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  • 53293-00-8 Structure
  • Basic information

    1. Product Name: 5-HEXYNOIC ACID
    2. Synonyms: 5-HEXYNOIC ACID 98%;4-Ethynylbutyric acid;HEX-5-YNOIC ACID;5-HEXYNOIC ACID;TIMTEC-BB SBB009090;RARECHEM AL BO 1092;5-Hexynoicacid,97%
    3. CAS NO:53293-00-8
    4. Molecular Formula: C6H8O2
    5. Molecular Weight: 112.13
    6. EINECS: -0
    7. Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;C6;Carbonyl Compounds;Carboxylic Acids
    8. Mol File: 53293-00-8.mol
    9. Article Data: 27
  • Chemical Properties

    1. Melting Point: 27°C (estimate)
    2. Boiling Point: 224-225 °C(lit.)
    3. Flash Point: 230 °F
    4. Appearance: yellow/Liquid
    5. Density: 1.016 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.042mmHg at 25°C
    7. Refractive Index: n20/D 1.449(lit.)
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. PKA: 4?+-.0.10(Predicted)
    11. Water Solubility: Miscible with water.
    12. BRN: 1743192
    13. CAS DataBase Reference: 5-HEXYNOIC ACID(CAS DataBase Reference)
    14. NIST Chemistry Reference: 5-HEXYNOIC ACID(53293-00-8)
    15. EPA Substance Registry System: 5-HEXYNOIC ACID(53293-00-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. RIDADR: 3265
    5. WGK Germany: 3
    6. RTECS:
    7. F: 10-23
    8. HazardClass: 8
    9. PackingGroup: III
    10. Hazardous Substances Data: 53293-00-8(Hazardous Substances Data)

53293-00-8 Usage

Description

5-Hexynoic acid, also known as an alkynoic acid, is a clear yellow liquid with a triple bond between the carbons at positions 5 and 6. It is characterized by its unique chemical properties, which include undergoing gold-catalyzed cyclization to form the corresponding methylene lactones.

Uses

Used in Chemical Synthesis:
5-Hexynoic acid is used as a key intermediate in the preparation of various chemical compounds, particularly hex-5-ynoic acid methyl ester. This synthesis process involves the use of p-toluenesulfonic acid as a reagent, highlighting the versatility of 5-hexynoic acid in chemical reactions and its importance in the synthesis of other valuable compounds.
Used in Pharmaceutical Industry:
While the provided materials do not explicitly mention the pharmaceutical applications of 5-hexynoic acid, its involvement in chemical synthesis suggests that it may play a role in the development of pharmaceutical compounds. The ability to form methylene lactones through gold-catalyzed cyclization could potentially be harnessed for the creation of novel drug candidates with unique therapeutic properties.

Check Digit Verification of cas no

The CAS Registry Mumber 53293-00-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,2,9 and 3 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 53293-00:
(7*5)+(6*3)+(5*2)+(4*9)+(3*3)+(2*0)+(1*0)=108
108 % 10 = 8
So 53293-00-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O2/c1-2-3-4-5-6(7)8/h1H,3-5H2,(H,7,8)/p-1

53293-00-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (H0882)  5-Hexynoic Acid  >96.0%(GC)(T)

  • 53293-00-8

  • 5g

  • 1,170.00CNY

  • Detail
  • TCI America

  • (H0882)  5-Hexynoic Acid  >96.0%(GC)(T)

  • 53293-00-8

  • 25g

  • 3,990.00CNY

  • Detail
  • Alfa Aesar

  • (B25132)  5-Hexynoic acid, 96%   

  • 53293-00-8

  • 1g

  • 398.0CNY

  • Detail
  • Alfa Aesar

  • (B25132)  5-Hexynoic acid, 96%   

  • 53293-00-8

  • 5g

  • 1233.0CNY

  • Detail
  • Alfa Aesar

  • (B25132)  5-Hexynoic acid, 96%   

  • 53293-00-8

  • 25g

  • 4114.0CNY

  • Detail

53293-00-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Hexynoic Acid

1.2 Other means of identification

Product number -
Other names 5-Hexynoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:53293-00-8 SDS

53293-00-8Synthetic route

5-hexyl-1-ol
928-90-5

5-hexyl-1-ol

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With jones' reagent In acetone for 1h; Ambient temperature;82%
With chromium(VI) oxide; hydrogen cation In acetone80%
With jones reagent at 0℃;76%
5-hexyl-1-ol
928-90-5

5-hexyl-1-ol

water
7732-18-5

water

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
In hexane; sulfuric acid; acetone72%
5-hexynonitrile
14918-21-9

5-hexynonitrile

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With sodium hydroxide In water for 10h; Heating;70%
With potassium hydroxide
With potassium hydroxide In methanol; water Heating;
With potassium hydroxide In ethanol; water for 4h; Heating; Yield given;
5,6-dibromohexanoic acid
279214-91-4

5,6-dibromohexanoic acid

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With sodium amide In diethyl ether at -33 - 25℃; Dehydrobromination;70%
With sodium amide In diethyl ether; ammonia at -33℃; for 1.5h;65%
hex-5-ynoic acid tert-butyl ester
73448-14-3

hex-5-ynoic acid tert-butyl ester

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 20h;65%
5,6-dibromohexanoic acid
279214-91-4

5,6-dibromohexanoic acid

A

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

B

6-bromohex-5(E)-enoic acid

6-bromohex-5(E)-enoic acid

Conditions
ConditionsYield
With sodium hydroxide; PEG-2000 at 80℃; for 8h; Dehydrobromination;A 49%
B 19.6%
5-hexyl-1-ol
928-90-5

5-hexyl-1-ol

A

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

B

hex-5-ynoic acid hex-5-ynyl ester

hex-5-ynoic acid hex-5-ynyl ester

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid; acetone
5-hexynoic acid ethyl ester
108545-38-6

5-hexynoic acid ethyl ester

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With potassium hydroxide
methanol
67-56-1

methanol

2-carbonyl-3-butenenitrile
60556-87-8

2-carbonyl-3-butenenitrile

allenyltrimethylsilane
14657-22-8

allenyltrimethylsilane

A

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

B

6-(trimethylsilyl)hex-5-ynoic acid:
101224-43-5

6-(trimethylsilyl)hex-5-ynoic acid:

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
methyl hex-5-ynoate
77758-51-1

methyl hex-5-ynoate

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With potassium hydroxide for 0.5h; Heating;
With water; potassium hydroxide In methanol at 20℃; for 0.5h; Inert atmosphere;
bromobutyric acid
2623-87-2

bromobutyric acid

lithium acetylide
70277-75-7

lithium acetylide

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With ammonia
5,6-dibromohexanoic acid
279214-91-4

5,6-dibromohexanoic acid

A

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

B

6ξ-bromo-hex-5-enoic acid

6ξ-bromo-hex-5-enoic acid

Conditions
ConditionsYield
With potassium hydroxide
5,6-dibromohexanoic acid
279214-91-4

5,6-dibromohexanoic acid

ethanolic KOH-solution

ethanolic KOH-solution

A

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

B

6ξ-bromo-hex-5-enoic acid

6ξ-bromo-hex-5-enoic acid

5,6-dibromohexanoic acid
279214-91-4

5,6-dibromohexanoic acid

A

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

B

hex-4-ynoic acid
41143-12-8

hex-4-ynoic acid

C

6-bromohex-5(E)-enoic acid

6-bromohex-5(E)-enoic acid

Conditions
ConditionsYield
With sodium hydroxide; PEG-2000 In water at 82℃; for 8h;
bromobutyric acid
2623-87-2

bromobutyric acid

lithium acetylide-ethylenediamine complex
1216963-74-4

lithium acetylide-ethylenediamine complex

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
In dimethyl sulfoxide
5-hexenoic acid
1577-22-6

5-hexenoic acid

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Br2 / CH2Cl2 / 1.5 h / -40 °C
2: 65 percent / NaNH2 / diethyl ether; liquid ammonia / 1.5 h / -33 °C
View Scheme
Multi-step reaction with 2 steps
1: Br2 / CH2Cl2 / 1.5 h / -40 °C
2: NaOH; PEG-2000 / H2O / 8 h / 82 °C
View Scheme
Multi-step reaction with 2 steps
1: petroleum ether; bromine
2: ethanolic KOH-solution
View Scheme
5-hexenoic acid
1577-22-6

5-hexenoic acid

Merrifield resin

Merrifield resin

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93.5 percent / Br2 / CH2Cl2 / 1.5 h / -40 °C
2: 70 percent / NaNH2 / diethyl ether / -33 - 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 93.5 percent / Br2 / CH2Cl2 / 1.5 h / -40 °C
2: 49 percent / 40 percent aq. NaOH; PEG-2000 / 8 h / 80 °C
View Scheme
hex-2-yn-1-ol
764-60-3

hex-2-yn-1-ol

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaNH2 / various solvent(s)
2: Jones reagent
View Scheme
methyl 5-hexenoate
2396-80-7

methyl 5-hexenoate

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aq. KOH / 0.5 h / Heating
View Scheme
6-(2-Nitro-phenylselanyl)-hexanoic acid methyl ester
108545-33-1

6-(2-Nitro-phenylselanyl)-hexanoic acid methyl ester

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / aq. H2O2 / tetrahydrofuran / 24 h
3: aq. KOH / 0.5 h / Heating
View Scheme
2-(chloromethyl)tetrahydropyran
18420-41-2, 130233-13-5, 130233-14-6

2-(chloromethyl)tetrahydropyran

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaNH2, liq. NH3 / tetrahydrofuran / -78 °C
2: Jones' reagent / acetone / 0 °C
View Scheme
Tetrahydropyran-2-methanol
100-72-1

Tetrahydropyran-2-methanol

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2, pyridine / 10 h / Ambient temperature
2: NaNH2, liq. NH3 / tetrahydrofuran / -78 °C
3: Jones' reagent / acetone / 0 °C
View Scheme
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 0.17 h / -10 °C
2: NaCN / dimethylsulfoxide / 0.5 h / 70 °C
3: KOH / ethanol; H2O / 4 h / Heating
View Scheme
4-pentynyl-1-tosylate
77758-50-0

4-pentynyl-1-tosylate

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaCN / dimethylsulfoxide / 0.5 h / 70 °C
2: KOH / ethanol; H2O / 4 h / Heating
View Scheme
1-chloro-4-pentyne
14267-92-6

1-chloro-4-pentyne

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 53 percent
2: 70 percent / NaOH / H2O / 10 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: acetone; sodium iodide
2: aqueous acetone
3: aqueous KOH-solution
View Scheme
With hydrogenchloride; potassium hydroxide In water; dimethyl sulfoxide
5-iodopent-1-yne
2468-55-5

5-iodopent-1-yne

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous acetone
2: aqueous KOH-solution
View Scheme
2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol
5244-34-8

2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Conditions
ConditionsYield
With n-butyllithium In hexane
aqueous potassium hydroxide

aqueous potassium hydroxide

5-hexynonitrile
14918-21-9

5-hexynonitrile

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

methanol
67-56-1

methanol

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

methyl hex-5-ynoate
77758-51-1

methyl hex-5-ynoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 36h; Reflux;100%
With toluene-4-sulfonic acid In dichloromethane for 24h; Esterification; Heating;97%
With toluene-4-sulfonic acid In dichloromethane for 24h; Heating;96%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

hex-5-in-carboxyl chloride
55183-45-4

hex-5-in-carboxyl chloride

Conditions
ConditionsYield
With oxalyl dichloride Inert atmosphere;100%
With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;83%
With oxalyl dichloride; N,N-dimethyl-formamide In benzene at 25 - 35℃; for 2h;82%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

methyl iodide
74-88-4

methyl iodide

methyl hex-5-ynoate
77758-51-1

methyl hex-5-ynoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide100%
With potassium carbonate In N,N-dimethyl-formamide at 5℃; for 5h; Cooling with ice;70%
With potassium carbonate In N,N-dimethyl-formamide
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

6-(trimethylsilyl)hex-5-ynoic acid:
101224-43-5

6-(trimethylsilyl)hex-5-ynoic acid:

Conditions
ConditionsYield
Stage #1: hex-5-ynoic acid With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere;
100%
Stage #1: hex-5-ynoic acid With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With water; acetic acid In tetrahydrofuran; hexane for 0.333333h;
76%
Stage #1: hex-5-ynoic acid With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; for 4h; Inert atmosphere;
65%
Stage #1: hex-5-ynoic acid With n-butyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
63%
Stage #1: hex-5-ynoic acid With n-butyllithium In tetrahydrofuran; Petroleum ether at -78℃;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; Petroleum ether at -78 - 0℃;
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

sodium 5-hexynoate
1219440-76-2

sodium 5-hexynoate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 20℃; for 0.166667h;100%
With sodium hydroxide In water
morpholine
110-91-8

morpholine

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

1-morpholinohex-5-yn-1-one
1293915-62-4

1-morpholinohex-5-yn-1-one

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 20℃;100%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 23℃; Inert atmosphere;62%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-methoxy-N-methylhex-5-ynamide
217087-88-2

N-methoxy-N-methylhex-5-ynamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; Inert atmosphere;100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 25℃; for 6h;98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 43h;94%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

6-(4-nitrophenyl)hex-5-ynoic acid
1084898-19-0

6-(4-nitrophenyl)hex-5-ynoic acid

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;100%
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; triphenylphosphine at 50℃; for 14h; Inert atmosphere; Schlenk technique;74%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere;22%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

2,3,5,6-tetraflourophenol
769-39-1

2,3,5,6-tetraflourophenol

2,3,5,6-tetrafluorophenyl hex-5-ynoate
1462237-48-4

2,3,5,6-tetrafluorophenyl hex-5-ynoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;100%
With pyridinium p-toluenesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Inert atmosphere;
1,3-dihydroxyacetone dimer
62147-49-3

1,3-dihydroxyacetone dimer

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

2-oxopropane-1,3-diyl bis(hex-5-ynoate)

2-oxopropane-1,3-diyl bis(hex-5-ynoate)

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;100%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

4-Iodophenol
540-38-5

4-Iodophenol

6-(4-hydroxyphenyl)hex-5-ynoic acid

6-(4-hydroxyphenyl)hex-5-ynoic acid

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 4.5h; Temperature; Inert atmosphere;100%
1-Boc-2-benzylpiperazine

1-Boc-2-benzylpiperazine

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

C22H30N2O3

C22H30N2O3

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;100%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

6-methylidenetetrahydro-2-pyrone
5636-66-8

6-methylidenetetrahydro-2-pyrone

Conditions
ConditionsYield
With [(1,1′-biphenyl-2-yl)di-tert-butylphosphine]gold(I) trifluoromethanesulfonate; silver trifluoromethanesulfonate In chloroform-d1 at 20℃; for 0.0833333h; Reagent/catalyst;99%
With C42H64P4Pd2S4 at 90℃; for 10h; Inert atmosphere;98%
With potassium carbonate; gold(I) chloride In acetonitrile at 20℃; for 2h;97%
N-(2-hydroxy-1-methylethyl)-3-iodobenzamide
863713-59-1

N-(2-hydroxy-1-methylethyl)-3-iodobenzamide

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

6-[3-(2-hydroxy-1-methylethylcarbamoyl)phenyl]hex-5-ynoic acid
863713-63-7

6-[3-(2-hydroxy-1-methylethylcarbamoyl)phenyl]hex-5-ynoic acid

Conditions
ConditionsYield
With pyrrolidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 20 - 60℃; for 3.3h; Sonogashira Coupling;99%
Stage #1: N-(2-hydroxy-1-methylethyl)-3-iodobenzamide; hex-5-ynoic acid With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 60℃; for 3h; Sonogashira coupling;
Stage #2: N-(2-hydroxy-1-methylethyl)-3-iodobenzamide; hex-5-ynoic acid In water; acetonitrile for 0.333333h; Further stages.;
97%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

(-)-englerin B

(-)-englerin B

C30H38O5

C30H38O5

Conditions
ConditionsYield
With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine In toluene at 20℃; Yamaguchi esterification; Inert atmosphere;99%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

cholesterol
57-88-5

cholesterol

(3β)-cholest-4-en-3yl hex-5-ynoate
949584-04-7

(3β)-cholest-4-en-3yl hex-5-ynoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 20h;99%
With dmap; dicyclohexyl-carbodiimide59%
2-(2'-hydroxyethylamino)-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine

2-(2'-hydroxyethylamino)-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

2-[2'-(5-hexynoyloxy)ethylamino]-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine
1391054-29-7

2-[2'-(5-hexynoyloxy)ethylamino]-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;99%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

methyl hex-5-ynoate
77758-51-1

methyl hex-5-ynoate

Conditions
ConditionsYield
With chloro-trimethyl-silane In methanol at 20℃; for 16h;99%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

dodeca-5,7-diynedioic acid
28393-04-6

dodeca-5,7-diynedioic acid

Conditions
ConditionsYield
With oxygen; ammonium chloride; copper(l) chloride In water at 20℃;98%
Stage #1: hex-5-ynoic acid With acetyl chloride In methanol at 20 - 80℃; for 12h; Inert atmosphere; Schlenk technique;
Stage #2: With copper(II) acetate monohydrate In acetonitrile at 80℃; for 4h; Reflux; Further stages;
69%
With ammonium chloride; water; copper(l) chloride Reagens 4: Luft;
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

3,4-dihydro-6-methyl-2H-pyran-2-one
3740-59-8

3,4-dihydro-6-methyl-2H-pyran-2-one

Conditions
ConditionsYield
With triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 16h; Inert atmosphere;98%
With zinc(II) carbonate
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

6-bromo-5-hexynoic acid
910028-80-7

6-bromo-5-hexynoic acid

Conditions
ConditionsYield
With N-Bromosuccinimide; silver nitrate In acetone for 2h;98%
With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 2h;96%
With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 2h;72%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

pentafluorophenyl 5-hexynoate
1219141-93-1

pentafluorophenyl 5-hexynoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 0℃;98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1h;95%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

C31H35NO7

C31H35NO7

C37H41NO8

C37H41NO8

Conditions
ConditionsYield
With dmap; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;98%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

5-ketohexanoic acid
3128-06-1

5-ketohexanoic acid

Conditions
ConditionsYield
In water at 90℃; for 45h;98%
With [RhCl2(p-cymene)]2; water at 20℃; for 12h;86%
With platinum catalyst In water at 37℃; for 30h;64%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

methanandamide
157182-49-5

methanandamide

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} 5-hexynoate
1313514-82-7

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} 5-hexynoate

Conditions
ConditionsYield
Stage #1: hex-5-ynoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: methanandamide In dichloromethane at 20℃; for 10h; Inert atmosphere;
98%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol
22323-82-6

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

(2'R)-2,3-O-isopropylidene-2,3-dihydroxy-1-prop-1-yl pent-4-ynoate
1341126-40-6

(2'R)-2,3-O-isopropylidene-2,3-dihydroxy-1-prop-1-yl pent-4-ynoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h; Inert atmosphere;98%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazol-1-yl)(piperazin-1-yl)methanone

(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazol-1-yl)(piperazin-1-yl)methanone

1-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-1-yl)hex-5-yn-1-one

1-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-1-yl)hex-5-yn-1-one

Conditions
ConditionsYield
Stage #1: hex-5-ynoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: (2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazol-1-yl)(piperazin-1-yl)methanone In N,N-dimethyl-formamide at 20℃; for 3h;
98%
formaldehyd
50-00-0

formaldehyd

hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

1-((S)-3-azido-2-isocyanopropyl)benzene
1223635-87-7

1-((S)-3-azido-2-isocyanopropyl)benzene

(S)-2-[(1-azido-3-phenylpropan-2-yl)amino]-2-oxoethyl hex-5-ynoate

(S)-2-[(1-azido-3-phenylpropan-2-yl)amino]-2-oxoethyl hex-5-ynoate

Conditions
ConditionsYield
In methanol at 20℃; Passerini Condensation;98%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

(E)-5,6-dibromopent-5-enoic acid

(E)-5,6-dibromopent-5-enoic acid

Conditions
ConditionsYield
With bromine; magnesium bromide ethyl etherate; sodium bromide In dichloromethane at 20℃;98%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

(7S)‐2‐(4‐phenoxyphenyl)‐7‐(piperidin‐4‐yl)‐4H,5H,6H,7H‐pyrazolo[1,5‐a]pyrimidine‐3‐carboxamide

(7S)‐2‐(4‐phenoxyphenyl)‐7‐(piperidin‐4‐yl)‐4H,5H,6H,7H‐pyrazolo[1,5‐a]pyrimidine‐3‐carboxamide

(S)-7-(1-(hex-5-ynoyl)piperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-3-carboxamide

(S)-7-(1-(hex-5-ynoyl)piperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-3-carboxamide

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;98%

53293-00-8Relevant articles and documents

A concise synthesis of xestospongic acid methyl ester with pancreatic lipase inhibitory activity

Gong, Jing-Xu,Wang, He-Yao,He, Wen-Fei,Wang, Zhen-Zhong,Xiao, Wei,Guo, Yue-Wei

, p. 916 - 919 (2013)

Xestospongic acid methyl ester, a naturally brominated fatty acid with potent pancreatic lipase inhibitory activity in vitro, was synthesized from 5-hexynol in 30% total yield.

Palladium-catalysed direct synthesis of optically active dienols

Jeffery

, p. 1133 - 1136 (1993)

A direct and highly chemo, regio and stereocontrolled method for constructing optically active conjugated dienols is described and illustrated by a short, convenient and efficient synthesis of methyl (9R)-9-hydroxytetradeca-5Z,7E-dienoate(-)-1.

Luminescence modulations of rhenium tricarbonyl complexes induced by structural variations

Bertrand, Helene C.,Clede, Sylvain,Guillot, Regis,Lambert, Francois,Policar, Clotilde

, p. 6204 - 6223 (2014/07/07)

Octahedral d6 low-spin Re(I) tricarbonyl complexes are of considerable interest as noninvasive imaging probes and have been deeply studied owing to their biological stability, low toxicity, large Stokes shifts, and long luminescence lifetimes. We reported recently the bimodal IR and luminescence imaging of a Re(I) tricarbonyl complex with a Pyta ligand (4-(2-pyridyl)-1,2,3-triazole) in cells and labeled such metal-carbonyl complexes SCoMPIs for single-core multimodal probes for imaging. Re(I) tricarbonyl complexes have unique photophysical properties allowing for their unequivocal detection in cells but also present some weaknesses such as a very low luminescence quantum yield in aqueous medium. Further optimizations would thus be desirable. We therefore developed new Re(I) tricarbonyl complexes prepared from different ancillary ligands. Complexes with benzothiadiazole- triazole ligands show interesting luminescent quantum yields in acetonitrile and may constitute valuable luminescent metal complexes in organic media. A series of complexes with bidentate 1-(2-quinolinyl)-1,2,3-triazole (Taquin) and 1-(2-pyridyl)-1,2,3-triazole (Tapy) ligands bearing various 4-substituted alkyl side chains has been designed and synthesized with efficient procedures. Their photophysical properties have been characterized in acetonitrile and in a H 2O/DMSO (98/2) mixture and compared with those of the parent Quinta- and Pyta-based complexes. Tapy complexes bearing long alkyl chains show impressive enhancement of their luminescent properties relative to the parent Pyta complex. Theoretical calculations have been performed to further characterize this new class of rhenium tricarbonyl complexes. Preliminary cellular imaging studies in MDA-MB231 breast cancer cells reveal a strong increase in the luminescence signal in cells incubated with the Tapy complex substituted with a C12 alkyl chain. This study points out the interesting potential of the Tapy ligand in coordination chemistry, which has been so far underexploited.

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