14267-92-6

Basic information

• Product Name: 5-Chloro-1-pentyne
• Synonyms: 4-PENTYNYL CHLORIDE;5-CHLORO-1-PENTYNE;1-Chloro-4-pentyne;1-Pentyne,5-chloro-;5-chloro-1-pentyn;5-chloro-pent-1-yne;5-chloropent-1-yne;5-Chloropentyne
• CAS NO: 14267-92-6
• Molecular Formula: C₅H₇Cl
• Molecular Weight: 102.56
• EINECS: 238-159-5
• Product Categories: Miscellaneous;Acetylenes;Functionalized Acetylenes;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 14267-92-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: -61°C (estimate)
• Boiling Point: 67-69 °C145 mm Hg(lit.)
• Flash Point: 60 °F
• Appearance: Clear colorless to light brown/Liquid
• Density: 0.968 g/mL at 25 °C(lit.)
• Vapor Pressure: 20.4mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: −20°C
• Water Solubility: Not miscible in water.
• BRN: 1736710
• CAS DataBase Reference: 5-Chloro-1-pentyne(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-1-pentyne(14267-92-6)
• EPA Substance Registry System: 5-Chloro-1-pentyne(14267-92-6)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-38-36/37/38
• Safety Statements: 23-24/25-16
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 14267-92-6(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO LIGHT BROWN LIQUID

Uses

Different sources of media describe the Uses of 14267-92-6 differently. You can refer to the following data:
1. 5-Chloro-1-pentyne is used with α-diazoesters in a copper-catalyzed synthesis of pyrazoles. It is also used in the synthesis of 5-chloro-2-trimethylstannyl-1-pentene by reacting with Me3SnCu.Me2S.
2. 5-Chloro-1-pentyne was used in the synthesis of 5-chloro-2-trimethylstannyl-1-pentene by reacting with Me3SnCu.Me2S. It was also used with α-diazoesters in a copper-catalyzed synthesis of pyrazoles.

InChI:InChI=1/C5H7Cl/c1-2-3-4-5-6/h1H,3-5H2

Synthetic route

pent-1-yn-5-ol (5390-04-5) → 1-chloro-4-pentyne (14267-92-6)

Conditions	Yield
With methanesulfonyl chloride; triethylamine at 15 - 20℃; for 2.5h; Temperature;	98.4%
With oxalyl dichloride; Tropone In chloroform at 75℃; for 0.5h; Inert atmosphere; Sealed tube;	84%
With pyridine; thionyl chloride
Stage #1: pent-1-yn-5-ol With N,N-dimethylthiourea In dichloromethane at 20℃; Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 1h; Irradiation;	72 %Chromat.

sodium acetylide (1066-26-8) + 1,3-chlorobromopropane (109-70-6) → 1-chloro-4-pentyne (14267-92-6)

Conditions	Yield
With ammonia at -40℃; for 3h;	78%
In ammonia at -35℃; for 4h;	34%
With ammonia at -35℃; for 4h;	34%
With ammonia
In ammonia

1,3-chlorobromopropane (109-70-6) + acetylene (74-86-2) → 1-chloro-4-pentyne (14267-92-6)

Conditions	Yield
(i) LiNH2, liq. NH3, (ii) /BRN= 605278/; Multistep reaction;
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -65℃;

ammonia (7664-41-7) + sodium acetylide (1066-26-8) + 1,3-chlorobromopropane (109-70-6) → 1-chloro-4-pentyne (14267-92-6)

Conditions	Yield
under 760 Torr;

1,3-chlorobromopropane (109-70-6) + calcium carbide → 1-chloro-4-pentyne (14267-92-6)

Conditions	Yield
With sodium hydroxide; diethylene glycol dibutyl ether

pent-1-yn-5-ol (5390-04-5) → 1-chloro-4-pentyne (14267-92-6) + C10H14O

Conditions	Yield
With hydrogenchloride In water at 120℃; under 5171.62 Torr; for 0.25h; Flow reactor;	A 12 %Spectr. B n/a

1-iodo-3-chloro-propane (6940-76-7) + trimethylsilylacetylene (1066-54-2) → 1-chloro-4-pentyne (14267-92-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;

1-chloro-4-pentyne (14267-92-6) → 5-iodopent-1-yne (2468-55-5)

Conditions	Yield
With sodium iodide In acetone Finkelstein Reaction; Reflux;	100%
With sodium iodide In acetone for 72h; Inert atmosphere; Reflux;	99%
With sodium iodide In acetone for 3h; Reflux;	99%

Indole-3-carboxaldehyde (487-89-8) + 1-chloro-4-pentyne (14267-92-6) → 1-(4-pentenyl)-1H-indole-3-carboxaldehyde (110206-34-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 75℃; for 5h; Alkylation;	100%
With sodium hydride 1.) DMF, 70 deg C, 30 min, 2.) DMF, RT, 1 h; Yield given. Multistep reaction;
With sodium hydride 1.) DMF, RT, 10 min, 2.) DMF, from 70 to 80 deg C, 2 h; Multistep reaction;
Stage #1: 1-chloro-4-pentyne With sodium iodide In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil for 48h; Inert atmosphere;

phthalimide (136918-14-4) + 1-chloro-4-pentyne (14267-92-6) → N-(pent-4-ynyl)phthalimide (6097-07-0)

Conditions	Yield
In N,N-dimethyl-formamide Gabriel Amine Synthesis;	100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 16h;	96%
With potassium carbonate; 18-crown-6 ether In benzene for 40h; Heating;	92%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 16h; Inert atmosphere;	87%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 16h; Inert atmosphere;	78%

1-chloro-4-pentyne (14267-92-6) + mercaptoacetic acid (68-11-1) → 2-(pent-4-ynylthio)acetic acid (1010447-29-6)

Conditions	Yield
Stage #1: mercaptoacetic acid With potassium hydroxide In methanol at 0℃; for 0.333333h; Stage #2: 1-chloro-4-pentyne In methanol at 40 - 50℃; for 2h; Inert atmosphere;	100%

1-chloro-4-pentyne (14267-92-6) + phenol (108-95-2) → (pent-4-yn-1-yloxy)benzene (92635-89-7)

Conditions	Yield
With caesium carbonate; potassium iodide In acetonitrile at 85℃;	100%

1-chloro-4-pentyne (14267-92-6) + 4-hydroxy-3-(trifluoromethyl)benzonitrile (124811-71-8) → 3-trifluoromethyl-4-(pent-4-yn-1-yloxy)benzonitrile

Conditions	Yield
With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 65℃; for 24h;	100%

(2S,3R,4S,5S)-(3-azido-4-hydroxy-6,6-dimethyltetrahydro-2H-pyran-2,5-diyl)dimethanol + 1-chloro-4-pentyne (14267-92-6) → (2S,3R,4S,5S)-{3-[4′-(3-chloropropyl)-1′H-1′,2′,3′-triazol-1-yl]-4-hydroxy-6,6-dimethyltetrahydro-2H-pyran-2,5-diyl}dimethanol

Conditions	Yield
With copper nanoparticles on activated carbon; triethylamine In 1,4-dioxane at 60℃; for 20h; Huisgen Cycloaddition; Inert atmosphere;	100%

1-chloro-4-pentyne (14267-92-6) + tert-butyl 4-(2-azidoacryloyl)piperazine-1-carboxylate → tert-butyl 4-(2-(4-(3-chloropropyl)-1H-1,2,3-triazol-1-yl)acryloyl)piperazine-1-carboxylate

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane at 20℃; for 24h;	100%

silicon dioxide hydrate (23382-09-4) + 1-chloro-4-pentyne (14267-92-6) + 3,5-dimethyl-4-hydroxybenzonitrile (4198-90-7) + 3-(3-methylisoxazol-5-yl)propyl chloride (130800-76-9) → 3,5-dimethyl-4-(pent-4-yn-1-yloxy)benzonitrile (134472-29-0)

Conditions	Yield
In ethyl acetate	99.4%
In ethyl acetate	99.4%

1-chloro-4-pentyne (14267-92-6) + 4-cyanophenol (767-00-0) → 4-(pent-4-yn-1-yloxy)benzonitrile (368453-52-5)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 21h;	99%
With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 65℃; for 24h;	70%

1-chloro-4-pentyne (14267-92-6) → 5-chloro-2-iodo-pent-1-ene (450406-22-1)

Conditions	Yield
With diphenyl hydrogen phosphite; diphenyl-phosphinic acid; iodine In chloroform at 20 - 30℃; for 16h; Inert atmosphere; regioselective reaction;	99%
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile at 25℃;	80%
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile at 20℃; for 3h;	60%
With iodine; Diphenylphosphine oxide In chloroform-d1 at 20℃; for 16h; Inert atmosphere; regioselective reaction;	59%
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile at 20℃; for 1h;

1-chloro-4-pentyne (14267-92-6) + 4,4'-diiodobiphenyl (3001-15-8) → 4,4'-bis-(5-chloropent-1-ynyl)biphenyl (568571-16-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 3h;	99%

1-chloro-4-pentyne (14267-92-6) + Phenyl azide (622-37-7) → 4-(3-chloropropyl)-1-phenyl-1H-1,2,3-triazole (1101825-01-7)

Conditions	Yield
With N,N’-bis-{2,6-(di-iso-propyl)phenyl}imidazol-2-ylidene-N,N’-(dicyclohexyl)imidazol-2-ylidenecopper(I) tetrafluoroborate In neat (no solvent) at 20℃; for 24h; Huisgen Cycloaddition;	99%
[(ICy)2Cu]PF6 at 20℃; for 0.416667h; Product distribution / selectivity; Huisgen cycloaddition;	98%
With [(ICy)2Cu]PF6 at 20℃; for 0.416667h; Huisgen cycloaddition; regioselective reaction;	98%
With copper diacetate; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1h;	90%
[(ICy)2Cu]PF6 at 20 - 40℃; for 18 - 43h; Conversion of starting material; Huisgen cycloaddition;

2-pyrrolidinon (616-45-5) + 1-chloro-4-pentyne (14267-92-6) → 1-((E)-5-chloropent-1-enyl)-2-pyrrolidin-2-one (863709-31-3)

Conditions	Yield
With dmap; ruthenium trichloride; tributylphosphine; water; potassium carbonate In toluene at 100℃; for 15h; optical yield given as %de;	99%

1-chloro-4-pentyne (14267-92-6) + N-(4-methylbenzyl)-4-pentyn-1-amine (143427-45-6) → C17H22ClN (1205551-53-6)

Conditions	Yield
With copper(I) bromide In 1,4-dioxane at 100℃; for 0.5h; Microwave irradiation; Inert atmosphere;	99%
With copper(I) bromide In 1,4-dioxane at 100℃; for 0.5h; Microwave irradiation; regioselective reaction;	99%

1-chloro-4-pentyne (14267-92-6) → 1,10-dichlorodeca-4,6-diyne

Conditions	Yield
With CuO-Fe3O4; potassium tert-butylate; oxygen at 60℃; for 48h; Glaser Coupling;	99%
With [2,2]bipyridinyl; oxygen; copper(l) chloride In N,N-dimethyl-formamide at 50℃; for 12h; Glaser Coupling;	99%
With piperidine; copper(l) chloride In toluene at 60℃;	92%

1-chloro-4-pentyne (14267-92-6) + benzyl azide (622-79-7) → 1-benzyl-4-(3-chloropropyl)-1H-[1,2,3]triazole (1228000-47-2)

Conditions	Yield
With triethylamine In water at 22℃; for 8h; Inert atmosphere; Micellar solution; Green chemistry;	99%
With sodium ascorbate In water; tert-butyl alcohol at 50℃; for 1.5h; Huisgen reaction;	96%
With copper diacetate; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1h;	85%

1-chloro-4-pentyne (14267-92-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(5-chloropent-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
With Cu(1+)*CF3O3S(1-)*C22H35N; triethylamine In benzene at 20℃; for 12h;	99%
With C31H43IrN2Si In benzene-d6 at 20℃; for 0.216667h; Glovebox; Inert atmosphere; chemoselective reaction;	99 %Spectr.
With C40H50IrNP2 In benzene-d6 at 60℃; for 2h;	99 %Spectr.
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With C31H41IrN2Si at 20℃; for 0.05h; Inert atmosphere; Glovebox; Stage #2: 1-chloro-4-pentyne In fluorobenzene at 20℃; for 0.1h;
With C37H47F6N3O4S2Zn In tetrahydrofuran at 60℃; for 5h;	73 %Spectr.

ethyl diazoalaninate (6111-99-5) + 1-chloro-4-pentyne (14267-92-6) → ethyl 7-chloro-2-methylhepta-2,3-dienoate

Conditions	Yield
With copper(I) bromide dimethylsulfide complex; C36H44N4O*BrH In dichloromethane at 30℃; for 2.5h; Inert atmosphere; enantioselective reaction;	99%

1-chloro-4-pentyne (14267-92-6) + tetraphenylphosphonium 2-[4-azidobutoxy]nonahydro-closo-decaborate → C9H24B10ClN3O(2-)*2C24H20P(1+)

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h;	99%

cis-1,2-Dichloroethylene (156-59-2) + 1-chloro-4-pentyne (14267-92-6) → (6Z)-1,12-dichloro-dodec-6-en-4,8-diyne

Conditions	Yield
With N-butylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 3h;	98%

chloro-trimethyl-silane (75-77-4) + 1-chloro-4-pentyne (14267-92-6) → (5-chloropent-1-ynyl)trimethylsilane (77113-48-5)

Conditions	Yield
With n-butyllithium 1.) THF, -20 degC, 2.) 15 min, 0 degC;	98%
Stage #1: 1-chloro-4-pentyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran Schlenk technique; Inert atmosphere;	94%
With n-butyllithium In tetrahydrofuran; hexane for 2h; -78 deg C to RT;	92%

Triallylborane (688-61-9, 53588-88-8, 90721-85-0, 151452-33-4, 151452-35-6) + 1-chloro-4-pentyne (14267-92-6) → 3-methoxy-7-(3-chloropropyl)-3-borabicyclo{3.3.1}non-6-ene (119352-32-8) + propene (187737-37-7)

Conditions	Yield
With methanol In methanol Ar atmosphere; heating of borane and pentyne derivatives (140°C, 1.5 h), cooling (-10 - 0°C), addn. of MeOH, refluxing (1 h); distn.; elem. anal.;	A 82% B 98%

Undecane-1-thiol (5332-52-5) + 1-chloro-4-pentyne (14267-92-6) → dodecyl(pent-4-ynyl)sulfane (1010447-20-7)

Conditions	Yield
Stage #1: Undecane-1-thiol With potassium hydroxide In methanol for 0.25h; Inert atmosphere; Stage #2: 1-chloro-4-pentyne In methanol at 50℃; for 2h;	98%

1-chloro-4-pentyne (14267-92-6) + 1-phenylpropane-2-thiol (4475-55-2) → pent-4-ynyl(1-phenylpropan-2-yl)sulfane (1010447-21-8)

Conditions	Yield
Stage #1: 1-phenylpropane-2-thiol With potassium hydroxide In methanol for 0.25h; Inert atmosphere; Stage #2: 1-chloro-4-pentyne In methanol at 50℃; for 2h;	98%

1-chloro-4-pentyne (14267-92-6) → (Z,Z)-1,4,7,10-tetrachloro-4,6-decadiene (1200438-18-1)

Conditions	Yield
With di(rhodium)tetracarbonyl dichloride; tris(2,4,6-trimethylphenyl)phosphine; trifluoroacetyl chloride In chlorobenzene at 130℃; for 3h; stereoselective reaction;	98%

1-chloro-4-pentyne (14267-92-6) + dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) → (E)-(5-chloropent-1-en-1-yl)dimethyl(phenyl)silane

Conditions	Yield
Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 22℃; for 0.5h; Inert atmosphere; Stage #2: 1-chloro-4-pentyne With methanol In tetrahydrofuran at 22℃; for 12h; Inert atmosphere; stereoselective reaction;	98%
Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With tributylphosphine; dimethyl zinc(II) In tetrahydrofuran; n-heptane at 20℃; for 0.5h; Schlenk technique; Stage #2: 1-chloro-4-pentyne In tetrahydrofuran; n-heptane at 75℃; for 18h; Schlenk technique; Sealed tube; Stage #3: With water In tetrahydrofuran; n-heptane Schlenk technique; Sealed tube;	80%

ethyl 4-(1,2,3-thiodiazole)carboxylate (3989-36-4) + 1-chloro-4-pentyne (14267-92-6) → ethyl 5-(3-chloropropyl)thiophene-3-carboxylate

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; chloro(1,5-cyclooctadiene)rhodium(I) dimer In chlorobenzene at 80℃; for 7h; Inert atmosphere; Schlenk technique; Glovebox;	98%

5-methoxylindole (1006-94-6) + 1-chloro-4-pentyne (14267-92-6) → C14H15NO

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 80℃; for 3h;	98%

Upstream product

• 7664-41-7 ammonia 
• 1066-26-8 sodium acetylide 
• 109-70-6 1.3-chlorobromopropane 
• 6940-76-7 1-iodo-3-chloro-propane 
• 1066-54-2 trimethylsilylacetylene 
• 5390-04-5 pent-1-yn-5-ol 
• 74-86-2 acetylene 

Downstream Products

• 2468-55-5 5-iodopent-1-yne 
• 55402-10-3 1-chloro-6,6-dimethylhept-4-yne 
• 5891-21-4 5-chloro-2-pentanone 
• 63305-45-3 4-oxopentyl formate 
• 28077-73-8 6-chlorohex-2-yne 
• 20074-80-0 5-chloro-pentanal 
• 174125-30-5 5-chloro-1-triethylsilyl-1-pentyne 
• 189116-17-4 (E)-7-chloro-1-phenylhept-1-en-3-yne 
• 162023-24-7 5-p-(trans-4-pentylcyclohexyl)phenoxy-1-pentyne 
• 37490-32-7 [(1E)-5-chloropent-1-en-1-yl]boronic acid 
• 42873-80-3 dofenapyn 

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