3-(triphenylphosphoranylidene)octane-2,6-dione

A

4-penten-3-one
1629-58-9

4-penten-3-one

B

oct-6-yn-3-one
26118-44-5

oct-6-yn-3-one

C

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at 650℃; under 0.01 - 0.1 Torr; for 2h;A 49%
B 39%
C n/a
...Expand
dimethylglyoxal
431-03-8

dimethylglyoxal

A

dimethylketene
598-26-5

dimethylketene

B

propene
187737-37-7

propene

C

carbon dioxide
124-38-9

carbon dioxide

D

methyl vinyl ketone
78-94-4

methyl vinyl ketone

E

prop-1-yne
74-99-7

prop-1-yne

F

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
With pyrographite at -196℃; Mechanism;A 2%
B 22.4%
C 9.4%
D 19%
E 2.3%
F 40.7%
...Expand
(p-fluorophenyl)dimethyl(1-propynyl)stannane
93247-03-1

(p-fluorophenyl)dimethyl(1-propynyl)stannane

4-ethynyl-N,N-dimethylaniline
17573-94-3

4-ethynyl-N,N-dimethylaniline

A

{(p-(dimethylamino)phenyl)ethynyl}(p-fluorophenyl)dimethylstannane
93246-99-2

{(p-(dimethylamino)phenyl)ethynyl}(p-fluorophenyl)dimethylstannane

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
In neat (no solvent) (vac.); mixing Sn-compd. with org. compd. in stream of Ar, heating (150°C), keeping (160-175°C, 10 h); distn. (vac.), collection (155°C and higher, 0.08 mm), recrystn. (hexane/CCl4); elem. anal.;A 36%
B n/a
In neat (no solvent) (vac.); mixing Sn-compd. with org. compd. in stream of Ar, heating (150°C), keeping (160-175°C, 5 h),; distn. (vac.), collection (155°C and higher, 0.08 mm), recrystn. (hexane/CCl4); elem. anal.;A 33%
B n/a
...Expand
3-(triphenylphosphoranylidene)heptane-2,6-dione
193155-13-4

3-(triphenylphosphoranylidene)heptane-2,6-dione

A

5-heptyne-2-one
22592-18-3

5-heptyne-2-one

B

methyl vinyl ketone
78-94-4

methyl vinyl ketone

C

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at 750℃; under 0.01 - 0.1 Torr; for 2h;A 33%
B 28%
C n/a
at 650℃; under 0.01 - 0.1 Torr; for 2h;A 26%
B 32%
C n/a
...Expand
1-Methyl-1-ethenylsilacyclobutane
3514-67-8

1-Methyl-1-ethenylsilacyclobutane

A

propene
187737-37-7

propene

B

ethene
74-85-1

ethene

C

1,2-propanediene
463-49-0

1,2-propanediene

D

buta-1,3-diene
106-99-0

buta-1,3-diene

E

prop-1-yne
74-99-7

prop-1-yne

F

1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane
22053-38-9

1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane

Conditions
ConditionsYield
at 775℃; under 0.008 - 0.08 Torr; Product distribution; Mechanism; other temperature;A 1.4%
B 8%
C 3.6%
D n/a
E 1.7%
F 28%
...Expand
1-Methyl-1-ethenylsilacyclobutane
3514-67-8

1-Methyl-1-ethenylsilacyclobutane

A

ethene
74-85-1

ethene

B

1,2-propanediene
463-49-0

1,2-propanediene

C

prop-1-yne
74-99-7

prop-1-yne

D

1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane
22053-38-9

1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane

Conditions
ConditionsYield
at 775℃; under 0.008 - 0.08 Torr; Further byproducts given;A 8%
B 3.6%
C 1.7%
D 28%
Kinetics; Thermodynamic data; low pressure pyrolysis; also co-pyrolysis with 1,1-dimethyl-1-silacyclobutane; var. temp.;
...Expand
2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

1,1-Divinyl-1-silacyclobutane
74045-42-4

1,1-Divinyl-1-silacyclobutane

A

propene
187737-37-7

propene

B

ethene
74-85-1

ethene

C

Allylmethylvinylsilan

Allylmethylvinylsilan

D

3,4-Dimethyl-1-sila-1-vinylcyclopent-3-en

3,4-Dimethyl-1-sila-1-vinylcyclopent-3-en

E

prop-1-yne
74-99-7

prop-1-yne

F

acetylene
74-86-2

acetylene

G

aromatic hydrocarbons, Si-compounds

aromatic hydrocarbons, Si-compounds

Conditions
ConditionsYield
at 820℃; under 0.008 - 0.08 Torr; Product distribution; Mechanism;A 3%
B 21%
C 8%
D 14%
E 4%
F 18%
G n/a
...Expand
furan
110-00-9

furan

A

ethene
74-85-1

ethene

B

prop-1-yne
74-99-7

prop-1-yne

C

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
at 700℃; Pyrolysis;
...Expand
pyridine
110-86-1

pyridine

2-Butynoic acid
590-93-2

2-Butynoic acid

A

2,4-hexadiyne
2809-69-0

2,4-hexadiyne

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
Reaktion des Kupfersalzes;
...Expand
methyl bromide
74-83-9

methyl bromide

sodium acetylide
1066-26-8

sodium acetylide

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With tetrahydrofuran; N,N-dimethyl-formamide
2-chloropropene
557-98-2

2-chloropropene

potassium cyanide
151-50-8

potassium cyanide

prop-1-yne
74-99-7

prop-1-yne

2-chloropropene
557-98-2

2-chloropropene

sodium ethanolate
141-52-6

sodium ethanolate

prop-1-yne
74-99-7

prop-1-yne

2-chloropropene
557-98-2

2-chloropropene

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With potassium carbonate
With sodium ethanolate
2,3-Dichloroprop-1-ene
78-88-6

2,3-Dichloroprop-1-ene

A

propene
187737-37-7

propene

B

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
With sodium
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

prop-1-yne
74-99-7

prop-1-yne

(E)-2-hepten-5-yn-4-ol
63124-69-6

(E)-2-hepten-5-yn-4-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; pentane at -78℃; for 0.833333h;100%
(i) EtMgBr, Et2O, (ii) /BRN= 1209254/; Multistep reaction;
2-iodobenzonitrile
4387-36-4

2-iodobenzonitrile

prop-1-yne
74-99-7

prop-1-yne

2-(prop-1-yn-1-yl)benzonitrile
110166-79-5

2-(prop-1-yn-1-yl)benzonitrile

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride for 6h; Ambient temperature;100%
N-methoxy-N-methyl-3,3-dimethylacrylamide
121712-53-6

N-methoxy-N-methyl-3,3-dimethylacrylamide

prop-1-yne
74-99-7

prop-1-yne

2-Methyl-2-hepten-5-yn-4-one
103576-51-8

2-Methyl-2-hepten-5-yn-4-one

Conditions
ConditionsYield
With n-butyllithium; triphenylmethane 1.) -78 deg C, 15 min, 2.) r.t., 3 h;100%
prop-1-yne
74-99-7

prop-1-yne

4-methyl-1,3,2-dithiazolium hexafluoroarsenate(V)
88047-50-1

4-methyl-1,3,2-dithiazolium hexafluoroarsenate(V)

Conditions
ConditionsYield
With dichlorodithionitronium hexafluoroarsenate In liquid sulphur dioxide100%
With dithionitronium hexafluoroarsenate In liquid sulphur dioxide Yield given;
With dithionitronium hexafluoroarsenate In liquid sulphur dioxide for 6h; Ambient temperature;
1-(Methoxymethoxy)-2-butanone
170450-99-4

1-(Methoxymethoxy)-2-butanone

prop-1-yne
74-99-7

prop-1-yne

3-<(Methoxymethoxy)methyl>-4-hexyn-3-ol
170450-89-2

3-<(Methoxymethoxy)methyl>-4-hexyn-3-ol

Conditions
ConditionsYield
With ethylmagnesium bromide In tetrahydrofuran 1.) -78 deg C to r.t.; r.t., 1 h, 2.) 0 deg C to r.t., 1 h;100%
2-iodophenylamine
615-43-0

2-iodophenylamine

prop-1-yne
74-99-7

prop-1-yne

1-(2-aminophenyl)prop-1-yne
220465-91-8

1-(2-aminophenyl)prop-1-yne

Conditions
ConditionsYield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In triethylamine at 20℃; for 27h; Arylation;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Condensation;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at -78 - 20℃; for 13h; Sonogashira coupling;90%
(3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester
211029-67-3

(3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester

prop-1-yne
74-99-7

prop-1-yne

(3-prop-1-ynyl-pyridin-4-yl)-carbamic acid tert-butyl ester
211029-71-9

(3-prop-1-ynyl-pyridin-4-yl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 20℃;100%
Stage #1: (3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester; prop-1-yne; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In DMF (N,N-dimethyl-formamide); triethylamine at -78 - 20℃;
Stage #2: With ammonium chloride In DMF (N,N-dimethyl-formamide); water; ethyl acetate; triethylamine		98%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at -78 - 20℃; for 5 - 6h;97%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at -78 - 20℃; for 1h;
prop-1-yne
74-99-7

prop-1-yne

2,4-dibromo-6-pentyl-pyrimidine
494194-57-9

2,4-dibromo-6-pentyl-pyrimidine

4-pentyl-2,6-di-prop-1-ynyl-pyrimidine
494194-56-8

4-pentyl-2,6-di-prop-1-ynyl-pyrimidine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 3h; Sonogashira coupling;100%
2,4-dibromo-pyrimidine
3921-01-5

2,4-dibromo-pyrimidine

prop-1-yne
74-99-7

prop-1-yne

2,4-di-prop-1-ynyl-pyrimidine

2,4-di-prop-1-ynyl-pyrimidine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;100%
2,4-dibromo-5-methyl-pyrimidine
494194-61-5

2,4-dibromo-5-methyl-pyrimidine

prop-1-yne
74-99-7

prop-1-yne

5-methyl-2,4-di-prop-1-ynyl-pyrimidine
494194-51-3

5-methyl-2,4-di-prop-1-ynyl-pyrimidine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 3h;99%
2,4-dibromo-6-methyl-pyrimidine

2,4-dibromo-6-methyl-pyrimidine

prop-1-yne
74-99-7

prop-1-yne

4-methyl-2,6-di-prop-ynyl-pyrimidine
494194-53-5

4-methyl-2,6-di-prop-ynyl-pyrimidine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 3h;
2,4-dibromo-5,6-dimethyl-pyrimidine
753470-32-5

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

prop-1-yne
74-99-7

prop-1-yne

4,5-dimethyl-2,6-di-prop-1-ynyl-pyrinidine
494194-54-6

4,5-dimethyl-2,6-di-prop-1-ynyl-pyrinidine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; Sonogashira coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 3h;
4-(tert-butyldiphenylsilanyloxy)-2-butyn-1-al
112213-42-0

4-(tert-butyldiphenylsilanyloxy)-2-butyn-1-al

prop-1-yne
74-99-7

prop-1-yne

1-(tert-butyldiphenylsilanyloxy)hepta-2,5-diyn-4-ol
874667-97-7

1-(tert-butyldiphenylsilanyloxy)hepta-2,5-diyn-4-ol

Conditions
ConditionsYield
Stage #1: prop-1-yne With n-butyllithium; lithium bromide In tetrahydrofuran; hexane at -20℃; for 2h;
Stage #2: 4-(tert-butyldiphenylsilanyloxy)-2-butyn-1-al In tetrahydrofuran; hexane at -20 - 20℃;		100%
prop-1-yne
74-99-7

prop-1-yne

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

Conditions
ConditionsYield
(Me2SiCp''2UBu)2O*2THF In tetrahydrofuran at 66℃; for 44h;100%
2-bromo-6-fluorobenzaldehyde
360575-28-6

2-bromo-6-fluorobenzaldehyde

prop-1-yne
74-99-7

prop-1-yne

2-fluoro-6-prop-1-ynylbenzaldehyde
608515-62-4

2-fluoro-6-prop-1-ynylbenzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In DMF (N,N-dimethyl-formamide) at -78 - 20℃; for 4h;100%
(η5-C5Me5)Nb(CO)4
80432-28-6

(η5-C5Me5)Nb(CO)4

prop-1-yne
74-99-7

prop-1-yne

C5(CH3)5Nb(HCCCH3)2CO

C5(CH3)5Nb(HCCCH3)2CO

Conditions
ConditionsYield
In pentane byproducts: CO; Irradiation (UV/VIS); passing a faint stream of methylacetylene through Nb complex soln. under N2; irradiation (Hg medium pressure burner, 450 W), -20°C, 8-20 min; filtration; evapn. to dryness;100%
C9H4F6INO2
1139688-61-1

C9H4F6INO2

prop-1-yne
74-99-7

prop-1-yne

C12H7F6NO2
1139688-65-5

C12H7F6NO2

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide Sonogashira coupling;100%
(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane
95337-97-6, 110171-85-2, 130659-83-5, 95338-04-8

(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane

prop-1-yne
74-99-7

prop-1-yne

(S)-1-((tert-butyldimethylsilyl)oxy)hept-5-yn-3-ol
960211-10-3

(S)-1-((tert-butyldimethylsilyl)oxy)hept-5-yn-3-ol

Conditions
ConditionsYield
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;
Stage #2: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;		100%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - 0℃; for 2h;		85%
Stage #1: prop-1-yne With n-butyllithium In hexane at -78℃; for 0.0833333h;
Stage #2: With potassium hexamethylsilazane In hexane; toluene at -78℃; for 0.5h;
Stage #3: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane; toluene at -78℃; for 2h;		83%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 0℃; for 2h;
Stage #3: With ammonium chloride In tetrahydrofuran; water		80%
5-chloro-3-iodo-2-aminopyridine
211308-81-5

5-chloro-3-iodo-2-aminopyridine

prop-1-yne
74-99-7

prop-1-yne

5-chloro-3-prop-1-ynyl-pyridin-2-ylamine
1312755-53-5

5-chloro-3-prop-1-ynyl-pyridin-2-ylamine

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 0 - 20℃; for 1h;100%
(R)-benzyl glycidol
14618-80-5

(R)-benzyl glycidol

prop-1-yne
74-99-7

prop-1-yne

(2R)-1-(benzyloxy)hex-4-yn-2-ol
171075-74-4

(2R)-1-(benzyloxy)hex-4-yn-2-ol

Conditions
ConditionsYield
Stage #1: prop-1-yne With n-butyllithium In hexane; toluene at 0℃; for 1.5h;
Stage #2: With diethylaluminium chloride In hexane; toluene at 0℃; for 2h;
Stage #3: (R)-benzyl glycidol In hexane; toluene for 0.166667h;		100%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 0.666667h; Inert atmosphere;
Stage #2: (R)-benzyl glycidol With boron trifluoride diethyl etherate In tetrahydrofuran; toluene at -78 - 0℃; Inert atmosphere;		98%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; 1,2-dimethoxyethane at -78 - -40℃; for 0.666667h; Inert atmosphere;
Stage #2: (R)-benzyl glycidol With boron trifluoride diethyl etherate In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 1.16667h; Inert atmosphere;		98%
tert-butyl 4-azidopiperidine-1-carboxylate
180695-80-1

tert-butyl 4-azidopiperidine-1-carboxylate

prop-1-yne
74-99-7

prop-1-yne

tert-butyl 4-(4-methyl-1H-1,2,3-triazol-1-yl)-piperidine-1-carboxylate

tert-butyl 4-(4-methyl-1H-1,2,3-triazol-1-yl)-piperidine-1-carboxylate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20 - 40℃; for 5h; Sealed tube;100%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 18h;100%
prop-1-yne
74-99-7

prop-1-yne

tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate
108492-14-4

tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate

C15H26N4O4

C15H26N4O4

Conditions
ConditionsYield
With copper diacetate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃;100%
prop-1-yne
74-99-7

prop-1-yne

2-methyl-1-penten-3-yne
926-55-6

2-methyl-1-penten-3-yne

Conditions
ConditionsYield
With methylaluminoxane In benzene-d6 at 20℃; under 1E-05 Torr; for 48h; Dimerization;99.4%
With formaldehyd; palladium(II) acetylacetonate; triethylaluminum; triphenylphosphine In toluene at 100℃; for 6h;44%
[(Et2N)3U][BPh4] In tetrahydrofuran-d8 at 110℃; for 24h; Dimerization;94 % Chromat.
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

prop-1-yne
74-99-7

prop-1-yne

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With methanesulfonic acid; 2-(diphenylphosphino)pyridine; palladium diacetate at 45℃;99%
With methanesulfonic acid; N,N-dimethyl-aniline; palladium complex with bis(3,5-dimethyl-4-methoxyphenyl) (6-methyl-2-pyridyl)phosphine at 65℃; for 7h; Product distribution / selectivity; Cooling with ethanol-dry ice; Autoclave;73%
With methanesulfonic acid; 2-(diphenylphosphino)pyridine; palladium diacetate at 45℃; Mechanism; var. reagents and reaction conditions;
...Expand
N-Methoxy-N-methyl-3-propyl-2-hexenamide
157731-55-0

N-Methoxy-N-methyl-3-propyl-2-hexenamide

prop-1-yne
74-99-7

prop-1-yne

6-Propyl-5-nonen-2-yn-4-one
120696-27-7

6-Propyl-5-nonen-2-yn-4-one

Conditions
ConditionsYield
With n-butyllithium; triphenylmethane 1.) -78 deg C, 15 min, 2.) r.t., 3 h;99%
1,4-dihexyl-2,5-diiodobenzene
162715-91-5

1,4-dihexyl-2,5-diiodobenzene

prop-1-yne
74-99-7

prop-1-yne

2,5-dihexyl-1,4-diprop-1-ynylbenzene
188781-60-4

2,5-dihexyl-1,4-diprop-1-ynylbenzene

Conditions
ConditionsYield
With piperidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride for 3h;99%
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide under 760 Torr; for 4h;82%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

prop-1-yne
74-99-7

prop-1-yne

ethyl 4-(prop-1-yn-1-29/122-yl)benzoate

ethyl 4-(prop-1-yn-1-29/122-yl)benzoate

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride 24 deg C, then 65 deg C;99%
prop-1-yne
74-99-7

prop-1-yne

(1R,2S,5R)-2-Methyl-5-((S)-(S)-3-oxiranyl-butyl)-6,8-dioxa-bicyclo[3.2.1]octane
585526-36-9

(1R,2S,5R)-2-Methyl-5-((S)-(S)-3-oxiranyl-butyl)-6,8-dioxa-bicyclo[3.2.1]octane

(3S,4R)-3-Methyl-1-((1R,2S,5S)-2-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-oct-6-yn-4-ol
585526-37-0

(3S,4R)-3-Methyl-1-((1R,2S,5S)-2-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-oct-6-yn-4-ol

Conditions
ConditionsYield
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 20℃;99%
1-indoline
496-15-1

1-indoline

prop-1-yne
74-99-7

prop-1-yne

4,4,6-trimethyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

4,4,6-trimethyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
With ammonium hexafluorophosphate; dodecacarbonyl-triangulo-triruthenium In benzene at 95℃; for 12h;99%
With [(PCy3)2(CO)(CH3CN)2RuCCPh][BF4] In benzene-d6 at 80℃;83 % Spectr.
(2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate
876288-81-2

(2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate

prop-1-yne
74-99-7

prop-1-yne

(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin
876288-82-3

(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

Conditions
ConditionsYield
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h;
Stage #2: (2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate In tetrahydrofuran at -78 - 24℃; for 3h;		99%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: (2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate In tetrahydrofuran at -78 - 25℃; for 3h;		97%

Propyne Chemical Properties

Chemical Name: Propyne
IUPAC NAME: Prop-1-yne
CAS No.: 74-99-7
EINECS: 200-828-4
RTECS: UK4250000
Molecular Formula: C3H4
Molecular Weight: 40.06 g/mol
Melting Point: −102.7 °C(lit.)
Density: 0.648 g/cm3
Following is the structure of MEthyl acetylene (74-99-7):


Product Categories about MEthyl acetylene (74-99-7) are Allyl Monomers ; Monomers ; Polymer Science ; Chemical Synthesis ; Compressed and Liquefied Gases ; Synthetic Reagents
The chemical synonymous of MEthyl acetylene (74-99-7) are Methylacetylene ; 1-Propyne ; Allylene ; Propyne ; Acetylene, methyl- ; Ch3cequivch ; Methyl-acetylen ; Propine

Propyne Toxicity Data With Reference

1.    

mmo-esc 10 pph

     MUREAV    Mutation Research. 307 (1994),335.
2.    

mmo-esc 25 pph

     MUREAV    Mutation Research. 307 (1994),335.
3.    

ihl-rat LC:>42,000 ppm/6H

     AMIHAB    AMA Archives of Industrial Health. 15 (1957),20.

Propyne Consensus Reports

Reported in EPA TSCA Inventory.

Propyne Safety Profile

This compound is a simple anesthetic and in high concentration is an asphyxiant. Mutation data reported. Dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. Localized heating of liquid-containing cylinders to 95°C may cause an explosion. Product of reaction with silver nitrate ignites at 150°C. A commercial mixture containing 30% propyne in MAPP gas is similar to ethylene in potential hazards and handling requirements. To fight fire, stop flow of gas. When heated to decomposition it emits acrid smoke and irritating fumes. See also ACETYLENE COMPOUNDS and ALKYNES.
Hazard Codes:
Xi: Irritant
F: Flammable
Risk Statements about MEthyl acetylene (74-99-7):
R11 Highly flammable.
R37 Irritating to respiratory system.
Safety Statements about MEthyl acetylene (74-99-7):
S16 Keep away from sources of ignition.
S36 Wear suitable protective clothing.
S38 In case of insufficient ventilation, wear suitable respiratory equipment. 
 

Propyne Standards and Recommendations

OSHA PEL: TWA 1000 ppm
ACGIH TLV: TWA 1000 ppm
DFG MAK: 1000 ppm (1700 mg/m3)

Propyne Specification

 MEthyl acetylene (74-99-7) is a convenient three-carbon building block for organic synthesis. Deprotonation with n-butyllithium gives propynyllithium. This nucleophilic reagent adds to carbonyl groups, producing alcohols and esters.Whereas purified propyne is expensive, MAPP gas can be used to cheaply generate large amounts of the reagent.It exists in equilibrium with allene, the mixture of methylacetylene and propadiene being called MAPD.Research by European space concerns into using light hydrocarbons with liquid oxygen as a relatively high performing propellant combination which would also be less toxic than the commonly used MMH/NTO (monomethylhydrazine/nitrogen tetroxide) systems, showed that propyne would be highly advantageous as a rocket fuel for craft intended for low Earth orbital operations. This conclusion was reached based upon a specific impulse expected to reach 370 s if oxygen is used as oxidizer, a high density, and energy/volume ratio, and the moderate boiling point, which causes the chemical to present fewer problems in storage than for example a fuel that needs to be kept at extremely low temperatures.

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