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935-14-8

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935-14-8 Usage

Chemical Properties

White or orange-brown crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 935-14-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 5 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 935-14:
(5*9)+(4*3)+(3*5)+(2*1)+(1*4)=78
78 % 10 = 8
So 935-14-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H6/c1-3-9-5-7-10(4-2)8-6-9/h1-2,5-8H

935-14-8 Well-known Company Product Price

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  • TCI America

  • (D2151)  1,4-Diethynylbenzene  >98.0%(GC)

  • 935-14-8

  • 1g

  • 525.00CNY

  • Detail
  • TCI America

  • (D2151)  1,4-Diethynylbenzene  >98.0%(GC)

  • 935-14-8

  • 5g

  • 1,590.00CNY

  • Detail
  • Aldrich

  • (632090)  1,4-Diethynylbenzene  96%

  • 935-14-8

  • 632090-5G

  • 1,888.38CNY

  • Detail

935-14-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-Diethynylbenzene

1.2 Other means of identification

Product number -
Other names para-diethynylbenzene

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:935-14-8 SDS

935-14-8Synthetic route

1,4-Bis(trimethylsilylethynyl)benzene
17938-13-5

1,4-Bis(trimethylsilylethynyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium carbonate In methanol; dichloromethane at 20℃; for 1h;100%
With water; potassium hydroxide In methanol for 1h;100%
With potassium carbonate In methanol at 20℃;97%
para-diiodobenzene
624-38-4

para-diiodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
Stage #1: para-diiodobenzene; trimethylsilylacetylene With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Sonogahira-Hagihara coupling reaction;
Stage #2: With potassium carbonate In methanol
100%
1,4-bis(2,2-dibromoethenyl)benzene
77295-67-1

1,4-bis(2,2-dibromoethenyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;99%
With caesium carbonate; dimethyl sulfoxide at 115℃; for 12h;95%
With Succinimide; potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Schlenk technique; Inert atmosphere;84%
1,4-bis(2-hydroxy-2-methyl-4-but-3-ynyl)benzene
2344-53-8

1,4-bis(2-hydroxy-2-methyl-4-but-3-ynyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium hydroxide In toluene for 3h; Reflux; Inert atmosphere; Darkness;98%
With sodium isopropylate In isopropyl alcohol for 4.5h; Heating;85%
With aluminum oxide; potassium hydroxide for 0.0166667h; microwave irradiation;84%
anti-3,3'-(1,4-phenylene)bis(2,3-dibromopropanoic acid)

anti-3,3'-(1,4-phenylene)bis(2,3-dibromopropanoic acid)

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h;98%
1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)trisilane

1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)trisilane

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; methanol at 0℃; Inert atmosphere;97%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

(dibromomethyl)(triphenyl)phosphonium bromide
56506-90-2

(dibromomethyl)(triphenyl)phosphonium bromide

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
Stage #1: terephthalaldehyde,; (dibromomethyl)(triphenyl)phosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.0833333h; Wittig-type condensation;
Stage #2: With potassium tert-butylate In tetrahydrofuran at -78℃; Elimination;
85%
1,1'-(1,4-phenylene)bis(3-phenylprop-2-yn-1-one)
52714-30-4

1,1'-(1,4-phenylene)bis(3-phenylprop-2-yn-1-one)

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium hydroxide; water In benzene at 80℃;83%
aqueous potassium hydroxide

aqueous potassium hydroxide

1,4-Bis(trimethylsilylethynyl)benzene
17938-13-5

1,4-Bis(trimethylsilylethynyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
In methanol; dichloromethane; water78%
1,4-Diacetylbenzene
1009-61-6

1,4-Diacetylbenzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
Stage #1: 1,4-Diacetylbenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Enolization;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran at -78℃; for 0.25h; Phosphorylation;
Stage #3: With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 4h; Dehydration;
77%
(i) PCl5, (ii) NaNH2, liq. NH3; Multistep reaction;
(Z,Z)-1,4-bis(2-bromoethenyl)benzene
88248-70-8

(Z,Z)-1,4-bis(2-bromoethenyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 25℃; for 3h;73%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene; trimethylsilylacetylene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran Sonogashira coupling; Inert atmosphere;
Stage #2: With potassium hydroxide In methanol
72%
Sonogashira Cross-Coupling;
1,4-phenylenebis(methyleneisoxazolone)

1,4-phenylenebis(methyleneisoxazolone)

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
at 750℃; for 1.5h; Pyrolysis;72%
2-methyl-4-(4-(3-methyl-3-((2-nitrobenzyl)oxy)but-1-yn-1-yl)phenyl)but-3-yn-2-ol
1453814-03-3

2-methyl-4-(4-(3-methyl-3-((2-nitrobenzyl)oxy)but-1-yn-1-yl)phenyl)but-3-yn-2-ol

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium hydroxide In toluene at 110℃; for 12h; Inert atmosphere; UV-irradiation;70%
tert-butyldimethyl((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)silane
1611483-95-4

tert-butyldimethyl((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)silane

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium trimethylsilonate In dimethyl sulfoxide at 70℃; for 12h; Sealed tube; Schlenk technique;70%
1,4-bis(1,2-dibromoethyl)benzene
25393-98-0

1,4-bis(1,2-dibromoethyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 In xylene Heating;63%
With potassium hydroxide
With potassium tert-butylate In tert-butyl alcohol for 1h; Heating;
dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

(4-bromophenyl)(trimethylsilyl)acetylene
16116-78-2

(4-bromophenyl)(trimethylsilyl)acetylene

A

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

B

(p-(dimethylsilyl)phenyl)acetylene
244307-32-2

(p-(dimethylsilyl)phenyl)acetylene

Conditions
ConditionsYield
Stage #1: (4-bromophenyl)(trimethylsilyl)acetylene With potassium carbonate In methanol for 5h;
Stage #2: With n-butyllithium In tetrahydrofuran at -78℃;
Stage #3: dimethylmonochlorosilane In tetrahydrofuran
A n/a
B 63%
(E)-3-Chloro-3-[4-((E)-1-chloro-3-oxo-propenyl)-phenyl]-propenal

(E)-3-Chloro-3-[4-((E)-1-chloro-3-oxo-propenyl)-phenyl]-propenal

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 80℃; for 0.5h;41%
1,4-diethynylcyclohexa-2,5-diene-1,4-diol
24936-01-4

1,4-diethynylcyclohexa-2,5-diene-1,4-diol

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With acetic acid; tin(ll) chloride at 40 - 45℃;
With tin(ll) chloride In acetic acid
trans-1,4-diethynyl-1,4-dihydroxy-2,5-cyclohexadiene
24936-01-4

trans-1,4-diethynyl-1,4-dihydroxy-2,5-cyclohexadiene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With sulfuric acid; tin(ll) chloride
1,4-Diethynyl-4-methoxy-cyclohexa-2,5-dienol

1,4-Diethynyl-4-methoxy-cyclohexa-2,5-dienol

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With sulfuric acid; tin(ll) chloride
1,4-di(1-chloroethenyl)benzene
125757-06-4

1,4-di(1-chloroethenyl)benzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With sodium amide In ammonia for 7h; Yield given;
C21H19Cl2NO2P(1+)*Cl(1-)

C21H19Cl2NO2P(1+)*Cl(1-)

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature; Yields of byproduct given;
With sodium hydroxide Ambient temperature; Yield given;
2,2'-bis-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-1,1'-p-phenylene-bis-ethanone
105070-00-6

2,2'-bis-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-1,1'-p-phenylene-bis-ethanone

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With sodium hydroxide; trichlorophosphate 1. dioxane, 80 degC, 4h; Yield given. Multistep reaction. Yields of byproduct given;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; copper(l) iodide 2.) toluene, 100 deg C; Multistep reaction;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

propargyl alcohol
107-19-7

propargyl alcohol

A

4-bromo-1-ethynylbenzene
766-96-1

4-bromo-1-ethynylbenzene

B

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With manganese(IV) oxide; potassium hydroxide; copper diacetate; diisopropylamine; triphenylphosphine; palladium dichloride 1.) reflux, 3 h, 2.) CH2Cl2, Et2O, 90 min; Yield given. Multistep reaction. Yields of byproduct given;
para-diiodobenzene
624-38-4

para-diiodobenzene

tributylethynyltin
994-89-8

tributylethynyltin

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃;
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 110℃;
1,4-bis(1,2-dibromoethyl)benzene
25393-98-0

1,4-bis(1,2-dibromoethyl)benzene

ethanolic KOH

ethanolic KOH

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

para-diiodobenzene
624-38-4

para-diiodobenzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(I) iodide; diisopropylamine; triethylamine / dichlorobis(triphenylphosphine)palladium(II) / tetrahydrofuran / 96 h / 60 °C
2: aq. potassium hydroxide / tetrahydrofuran; methanol / 1 h
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / TBAF / tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
1: 93 percent / CuI; diisopropylamine / Pd(PPh3)4 / toluene / 24 h / 50 °C
2: 92 percent / K2CO3 / tetrahydrofuran; methanol / 1 h / 20 °C
View Scheme
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

phenylacetylene
536-74-3

phenylacetylene

star-poly(phenylacetylene), Mn: 37500 (GPC), Mw/Mn: 1.2 (GPC), methanol-insoluble; monomer(s): phenylacetylene; 1,4-diethynylbenzene

star-poly(phenylacetylene), Mn: 37500 (GPC), Mw/Mn: 1.2 (GPC), methanol-insoluble; monomer(s): phenylacetylene; 1,4-diethynylbenzene

Conditions
ConditionsYield
Stage #1: phenylacetylene With triphenylvinyllithium; triphenylphosphine; [(nbd)RhCl]2 In diethyl ether; toluene at 30℃; for 0.5h;
Stage #2: 1,4-diethynylbenzene In diethyl ether; toluene at 30℃; for 0.166667h;
100%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4,4'-(1,4-phenylenebis(ethyne-2,1-diyl))dibenzaldehyde
192188-70-8

4,4'-(1,4-phenylenebis(ethyne-2,1-diyl))dibenzaldehyde

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran for 30h; Sonogashira coupling; Heating;100%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-bis((2-bromophenyl)ethynyl)benzene
852066-26-3

1,4-bis((2-bromophenyl)ethynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Sonogashira Cross-Coupling;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile at 80℃; for 12h; Sonogashira coupling; Inert atmosphere;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile at 80℃; for 12h; Sonogashira coupling; Inert atmosphere;99%
C23H20N8O4
919363-64-7

C23H20N8O4

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

C56H46N16O8
919363-69-2

C56H46N16O8

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In water; acetone; tert-butyl alcohol at 20℃; for 24h;100%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-di(2-iodoethynyl)benzene
878-06-8

1,4-di(2-iodoethynyl)benzene

Conditions
ConditionsYield
With aluminum oxide; N-iodo-succinimide In acetonitrile at 80℃; for 1h; Molecular sieve;99%
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;98%
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;98%
trans-dichloro-bis(tri-n-butylphosphine)platinum(II)
15391-01-2, 15076-72-9, 15390-92-8

trans-dichloro-bis(tri-n-butylphosphine)platinum(II)

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

trans-{Pt(PBu3)2CCC6H4CC-}n

trans-{Pt(PBu3)2CCC6H4CC-}n

Conditions
ConditionsYield
With copper(l) iodide; diethylamine In tetrahydrofuran refluxed under N2; pptd., concd., dried (vac.), dissolved in CHCl3, poured into MeOH;99%
2-iodoprop-2-en-1-ol
84201-43-4

2-iodoprop-2-en-1-ol

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

4,4'-(1,4-phenylene)bis(2-methylenebut-3-yn-1-ol)
1272632-90-2

4,4'-(1,4-phenylene)bis(2-methylenebut-3-yn-1-ol)

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 65℃; for 16h; Sonogashira coupling; Inert atmosphere;99%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1-butyl-4-((4-iodophenyl)ethynyl)benzene

1-butyl-4-((4-iodophenyl)ethynyl)benzene

1,4-bis((4-(4-butylphenylethynyl)phenyl)ethynyl)benzene

1,4-bis((4-(4-butylphenylethynyl)phenyl)ethynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 20℃; for 12h; Sonogashira Cross-Coupling; Inert atmosphere;99%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

2–(3-phenylpropiolyl)benzaldehyde

2–(3-phenylpropiolyl)benzaldehyde

C42H22O2

C42H22O2

Conditions
ConditionsYield
Stage #1: 1,4-diethynylbenzene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 2–(3-phenylpropiolyl)benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 6h; Inert atmosphere;
Stage #3: With hydrogenchloride In water at 20℃; for 3h; Inert atmosphere;
98.8%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Poly(1,4-phenyleneethynylene)

Poly(1,4-phenyleneethynylene)

Conditions
ConditionsYield
With copper(l) iodide; di-n-propylamine; bis-triphenylphosphine-palladium(II) chloride at 75℃; for 0.666667h;98%
4-acetoxyiodobenzene
33527-94-5

4-acetoxyiodobenzene

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-bis(4-acetoxyphenyl)ethynylbenzene
1256281-23-8

1,4-bis(4-acetoxyphenyl)ethynylbenzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 18h; Inert atmosphere;98%
pyrrolidine
123-75-1

pyrrolidine

formaldehyd
50-00-0

formaldehyd

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

A

1-[3-(4-ethynylphenyl)prop-2-yn-1-yl]pyrrolidine

1-[3-(4-ethynylphenyl)prop-2-yn-1-yl]pyrrolidine

B

1,4-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]benzene

1,4-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]benzene

Conditions
ConditionsYield
With copper(I) (2-biphenyl)di-tert-butylphosphane-aniline hexaflurophosphate In toluene at 50℃; under 1500.15 Torr; Reagent/catalyst; Solvent; Time; Inert atmosphere;A n/a
B 98%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

benzyl chloride
100-44-7

benzyl chloride

1-benzyl-4-(4-ethynylphenyl)-1H-1,2,3-triazole
1248568-43-5

1-benzyl-4-(4-ethynylphenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide In water at 20℃; for 2h; Huisgen Cycloaddition; Green chemistry;98%
4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide
16352-18-4

4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

C22H32O6P2

C22H32O6P2

Conditions
ConditionsYield
With tris(triphenylphosphine)rhodium(I) chloride In acetone at 25℃; for 20h;97%
C15H27N3O6
1028208-44-7

C15H27N3O6

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

C40H60N6O12
1095278-08-2

C40H60N6O12

Conditions
ConditionsYield
With sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; water; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water Inert atmosphere;97%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

8-bromoguanosine
4016-63-1

8-bromoguanosine

8,8'-[benzene-1,4-diyl-di(ethyn-2,1-diyl)]diguanosine
1190592-50-7

8,8'-[benzene-1,4-diyl-di(ethyn-2,1-diyl)]diguanosine

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 70℃; for 16h; Sonogashira-Hagihara coupling; Inert atmosphere;97%
4-Iodoacetophenone
13329-40-3

4-Iodoacetophenone

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-Bis(4-acetylphenylethynyl)benzene

1,4-Bis(4-acetylphenylethynyl)benzene

Conditions
ConditionsYield
With C16H20Cl2N2O2Pd; potassium hydroxide In water; acetonitrile at 20℃; for 1h; Sonogashira Cross-Coupling;97%
With 2,2′-(1,2-phenylene)bis(4,4-di-methyl-4,5-dihydrooxazole)-N,N′-dichloridopalladium(II); potassium hydroxide In water; acetonitrile at 20℃; for 1h; Sonogashira Cross-Coupling;97%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; silica gel for 0.333333h; Sonogashira coupling; Neat (no solvent); ball mill; chemoselective reaction;69 %Spectr.
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-di(1H-1,2,3-triazol-4-yl)benzene
1244804-05-4, 935747-92-5

1,4-di(1H-1,2,3-triazol-4-yl)benzene

Conditions
ConditionsYield
With sodium azide In water at 100℃; Green chemistry; regioselective reaction;97%
With copper(l) iodide; trimethylsilylazide In methanol; N,N-dimethyl-formamide at 90℃; for 44h; Inert atmosphere;82%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

PPh3*B(C6F5)3
856827-93-5

PPh3*B(C6F5)3

E-HCtCC6H4C(PPh3)=C(H)B(C6F5)3
1257311-31-1

E-HCtCC6H4C(PPh3)=C(H)B(C6F5)3

Conditions
ConditionsYield
In dichloromethane (N2); addn. of acetylene deriv. to CH2Cl2 suspn. of triphenylphosphine-borane deriv., stirring overnight; concg., layering with pentane, cooling to -35°C overnight, isolation of ppt., elem. anal.;97%
In dichloromethane Inert atmosphere;97%
3-iodopyridine
1120-90-7

3-iodopyridine

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-bis(pyridin-3-ylethynyl)benzene
271250-99-8

1,4-bis(pyridin-3-ylethynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 50℃; for 48h; Sonogashira coupling;97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18h; Sonogashira coupling; Inert atmosphere;65%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2,2'-(1,4-phenylenebis(ethyne-2,1-diyl))dibenzaldehyde
1301742-81-3

2,2'-(1,4-phenylenebis(ethyne-2,1-diyl))dibenzaldehyde

Conditions
ConditionsYield
Stage #1: ortho-bromobenzaldehyde With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Sonogashira Cross-Coupling;
Stage #2: 1,4-diethynylbenzene With copper(l) iodide In tetrahydrofuran at 20℃; for 24h; Sonogashira Cross-Coupling;
97%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile at 80℃; for 18h; Sonogashira coupling; Inert atmosphere;80%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

1,4-Bis(trimethylsilylethynyl)benzene
17938-13-5

1,4-Bis(trimethylsilylethynyl)benzene

Conditions
ConditionsYield
With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine In toluene at 80℃; for 24h; Inert atmosphere;97%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-4-(4-(1-benzyl-1H-1,2,3-triazole-4-yl)phenyl)-1H-1,2,3-triazole
115415-19-5

1-benzyl-4-(4-(1-benzyl-1H-1,2,3-triazole-4-yl)phenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide; [CuI(3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane)3] In water; acetonitrile at 125℃; for 0.25h; Catalytic behavior; Huisgen Cycloaddition; Sealed tube; Microwave irradiation;97%
With sodium azide; [(tris(3,5-dimethyl-1-pyrazolyl)methane)2Cu](BF4)2 In methanol; water at 125℃; for 0.5h; Catalytic behavior; Microwave irradiation;95%
With sodium azide In water at 40℃; for 3h;89%
1,4-diethynylbenzene
935-14-8

1,4-diethynylbenzene

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

1,4-<1,2-bis(diphenylphosphinoxido)ethyl>ethynylbenzene

1,4-<1,2-bis(diphenylphosphinoxido)ethyl>ethynylbenzene

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In water; benzene for 1h;96.5%

935-14-8Relevant articles and documents

A Heterobimetallic AuIII-PtII Photocatalyst for Water Reduction to Hydrogen

Su, Yi-Bing,Yuan, Yong-Jun,Liu, Xiao-Le,Chen, Guang-Hui,Chen, Xin,Yu, Zhen-Tao,Zou, Zhi-Gang

, p. 527 - 531 (2019)

A supramolecular complex, [Au(C^N^C)(C≡CC6H4C≡C)Pt(terpy)]+, has been synthesized as a photocatalyst for water reduction. This compound consists of a cyclometalated alkyne-gold(III) photosensitizer and a platinum(II) terpyridine complex bridged through a central phenylethynyl group.

2D arrays of organic qubit candidates embedded into a pillared-paddlewheel metal-organic framework

Forbes, Malcolm D. E.,Garcia-Garibay, Miguel A.,Jellen, Marcus J.,Ayodele, Mayokun J.,Cantu, Annabelle

supporting information, p. 18513 - 18521 (2020/11/27)

The creation of ordered arrays of qubits that can be interfaced from the macroscopic world is an essential challenge for the development of quantum information science (QIS) currently being explored by chemists and physicists. Recently, porous metal?organic frameworks (MOFs) have arisen as a promising solution to this challenge as they allow for atomic-level spatial control of the molecular subunits that comprise their structures. To date, no organic qubit candidates have been installed in MOFs despite their structural variability and promise for creating systems with adjustable properties. With this in mind, we report the development of a pillared-paddlewheel-type MOF structure that contains 4,7-bis(2-(4-pyridyl)-ethynyl) isoindoline N-oxide and 1,4-bis(2-(4-pyridyl)-ethynyl)-benzene pillars that connect 2D sheets of 9,10-dicarboxytriptycene struts and Zn2(CO2)4 secondary binding units. The design allows for the formation of ordered arrays of reorienting isoindoline nitroxide spin centers with variable concentrations through the use of mixed crystals containing the secondary 1,4-phenylene pillar. While solvent removal causes decomposition of the MOF, magnetometry measurements of the MOF containing only N-oxide pillars demonstrated magnetic interactions with changes in magnetic moment as a function of temperature between 150 and 5 K. Variable-temperature electron paramagnetic resonance (EPR) experiments show that the nitroxides couple to one another at distances as long as 2 nm, but act independently at distances of 10 nm or more. We also use a specially designed resonance microwave cavity to measure the face-dependent EPR spectra of the crystal, demonstrating that it has anisotropic interactions with impingent electromagnetic radiation.

Synthesis and characterization of propeller-shaped mono- to hexacationic quinolinium-substituted benzenes

Batsyts, Sviatoslav,Hübner, Eike G.,Namyslo, Jan C.,Gjikaj, Mimoza,Schmidt, Andreas

, p. 4102 - 4114 (2019/04/30)

Diels-Alder reaction of 2-, 3- and 4-(phenylethynyl)quinolines and tetraphenylcyclopentadienone gave three regioisomeric 2,3,4,5,6-pentaphenyl-1-(quinolin-2-yl, -3-yl, and -4-yl)benzenes. Restricted rotation of the 3-yl and 4-yl substituted derivatives is observed between the central core and the substituents, resulting in propeller-shaped molecules. Likewise, 1,2-diquinolinyl-3,4,5,6-tetraphenylbenzenes with 3-yl,3-yl and 3-yl,4-yl connectivity were prepared. As evidenced by NMR spectroscopy, they form two diasteromers due to their restricted rotation. A cobalt-catalyzed [2 + 2 + 2]-cyclotrimerization of 2-(phenylethynyl)quinoline resulted in the formation of triphenyl-2,4,6- and -3,5,6-tri(quinolin-2-yl)benzenes. The same reaction was applied to 3,3′-ethyne-1,2-diyldiquinoline which formed hexa(quinolin-3-yl)benzene. N-Methylation gave the title compounds. Among those, the hexacationic hexa(N-methylquinolinio-3-yl)benzene is described. Stereochemical aspects are predominantly discussed by means of results of NMR experiments. DFT-calculations on the most stable conformations and the frontier orbital profiles of the hexacation as well as of its neutral precursor have been carried out.

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