Azulene

Modify Date: 2025-08-21 14:09:29

Azulene structure	Common Name	Azulene
	CAS Number	275-51-4	Molecular Weight	128.171
	Density	1.0±0.1 g/cm3	Boiling Point	220.7±7.0 °C at 760 mmHg
	Molecular Formula	C₁₀H₈	Melting Point	98-100 °C(lit.)
	MSDS	Chinese USA	Flash Point	76.7±8.9 °C
	Symbol	GHS09	Signal Word

Use of Azulene

Azulene (Cyclopentacycloheptene) is as an isomer of naphthalene with high anti-HIV activity. Azulene, isolated from the distillation of chamomile oil, is a scaffold in medicinal chemistry[1][2][3].

Name	azulene
Synonym	More Synonyms

Description	Azulene (Cyclopentacycloheptene) is as an isomer of naphthalene with high anti-HIV activity. Azulene, isolated from the distillation of chamomile oil, is a scaffold in medicinal chemistry[1][2][3].
Related Catalog	Signaling Pathways >> Anti-infection >> HIV Research Areas >> Infection
Target	HIV
In Vitro	Azulene is an interesting scaffold in medicinal chemistry as it resembles several other bicyclic aromatics that are frequently found in drugs. Azulene, a structural isomer of naphthalene, is a bicyclic nonbenzenoid aromatic hydrocarbon having a dipole moment due to the electron-rich five-membered ring and electron-deficient sevenmembered ring[1].
References	[1]. Teppo O Leino, et al. Azulene-based Compounds for Targeting Orexin Receptors. Eur J Med Chem. 2018 Sep 5;157:88-100. [2]. Julia Peet, et al. Antiretroviral (HIV-1) Activity of Azulene Derivatives. Bioorg Med Chem. 2016 Apr 15;24(8):1653-7. [3]. David A. Becker, et al. A new synthesis of substituted azulenes. Journal of the American Chemical Society, 111(1), 389-391.

Density	1.0±0.1 g/cm3
Boiling Point	220.7±7.0 °C at 760 mmHg
Melting Point	98-100 °C(lit.)
Molecular Formula	C₁₀H₈
Molecular Weight	128.171
Flash Point	76.7±8.9 °C
Exact Mass	128.062607
LogP	3.45
Vapour Pressure	0.2±0.2 mmHg at 25°C
Index of Refraction	1.632
InChIKey	CUFNKYGDVFVPHO-UHFFFAOYSA-N
SMILES	c1ccc2cccc-2cc1
Stability	Stable. Combustible. Incompatible with strong oxidizing agents.

Azulene MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CO4570000

CHEMICAL NAME :: Azulene

CAS REGISTRY NUMBER :: 275-51-4

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C10-H8

MOLECULAR WEIGHT :: 128.18

WISWESSER LINE NOTATION :: L57J

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 520 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 108 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 145 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#07952 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - E0278 No. of Facilities: 2232 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 20256 (estimated) No. of Female Employees: 17049 (estimated)

Symbol	GHS09
Hazard Statements	H411
Precautionary Statements	P273
Personal Protective Equipment	Eyeshields;Gloves
Hazard Codes	N
Risk Phrases	R51/53
Safety Phrases	S61
RIDADR	UN 3077 9/PG 3
WGK Germany	2
RTECS	CO4570000
HS Code	2902909090

Precursor 9
CAS#:23306-02-7 1-chloroazulene CAS#:36044-41-4 2-Iodoazulene CAS#:36044-31-2 2-Chloroazulene CAS#:607393-61-3 2-azulenyl trif...
CAS#:52487-41-9 3,4-Dihydro-1(2... CAS#:90266-03-8 3,8a-dihydro-2H... CAS#:84176-25-0 Trimethylen-cyc... CAS#:544-25-2 Cycloheptatriene
CAS#:393091-18-4 3-Chloro-8,8a-d...
DownStream 10
CAS#:10487-55-5 1-(3-acetylazul... CAS#:14658-95-8 1,3-dibromoazulene CAS#:61035-76-5 1-bromoazulene CAS#:19384-00-0 2-Hydroxyazulene
CAS#:2048-68-2 N,N-dimethylazu... CAS#:121-69-7 N,N-Dimethylaniline CAS#:275-51-4 Azulene CAS#:34505-30-1 1-methyl-2-nitr...
CAS#:35963-33-8 CAS#:460-12-8 Diacetylene

HS Code	2902909090
Summary	2902909090 other aromatic hydrocarbons。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0%

Determination of descriptors for polycyclic aromatic hydrocarbons and related compounds by chromatographic methods and liquid-liquid partition in totally organic biphasic systems.

J. Chromatogr. A. 1361 , 240-54, (2014)

Retention factors on several columns and at various temperatures using gas chromatography and from reversed-phase liquid chromatography on a SunFire C18 column with various mobile phase compositions c...

Novel azulene-based derivatives as potent multi-receptor tyrosine kinase inhibitors.

Bioorg. Med. Chem. Lett. 20(20) , 6129-32, (2010)

A series of azulene-based derivatives were synthesized as potent inhibitors for receptor tyrosine kinases such as FMS-like tyrosine kinase 3 (FLT-3). Systematic side chain modification of prototype 1a...

Total synthesis of a CD-ring: side-chain building block for preparing 17-epi-calcitriol derivatives from the Hajos-Parrish dione.

J. Org. Chem. 76(16) , 6906-11, (2011)

An efficient synthesis of the key building block for 17-epi-calctriol from the Hajos-Parrish dione involving a sequence of diastereoselective transformation of the azulene core and the side-chain cons...

Bicyclo[5.3.0]deca-2,4,6,8,10-pentaene

EINECS 205-993-6

Cyclopentacycloheptene

Azunol

Bicyclo(5.3.0)-deca-2,4,6,8,10-pentaene

MFCD00003810

Azulene

Bicyclo(5.3.0)-1,3,5,7,9-decapentaene

Bicyclo[5.3.0]decapentaene

Bicyclo[0.3.5]deca-1,3,5,7,9-pentaene

Azunamic

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Azulene

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