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Azulene

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Name

Azulene

EINECS 205-993-6
CAS No. 275-51-4 Density 1.037 g/cm3
PSA 0.00000 LogP 2.79140
Solubility Soluble in common solvents, insoluble in water Melting Point 98-100 °C(lit.)
Formula C10H8 Boiling Point 220.718 °C at 760 mmHg
Molecular Weight 128.174 Flash Point 76.66 °C
Transport Information N/A Appearance Blue Crystal
Safety 61 Risk Codes 51/53
Molecular Structure Molecular Structure of 275-51-4 (Azulene) Hazard Symbols DangerousN
Synonyms

Bicyclo[5.3.0]decapentaene;Cyclopentacycloheptene;NSC 89248;

Article Data 81

Azulene Synthetic route

92622-71-4

tetracyclo<5.3.0.02.4.03.5>deca-6,8,10-triene

275-51-4

azulene

Conditions
ConditionsYield
In cyclohexane Quantum yield; Irradiation;100%
In (2)H8-toluene at 90 - 120℃; Thermodynamic data; Rate constant; ΔH (excit.), ΔS (excit.), Ea;
607393-61-3

2-azulenyl trifluoromethanesulfonate

275-51-4

azulene

Conditions
ConditionsYield
With formic acid; tributyl-amine; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 24h; Heating;96%
696-68-4

6-(dimethylamino)fulvene

(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

A

131-11-3

phthalic acid dimethyl ester

B

275-51-4

azulene

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 44h; Product distribution; Decomposition; retro-Diels-Alder reaction; Heating;A 94%
B 31%
23306-02-7

1-chloroazulene

275-51-4

azulene

Conditions
ConditionsYield
With potassium phosphate; poly(methylhydrosiloxane); palladium diacetate In tetrahydrofuran at 80℃; for 12h;92%
1201-25-8

azulene-1-carboxylic acid

275-51-4

azulene

Conditions
ConditionsYield
With trichloroacetic acid In benzene for 6h; Heating;90%
586-78-7

para-nitrophenyl bromide

441292-61-1

6-(tri-n-butylstannyl)azulene

A

6-(4-nitrophenyl)azulene

B

275-51-4

azulene

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In 1,4-dioxane for 2h; Heating;A 83%
B 5%
35046-05-0

6-bromoazulene

586-78-7

para-nitrophenyl bromide

A

6-(4-nitrophenyl)azulene

B

275-51-4

azulene

Conditions
ConditionsYield
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%
111-26-2

hexan-1-amine

620634-44-8

2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

563-96-2

2,2-dihydroxyacetic acid

A

2-(azulen-1-yl)-N-hexylglycine

B

275-51-4

azulene

Conditions
ConditionsYield
In methanol at 20℃; for 3h; Petasis Reaction; Inert atmosphere;A 82%
B 6%
52866-26-9

((E)-Buta-1,3-dienyl)-diethyl-amine

82215-26-7

6-<(p-Nitrobenzoyl)oxy>fulvene

A

82215-27-8

6-(1-azulenyl)fulvene

B

275-51-4

azulene

Conditions
ConditionsYield
In benzene for 7h; Ambient temperature;A n/a
B 68%
104-92-7

1-bromo-4-methoxy-benzene

441292-61-1

6-(tri-n-butylstannyl)azulene

A

6-(4-methoxyphenyl)azulene

B

275-51-4

azulene

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

Azulene History

Dating back to the 15th century as the azure-blue chromophore, Azulene (CAS NO.275-51-4) obtained by steam distillation of German chamomile.Its structure and first synthesis were reported by Lavoslav Ru?i?ka, followed in 1937 by Placidus Plattner.The chromophore was discovered in yarrow and wormwood and named in 1863 by Septimus Piesse.

Azulene Consensus Reports

Reported in EPA TSCA Inventory.

Azulene Specification

Azulene is an organic compound with the formula C10H8, and its systematic name is the same with the product name. With the CAS registry number 275-51-4, it is also named as Cyclopentacycloheptene. It belongs to the product categories of Aromatic Hydrocarbons (substituted) & Derivatives; Tropolones & Azulenes; Azulenes. Its EINECS number is 205-993-6. In addition, the molecular weight is 128.17. Its classification codes are: (1)Analgesics; (2)Analgesics, Non-Narcotic; (3)Anti-Inflammatory Agents; (4)Anti-inflammatory agents, non-steroidal; (5)Antirheumatic Agents; (6)Peripheral Nervous System Agents; (7)Sensory System Agents. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from light. In organometallic chemistry, azulene serves as a ligand for low-valent metal centers. It is reported to be anti-inflammatory principle of Matricaria. When heated, it can rearrange into naphthalene. 

Physical properties of Azulene are: (1)ACD/LogP: 3.361; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.36; (4)ACD/LogD (pH 7.4): 3.36; (5)ACD/BCF (pH 5.5): 211.02; (6)ACD/BCF (pH 7.4): 211.02; (7)ACD/KOC (pH 5.5): 1604.58; (8)ACD/KOC (pH 7.4): 1604.58; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.632; (13)Molar Refractivity: 44.095 cm3; (14)Molar Volume: 123.549 cm3; (15)Polarizability: 17.481×10-24cm3; (16)Surface Tension: 40.2 dyne/cm; (17)Density: 1.037 g/cm3; (18)Flash Point: 76.66 °C; (19)Enthalpy of Vaporization: 43.854 kJ/mol; (20)Boiling Point: 220.718 °C at 760 mmHg; (21)Vapour Pressure: 0.17 mmHg at 25°C.

Preparation: this chemical can be prepared by azulene-1-carboxylic acid by heating. This reaction will need reagent CCl3COOH and solvent benzene with the reaction time of 6 hours. The yield is about 90%.

Azulene can be prepared by azulene-1-carboxylic acid by heating

Uses of Azulene: it can be used to produce 1,3-dibromo-azulene at the ambient temperature. It will need reagent NBS and solvent benzene with the reaction time of 2 hours. The yield is about 95%.

Azulene can be used to produce 1,3-dibromo-azulene at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemcial is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. You must avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cccc2cccc2c1
(2)Std. InChI: InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
(3)Std. InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 108mg/kg (108mg/kg)   Drugs in Japan Vol. 6, Pg. 13, 1982.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07952,
mouse LD50 oral > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 13, 1982.
mouse LD50 subcutaneous 145mg/kg (145mg/kg)   Drugs in Japan Vol. 6, Pg. 13, 1982.
rat LD50 intraperitoneal 180mg/kg (180mg/kg)   Drugs in Japan Vol. 6, Pg. 13, 1982.
rat LD50 oral > 4gm/kg (4000mg/kg)   Drugs in Japan Vol. 6, Pg. 13, 1982.
rat LD50 subcutaneous 520mg/kg (520mg/kg)   Drugs in Japan Vol. 6, Pg. 13, 1982.

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