Product Name

  • Name

    3-Chloro-1-propyne

  • EINECS 210-856-9
  • CAS No. 624-65-7
  • Article Data34
  • CAS DataBase
  • Density 1.017 g/cm3
  • Solubility
  • Melting Point <-50 °C
  • Formula C3H3Cl
  • Boiling Point 57 °C at 760 mmHg
  • Molecular Weight 74.5098
  • Flash Point 18.9 °C
  • Transport Information UN 3286 3/PG 2
  • Appearance colorless flammable liquid
  • Safety 16-26-36/37/39-45-27
  • Risk Codes 11-23/24/25-34
  • Molecular Structure Molecular Structure of 624-65-7 (3-Chloro-1-propyne)
  • Hazard Symbols FlammableF, ToxicT, CorrosiveC
  • Synonyms Propyne,3-chloro- (6CI,8CI);1-Chloroprop-2-yne;2-Propynyl chloride;3-Chloro-1-propyne;NSC 66411;Propargyl chloride;
  • PSA 0.00000
  • LogP 0.85840

Synthetic route

1,1-dimethylprop-3-ynylamine
2978-58-7

1,1-dimethylprop-3-ynylamine

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
With 3,5-dichlorobenzoyl chloride; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; Time; Reagent/catalyst;97.98%
propargyl alcohol
107-19-7

propargyl alcohol

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
With thionyl chloride; tetramethylurea In toluene at 40℃; for 3.16h;94%
With benzoyl chloride; N,N-dimethyl-formamide at 0 - 20℃; for 14.25h;75%
With pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran Heating;63%
N,N-Dichlorobenzenesulfonamide
473-29-0

N,N-Dichlorobenzenesulfonamide

propargyl alcohol
107-19-7

propargyl alcohol

A

benzenesulfonamide
98-10-2

benzenesulfonamide

B

N-chlorobenzenesulfonamide
80-16-0

N-chlorobenzenesulfonamide

C

2-propynyl chloride
624-65-7

2-propynyl chloride

D

3-hydroxy-2,2-dichloro-1,1-di(N-benzenesulfonamide)propane

3-hydroxy-2,2-dichloro-1,1-di(N-benzenesulfonamide)propane

Conditions
ConditionsYield
In tetrachloromethane at 30 - 35℃; for 6h; Irradiation;A 32%
B 4%
C 7 % Chromat.
D 16%
...Expand
phosgene
75-44-5

phosgene

propargyl alcohol
107-19-7

propargyl alcohol

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
at 0℃; Erhitzen des erhaltenen Chlorameisensaeure-prop-2-inylesters mit Triaethylamin-hydrochlorid auf 100grad;
3-bromo-2-chloroprop-1-ene
4860-96-2

3-bromo-2-chloroprop-1-ene

A

bromoallene
10024-18-7

bromoallene

B

chloroallene
3223-70-9

chloroallene

C

2-propynyl chloride
624-65-7

2-propynyl chloride

D

propargyl bromide
106-96-7

propargyl bromide

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol Yield given;
...Expand
2-bromo-3-chloro-propene
16400-63-8

2-bromo-3-chloro-propene

A

bromoallene
10024-18-7

bromoallene

B

chloroallene
3223-70-9

chloroallene

C

2-propynyl chloride
624-65-7

2-propynyl chloride

D

propargyl bromide
106-96-7

propargyl bromide

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol Yield given;
...Expand
propargyl alcohol
107-19-7

propargyl alcohol

A

N,N,2-trimethylpropionamide
21678-37-5

N,N,2-trimethylpropionamide

B

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1). 0 deg C; 2.) rt., 3h;A n/a
B 99 % Spectr.
propargyl bromide
106-96-7

propargyl bromide

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
With pyridine; tributyltin chloride at 50℃; Thermodynamic data; Equilibrium constant; Δ G;
propargyl iodide
659-86-9

propargyl iodide

A

chloroallene
3223-70-9

chloroallene

B

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
With pyridine; tributyltin chloride at 50℃; Thermodynamic data; Equilibrium constant; Δ G;
chloroallene
3223-70-9

chloroallene

2-propynyl chloride
624-65-7

2-propynyl chloride

Conditions
ConditionsYield
at 661.85℃; under 125 Torr; Equilibrium constant; var. temp. and pressures;
propargyl alcohol
107-19-7

propargyl alcohol

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

2-propynyl chloride
624-65-7

2-propynyl chloride

2-propynyl chloride
624-65-7

2-propynyl chloride

ethyl 4-(benzyloxy)-7-bromo-1H-indole-2-carboxylate
290333-14-1

ethyl 4-(benzyloxy)-7-bromo-1H-indole-2-carboxylate

ethyl 4-(benzyloxy)-7-bromo-1-prop-2-ynyl-1H-indole-2-carboxylate
922507-01-5

ethyl 4-(benzyloxy)-7-bromo-1-prop-2-ynyl-1H-indole-2-carboxylate

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 50℃; for 24h;100%
cyclopropyl phenyl ketone
3481-02-5

cyclopropyl phenyl ketone

2-propynyl chloride
624-65-7

2-propynyl chloride

1-cyclopropyl-1-phenyl-3-butyn-1-ol
91909-17-0

1-cyclopropyl-1-phenyl-3-butyn-1-ol

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran for 6h; Barbier type propargylation; Inert atmosphere;100%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

2-propynyl chloride
624-65-7

2-propynyl chloride

1-methyl-3-(2-propyn-1-yl)-imidazolium chloride
98379-44-3

1-methyl-3-(2-propyn-1-yl)-imidazolium chloride

Conditions
ConditionsYield
In toluene Reflux;99%
In benzene for 5h; Heating;
p-cresol
106-44-5

p-cresol

2-propynyl chloride
624-65-7

2-propynyl chloride

A

dipropargyl ether
6921-27-3

dipropargyl ether

B

1-methyl-4-(2-propynyloxy)benzene
5651-90-1

1-methyl-4-(2-propynyloxy)benzene

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodideA n/a
B 99%
...Expand
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

2-propynyl chloride
624-65-7

2-propynyl chloride

C11H11ClO
1340170-80-0

C11H11ClO

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 7h; Barbier Coupling Reaction; Inert atmosphere; chemoselective reaction;99%
caprinaldehyde
112-31-2

caprinaldehyde

Decan-2-one
693-54-9

Decan-2-one

2-propynyl chloride
624-65-7

2-propynyl chloride

tridec-1-yn-4-ol
74646-37-0

tridec-1-yn-4-ol

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 7h; Barbier Coupling Reaction; Inert atmosphere; chemoselective reaction;99%
...Expand
2-propynyl chloride
624-65-7

2-propynyl chloride

triethylamine
121-44-8

triethylamine

C9H18N(1+)*Cl(1-)

C9H18N(1+)*Cl(1-)

Conditions
ConditionsYield
In toluene Reflux;99%
2-propynyl chloride
624-65-7

2-propynyl chloride

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

Conditions
ConditionsYield
With piperazine; hydrogen In ethanol at 80℃; under 4500.45 Torr; for 24h;99%
With piperazine; hydrogen In ethanol at 100℃; under 4500.45 Torr; for 15h; Green chemistry;
With hydrogen In ethanol at 100℃; under 4500.45 Torr; for 24h; chemoselective reaction;87 %Chromat.
dimethyl iminodiacetate hydrochloride
39987-25-2, 62491-02-5

dimethyl iminodiacetate hydrochloride

2-propynyl chloride
624-65-7

2-propynyl chloride

N,N-bis(methoxycarbonylmethyl)propargylamine

N,N-bis(methoxycarbonylmethyl)propargylamine

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;99%
4-(4-chlorophenyl)-4-hydroxypiperidine
39512-49-7

4-(4-chlorophenyl)-4-hydroxypiperidine

2-propynyl chloride
624-65-7

2-propynyl chloride

N-propargyl-4-(4'-chlorophenyl)-4-piperidinol
43141-21-5

N-propargyl-4-(4'-chlorophenyl)-4-piperidinol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;98%
3-vinyloxy-propan-1-ol
6118-22-5

3-vinyloxy-propan-1-ol

2-propynyl chloride
624-65-7

2-propynyl chloride

3-(3-vinyloxy-propoxy)-propyne
6188-75-6

3-(3-vinyloxy-propoxy)-propyne

Conditions
ConditionsYield
With sodium hydroxide; tributyl-amine In water at 50 - 60℃; for 3h;98%
trans-benzoic acid 4-oxo-but-2-enyl ester
118017-13-3

trans-benzoic acid 4-oxo-but-2-enyl ester

2-propynyl chloride
624-65-7

2-propynyl chloride

rac-1-benzoyloxy-7-chlorohept-2(E)-en-5-yn-4-ol
213545-10-9

rac-1-benzoyloxy-7-chlorohept-2(E)-en-5-yn-4-ol

Conditions
ConditionsYield
Stage #1: 2-propynyl chloride With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667h; Metallation;
Stage #2: trans-benzoic acid 4-oxo-but-2-enyl ester In diethyl ether at -78℃; for 0.5h; Condensation;		98%
2-propynyl chloride
624-65-7

2-propynyl chloride

4-methoxy-phenol
150-76-5

4-methoxy-phenol

1-methoxy-4-(2-propynyloxy)benzene
17061-86-8

1-methoxy-4-(2-propynyloxy)benzene

Conditions
ConditionsYield
Stage #1: 4-methoxy-phenol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
Stage #2: 2-propynyl chloride In N,N-dimethyl-formamide at 0 - 20℃;		98%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;93%
trans-PdEt2(PMe2Ph)2
75108-70-2

trans-PdEt2(PMe2Ph)2

2-propynyl chloride
624-65-7

2-propynyl chloride

trans-[ClPd(η1-allenyl)(PMe2Ph)2]
1428586-22-4

trans-[ClPd(η1-allenyl)(PMe2Ph)2]

Conditions
ConditionsYield
Stage #1: trans-PdEt2(PMe2Ph)2 With styrene In tetrahydrofuran at 55℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: 2-propynyl chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique;		98%
2-propynyl chloride
624-65-7

2-propynyl chloride

(Z,Z)-bis(2,3-dichloroprop-1-en-1-yl)tellurium dichloride

(Z,Z)-bis(2,3-dichloroprop-1-en-1-yl)tellurium dichloride

Conditions
ConditionsYield
With tellurium tetrachloride In benzene at 80℃; for 4h; stereospecific reaction;98%
[Pd(η2-dmfu)(Ph2PC9H5(Me)N)
1038998-45-6

[Pd(η2-dmfu)(Ph2PC9H5(Me)N)

2-propynyl chloride
624-65-7

2-propynyl chloride

C25H21ClNPPd

C25H21ClNPPd

Conditions
ConditionsYield
In dichloromethane for 0.333333h; Kinetics; Inert atmosphere; regioselective reaction;98%
(S)-N-(2-formyl-benzyl-4-chlorophenyl)-1-benzyl-pyrrolidine-2-carboxamide-glycine nickel complex

(S)-N-(2-formyl-benzyl-4-chlorophenyl)-1-benzyl-pyrrolidine-2-carboxamide-glycine nickel complex

2-propynyl chloride
624-65-7

2-propynyl chloride

(S)-2-((E)-((2-((S)-1-benzylpyrrolidine-2-carboxamido)-5-chlorophenyl) (phenyl)methylene)amino)pent-4-ynoic acid nickel complex

(S)-2-((E)-((2-((S)-1-benzylpyrrolidine-2-carboxamido)-5-chlorophenyl) (phenyl)methylene)amino)pent-4-ynoic acid nickel complex

Conditions
ConditionsYield
Stage #1: (S)-N-(2-formyl-benzyl-4-chlorophenyl)-1-benzyl-pyrrolidine-2-carboxamide-glycine nickel complex With sodium hydroxide In water; N,N-dimethyl-formamide at -10℃; for 0.5h;
Stage #2: 2-propynyl chloride In water; N,N-dimethyl-formamide Solvent; Temperature; enantioselective reaction;		97.8%
With sodium hydroxide In water; N,N-dimethyl-formamide at -10℃; for 1.5h; Solvent;93.87 %Chromat.
2-propynyl chloride
624-65-7

2-propynyl chloride

2-Fluoro-2-phenyl-2-phenylthioacetonitrile
210217-98-4

2-Fluoro-2-phenyl-2-phenylthioacetonitrile

2-Fluoro-2-phenyl-pent-4-ynenitrile

2-Fluoro-2-phenyl-pent-4-ynenitrile

Conditions
ConditionsYield
With Triethylgermyl-natrium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1.) -60 deg C, 0.25 h, 2.) -80 deg C, 0.5 h;97%
5-(hydroxymethyl)benzene-1,3-diol
29654-55-5

5-(hydroxymethyl)benzene-1,3-diol

2-propynyl chloride
624-65-7

2-propynyl chloride

3,5-dipropargyloxybenzyl alcohol
176038-84-9

3,5-dipropargyloxybenzyl alcohol

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone Heating / reflux;97%
With Ki; potassium carbonate In acetone97%
With potassium carbonate; potassium iodide In acetone Heating / reflux;97%
With potassium carbonate; potassium iodide In acetone Heating;88%
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one
79-77-6

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

2-propynyl chloride
624-65-7

2-propynyl chloride

(E)-3-Methyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-1-en-5-yn-3-ol
14168-34-4

(E)-3-Methyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-1-en-5-yn-3-ol

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran for 6h; Barbier type propargylation; Inert atmosphere;97%
2-propynyl chloride
624-65-7

2-propynyl chloride

N-acetyl-5-methoxy-2,4,6-tribromotryptamine
300662-21-9

N-acetyl-5-methoxy-2,4,6-tribromotryptamine

N-acetyl-5-methoxy-1-propargyl-2,4,6-tribromotryptamine

N-acetyl-5-methoxy-1-propargyl-2,4,6-tribromotryptamine

Conditions
ConditionsYield
Stage #1: N-acetyl-5-methoxy-2,4,6-tribromotryptamine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: 2-propynyl chloride In N,N-dimethyl-formamide at 20℃; for 4h;		97%
tris-(trimethylsilyl)silane
1873-77-4

tris-(trimethylsilyl)silane

2-propynyl chloride
624-65-7

2-propynyl chloride

A

(Me3SiO)2Si(H)SiMe3

(Me3SiO)2Si(H)SiMe3

B

2-((Z)-3-chloroprop-1-enyl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane

2-((Z)-3-chloroprop-1-enyl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane

Conditions
ConditionsYield
With oxygen; 2-hydroxyethanethiol In water at 20℃; for 24h; optical yield given as %de; stereoselective reaction;A 5 %Chromat.
B 97%
...Expand
trans-diethylbis(Et3phosphine)palladium(II)
60885-31-6

trans-diethylbis(Et3phosphine)palladium(II)

2-propynyl chloride
624-65-7

2-propynyl chloride

trans-[ClPd(η1-allenyl)(PEt3)2]
1428586-21-3

trans-[ClPd(η1-allenyl)(PEt3)2]

Conditions
ConditionsYield
Stage #1: trans-diethylbis(Et3phosphine)palladium(II) With styrene In tetrahydrofuran at 55℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: 2-propynyl chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique;		97%
p-9-(2-methylisoxazolidin-5-yl)non-1-yloxycinnamaldehyde

p-9-(2-methylisoxazolidin-5-yl)non-1-yloxycinnamaldehyde

2-propynyl chloride
624-65-7

2-propynyl chloride

p-9-[2-methyl-2-(2-popyn-1-yl) isoxazolidinium-5-yl]non-1-yloxycinnamaldehyde chloride

p-9-[2-methyl-2-(2-popyn-1-yl) isoxazolidinium-5-yl]non-1-yloxycinnamaldehyde chloride

Conditions
ConditionsYield
In acetone at 20℃; for 24h;97%
pyrrolidine
123-75-1

pyrrolidine

2-propynyl chloride
624-65-7

2-propynyl chloride

1-(prop-2-yn-1-yl)pyrrolidine
7223-42-9

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

Conditions
ConditionsYield
In acetonitrile at 60℃; for 48.5h;97%
With sodium hydrogencarbonate In ethanol at 25℃; for 3h;
5,7-dihydroxy-2H-chromen-2-one
2732-18-5

5,7-dihydroxy-2H-chromen-2-one

2-propynyl chloride
624-65-7

2-propynyl chloride

5,7-bis(prop-2-yn-1-yloxy)-2H-chromene-2-one

5,7-bis(prop-2-yn-1-yloxy)-2H-chromene-2-one

Conditions
ConditionsYield
With caesium carbonate In acetone at 110℃; for 2h; Microwave irradiation;97%
benzyl 4-oxo-1-piperidinecarboxylate
19099-93-5

benzyl 4-oxo-1-piperidinecarboxylate

2-propynyl chloride
624-65-7

2-propynyl chloride

benzyl 4-(3-chloroprop-1-ynyl)-4-hydroxypiperidine-1-carboxylate

benzyl 4-(3-chloroprop-1-ynyl)-4-hydroxypiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2-propynyl chloride With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: benzyl 4-oxo-1-piperidinecarboxylate In tetrahydrofuran; hexane at -78℃; for 6h; Inert atmosphere;		97%
2-hydroxyethyl vinyl ether
764-48-7

2-hydroxyethyl vinyl ether

2-propynyl chloride
624-65-7

2-propynyl chloride

ethylene glycol vinyl propargyl diether
14846-79-8

ethylene glycol vinyl propargyl diether

Conditions
ConditionsYield
With sodium hydroxide; tributyl-amine In water at 50 - 60℃; for 3h; Product distribution; other catalyst;96.8%
With sodium hydroxide; tributyl-amine In water at 50 - 60℃; for 3h;96.8%
ethylene glycol
107-21-1

ethylene glycol

2-propynyl chloride
624-65-7

2-propynyl chloride

α,ω-bis(O-propargyl)ethylene glycol
40842-04-4

α,ω-bis(O-propargyl)ethylene glycol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 29 - 32℃; for 2h;96%

3-Chloropropyne Chemical Properties

IUPAC Name: 3-Chloroprop-1-yne
Molecular Formula: C3H3Cl
Molecular Weight: 74.508920 g/mol
Appearance: Colorless flammable liquid
Melting Point: <-50°C
Boiling Point: 58 °C(lit.)
Flash Point: 7 °F
Insolubility: Water, glycerol
Density: 1.03 g/mL at 25 °C(lit.)
Structure of 3-Chloropropyne (CAS NO.624-65-7):
                      
Categories of 3-Chloropropyne (CAS NO.624-65-7): Aliphatics;Halides;Acetylenes;Functionalized Acetylenes

3-Chloropropyne Uses

 3-Chloropropyne (CAS NO.624-65-7) is  engineering plastics modifier. It is used as intermediate in organic synthesis, and is used in the manufacture of Excellent drop-ning and soil fumigant.

3-Chloropropyne Safety Profile

Hazard Codes: F  ,T  ,C 
Risk Statements: 11-23/24/25-34
11:Highly Flammable
23/24/25:Toxic by inhalation, in contact with skin and if swallowed   
34:Causes burns 
Safety Statements: 16-26-36/37/39-45-27
16:Keep away from sources of ignition-Nosmoking
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection 
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
27:Take off immediately all contaminated clothing     
A pressure-sensitive explosive. Reacts explosively with ammonia in a closed container. When heated to decomposition it emits toxic fumes of Cl−. See also ACETYLENE COMPOUNDS and ALKYNES; CHLORINATED HYDROCARBONS, ALIPHATIC; and EXPLOSIVES, HIGH; EXPLOSIVES, LOW; EXPLOSIVES, PERMITTED.

3-Chloropropyne Specification

 3-Chloropropyne , its cas register number is 624-65-7. It also can be called 3-Chloro-1-propyne ; and Propargyl chloride .

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