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5-Chloro-1-pentyne

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Name

5-Chloro-1-pentyne

EINECS 238-159-5
CAS No. 14267-92-6 Density 0.966 g/cm3
PSA 0.00000 LogP 1.63860
Solubility Not miscible in water. Melting Point -61°C (estimate)
Formula C5H7Cl Boiling Point 117.888 °C at 760 mmHg
Molecular Weight 102.564 Flash Point 15.556 °C
Transport Information UN 1993 3/PG 2 Appearance clear, colorless clear liquid
Safety 23-24/25-16 Risk Codes 11-38-36/37/38
Molecular Structure Molecular Structure of 14267-92-6 (5-Chloro-1-pentyne) Hazard Symbols FlammableF,IrritantXi
Synonyms

(3-Chloropropyl)acetylene;1-Chloro-4-pentyne;4-Pentynyl chloride;

Article Data 21

5-Chloro-1-pentyne Synthetic route

5390-04-5

pent-1-yn-5-ol

14267-92-6

1-chloro-4-pentyne

Conditions
ConditionsYield
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.
1066-26-8

sodium acetylide

109-70-6

1,3-chlorobromopropane

14267-92-6

1-chloro-4-pentyne

Conditions
ConditionsYield
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
109-70-6

1,3-chlorobromopropane

74-86-2

acetylene

14267-92-6

1-chloro-4-pentyne

Conditions
ConditionsYield
(i) LiNH2, liq. NH3, (ii) /BRN= 605278/; Multistep reaction;
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -65℃;
7664-41-7

ammonia

1066-26-8

sodium acetylide

109-70-6

1,3-chlorobromopropane

14267-92-6

1-chloro-4-pentyne

Conditions
ConditionsYield
under 760 Torr;
109-70-6

1,3-chlorobromopropane

calcium carbide

calcium carbide

14267-92-6

1-chloro-4-pentyne

Conditions
ConditionsYield
With sodium hydroxide; diethylene glycol dibutyl ether
5390-04-5

pent-1-yn-5-ol

A

14267-92-6

1-chloro-4-pentyne

B

C10H14O

Conditions
ConditionsYield
With hydrogenchloride In water at 120℃; under 5171.62 Torr; for 0.25h; Flow reactor;A 12 %Spectr.
B n/a
6940-76-7

1-iodo-3-chloro-propane

1066-54-2

trimethylsilylacetylene

14267-92-6

1-chloro-4-pentyne

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;
14267-92-6

1-chloro-4-pentyne

2468-55-5

5-iodopent-1-yne

Conditions
ConditionsYield
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%
487-89-8

Indole-3-carboxaldehyde

14267-92-6

1-chloro-4-pentyne

110206-34-3

1-(4-pentenyl)-1H-indole-3-carboxaldehyde

Conditions
ConditionsYield
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;
136918-14-4

phthalimide

14267-92-6

1-chloro-4-pentyne

6097-07-0

N-(pent-4-ynyl)phthalimide

Conditions
ConditionsYield
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%

5-Chloro-1-pentyne Specification

The CAS register number of is 5-Chloro-1-pentyne 14267-92-6. It also can be called as 1-Pentyne, 5-chloro- and the IUPAC name about this chemical is 5-chloropent-1-yne. The molecular formula about this chemical is C5H7Cl and the molecular weight is 102.56. It belongs to the following product categories, such as Miscellaneous; Acetylenes; Functionalized Acetylenes; Alkynyl; Halogenated Hydrocarbons; Organic Building Blocks and so on.

Physical properties about 5-Chloro-1-pentyne are: (1)ACD/LogP: 1.85; (2)ACD/LogD (pH 5.5): 1.85; (3)ACD/LogD (pH 7.4): 1.85; (4)ACD/BCF (pH 5.5): 14.997; (5)ACD/BCF (pH 7.4): 14.997; (6)ACD/KOC (pH 5.5): 241.769; (7)ACD/KOC (pH 7.4): 241.769 ; (8)#Freely Rotating Bonds: 2; (9)Index of Refraction: 1.438; (10)Molar Refractivity: 27.89 cm3; (11)Molar Volume: 106.219 cm3; (12)Polarizability: 11.057x10-24cm3; (13)Surface Tension: 29.964 dyne/cm; (14)Enthalpy of Vaporization: 34.14 kJ/mol; (15)Boiling Point: 117.888 °C at 760 mmHg; (16)Vapour Pressure: 20.377 mmHg at 25°C.

Preparation of 5-Chloro-1-pentyne: This chemical can be prepared by ethynylsodium and 1-bromo-3-chloro-propane. This reaction will need reagent liquid ammonia.

Preparation of 5-Chloro-1-pentyne

Uses of 5-Chloro-1-pentyne: it can be used to produce 27-chloro-hept-3-yn-1-ol with oxirane at temperature of -78 ℃. This reaction will need reagent n-BuLi, BF3*Et2O with reaction time of 1 hours. The yield is about 45%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin, it is highly flammable. When you are using it, please do not breathe vapour and avoid contact with skin and eyes, you need also keep away from sources of ignition.

You can still convert the following datas into molecular structure:
(1)SMILES: C#CCCCCl
(2)InChI: InChI=1/C5H7Cl/c1-2-3-4-5-6/h1H,3-5H2
(3)InChIKey: UXFIKVWAAMKFQE-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C5H7Cl/c1-2-3-4-5-6/h1H,3-5H2
(5)Std. InChIKey: UXFIKVWAAMKFQE-UHFFFAOYSA-N

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