275-51-4

Basic information

• Product Name: AZULENE
• Synonyms: AZULEN;AZULENE;BICYCLO(5.3.0)-DECA-1,3,5,7,9-PENTAENE;BICYCLO[5.3.0]DECAPENTAENE;LABOTEST-BB LT00007822;CYCLOPENTACYCLOHEPTEN;CYCLOPENTACYCLOHEPTENE;Azunamic
• CAS NO: 275-51-4
• Molecular Formula: C₁₀H₈
• Molecular Weight: 128.17
• EINECS: 205-993-6
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Tropolones & Azulenes;Azulenes
• Mol File: 275-51-4.mol
• Article Data: 46

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 242 °C(lit.)
• Flash Point: 241-243°C
• Appearance: Dark blue/Fine Crystalline Powder
• Density: 1.0530
• Vapor Pressure: 0.165mmHg at 25°C
• Refractive Index: 1.5736 (estimate)
• Storage Temp.: Store at +2°C to +8°C.
• Solubility: Soluble in organic solvents.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,926
• BRN: 969517
• CAS DataBase Reference: AZULENE(CAS DataBase Reference)
• NIST Chemistry Reference: AZULENE(275-51-4)
• EPA Substance Registry System: AZULENE(275-51-4)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: CO4570000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 275-51-4(Hazardous Substances Data)

Usage

Chemical Description

Azulene is a bicyclic aromatic hydrocarbon with a blue color and a characteristic odor.

Chemical Properties

Blue Crystal

Uses

Different sources of media describe the Uses of 275-51-4 differently. You can refer to the following data:
1. Azulene is used as an additive in ointments. It is an active ingredient in cosmetics, shaving creams and other topicals. It is used as antioxidant and in anti-inflammatory activities. It is involved in the colorimetric determination of furfural. It acts as ligand for low valent metals and forms pi complexes with both cyclopentadienyl and cylcloheptatrienyl ligands in organometallic chemistry. It is also used as precursor for the preparation of (azulene)Mo2 (CO)6 and (azulene)Fe2 (CO)5.
2. azulene is renowned as an anti-inflammatory, calming, and soothing agent. excellent for sensitive skin, azulene is a german chamomile derivative with a characteristic deep blue color. Careful, it stains!

Definition

Different sources of media describe the Definition of 275-51-4 differently. You can refer to the following data:
1. A blue crystalline compound having a seven-membered ring fused to a five-membered ring. It converts to naphthalene on heating.
2. azulene: A blue crystalline compound,C10H8; m.p. 99°C. It contains afive-membered ring fused to a sevenmemberedring and has aromaticproperties. When heated it is convertedinto naphthalene.
3. ChEBI: A mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 2386, 1953 DOI: 10.1021/ja01106a030Tetrahedron Letters, 23, p. 495, 1982 DOI: 10.1016/S0040-4039(00)86871-9

Safety Profile

Poison by intraperitoneal,intravenous, and subcutaneous routes. When heated todecomposition it emits acrid smoke and irritating vapors.

Purification Methods

Crystallise azulene from EtOH. It has UV max 270nm (log 4.72) in hexane. [Platner & Magyar Helv Chim Acta 25 581 1942, Beilstein 5 IV 1636.]

InChI:InChI=1/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H

Synthetic route

tetracyclo<5.3.0.02.4.03.5>deca-6,8,10-triene (92622-71-4) → azulene (275-51-4)

Conditions	Yield
In cyclohexane Quantum yield; Irradiation;	100%
In (2)H8-toluene at 90 - 120℃; Thermodynamic data; Rate constant; ΔH (excit.), ΔS (excit.), Ea;

2-azulenyl trifluoromethanesulfonate (607393-61-3) → azulene (275-51-4)

Conditions	Yield
With formic acid; tributyl-amine; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 24h; Heating;	96%

6-(dimethylamino)fulvene (696-68-4) + (1R,2S,6R,7R)-3,3-Dioxo-3λ6-thia-tricyclo[5.2.2.02,6]undeca-4,8,10-triene-8,9-dicarboxylic acid dimethyl ester → phthalic acid dimethyl ester (131-11-3) + azulene (275-51-4)

Conditions	Yield
In 1,2-dichloro-ethane for 44h; Product distribution; Decomposition; retro-Diels-Alder reaction; Heating;	A 94% B 31%

1-chloroazulene (23306-02-7) → azulene (275-51-4)

Conditions	Yield
With potassium phosphate; poly(methylhydrosiloxane); palladium diacetate In tetrahydrofuran at 80℃; for 12h;	92%

azulene-1-carboxylic acid (1201-25-8) → azulene (275-51-4)

Conditions	Yield
With trichloroacetic acid In benzene for 6h; Heating;	90%

para-nitrophenyl bromide (586-78-7) + 6-(tri-n-butylstannyl)azulene (441292-61-1) → 6-(4-nitrophenyl)azulene + azulene (275-51-4)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In 1,4-dioxane for 2h; Heating;	A 83% B 5%

6-bromoazulene (35046-05-0) + para-nitrophenyl bromide (586-78-7) → 6-(4-nitrophenyl)azulene + azulene (275-51-4)

Conditions	Yield
Stage #1: 6-bromoazulene With bis(tri-n-butyltin); tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Heating; Stage #2: para-nitrophenyl bromide With tri-tert-butyl phosphine; cesium fluoride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 2h; Stille cross-coupling; Heating; Further stages.;	A 83% B 5%

hexan-1-amine (111-26-2) + 2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (620634-44-8) + 2,2-dihydroxyacetic acid (563-96-2) → 2-(azulen-1-yl)-N-hexylglycine + azulene (275-51-4)

Conditions	Yield
In methanol at 20℃; for 3h; Petasis Reaction; Inert atmosphere;	A 82% B 6%

((E)-Buta-1,3-dienyl)-diethyl-amine (52866-26-9) + 6-<(p-Nitrobenzoyl)oxy>fulvene (82215-26-7) → 6-(1-azulenyl)fulvene (82215-27-8) + azulene (275-51-4)

Conditions	Yield
In benzene for 7h; Ambient temperature;	A n/a B 68%

1-bromo-4-methoxy-benzene (104-92-7) + 6-(tri-n-butylstannyl)azulene (441292-61-1) → 6-(4-methoxyphenyl)azulene + azulene (275-51-4)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In 1,4-dioxane for 6h; Heating;	A 63% B 6%

1-bromo-4-methoxy-benzene (104-92-7) + 6-bromoazulene (35046-05-0) → 6-(4-methoxyphenyl)azulene + azulene (275-51-4)

Conditions	Yield
Stage #1: 6-bromoazulene With bis(tri-n-butyltin); tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Heating; Stage #2: 1-bromo-4-methoxy-benzene With tri-tert-butyl phosphine; cesium fluoride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 6h; Stille cross-coupling; Heating; Further stages.;	A 63% B 6%

5-(2-azulenyl)tetrazole → naphthalene (91-20-3) + 1H-Cyclopentindene (209-69-8) + 2-Cyanoazulene (58081-28-0) + azulene (275-51-4)

Conditions	Yield
at 600℃; under 0.000750075 - 0.0750075 Torr; for 0.833333h;	A 9% B 5% C 62% D 8%

cyclohepta[b]furan-2(2H)-one (4481-35-0) + acetaldehyde (75-07-0) → azulene (275-51-4)

Conditions	Yield
With diethylamine for 3h; Heating;	60%

tricyclo<5.3.0.02,5>deca-3,6,8,10-tetraene (92622-72-5) → azulene (275-51-4)

Conditions	Yield
In cyclohexane Quantum yield; Irradiation;	60%
In (2)H8-toluene at 120 - 140℃; Thermodynamic data; Ea, half-life;

2-chloroazulene (36044-31-2) → 2,2′-biazulene (82893-99-0) + azulene (275-51-4)

Conditions	Yield
With trifuran-2-yl-phosphane; tetraethylammonium iodide; zinc; bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 24h;	A 60% B n/a

para-bromotoluene (106-38-7) + 6-bromoazulene (35046-05-0) → 6,6'-Biazulenyl (73393-11-0) + 6-(p-Methylphenyl)azulen (102435-38-1) + azulene (275-51-4)

Conditions	Yield
Stage #1: 6-bromoazulene With bis(tri-n-butyltin); tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Heating; Stage #2: para-bromotoluene With tri-tert-butyl phosphine; cesium fluoride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 24h; Stille cross-coupling; Heating; Further stages.;	A 12% B 60% C 5%

para-bromotoluene (106-38-7) + 6-(tri-n-butylstannyl)azulene (441292-61-1) → 6,6'-Biazulenyl (73393-11-0) + 6-(p-Methylphenyl)azulen (102435-38-1) + azulene (275-51-4)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In 1,4-dioxane for 24h; Heating;	A 31% B 58% C 10%
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In 1,4-dioxane for 24h; Heating;	A 32% B 27% C 18%

1,3-dibromoazulene (14658-95-8) + sodium phenoxide (139-02-6) → 1-phenoxyazulene (78049-27-1) + azulene (275-51-4)

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide at 150℃; for 6h;	A 15% B 55%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 6-iodoazulene (691897-66-2) → azulene (275-51-4) + 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)azulene

Conditions	Yield
Stage #1: 6-iodoazulene With tri-n-butyllithium magnesate complex In diethyl ether for 0.5h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether Further stages.;	A 8% B 55%

2-iodoazulene (36044-41-4) → 2,2′-biazulene (82893-99-0) + azulene (275-51-4)

Conditions	Yield
With copper at 180℃; for 6h;	A 54% B n/a
With trifuran-2-yl-phosphane; tetraethylammonium iodide; zinc; bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 4h;	A 42% B 28%

1,3-diiodoazulene (36044-42-5) + diphenylamine (122-39-4) → 1-diphenylaminoazulene (78049-26-0) + azulene (275-51-4)

Conditions	Yield
With copper(l) iodide; copper; potassium carbonate at 160 - 170℃; for 2h;	A 19% B 54%

chloro-diphenylphosphine (1079-66-9) + 1,6-di-tert-butyl-3-iodoazulene (691897-73-1) → azulene (275-51-4) + (3,6-di-tert-butyl-azulen-1-yl)-diphenyl-phosphane

Conditions	Yield
Stage #1: 1,6-di-tert-butyl-3-iodoazulene With tri-n-butyllithium magnesate complex In diethyl ether for 0.5h; Stage #2: chloro-diphenylphosphine In diethyl ether Further stages.;	A 7% B 52%

4-tolyl iodide (624-31-7) + 2-(azulen-2-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (457644-50-7) → 2-(4-tolyl)azulene (111679-38-0) + azulene (275-51-4)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; caesium carbonate In 1,4-dioxane at 80℃; for 24h; Miyaura-Suzuki cross-coupling;	A 51% B 4%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 1-azulenyl iodide (76279-71-5) → 2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (620634-44-8) + azulene (275-51-4)

Conditions	Yield
Stage #1: 1-azulenyl iodide With phenyllithium In tetrahydrofuran; diethyl ether; cyclohexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; diethyl ether; cyclohexane at -78 - 20℃; for 3h; Inert atmosphere;	A 51% B n/a

1,2,3,4-tetrahydroazulen-1-one (52487-41-9) → azulene (275-51-4)

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 60℃;	50%
Multi-step reaction with 2 steps 1: 87 percent / aluminum hydride / tetrahydrofuran / 0.5 h / 0 °C 2: 37 percent / 10percent Pd/C / benzene; hexane / 480 °C View Scheme

1-methylazulene (769-31-3) + 1-(3-methylazulen-1-ylmethylene)azulenium perchlorate → 1-methyl-3-(3-methylazulen-1-yl)azulenium perchlorate + azulene (275-51-4)

Conditions	Yield
In acetic acid for 2h; from boiling point to r.t.;	A 24 mg B 50%

1-formylazulene (7206-61-3) → azulene (275-51-4)

Conditions	Yield
With pyrrole In acetic acid at 20℃; for 72h; decarbonylation;	49%

1.4-dibromobenzene (106-37-6) + 2-(azulen-2-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (457644-50-7) → 2-phenylazulene (19227-07-7) + azulene (275-51-4) + 1,4-di(2-azulenyl)benzene

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; caesium carbonate In 1,4-dioxane at 80℃; for 24h; Miyaura-Suzuki cross-coupling;	A 2% B 2% C 44%

(E)-sesquifulvatriene (67052-42-0) → benzene (71-43-2) + azulene (275-51-4)

Conditions	Yield
at 500℃; under 0.001 Torr; Product distribution;	A n/a B 42%

para-chlorotoluene (106-43-4) + 2-(azulen-2-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (457644-50-7) → 2,2′-biazulene (82893-99-0) + 2-(4-tolyl)azulene (111679-38-0) + azulene (275-51-4)

Conditions	Yield
With barium dihydroxide; cesium carbonate; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In 1,4-dioxane at 80℃; for 24h;	A 40% B 12% C 4%

azulene (275-51-4) → 1,3-dibromoazulene (14658-95-8)

Conditions	Yield
With N-Bromosuccinimide; acetic anhydride In diethyl ether	100%
With N-Bromosuccinimide In benzene for 2h; Ambient temperature;	95%
With N-Bromosuccinimide In hexane at 20℃;	89%

azulene (275-51-4) → 1-azulenyl iodide (76279-71-5)

Conditions	Yield
With N-iodo-succinimide In dichloromethane at 0℃; for 0.25h; Inert atmosphere;	100%
With N-iodo-succinimide In dichloromethane at 20℃; for 2h;	98%
With N-iodo-succinimide In dichloromethane at 0℃; for 0.25h; Inert atmosphere;	87%

2,2,3,3,3-pentafluoropropanoic anhydride (356-42-3) + azulene (275-51-4) → 1-(pentafluoropropionyl)azulene (73017-88-6)

Conditions	Yield
for 0.25h;	100%

azulene (275-51-4) → 1,3-diiodoazulene (36044-42-5)

Conditions	Yield
With aluminum oxide; iodine In solid for 20h; Ambient temperature;	100%
With N-iodo-succinimide In dichloromethane-d2	98%
With N-iodo-succinimide In benzene at 50℃; for 3h;	96%

azulene (275-51-4) → bicyclo<5.3.0>decane (5661-80-3)

Conditions	Yield
With Pd/C; hydrogen In chloroform at 20℃; under 760.051 Torr; for 5h; Catalytic behavior;	100%
With lithium; nickel dichloride In tetrahydrofuran at 20℃; Reduction;	72 % Chromat.

acridine (260-94-6) + trifluoromethylsulfonic anhydride (358-23-6) + azulene (275-51-4) → C38H24F6N2O4S2 (929021-11-4)

Conditions	Yield
In dichloromethane at 20℃;	99%
In dichloromethane at 20℃; for 2h;	99%

racemic methyl phenyl sulfoxide (1193-82-4) + trifluoroacetic anhydride (407-25-0) + azulene (275-51-4) → (1-azulenyl)methylphenylsulfonium trifluoroacetate (1029874-10-9)

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h;	99%

1,1'-sulfinylbisbenzene (945-51-7) + trifluoroacetic anhydride (407-25-0) + azulene (275-51-4) → (1-azulenyl)diphenylsulfonium trifluoroacetate (1029874-04-1)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	99%

dimethyl sulfoxide (67-68-5) + trifluoroacetic anhydride (407-25-0) + azulene (275-51-4) → (1-azulenyl)dimethylsulfonium trifluoroacetate (1029874-01-8)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	99%

dimethyl sulfoxide (67-68-5) + azulene (275-51-4) → 1,3-bis(methylthio)azulene (2978-83-8)

Conditions	Yield
Stage #1: dimethyl sulfoxide; azulene With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 0.5h; Stage #2: With triethylamine In ethanol for 2h; Reflux;	98%

isoquinoline (119-65-3) + trifluoromethylsulfonic anhydride (358-23-6) + azulene (275-51-4) → C30H20F6N2O4S2

Conditions	Yield
In dichloromethane at 20℃;	97%
In dichloromethane at 20℃; for 2h;	97%

1,3-Benzothiazole (95-16-9) + trifluoromethylsulfonic anhydride (358-23-6) + azulene (275-51-4) → C26H16F6N2O4S4 (929021-13-6)

Conditions	Yield
In dichloromethane at 20℃;	97%

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene (1203707-11-2) + azulene (275-51-4) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9) + 2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene (1314045-03-8)

Conditions	Yield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;	A 97% B 58%

1,3-dimethylbarbituric acid (769-42-6) + 2,2-dihydroxy-1-[4-(trifluoromethyl)phenyl]ethanone (101906-05-2) + azulene (275-51-4) → C25H19F3N2O4

Conditions	Yield
In isopropyl alcohol at 80℃;	97%

azulene (275-51-4) → 1-formylazulene (7206-61-3)

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide at 0 - 20℃;	95%
With Vilsmeier reagent In dichloromethane at 0 - 25℃; for 0.75h; Inert atmosphere;	90%
With N,N-dimethyl-formamide; trichlorophosphate
With N-methyl-N-phenylformamide
Multi-step reaction with 2 steps 1: aq. HClO4 / ethanol 2: aq. KMnO4 / acetone View Scheme

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + azulene (275-51-4) → 1-formylazulene (7206-61-3)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.5h; Stage #2: azulene at 20℃; for 1h;	95%
With trichlorophosphate at 0 - 20℃; for 1.5h;	95%
Stage #1: N,N-dimethyl-formamide With phosphorus trichloride at 0℃; for 0.5h; Stage #2: azulene In N,N-dimethyl-formamide at 25℃; for 2h;	95%

trifluoromethylsulfonic anhydride (358-23-6) + dimethyl sulfoxide (67-68-5) + azulene (275-51-4) → 1,3-azulenyldiylbis(dimethylsulfonium) bis(trifluoromethanesulfonate)

Conditions	Yield
In dichloromethane at 20℃; for 2h;	95%

2,6-dimethylpyrone (1004-36-0) + azulene (275-51-4) → 4-(azulen-1-yl)-2,6-dimethyl-pyranylium perchlorate

Conditions	Yield
Stage #1: 2,6-dimethylpyrone With trichlorophosphate In nitromethane for 1h; Stage #2: azulene In nitromethane for 0.25h; Stage #3: With perchloric acid In nitromethane at 70 - 80℃; for 0.333333h;	94%

1,10-Phenanthroline (66-71-7) + trifluoromethylsulfonic anhydride (358-23-6) + azulene (275-51-4) → C36H22F6N4O4S2 (929021-12-5)

Conditions	Yield
In dichloromethane at 20℃;	94%
In dichloromethane at 20℃; for 2h;	94%

1-(4-methylbenzenesulfonyl)-4-[4-(trifluoromethyl)phenyl]-1,2,3-triazole + azulene (275-51-4) → N-((Z)-2-(azulen-1-yl)-2-(4-(trifluoromethyl)phenyl)vinyl)-4-methylbenzenesulfonamide

Conditions	Yield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 60℃; for 12h; diastereoselective reaction;	94%
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 60℃; for 3h;	94%

azulene (275-51-4) → 1,6-dihydroazulene (63320-32-1)

Conditions	Yield
With ammonia; sodium In diethyl ether at -78℃; for 0.5h; Birch reduction;	93%

azulene (275-51-4) + 1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene (741737-71-3) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9) + 1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene (1314045-02-7) + 2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

Conditions	Yield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;	A 93% B 19% C 34%

Methyl phenyldiazoacetate (22979-35-7) + azulene (275-51-4) → methyl 2-phenyl-2H-benzo[7]annulene-2-carboxylate

Conditions	Yield
With copper(II) hexafluoroacetylacetonate In 1,2-dichloro-ethane at 20℃; for 0.5h;	93%

2-diazo-1,3-dicyano-6-oxo-2,6-azulenequinone (53535-47-0) + azulene (275-51-4) → 6-hydroxy-1,3-dicyanoazulene + 2-(1-azulenyl)-1,3-dicyanoazulen-6-ol + 2-(5-azulenyl)-1,3-dicyanoazulen-6-ol

Conditions	Yield
In ethyl acetate for 1.5h; Condensation; dediazotization; Photolysis;	A 1% B 92% C 5%

isoquinoline (119-65-3) + trifluoromethylsulfonic anhydride (358-23-6) + azulene (275-51-4) → C20H14F3NO2S + C30H20F6N2O4S2

Conditions	Yield
In dichloromethane at 20℃;	A 92% B 6%
In dichloromethane at 20℃; for 0.5h;	A 92% B 6%

trifluoromethylsulfonic anhydride (358-23-6) + 1,1'-sulfinylbisbenzene (945-51-7) + azulene (275-51-4) → 1-azulenediylbis(diphenylsulfonium) bis(trifluoromethanesulfonate)

Conditions	Yield
In dichloromethane at 20℃; for 2h;	92%

Upstream product

• 29648-84-8 1,4,5,6,7,8-hexahydro-azulene 
• 88-72-2 1-methyl-2-nitrobenzene 
• 61035-76-5 2-bromoazulene 
• 5622-76-4 1-phenylbut-1-en-3-yne 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 34509-94-9 Azulene radical anion 
• 935-89-7 <1-3H>azulene 
• 36044-42-5 1,3-diiodoazulene 
• 122-39-4 diphenylamine 
• 38337-21-2 azulene-1,3-dicarbaldehyde 
• 696-68-4 6-(dimethylamino)fulvene 
• 293-96-9 cyclodecane 
• 1502-06-3 cyclodecanone 
• 5661-80-3 bicyclo<5.3.0>decane 

Downstream Products

• 16430-62-9 1-triphenylmethylazulene 
• 23781-83-1 4-phenylazulene 
• 38717-96-3 azulen-1-yl(phenyl)methanone 
• 16458-19-8 1,3-bis(diphenylmethyl)azulene 
• 16430-63-0 1,3-bis(triphenylmethyl)azulene 
• 130986-62-8 1-Pikryl-azulen 
• 16458-38-1 1-<2,4,6-Trimethyl-benzyl>-azulen 
• 16458-39-2 1.3-Bis-<2.4.6-trimethyl-benzyl>-azulen 
• 16430-64-1 1-<α-Methyl-benzhydryl>-azulen 
• 16458-20-1 1--azulen 
• 16458-55-2 di(1-azulenyl)phenylmethane 
• 16458-54-1 Azulenyl-⁽¹⁾-p-tolyl-malonsaeure-diethylester 
• 93319-67-6 4-benzyl-azulene 
• 61035-79-8 1,3-Di-(p-tolylthio)-azulen 

Relevant articles and documents

A Convenient Synthesis of Azulene

An improved and scalable synthesis of azulene has been developed by the application of pyrrolidine as a reagent and continuous steam distillation and extraction for workup. Applications for the coloration of perfluorinated media and silicones were demonstrated.

Preparation of azulenyllithium and magnesium reagents utilizing halogen-metal exchange reaction of several iodoazulenes with organolithium or magnesium ate complex

Preparation of several azulenyllithium and magnesium reagents was achieved by the halogen-metal exchange reaction of iodoazulenes with n-butyllithium or lithium tri(n-butyl)magnesate at low temperature and the synthetic application of the reagents was explored.

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Coupling reaction of azulenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes with haloazulenes

In order to study the physicochemical properties of azulene oligomers, the synthesis and a coupling reaction of 2-(2-amino-1,3-bisethoxycarbonyl-6-azulenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (1) and 2-(2-azulenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2) were examined.

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Gold-Catalyzed Direct Alkynylation of Azulenes

A novel catalytic method for the direct C-H alkynylation of azulenes is developed. The gold catalyzed functionalization of this special carbacycle is achieved with hypervalent iodonium reagent TIPS-EBX under mild reaction conditions. With the aid of the developed procedure, several TIPS alkynylated azulene derivatives were synthesized bearing important functional groups for further functionalization.