Benzene, 1,3,5-triiodo- supplier

Name
1,3,5-TRIIODOBENZENE
EINECS 604-604-1
CAS No. 626-44-8
Article Data25
CAS DataBase
Density 2.928 g/cm³
Solubility
Melting Point 184.2°C
Formula C₆H₃I₃
Boiling Point 383.8 °C at 760 mmHg
Molecular Weight 455.803
Flash Point 209 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,3,5-Triiodobenzene;
PSA 0.00000
LogP 3.50040

Synthetic route

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

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

Conditions

Conditions	Yield
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%

: 24154-37-8
2,4,6-triiodoaniline

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

Conditions

Conditions	Yield
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;

: 626-39-1
1,3,5-trisbromobenzene

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

Conditions

Conditions	Yield
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 sulfoxide	72%

: 35122-96-4
3,5-diiodoaniline

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

Conditions

Conditions	Yield
With hydrogenchloride; potassium iodide; sodium nitrite In acetonitrile at 0℃;	79%

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

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

Conditions

Conditions	Yield
With potassium iodide at 20℃;	68%

: 111938-17-1
1-iodo-3,5-diaminobenzene

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

Conditions

Conditions	Yield
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

: 626-39-1
1,3,5-trisbromobenzene

A: 626-00-6
1,3-Diiodobenzene

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

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

Conditions

Conditions	Yield
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

...Expand

: 71-43-2
benzene

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

Conditions

Conditions	Yield
With sulfuric acid; iodine

: 108673-30-9
3,4,5-triiodoaniline

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

Conditions

Conditions	Yield
(deamination);

: 100-01-6
4-nitro-aniline

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

Conditions

Conditions	Yield
Yield given;

: 7664-93-9
sulfuric acid

: 7553-56-2
iodine

: 71-43-2
benzene

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

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

...Expand

diazotized 3.5-diiodo-aniline: diazotized 3.5-diiodo-aniline

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

Conditions

Conditions	Yield
With potassium iodide

: 62-53-3
aniline

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

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

Conditions

Conditions	Yield
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

: 6276-04-6
3,5-dinitroiodobenzene

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

Conditions

Conditions	Yield
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

: 62-53-3
aniline

2-halogen-aniline: 2-halogen-aniline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: I2 2: deamination View Scheme

: 62-53-3
aniline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrochloric acid; iodine chloride 2: sodium nitrite; sulfuric acid; alcohol containing benzene View Scheme

: 108-70-3
1,3,5-trichlorobenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 20 °C / Reflux 2: Iodine monochloride / dichloromethane / 0 - 20 °C View Scheme

: 24154-37-8
2,4,6-triiodoaniline

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

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

Conditions

Conditions	Yield
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

: 62-53-3
aniline

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

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

Conditions

Conditions	Yield
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

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

: 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

Conditions

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 60℃; for 48h; Sonogashira-Heck-Cassar cross-coupling;	100%

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

: 1066-54-2
trimethylsilylacetylene

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

Conditions

Conditions	Yield
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%

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

: 98-80-6
phenylboronic acid

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

Conditions

Conditions	Yield
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%

: 1004305-27-4
(2,6-dimethoxy-4-pentylphenyl)boronic acid

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

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

Conditions

Conditions	Yield
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%

: 912814-89-2
2-[(4-ethynylbenzyl)oxy]ethanol

: 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

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at -78 - 20℃; for 48h; Inert atmosphere; Cooling with acetone-dry ice;	98%

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

: C33H47ClO5

: C105H138O15

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 72h; Sonogashira Cross-Coupling; Inert atmosphere; Sonication;	96.1%

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

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

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

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene for 5h; Sonogashira coupling; Heating;	94%

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

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

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

Conditions

Conditions	Yield
With copper (I) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride	93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 12h;	93%

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

: C28H18F4N2

: C90H54F12N6

Conditions

Conditions	Yield
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;

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

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

: C42H18F12

Conditions

Conditions	Yield
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%

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

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

: C54H60S18

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In benzene Sonogashira coupling;	92%

: 949922-97-8
3-ethynyl-2-(4-hydroxy-2,6-dimethylphenyl)-9-mesityl-[1,10]phenanthroline

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

: 1084886-23-6
C99H78N6O3

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Sonogashira coupling; Inert atmosphere;	91%

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

: 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

Conditions

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water for 72h; Suzuki coupling; Inert atmosphere; Reflux;	90%

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

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

: C42H36S18

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In benzene Sonogashira coupling;	89%

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

: 191171-55-8
2-anilineboronic acid pinacol ester

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

Conditions

Conditions	Yield
With barium dihydroxide; CyJohnPhos; palladium diacetate In 1,4-dioxane at 85℃; for 24h; Suzuki-Miyaura cross-coupling;	89%

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

: 89343-06-6
tris-iso-propylsilyl acetylene

: 1,3,5-tris(triisopropylsilylethynyl)benzene

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine for 18h; Sonogashira Cross-Coupling; Darkness; Inert atmosphere;	89%

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

: 56041-85-1
4-ethynylthioanisole

: 1226915-45-2
C33H24S3

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In toluene for 10h; Inert atmosphere; Heating;	88.5%

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

: 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

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide Condensation;	88%

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

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

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

Conditions

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Sonogashira coupling reaction;	88%

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

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

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

Conditions

Conditions	Yield
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 1h;	87%

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

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

: C105H126O6

Conditions

Conditions	Yield
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

: 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]

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine In toluene at 35℃; Sonogashira coupling;	87%

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

: 5570-18-3
2-aminophenylboronic acid

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

Conditions

Conditions	Yield
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)

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

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

Conditions

Conditions	Yield
With CuI; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran	87%
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%

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

: 106-95-6
allyl bromide

A: 626-00-6
1,3-Diiodobenzene

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

Conditions

Conditions	Yield
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%

...Expand

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

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

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

Conditions

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In tetrahydrofuran; diethyl ether at 20℃; for 48h; Kumada coupling reaction; Inert atmosphere; Cooling with ice;	86%

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

: 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

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 60℃; for 5h;	85%

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

: 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

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In triethylamine; N,N-dimethyl-formamide at 60℃; for 6h; Sonogashira reaction;	85%

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

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

: C114H108O15

Conditions

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

Benzene, 1,3,5-triiodo- Specification

This chemical is called Benzene, 1,3,5-triiodo-, and its CAS registry number is 626-44-8. With the molecular formula of C₆H₃I₃, its molecular weight is 455.80.

Other characteristics of the Benzene, 1,3,5-triiodo- can be summarised as followings: (1)ACD/LogP: 3.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.94; (4)ACD/LogD (pH 7.4): 3.94; (5)ACD/BCF (pH 5.5): 584.83; (6)ACD/BCF (pH 7.4): 584.83; (7)ACD/KOC (pH 5.5): 3328.44; (8)ACD/KOC (pH 7.4): 3328.44; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.774; (13)Molar Refractivity: 64.97 cm³; (14)Molar Volume: 155.6 cm³; (15)Polarizability: 25.75×10^-24cm³; (16)Surface Tension: 60.4 dyne/cm; (17)Density: 2.928 g/cm³; (18)Flash Point: 209 °C; (19)Enthalpy of Vaporization: 60.77 kJ/mol; (20)Boiling Point: 383.8 °C at 760 mmHg; (21)Vapour Pressure: 9.43E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: Ic1cc(I)cc(I)c1
2.InChI: InChI=1/C6H3I3/c7-4-1-5(8)3-6(9)2-4/h1-3H
3.InChIKey: WXLJJIHGDBUBJM-UHFFFAOYAM

Product Name

1,3,5-TRIIODOBENZENE

Synthetic route

Benzene, 1,3,5-triiodo- Specification

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