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626-44-8

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626-44-8 Usage

Uses

1,3,5-Triiodobenzene is used in the synthesis of conjugated microporous polymers through cationic cyclization polymerization. It also can be used in optical materials.

Synthesis

1,3,5-Triiodobenzene was synthesized by reacting 2,4,6-triiodoaniline with NaNO2 in the presence of copper(I) oxide.Experimental procedure: Finely ground NaNO2 (1.95 g, 0.028 mol) was slowly added with stirring to sulfuric acid (3.5 mL). Then a solution of 2,4,6-triiodoaniline(2.90 g, 6.16 mmol) in glacial AcOH (130 mL) was added dropwise with stirring and cooling at such a rate that the temperature of the reaction mixture was kept below 20 °C. Following addition of the amine, the reaction mixture was stirred at ≈20 °C for about 30 min. The resulting solution of the diazonium salt was added dropwise to a suspension of copper(I) oxide (2.52 g) in dry ethanol (70 mL) with vigorous stirring over 15 min. The reaction mixture was brought to boiling and stirred for 30 min until elimination of nitrogen ceased. Then the mixture was cooled, kept for one day, poured into ice water (300 mL), and extracted with benzene (3×50 mL). The benzene extracts were dried with anhydrous Na2SO4 and the solvent was distilled off in vacuo. The residue was repeatedly recrystallized from benzene. The yield was 2.01 g (84%), m.p. 182 °C (cf. lit. data11: m.p. 183 °C). 1H NMR (CDCl3), δ: 8.02 (s, 3 H, CH). 13C NMR (CDCl3), δ: 79; 128.

Check Digit Verification of cas no

The CAS Registry Mumber 626-44-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 6 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 626-44:
(5*6)+(4*2)+(3*6)+(2*4)+(1*4)=68
68 % 10 = 8
So 626-44-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H3I3/c7-4-1-5(8)3-6(9)2-4/h1-3H

626-44-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3,5-TRIIODOBENZENE

1.2 Other means of identification

Product number -
Other names 1,3,5-triodobenzene

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:626-44-8 SDS

626-44-8Synthetic route

1,3,5-tris(trimethylsilyl)benzene
5624-60-2

1,3,5-tris(trimethylsilyl)benzene

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 0 - 20℃;92%
With Iodine monochloride In dichloromethane at 0 - 20℃;91%
With Iodine monochloride In dichloromethane at 0℃;90%
With Iodine monochloride In tetrachloromethane at 20℃; for 24h;36%
2,4,6-triiodoaniline
24154-37-8

2,4,6-triiodoaniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Stage #1: 2,4,6-triiodoaniline With sulfuric acid; acetic acid; sodium nitrite at 20℃; for 0.5h;
Stage #2: With copper(I) oxide In ethanol for 0.5h; Heating;
84%
With sulfuric acid; sodium nitrite; benzene
deamination; Yield given;
1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
With iodine; nickel; potassium iodide In N,N-dimethyl-formamide at 187℃; for 8h; Schlenk technique; Inert atmosphere;83%
With nickel; potassium iodide In N,N-dimethyl-formamide at 185 - 190℃; for 3h;75%
With iodine; nickel; potassium iodide In dimethyl sulfoxide72%
3,5-diiodoaniline
35122-96-4

3,5-diiodoaniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
With hydrogenchloride; potassium iodide; sodium nitrite In acetonitrile at 0℃;79%
C6H3IN4(2+)*2HO4S(1-)

C6H3IN4(2+)*2HO4S(1-)

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
With potassium iodide at 20℃;68%
1-iodo-3,5-diaminobenzene
111938-17-1

1-iodo-3,5-diaminobenzene

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Stage #1: 1-iodo-3,5-diaminobenzene With sulfuric acid; sodium nitrite at 0℃;
Stage #2: With water; potassium iodide
68%
Multi-step reaction with 2 steps
1: NaNO2 / H2SO4 / -10 - -5 °C
2: 68 percent / KI / 20 °C
View Scheme
1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

A

1,3-Diiodobenzene
626-00-6

1,3-Diiodobenzene

B

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

C

1,3-diiodo-5-bromobenzene
149428-64-8

1,3-diiodo-5-bromobenzene

Conditions
ConditionsYield
With 1,3-dimethyl-1,3-diazacyclohexane; copper(l) iodide; potassium iodide at 155℃; for 24.5h; Substitution;A n/a
B 33%
C n/a
benzene
71-43-2

benzene

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
With sulfuric acid; iodine
3,4,5-triiodoaniline
108673-30-9

3,4,5-triiodoaniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
(deamination);
4-nitro-aniline
100-01-6

4-nitro-aniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Yield given;
sulfuric acid
7664-93-9

sulfuric acid

iodine
7553-56-2

iodine

benzene
71-43-2

benzene

A

1,2,4-triiodobenzene
615-68-9

1,2,4-triiodobenzene

B

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

diazotized 3.5-diiodo-aniline

diazotized 3.5-diiodo-aniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
With potassium iodide
aniline
62-53-3

aniline

[(Xantphos)2Pd(3-methyl-1-butenyl]OTf

[(Xantphos)2Pd(3-methyl-1-butenyl]OTf

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 87 percent / potassium dichloroiodate; aq. HCl / 20 °C
2.1: NaNO2; sulfuric acid; glacial AcOH / 0.5 h / 20 °C
2.2: 84 percent / copper(I) oxide / ethanol / 0.5 h / Heating
View Scheme
3,5-dinitroiodobenzene
6276-04-6

3,5-dinitroiodobenzene

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 98 percent / SnCl2 / ethyl acetate / Heating
2.1: NaNO2; aq. H2SO4 / 0 °C
2.2: 68 percent / KI; H2O
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / stannous chloride / ethyl acetate
2: NaNO2 / H2SO4 / -10 - -5 °C
3: 68 percent / KI / 20 °C
View Scheme
aniline
62-53-3

aniline

2-halogen-aniline

2-halogen-aniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: I2
2: deamination
View Scheme
aniline
62-53-3

aniline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrochloric acid; iodine chloride
2: sodium nitrite; sulfuric acid; alcohol containing benzene
View Scheme
1,3,5-trichlorobenzene
108-70-3

1,3,5-trichlorobenzene

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium / tetrahydrofuran / 20 °C / Reflux
2: Iodine monochloride / dichloromethane / 0 - 20 °C
View Scheme
2,4,6-triiodoaniline
24154-37-8

2,4,6-triiodoaniline

A

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

B

2-chloro-1,3,5-triiodo-benzene
57830-61-2

2-chloro-1,3,5-triiodo-benzene

Conditions
ConditionsYield
Stage #1: 2,4,6-triiodoaniline With toluene-4-sulfonic acid; sodium nitrite In water; acetonitrile at 20℃; for 1.5h; Sandmeyer Reaction;
Stage #2: With copper(l) chloride In water; acetonitrile at 20℃; for 0.666667h; Sandmeyer Reaction; Overall yield = 0.69 g;
A n/a
B 0.69 g
aniline
62-53-3

aniline

A

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

B

2-chloro-1,3,5-triiodo-benzene
57830-61-2

2-chloro-1,3,5-triiodo-benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium iodide; sulfuric acid; dihydrogen peroxide / methanol / 6 h / Reflux
2.1: sodium nitrite; toluene-4-sulfonic acid / acetonitrile; water / 1.5 h / 20 °C
2.2: 0.67 h / 20 °C
View Scheme
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

3,7:10,14-dianhydro-4,5,6,11,12,13,15-hepta-O-benzyl-1,2,8,9-tetradeoxy-D-erythro-L-talo-D-gulo-pentadec-1-ynitol
499134-86-0

3,7:10,14-dianhydro-4,5,6,11,12,13,15-hepta-O-benzyl-1,2,8,9-tetradeoxy-D-erythro-L-talo-D-gulo-pentadec-1-ynitol

C198H198O27

C198H198O27

Conditions
ConditionsYield
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 60℃; for 48h; Sonogashira-Heck-Cassar cross-coupling;100%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,3,5-tris-(1-trimethylsilylethynyl)benzene
18772-58-2

1,3,5-tris-(1-trimethylsilylethynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 3h;99%
Stage #1: 1,3,5-Triiodobenzene With copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; isopropylamine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilylacetylene In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;
90%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

1,3,5-triphenylbenzene
612-71-5

1,3,5-triphenylbenzene

Conditions
ConditionsYield
With potassium carbonate In 1,2-dimethoxyethane at 100℃; for 24h; Suzuki Coupling;99%
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide; caesium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 125 - 130℃; for 48h; Suzuki-Miyaura cross-coupling;48%
(2,6-dimethoxy-4-pentylphenyl)boronic acid
1004305-27-4

(2,6-dimethoxy-4-pentylphenyl)boronic acid

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

1,3,5-tris(2,6-dimethoxy-4-pentylphenyl)benzene
1039358-36-5

1,3,5-tris(2,6-dimethoxy-4-pentylphenyl)benzene

Conditions
ConditionsYield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 42h; Suzuki coupling;98%
2-[(4-ethynylbenzyl)oxy]ethanol
912814-89-2

2-[(4-ethynylbenzyl)oxy]ethanol

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2,2',2''-((((benzene-1,3,5-triyltris(ethyne-2,1-diyl))tris(benzene-4,1-diyl))tris(methylene))tris(oxy))triethanol

2,2',2''-((((benzene-1,3,5-triyltris(ethyne-2,1-diyl))tris(benzene-4,1-diyl))tris(methylene))tris(oxy))triethanol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at -78 - 20℃; for 48h; Inert atmosphere; Cooling with acetone-dry ice;98%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

C33H47ClO5

C33H47ClO5

C105H138O15

C105H138O15

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 72h; Sonogashira Cross-Coupling; Inert atmosphere; Sonication;96.1%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

3-ethylnyl-10-methyl-10H-phenothiazine
250347-36-5

3-ethylnyl-10-methyl-10H-phenothiazine

1,3,5-tris(10-methyl-10H-phenothiazin-3-ylethynyl)benzene

1,3,5-tris(10-methyl-10H-phenothiazin-3-ylethynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene for 5h; Sonogashira coupling; Heating;94%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

3,5-bis(trimethylsilylethynyl)-1-ethynylbenzene
599187-53-8

3,5-bis(trimethylsilylethynyl)-1-ethynylbenzene

1,3,5-tris[(3,5-bis-trimethylsilylethynylphenyl)ethynyl]benzene

1,3,5-tris[(3,5-bis-trimethylsilylethynylphenyl)ethynyl]benzene

Conditions
ConditionsYield
With copper (I) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 12h;93%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

C28H18F4N2

C28H18F4N2

C90H54F12N6

C90H54F12N6

Conditions
ConditionsYield
Stage #1: C28H18F4N2 With copper(l) chloride; lithium tert-butoxide In N,N-dimethyl-formamide at 25℃; for 1h; Sealed tube; Glovebox; Sonication;
Stage #2: 1,3,5-Triiodobenzene With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 12h; Sealed tube; Glovebox;
93%
With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride; lithium tert-butoxide In N,N-dimethyl-formamide Inert atmosphere;
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2,3,5,6-tetrafluorobiphenyl
834-89-9

2,3,5,6-tetrafluorobiphenyl

C42H18F12

C42H18F12

Conditions
ConditionsYield
Stage #1: 2,3,5,6-tetrafluorobiphenyl With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;
Stage #2: 1,3,5-Triiodobenzene With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 12h; Inert atmosphere; Glovebox; Sealed tube; Heating;
93%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

4'-ethynyl-4,5-bis(butylthio)tetrathiafulvalene

4'-ethynyl-4,5-bis(butylthio)tetrathiafulvalene

C54H60S18

C54H60S18

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In benzene Sonogashira coupling;92%
3-ethynyl-2-(4-hydroxy-2,6-dimethylphenyl)-9-mesityl-[1,10]phenanthroline
949922-97-8

3-ethynyl-2-(4-hydroxy-2,6-dimethylphenyl)-9-mesityl-[1,10]phenanthroline

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

C99H78N6O3
1084886-23-6

C99H78N6O3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Sonogashira coupling; Inert atmosphere;91%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2,2'-bithiophene-5-boronic acid
132898-95-4

2,2'-bithiophene-5-boronic acid

2-{3,5-bis[5-(thiophen-2-yl)thiophen-2-yl]phenyl}-5-(thiophen-2-yl)thiophene

2-{3,5-bis[5-(thiophen-2-yl)thiophen-2-yl]phenyl}-5-(thiophen-2-yl)thiophene

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water for 72h; Suzuki coupling; Inert atmosphere; Reflux;90%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

4,5-bis-ethylsulfanyl-4'-ethynyl-[2,2']bi[[1,3]dithiolylidene]
475113-97-4

4,5-bis-ethylsulfanyl-4'-ethynyl-[2,2']bi[[1,3]dithiolylidene]

C42H36S18

C42H36S18

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In benzene Sonogashira coupling;89%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

1,3,5-tris(2'-aminophenyl)benzene
923027-14-9

1,3,5-tris(2'-aminophenyl)benzene

Conditions
ConditionsYield
With barium dihydroxide; CyJohnPhos; palladium diacetate In 1,4-dioxane at 85℃; for 24h; Suzuki-Miyaura cross-coupling;89%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

1,3,5-tris(triisopropylsilylethynyl)benzene

1,3,5-tris(triisopropylsilylethynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine for 18h; Sonogashira Cross-Coupling; Darkness; Inert atmosphere;89%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

4-ethynylthioanisole
56041-85-1

4-ethynylthioanisole

C33H24S3
1226915-45-2

C33H24S3

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In toluene for 10h; Inert atmosphere; Heating;88.5%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

(1R,2S)-2-({4-[3-Ethynyl-5-(4-{[((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phenylethynyl)-phenylethynyl]-benzyl}-methyl-amino)-1-phenyl-propan-1-ol
283597-76-2

(1R,2S)-2-({4-[3-Ethynyl-5-(4-{[((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phenylethynyl)-phenylethynyl]-benzyl}-methyl-amino)-1-phenyl-propan-1-ol

C144H132N6O6

C144H132N6O6

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide Condensation;88%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2-ethynyl-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane
73022-81-8

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

1,3,5-tris[2-(tris(trimethylsilyl)silyl)ethynyl]benzene
874396-92-6

1,3,5-tris[2-(tris(trimethylsilyl)silyl)ethynyl]benzene

Conditions
ConditionsYield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Sonogashira coupling reaction;88%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

(E)-(2-ethynylcyclopropyl) ethyl ether
20834-16-6, 98065-83-9, 98065-84-0

(E)-(2-ethynylcyclopropyl) ethyl ether

1,3,5-tris<(trans-2-ethoxycyclopropyl)ethynyl>benzene

1,3,5-tris<(trans-2-ethoxycyclopropyl)ethynyl>benzene

Conditions
ConditionsYield
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 1h;87%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2-[4-(4-ethynyl-2,5-dihexyl-phenylethynyl)-phenoxy]-tetrahydro-pyran
312624-90-1

2-[4-(4-ethynyl-2,5-dihexyl-phenylethynyl)-phenoxy]-tetrahydro-pyran

C105H126O6

C105H126O6

Conditions
ConditionsYield
With piperidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; for 6.5h; coupling;87%
5-ethynyl-10,20-bis[3,5-bis(1,1-dimethylethyl)phenyl]-15-[(pyrid-4-yl)ethynyl]-21H,23H-porphine

5-ethynyl-10,20-bis[3,5-bis(1,1-dimethylethyl)phenyl]-15-[(pyrid-4-yl)ethynyl]-21H,23H-porphine

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

5,5',5''-[1,3,5-benzenetriyltris(2,1-ethynediyl)]tris-[10,20-bis(3,5-bis(1,1-dimethylethyl)phenyl)-15-[(pyrid-4-yl)ethynyl]-21H,23H-porphine]

5,5',5''-[1,3,5-benzenetriyltris(2,1-ethynediyl)]tris-[10,20-bis(3,5-bis(1,1-dimethylethyl)phenyl)-15-[(pyrid-4-yl)ethynyl]-21H,23H-porphine]

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine In toluene at 35℃; Sonogashira coupling;87%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2-aminophenylboronic acid
5570-18-3

2-aminophenylboronic acid

1,3,5-tris(2'-aminophenyl)benzene
923027-14-9

1,3,5-tris(2'-aminophenyl)benzene

Conditions
ConditionsYield
With barium dihydroxide; CyJohnPhos; palladium diacetate In 1,4-dioxane at 85℃; for 24h; Suzuki-Miyaura cross-coupling;87%
Cp*Co(2,3-Et2C2B3H4-5-CCH)

Cp*Co(2,3-Et2C2B3H4-5-CCH)

1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

(Cp*Co(2,3-Et2C2B3H4-5-CC))3C6H3

(Cp*Co(2,3-Et2C2B3H4-5-CC))3C6H3

Conditions
ConditionsYield
With CuI; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran87%
With CuI; Et3N; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran under N2 atm. to mixt. cobaltacarborane, Pd(PPh3)2Cl2, CuI, and C6H3I3 were added THF and Et3N and stirred for 4 h; solvent was removed in vacuo, residue was taken up in CH2Cl2 and chromed. on silica (hexane); elem. anal.;87%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

allyl bromide
106-95-6

allyl bromide

A

1,3-Diiodobenzene
626-00-6

1,3-Diiodobenzene

B

1-allyl-3,5-diiodobenzene
528577-29-9

1-allyl-3,5-diiodobenzene

Conditions
ConditionsYield
Stage #1: 1,3,5-Triiodobenzene With n-butyllithium In hexane; toluene at 20℃; for 72h;
Stage #2: allyl bromide In hexane; toluene for 24h;
A n/a
B 86%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

thiophen-2-yl magnesium bromide
5713-61-1

thiophen-2-yl magnesium bromide

1,3,5-tris(2-thienyl)benzene
15509-95-2

1,3,5-tris(2-thienyl)benzene

Conditions
ConditionsYield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In tetrahydrofuran; diethyl ether at 20℃; for 48h; Kumada coupling reaction; Inert atmosphere; Cooling with ice;86%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside
346420-68-6

Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside

C123H126O54

C123H126O54

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 60℃; for 5h;85%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

2-propynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
211688-84-5

2-propynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

1,3,5-tris[3'-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)prop-1'-enyl]benzene

1,3,5-tris[3'-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)prop-1'-enyl]benzene

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In triethylamine; N,N-dimethyl-formamide at 60℃; for 6h; Sonogashira reaction;85%
1,3,5-Triiodobenzene
626-44-8

1,3,5-Triiodobenzene

(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran
168253-07-4

(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran

C114H108O15

C114H108O15

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) Sonogashira-Heck-Cassar cross-coupling;85%

626-44-8Relevant articles and documents

Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions

Desaintjean, Alexandre,Danton, Fanny,Knochel, Paul

supporting information, p. 4461 - 4476 (2021/08/13)

A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents are prepared in toluene within 10 to 120 minutes between 78 C and 25 C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as triazene or nitro, are tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arene and alkene derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.

Size-controlled synthesis of conjugated polymer nanoparticles in confined nanoreactors

Deng, Sheng,Zhi, Jian,Zhang, Xianmei,Wu, Qingqing,Ding, Yun,Hu, Aiguo

supporting information, p. 14144 - 14148 (2015/02/19)

Soluble conjugated polymeric nanoparticles are synthesized by Suzuki-type polycondensation of two monomers (Ax + By, x>2, y≥2) in the channel of ordered mesoporous silica-supported carbon nano-membranes (nanoreactors). These synthesized soluble conjugated microporous polymers (SCMPs) exhibit uniform particle-size distributions and well-controlled particle sizes. The control of particle size stems from the fact that the polycondensations exclusively take place inside the mesochannels of the nano-reactors. Photo-luminescence studies show that polymeric nanoparticles with tetraphenylethene and pyrene substructures are highly fluorescent. The combination of both physical stability and process-ability offered by the soluble polymeric nanoparticles makes them particularly attractive in light emitting and other optoelectronic applications.

Facile aromatic finkelstein iodination (AFI) reaction in 1,3-dimethyl-2-imidazolidinone (DMI)

Yamashita, Ken-Ichi,Tsuboi, Michihiro,Asano, Motoko S.,Sugiura, Ken-Ichi

experimental part, p. 170 - 175 (2011/11/29)

In this communication, we report the superior role of 1,3-dimethyl-2- imidazolidinone (DMI) as a solvent for aromatic Finkelstein iodination (AFI), the conversion of aryl bromides to aryl iodides. DMI accelerates the reaction rate and affords product(s) that could not be prepared using previous methods. Our findings for AFI avoid the use of toxic solvents such as N,N-dimethylformamide and hexamethylphosphoramide. Taylor & Francis Group, LLC.

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