1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene
azulene
A
7-isopropyl-1,4-dimethyl-azulene
B
2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h; | A 97% B 58% |
1-chloro-7-isopropyl-4-methyl-azulene
dihydroxy-methyl-borane
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h; | 94% |
azulene
1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene
A
7-isopropyl-1,4-dimethyl-azulene
B
1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h; | A 93% B 19% C 34% |
1,1-bis[4-(dimethylamino)phenyl]-2-(3-guaiazulenyl)ethylene
azulene
A
7-isopropyl-1,4-dimethyl-azulene
B
2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene
C
1,1-di(azulen-1-yl)-2,2-bis[4-(dimethylamino)phenyl]ethane
D
1,3-bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}azulene
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h; | A 91% B 46% C 13% D 19% |
A
7-isopropyl-1,4-dimethyl-azulene
B
dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate
Conditions | Yield |
---|---|
In acetonitrile at 110℃; for 1h; | A 29% B 71% |
In acetonitrile at 100℃; for 1h; in sealed tube; | A 29% B 71% |
A
7-isopropyl-1,4-dimethyl-azulene
B
2,2'-biguaiazulenyl
Conditions | Yield |
---|---|
With methanol Title compound not separated from byproducts; | A 50% B 20% |
ethanol
bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone
A
7-isopropyl-1,4-dimethyl-azulene
B
ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.166667h; Heating; | |
With toluene-4-sulfonic acid for 0.166667h; Mechanism; Heating; regioselectivity; other substrates; |
ethanol
Azulen-1-yl-(5-isopropyl-3,8-dimethyl-azulen-1-yl)-methanone
A
7-isopropyl-1,4-dimethyl-azulene
B
ethyl azulene-1-carboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 6h; Heating; |
ethanol
(5-Isopropyl-3,8-dimethyl-azulen-1-yl)-(4,6,8-trimethyl-azulen-1-yl)-methanone
A
7-isopropyl-1,4-dimethyl-azulene
B
ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
D
azulene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.166667h; Heating; |
ethanol
1-[3-(5-Isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone
A
7-isopropyl-1,4-dimethyl-azulene
B
1-acetyl-4,6,8-trimethylazulene
C
ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 1h; Heating; |
ethanol
2,2,2-Trifluoro-1-[3-(5-isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone
A
7-isopropyl-1,4-dimethyl-azulene
B
ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
C
1-trifluoroacetyl-4,6,8-trimethylazulene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 2.5h; Heating; Further byproducts given; |
guaia-1(5),6-diene
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
palladium on activated charcoal In xylene for 36h; Heating; |
3-bromo-7-isopropyl-1,4-dimethylazulene
A
7-isopropyl-1,4-dimethyl-azulene
B
2,2'-biguaiazulenyl
C
7-(2-bromo-1-methylethyl)-1,4-dimethylazulene
D
7-<(Z)-2-bromo-1-methylethenyl>-1,4-dimethylazulene
E
7-<(E)-2-bromo-1-methylethenyl>-1,4-dimethylazulene
F
7-(1-bromomethyl-2-bromoethyl)-1,4-dimethylazulene
Conditions | Yield |
---|---|
In benzene for 0.333333h; Product distribution; Ambient temperature; different solvent and reaction times; |
ergolide
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With selenium at 300 - 350℃; for 0.833333h; |
6-(3-guaiazulenyl)-1(6H)-guaiazulenone
A
7-isopropyl-1,4-dimethyl-azulene
B
5-isopropylidene-3,8-dimethyl-1(5H)-azulenone
C
1-(3-guaiazulenyl)-6a-isopropyl-2,5-dimethyl-1,1a,3,6a-tetrahydrocyclopropainden-3-one
Conditions | Yield |
---|---|
In octane at 80℃; |
5-Isopropenyl-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulen-1-ol
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 1) benzene, reflux, 2 h, 2) decaline, reflux, 2 h; Yield given. Multistep reaction; |
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
palladium on activated charcoal at 320 - 330℃; for 0.0833333h; Heating; |
5-(1-guaiazulenyl)-5,6-dihydro-9-isopropyl-1-methyl-4-nitrocyclopentaheptalene
A
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With phosphoric acid |
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
palladium on activated charcoal at 320 - 330℃; for 0.0833333h; Heating; |
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With 4,6,8-trimethylazulene In acetic acid for 2h; from boiling point to r.t.; Yield given; |
A
7-isopropyl-1,4-dimethyl-azulene
B
dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate
C
dimethyl (Z)-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethene-1,2-dicarboxylate
Conditions | Yield |
---|---|
In decane at 60 - 80℃; Kinetics; Thermodynamic data; Mechanism; var. solv. and temp; |
7-isopropyl-1,4-dimethyl-azulene
o-benzenedisulfonimide
4-methoxy-benzaldehyde
Conditions | Yield |
---|---|
In acetonitrile at 20 - 25℃; for 2h; | 99% |
7-isopropyl-1,4-dimethyl-azulene
trichloroacetic acid anhydride
3-trichloroacetylguaiazulene
Conditions | Yield |
---|---|
In dichloromethane | 98% |
In dichloromethane | 76% |
In dichloromethane | |
In dichloromethane at 20℃; for 2h; |
Conditions | Yield |
---|---|
In diethyl ether; acetonitrile at 25℃; | 98% |
With hexafluorophosphoric acid In water; acetic acid at 25℃; for 2h; | 88% |
7-isopropyl-1,4-dimethyl-azulene
Glyoxal
Conditions | Yield |
---|---|
With tetrafluoroboric acid; acetic acid In water at 25℃; for 1h; | 98% |
With tetrafluoroboric acid; acetic acid at 25℃; for 1h; | 98% |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol at 25℃; for 0.5h; | 98% |
7-isopropyl-1,4-dimethyl-azulene
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.75h; Vilsmeier Reaction; Stage #2: 7-isopropyl-1,4-dimethyl-azulene at 0 - 40℃; Vilsmeier Reaction; Stage #3: With tetrafluoroboric acid In water | 98% |
7-isopropyl-1,4-dimethyl-azulene
1,2-bis(4-methoxyphenyl)-1,2-ethanediol
1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 60℃; for 3h; | 97% |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol; water at 25℃; for 2h; | 97% |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol; water at 25℃; for 2h; | 97% |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol; water at 25℃; | 97% |
7-isopropyl-1,4-dimethyl-azulene
(E)-4-((4-methoxyphenyl)diazenyl)benzaldehyde
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol at 25℃; for 2h; | 97% |
7-isopropyl-1,4-dimethyl-azulene
4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol; water at 20℃; for 2h; | 97% |
7-isopropyl-1,4-dimethyl-azulene
3-Bromoazulene-1,5-quinone
Conditions | Yield |
---|---|
In methanol Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol; water at 25℃; for 1.5h; | 96% |
With hexafluorophosphoric acid In methanol at 25℃; for 1.5h; | 96% |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In diethyl ether; water; acetonitrile at 25℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With tetrafluoroboric acid In methanol; water at 25℃; for 2h; | 96% |
4-aminobenzaldehyde
7-isopropyl-1,4-dimethyl-azulene
4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 0.25h; Stage #2: 7-isopropyl-1,4-dimethyl-azulene In ethanol; water at 20℃; for 2h; | 96% |
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With dirhodium tetraacetate In 1,2-dichloro-ethane at 60℃; for 2h; diastereoselective reaction; | 96% |
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 60℃; for 3h; | 96% |
7-isopropyl-1,4-dimethyl-azulene
Conditions | Yield |
---|---|
With dirhodium tetraacetate In 1,2-dichloro-ethane at 60℃; for 3h; diastereoselective reaction; | 96% |
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 60℃; for 3h; | 96% |
formaldehyd
7-isopropyl-1,4-dimethyl-azulene
3,3-methylenebis(guaiazulene)
Conditions | Yield |
---|---|
With acetic acid at 25℃; for 1h; | 95% |
With ethanol; sodium hydrogencarbonate |
7-isopropyl-1,4-dimethyl-azulene
N,N-dimethyl-formamide
5-isopropyl-3,8-dimethylazulene-1-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 7-isopropyl-1,4-dimethyl-azulene; N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1h; Vilsmeier formylation; Stage #2: With potassium hydroxide; water | 95% |
Stage #1: 7-isopropyl-1,4-dimethyl-azulene; N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1h; Stage #2: With water; potassium hydroxide | 94% |
With trichlorophosphate In benzene for 0.666667h; | 92% |
7-isopropyl-1,4-dimethyl-azulene
3-bromo-7-isopropyl-1,4-dimethylazulene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; hexamethylenetetramine In hexane | 95% |
Multi-step reaction with 2 steps 1: Br2 / hexane / -20 °C 2: 100 percent / alkali View Scheme |
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In acetic acid at 25℃; for 2h; | 95% |
7-isopropyl-1,4-dimethyl-azulene
4-<<4'-(N,N-dimethylamino)phenyl-1'>azo>benzaldehyde
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol; water at 25℃; | 95% |
7-isopropyl-1,4-dimethyl-azulene
methyl 3,3,3-trifluoropyruvate
3,3,3-trifluoro-2-hydroxy-2-(5-isopropyl-3,8-dimethylazulen-1-yl)propionic acid methyl ester
Conditions | Yield |
---|---|
In hexane at 0℃; for 0.25h; | 95% |
7-isopropyl-1,4-dimethyl-azulene
(E)-4-((4-(dimethylamino)phenyl)diazenyl)benzaldehyde
Conditions | Yield |
---|---|
With hexafluorophosphoric acid In methanol at 25℃; for 2h; | 95% |
7-isopropyl-1,4-dimethyl-azulene
ethyl 2-benzoyl-4-(4-methoxyphenyl)-4-oxobut-2-enoate
ethyl 3-(guaiazulen-1-yl)-5-(4-methoxyphenyl)-2-phenylfuran-3-carboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane for 5h; Reflux; | 95% |
7-isopropyl-1,4-dimethyl-azulene
4,4'-bis(dimethylamino)benzhydrol
bis(4-dimethylaminophenyl)(3-guaiazulenyl)methane
Conditions | Yield |
---|---|
With o-benzenedisulfonimide In neat (no solvent) at 30℃; for 5.5h; Friedel-Crafts Alkylation; | 95% |
7-isopropyl-1,4-dimethyl-azulene
trifluoroacetic anhydride
2,2,2-trifluoro-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethanone
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2.3h; | 94% |
In dichloromethane |
Chemical Name: Guaiazulene
IUPAC NAME: 1,4-Dimethyl-7-propan-2-ylazulene
CAS No.: 489-84-9
EINECS: 207-701-2
RTECS: CO4790000
Molecular Formula: C15H18
Molecular Weight: 198.3 g/mol
Melting Point: 27-29 °C(lit.)
Density: 0.961 g/cm3
Flash Point: 142.3 °C
Boiling Point: 305.4 °C at 760 mmHg
Following is the structure of Guaiazulene (489-84-9):
Product Categories about Guaiazulene (489-84-9) are Azulenes ; Biochemistry ; Terpenes ; Terpenes (Others) ; Tropolones & Azulenes
The chemical synonymous of Guaiazulene (489-84-9) are 1,4-Dimethyl-7-(1-methylethyl)-azulen ; 1,4-Dimethyl-7-(1-methylethyl)azulene ; 1,4-Dimethyl-7-(1-methylethyl)-azulene ; 1,4-Dimethyl-7-isopropyl-azulen ; 3,8-Dimethyl-5-(2-propyl)azulene ; AZ-8 ; AZ-8 beris ; Azulen-Beris
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 525mg/kg (525mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 362, 1958. |
mouse | LD50 | oral | 1220mg/kg (1220mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 362, 1958. |
rat | LD50 | oral | 1550mg/kg (1550mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 615, 1969. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
Xn: Harmful
Risk Statements about Guaiazulene (489-84-9):
R22 Harmful if swallowed.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements about Guaiazulene (489-84-9):
S22 Do not breathe dust.
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
Attentions:
1. Storage: Keep container closed when not in use. Refrigerator (approx 4 °C). Store in a cool, dry area away from incompatible substances.
2. Handling: Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Do not breathe dust. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation
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