Product Name

  • Name

    Cyclopropyl acetylene

  • EINECS 425-430-1
  • CAS No. 6746-94-7
  • Article Data46
  • CAS DataBase
  • Density 0.85 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point 294 °C (decomp)
  • Formula C5H6
  • Boiling Point 31.4 °C at 760 mmHg
  • Molecular Weight 66.1026
  • Flash Point -5 °C
  • Transport Information UN 1294 3/PG 2
  • Appearance clear colorless to light yellow liquid
  • Safety 26-36/37-62-37/39-16
  • Risk Codes 11-36/37/38-48/20-63-65-67
  • Molecular Structure Molecular Structure of 6746-94-7 (Cyclopropyl acetylene)
  • Hazard Symbols FlammableF, HarmfulXn, IrritantXi
  • Synonyms Acetylene,cyclopropyl-;Cyclopropylethyne;Ethyne, cyclopropyl-;Ethynylcyclopropane;
  • PSA 0.00000
  • LogP 1.02960

Synthetic route

1-chloro-1-cyclopropylethene
24154-06-1

1-chloro-1-cyclopropylethene

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With potassium hydroxide In decane; water at 90℃; for 4h;96%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

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

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

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

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

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 94%
...Expand
1-chloro-4-pentyne
14267-92-6

1-chloro-4-pentyne

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
90%
With n-butyllithium; ammonium chloride In cyclohexane at 0 - 80℃;65%
With n-butyllithium In cyclohexane at 0 - 78℃; Inert atmosphere;58%
With n-butyllithium In cyclohexane other reagent: n-hexyllithium;
With n-butyllithium In cyclohexane at -20 - 78℃; for 4h; Inert atmosphere;
4-methylpentyne
7154-75-8

4-methylpentyne

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

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

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

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

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 120℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 90%
...Expand
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

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

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

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

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

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 90%
...Expand
α,α-dichloroethylcyclopropane
40459-85-6

α,α-dichloroethylcyclopropane

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With sodium hydroxide In 2-ethoxy-ethanol at 60℃;89%
With potassium tert-butylate In dimethyl sulfoxide
With ammonia; sodium amide
With potassium tert-butylate In toluene at 40℃; for 4h; Dehydrochlorination;
1,1-dichloro-2-cyclopropylethylene
58822-70-1

1,1-dichloro-2-cyclopropylethylene

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Dehalogenation;89%
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h;89%
diazomethane
186581-53-3, 908094-01-9

diazomethane

chloroprene
126-99-8

chloroprene

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
Stage #1: chloroprene With 5,10,15,20-tetraphenyl porphyrin iron In acetone at 0℃; for 0.5h; Inert atmosphere;
Stage #2: diazomethane In acetone Reagent/catalyst; Solvent; Temperature;		87.1%
N-benzyl 3-cyclopropyl-prop-2-ynylamine

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

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

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

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

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

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

6,6-dimethyl-1-phenyl-2-aza-6-sila-4-heptyne
101911-12-0

6,6-dimethyl-1-phenyl-2-aza-6-sila-4-heptyne

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

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

hex-1-yne
693-02-7

hex-1-yne

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

N-benzylhept-2-yn-1-amine

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

(2-bromovinyl)cyclopropane

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With potassium hydroxide In iso-butanol85%
With potassium hydroxide In tert-Amyl alcohol75%
diazomethane
186581-53-3, 908094-01-9

diazomethane

1-trimethylsilanylvinylacetylene

1-trimethylsilanylvinylacetylene

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
Stage #1: 2-(trimethylsilyl)-1-buten-3-yne With tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl methyl ether at -10℃; for 0.5h; Inert atmosphere;
Stage #2: diazomethane In tert-butyl methyl ether Reagent/catalyst; Solvent; Temperature;		83.9%
cyclopropanone
5009-27-8

cyclopropanone

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With 1,4-benzenedicarboxylic acid dimethyl ester; phosphorus pentachloride; potassium hydroxide In methanol at 0℃; for 5h;74%
spiropentyl bromide
75522-03-1

spiropentyl bromide

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

spiropentene
661-39-2

spiropentene

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 90℃; under 80 Torr; Title compound not separated from byproducts;A 4%
B 70%
N-benzyl 3-cyclopropyl-prop-2-ynylamine

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

phenylacetylene
536-74-3

phenylacetylene

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

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

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 60%
...Expand
4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

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

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

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

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

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

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 57%
...Expand
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With potassium hydroxide; phosphorus pentachloride In quinoline; dodecane; dimethyl sulfoxide; toluene55.6%
With phosphorus pentachloride In quinoline; n-heptane
With phosphorus pentachloride In quinoline; chlorobenzene
Multi-step reaction with 3 steps
1: 2 h / 20 °C
2: aluminum oxide
3: n-butyllithium / 5 h / 110 °C
View Scheme
Stage #1: Cyclopropyl methyl ketone With triphenyl phosphite; bromine; triethylamine In dichloromethane at -10℃; for 2h; Reflux; Green chemistry;
Stage #2: With potassium hydroxide In dimethyl sulfoxide at 40 - 110℃; for 2h; Reagent/catalyst; Solvent; Green chemistry;		102.2 g
(1-methoxyethenyl)cyclopropane
66031-87-6

(1-methoxyethenyl)cyclopropane

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With n-butyllithium at 110℃; for 5h;39%
With n-butyllithium at 100℃; for 5h;
1',2'-Dibromethylcyclopropan
58673-27-1

1',2'-Dibromethylcyclopropan

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With 2-ethoxy-ethanol; potassium hydroxide
1-chloro-1-cyclopropylethene
24154-06-1

1-chloro-1-cyclopropylethene

A

Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

B

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With silver perchlorate In acetic acid
α,α-dichloroethylcyclopropane
40459-85-6

α,α-dichloroethylcyclopropane

A

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

B

1-chloro-1-cyclopropylethene
24154-06-1

1-chloro-1-cyclopropylethene

C

2-methyl-1-buten-3-yne
78-80-8

2-methyl-1-buten-3-yne

Conditions
ConditionsYield
With potassium hydroxide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol
...Expand
(1-iodovinyl)cyclopropane
24154-05-0

(1-iodovinyl)cyclopropane

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With triethylamine at 150℃;
1,1-dibromo-2-cyclopropylehylene
122244-78-4

1,1-dibromo-2-cyclopropylehylene

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran for 0.5h; Heating;
α,α-dichloroethylcyclopropane
40459-85-6

α,α-dichloroethylcyclopropane

A

pent-1-en-3-yne
646-05-9

pent-1-en-3-yne

B

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With potassium tert-butylate In toluene; tert-butyl alcohol at 40℃; Dehydrochlorination;
α-(dichloromethyl)cyclopropanemethanol 4-methylbenzenesulfonate

α-(dichloromethyl)cyclopropanemethanol 4-methylbenzenesulfonate

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Elimination;94 % Chromat.
With methyllithium
α-(dibromomethyl)cyclopropanemethanol 4-methylbenzenesulfonate

α-(dibromomethyl)cyclopropanemethanol 4-methylbenzenesulfonate

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With sodium amide In dimethyl sulfoxide at 15 - 20℃; for 1h; Elimination;67 % Chromat.
α-(trichloromethyl)cyclopropanemethanol methanesulfonate

α-(trichloromethyl)cyclopropanemethanol methanesulfonate

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether at -10 - 0℃; for 1h; Elimination;95 % Chromat.

Cyclopropyl acetylene Chemical Properties

Molecular Structure of Cyclopropyl acetylene (CAS NO.6746-94-7):

IUPAC Name: Ethynylcyclopropane 
Molecular Formula: C5H6 
Molecular Weight: 66.10
Index of Refraction: 1.455
Molar Refractivity: 20.92 cm3
Molar Volume: 77 cm3
Surface Tension: 28.4 dyne/cm
Density: 0.85 g/cm3
Flash Point: -5 °C
Enthalpy of Vaporization: 26.54 kJ/mol
Boiling Point: 31.4 °C at 760 mmHg
Vapour Pressure: 605 mmHg at 25 °C
Storage temp.: Flammables area
Appearance: clear colorless to light yellow liquid
Canonical SMILES: C#CC1CC1
InChI: InChI=1S/C5H6/c1-2-5-3-4-5/h1,5H,3-4H2
InChIKey: NPTDXPDGUHAFKC-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; pharmacetical; API intermediates; Acetylenes; Cyclopropanes; Functionalized Acetylenes; Simple 3-Membered Ring Compounds

Cyclopropyl acetylene Uses

 Cyclopropyl acetylene (CAS NO.6746-94-7) is used as an intermediate for medicine and pesticide.

Cyclopropyl acetylene Safety Profile

Safety Information of Cyclopropyl acetylene (CAS NO.6746-94-7):
Hazard Codes: FlammableF,HarmfulXn,IrritantXi
Risk Statements: 11-36/37/38-48/20-63-65-67
11: Highly Flammable
36/37/38: Irritating to eyes, respiratory system and skin 
48/20: Harmful:  danger of serious damage to health by prolonged exposure through inhalation 
63: Possible risk of harm to the unborn child  
65: Harmful:  May cause lung damage if swallowed 
67: Vapors may cause drowsiness and dizziness 
Safety Statements: 26-36/37-62-37/39-16
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37: Wear suitable protective clothing and gloves
62: If swallowed, do not induce vomiting:  seek medical advice immediately and show this container or label
37/39: Wear suitable gloves and eye/face protection      
16: Keep away from sources of ignition - No smoking
RIDADR: UN 1294 3/PG 2
WGK Germany: 2
HazardClass: IRRITANT, FLAMMABLE

Cyclopropyl acetylene Specification

 Cyclopropyl acetylene (CAS NO.6746-94-7), its Synonyms are Acetylene,cyclopropyl- ; Cyclopropylacetylene ; Cyclopropylethyne ; Ethyne, cyclopropyl- ; Ethynylcyclopropane ; Cyclopropane,ethynyl- .

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