CAS No.275-51-4,Azulene Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	275-51-4
Name:	Azulene
Article Data:	81

Formula:	C₁₀H₈
Molecular Weight:	128.174
Synonyms:	Bicyclo[5.3.0]decapentaene;Cyclopentacycloheptene;NSC 89248;
EINECS:	205-993-6
Density:	1.037 g/cm³
Melting Point:	98-100 °C(lit.)
Boiling Point:	220.718 °C at 760 mmHg
Flash Point:	76.66 °C
Solubility:	Soluble in common solvents, insoluble in water
Appearance:	Blue Crystal
Hazard Symbols:	N
Risk Codes:	51/53
Safety:	61
PSA:	0.00000
LogP:	2.79140

Synthetic route

: 92622-71-4
tetracyclo<5.3.0.02.4.03.5>deca-6,8,10-triene

: 275-51-4
azulene

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 23306-02-7
1-chloroazulene

: 275-51-4
azulene

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 35046-05-0
6-bromoazulene

: 586-78-7
para-nitrophenyl bromide

A: 6-(4-nitrophenyl)azulene

B: 275-51-4
azulene

Conditions

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%

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

Raw Materials

74-86-2

4481-35-0

624-31-7

88-72-2

98-46-4

Downstream Products

74-86-2

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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.

Consensus Reports

Reported in EPA TSCA Inventory.

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)	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.