Product Name

  • Name

    Guaiazulene

  • EINECS 207-701-2
  • CAS No. 489-84-9
  • Article Data93
  • CAS DataBase
  • Density 0.976
  • Solubility
  • Hazard Symbols
  • Synonyms Azulene,7-isopropyl-1,4-dimethyl- (8CI); 1,4-Dimethyl-7-(1-methylethyl)Azulene;1,4-Dimethyl-7-isopropylazulene; 3,8-Dimethyl-5-(2-propyl)azulene;7-Isopropyl-1,4-dimethylazulene; AZ 8; AZ 8 Beris; Azulen-Beris; Azulon;Azunol; Cuteazul; Eucazulen; Guaiazulene; Guaiazulene blue; Kessazulen; NSC4714; Purazulen; S-Guaiazulene; Silazulon; Uroazulen; Vaumigan; Vetivazulen
  • PSA 0.00000
  • LogP 4.53160

Synthetic route

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene
1203707-11-2

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene

azulene
275-51-4

azulene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene
1314045-03-8

2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 97%
B 58%
1-chloro-7-isopropyl-4-methyl-azulene
867380-19-6

1-chloro-7-isopropyl-4-methyl-azulene

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;94%
azulene
275-51-4

azulene

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene
741737-71-3

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene
1314045-02-7

1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene

C

2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

Conditions
ConditionsYield
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
1103995-55-6

1,1-bis[4-(dimethylamino)phenyl]-2-(3-guaiazulenyl)ethylene

azulene
275-51-4

azulene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene
1314044-93-3

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
1314044-97-7

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
1314044-96-6

1,3-bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}azulene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 91%
B 46%
C 13%
D 19%
dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate
98525-07-6, 72898-39-6, 98525-12-3, 98525-13-4

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 110℃; for 1h;A 29%
B 71%
In acetonitrile at 100℃; for 1h; in sealed tube;A 29%
B 71%
3-bromoguaiazulenium bromide

3-bromoguaiazulenium bromide

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2,2'-biguaiazulenyl
17509-79-4

2,2'-biguaiazulenyl

Conditions
ConditionsYield
With methanol Title compound not separated from byproducts;A 50%
B 20%
ethanol
64-17-5

ethanol

bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone
10487-58-8

bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.166667h; Heating;
With toluene-4-sulfonic acid for 0.166667h; Mechanism; Heating; regioselectivity; other substrates;
ethanol
64-17-5

ethanol

Azulen-1-yl-(5-isopropyl-3,8-dimethyl-azulen-1-yl)-methanone
150985-85-6

Azulen-1-yl-(5-isopropyl-3,8-dimethyl-azulen-1-yl)-methanone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl azulene-1-carboxylate
1206-88-8

ethyl azulene-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating;
ethanol
64-17-5

ethanol

(5-Isopropyl-3,8-dimethyl-azulen-1-yl)-(4,6,8-trimethyl-azulen-1-yl)-methanone
150985-81-2

(5-Isopropyl-3,8-dimethyl-azulen-1-yl)-(4,6,8-trimethyl-azulen-1-yl)-methanone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

C

4,6,8-Trimethyl-azulene-1-carboxylic acid ethyl ester

4,6,8-Trimethyl-azulene-1-carboxylic acid ethyl ester

D

azulene
275-51-4

azulene

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.166667h; Heating;
ethanol
64-17-5

ethanol

1-[3-(5-Isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone
150985-82-3

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
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1-acetyl-4,6,8-trimethylazulene
834-97-9

1-acetyl-4,6,8-trimethylazulene

C

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

D

3-Acetyl-4,6,8-trimethyl-azulene-1-carboxylic acid ethyl ester

3-Acetyl-4,6,8-trimethyl-azulene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 1h; Heating;
ethanol
64-17-5

ethanol

2,2,2-Trifluoro-1-[3-(5-isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone
150985-83-4

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
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

C

1-trifluoroacetyl-4,6,8-trimethylazulene
841-83-8

1-trifluoroacetyl-4,6,8-trimethylazulene

D

4,6,8-Trimethyl-3-(2,2,2-trifluoro-acetyl)-azulene-1-carboxylic acid ethyl ester

4,6,8-Trimethyl-3-(2,2,2-trifluoro-acetyl)-azulene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 2.5h; Heating; Further byproducts given;
guaia-1(5),6-diene
105369-35-5

guaia-1(5),6-diene

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
palladium on activated charcoal In xylene for 36h; Heating;
3-bromo-7-isopropyl-1,4-dimethylazulene
90052-61-2

3-bromo-7-isopropyl-1,4-dimethylazulene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2,2'-biguaiazulenyl
17509-79-4

2,2'-biguaiazulenyl

C

7-(2-bromo-1-methylethyl)-1,4-dimethylazulene
90052-62-3, 123287-97-8

7-(2-bromo-1-methylethyl)-1,4-dimethylazulene

D

7-<(Z)-2-bromo-1-methylethenyl>-1,4-dimethylazulene
123279-26-5

7-<(Z)-2-bromo-1-methylethenyl>-1,4-dimethylazulene

E

7-<(E)-2-bromo-1-methylethenyl>-1,4-dimethylazulene
123257-39-6

7-<(E)-2-bromo-1-methylethenyl>-1,4-dimethylazulene

F

7-(1-bromomethyl-2-bromoethyl)-1,4-dimethylazulene
123257-26-1

7-(1-bromomethyl-2-bromoethyl)-1,4-dimethylazulene

Conditions
ConditionsYield
In benzene for 0.333333h; Product distribution; Ambient temperature; different solvent and reaction times;
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With selenium at 300 - 350℃; for 0.833333h;
6-(3-guaiazulenyl)-1(6H)-guaiazulenone
111873-85-9, 119439-50-8

6-(3-guaiazulenyl)-1(6H)-guaiazulenone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

5-isopropylidene-3,8-dimethyl-1(5H)-azulenone
111873-87-1

5-isopropylidene-3,8-dimethyl-1(5H)-azulenone

C

1-(3-guaiazulenyl)-6a-isopropyl-2,5-dimethyl-1,1a,3,6a-tetrahydrocyclopropainden-3-one
111873-84-8, 119479-40-2

1-(3-guaiazulenyl)-6a-isopropyl-2,5-dimethyl-1,1a,3,6a-tetrahydrocyclopropainden-3-one

Conditions
ConditionsYield
In octane at 80℃;
5-Isopropenyl-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulen-1-ol
144126-95-4

5-Isopropenyl-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulen-1-ol

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With toluene-4-sulfonic acid 1) benzene, reflux, 2 h, 2) decaline, reflux, 2 h; Yield given. Multistep reaction;
alismol

alismol

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
palladium on activated charcoal at 320 - 330℃; for 0.0833333h; Heating;
5-(1-guaiazulenyl)-5,6-dihydro-9-isopropyl-1-methyl-4-nitrocyclopentaheptalene
151621-28-2

5-(1-guaiazulenyl)-5,6-dihydro-9-isopropyl-1-methyl-4-nitrocyclopentaheptalene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

9-isopropyl-1-methyl-4-nitroaceheptylene

9-isopropyl-1-methyl-4-nitroaceheptylene

Conditions
ConditionsYield
With phosphoric acid
alismoxide

alismoxide

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
palladium on activated charcoal at 320 - 330℃; for 0.0833333h; Heating;
1-ethylideneguaiazulenium perchlorate

1-ethylideneguaiazulenium perchlorate

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With 4,6,8-trimethylazulene In acetic acid for 2h; from boiling point to r.t.; Yield given;
dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate
98525-07-6, 72898-39-6, 98525-12-3, 98525-13-4

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
145948-89-6

dimethyl (Z)-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethene-1,2-dicarboxylate

Conditions
ConditionsYield
In decane at 60 - 80℃; Kinetics; Thermodynamic data; Mechanism; var. solv. and temp;
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

o-benzenedisulfonimide
4482-01-3

o-benzenedisulfonimide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(3-guaiazulenyl)(4-methoxyphenyl)methylium o-benzenedisulfonimide

(3-guaiazulenyl)(4-methoxyphenyl)methylium o-benzenedisulfonimide

Conditions
ConditionsYield
In acetonitrile at 20 - 25℃; for 2h;99%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

trichloroacetic acid anhydride
4124-31-6

trichloroacetic acid anhydride

3-trichloroacetylguaiazulene
846-33-3

3-trichloroacetylguaiazulene

Conditions
ConditionsYield
In dichloromethane98%
In dichloromethane76%
In dichloromethane
In dichloromethane at 20℃; for 2h;
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

Conditions
ConditionsYield
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
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Glyoxal
131543-46-9

Glyoxal

α,α'-bis(3-guaiazulenylmethylium) bis(tetrafluoroborate)

α,α'-bis(3-guaiazulenylmethylium) bis(tetrafluoroborate)

Conditions
ConditionsYield
With tetrafluoroboric acid; acetic acid In water at 25℃; for 1h;98%
With tetrafluoroboric acid; acetic acid at 25℃; for 1h;98%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(3-guaiazulenyl)(2-thienyl)methylium hexafluorophosphate

(3-guaiazulenyl)(2-thienyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol at 25℃; for 0.5h;98%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-[(5-isopropyl-3,8-dimethylazulen-1-yl)methylene]-N-methylmethanaminium tetrafluoroborate

N-[(5-isopropyl-3,8-dimethylazulen-1-yl)methylene]-N-methylmethanaminium tetrafluoroborate

Conditions
ConditionsYield
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
489-84-9

7-isopropyl-1,4-dimethyl-azulene

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene
741737-71-3

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol at 60℃; for 3h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(3-guaiazulenyl)(4-hydroxyphenyl)methylium hexafluorophosphate

(3-guaiazulenyl)(4-hydroxyphenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(3-guaiazulenyl)(4-methoxyphenyl)methylium hexafluorophosphate

(3-guaiazulenyl)(4-methoxyphenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4'-methoxyazobenzene-4-carbaldehyde
3516-77-6

4'-methoxyazobenzene-4-carbaldehyde

(3-guaiazulenyl)[4-(4-methoxyphenylazo)phenyl]methylium hexafluorophosphate

(3-guaiazulenyl)[4-(4-methoxyphenylazo)phenyl]methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(E)-4-((4-methoxyphenyl)diazenyl)benzaldehyde
107321-41-5

(E)-4-((4-methoxyphenyl)diazenyl)benzaldehyde

C29H29N2O(1+)*F6P(1-)

C29H29N2O(1+)*F6P(1-)

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol at 25℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
1609117-40-9

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde

{4-[(E)-2-(3-guaiazulenyl)diazenyl]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

{4-[(E)-2-(3-guaiazulenyl)diazenyl]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 20℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3-Bromoazulene-1,5-quinone
161126-12-1

3-Bromoazulene-1,5-quinone

5'-Isopropyl-3',8'-dimethyl-[1,1']biazulenyl-3,7-dione

5'-Isopropyl-3',8'-dimethyl-[1,1']biazulenyl-3,7-dione

Conditions
ConditionsYield
In methanol Ambient temperature;96%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

benzaldehyde
100-52-7

benzaldehyde

(3-guaiazulenyl)phenylmethylium hexafluorophosphate

(3-guaiazulenyl)phenylmethylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃; for 1.5h;96%
With hexafluorophosphoric acid In methanol at 25℃; for 1.5h;96%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

(2E)-1-(3-guaiazulenyl)-3-phenyl-2-propen-1-ylium hexafluorophosphate

(2E)-1-(3-guaiazulenyl)-3-phenyl-2-propen-1-ylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In diethyl ether; water; acetonitrile at 25℃; for 1h;96%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

(3-guaiazulenyl)(2-methoxyphenyl)methylium tetrafluoroborate

(3-guaiazulenyl)(2-methoxyphenyl)methylium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid In methanol; water at 25℃; for 2h;96%
4-aminobenzaldehyde
556-18-3

4-aminobenzaldehyde

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
1609117-40-9

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde

Conditions
ConditionsYield
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
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-phenylvinyl)-4-methylbenzenesulfonamide

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-phenylvinyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
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%
1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole

1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-p-tolylvinyl)-4-methylbenzenesulfonamide

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-p-tolylvinyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
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
50-00-0

formaldehyd

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3,3-methylenebis(guaiazulene)
55544-35-9

3,3-methylenebis(guaiazulene)

Conditions
ConditionsYield
With acetic acid at 25℃; for 1h;95%
With ethanol; sodium hydrogencarbonate
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

5-isopropyl-3,8-dimethylazulene-1-carbaldehyde
3331-47-3

5-isopropyl-3,8-dimethylazulene-1-carbaldehyde

Conditions
ConditionsYield
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
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3-bromo-7-isopropyl-1,4-dimethylazulene
90052-61-2

3-bromo-7-isopropyl-1,4-dimethylazulene

Conditions
ConditionsYield
With N-Bromosuccinimide; hexamethylenetetramine In hexane95%
Multi-step reaction with 2 steps
1: Br2 / hexane / -20 °C
2: 100 percent / alkali
View Scheme
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

1-isopropyl-4-(3-guaiazulenylmethylium)benzene hexafluorophosphate

1-isopropyl-4-(3-guaiazulenylmethylium)benzene hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In acetic acid at 25℃; for 2h;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-<<4'-(N,N-dimethylamino)phenyl-1'>azo>benzaldehyde
39208-00-9

4-<<4'-(N,N-dimethylamino)phenyl-1'>azo>benzaldehyde

{4-[4-(dimethylamino)phenylazo]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

{4-[4-(dimethylamino)phenylazo]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(5-isopropyl-3,8-dimethylazulen-1-yl)propionic acid methyl ester
1198330-30-1

3,3,3-trifluoro-2-hydroxy-2-(5-isopropyl-3,8-dimethylazulen-1-yl)propionic acid methyl ester

Conditions
ConditionsYield
In hexane at 0℃; for 0.25h;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(E)-4-((4-(dimethylamino)phenyl)diazenyl)benzaldehyde
39208-00-9

(E)-4-((4-(dimethylamino)phenyl)diazenyl)benzaldehyde

C30H32N3(1+)*F6P(1-)

C30H32N3(1+)*F6P(1-)

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol at 25℃; for 2h;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

ethyl 2-benzoyl-4-(4-methoxyphenyl)-4-oxobut-2-enoate
1316302-31-4

ethyl 2-benzoyl-4-(4-methoxyphenyl)-4-oxobut-2-enoate

ethyl 3-(guaiazulen-1-yl)-5-(4-methoxyphenyl)-2-phenylfuran-3-carboxylate
1447465-53-3

ethyl 3-(guaiazulen-1-yl)-5-(4-methoxyphenyl)-2-phenylfuran-3-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 5h; Reflux;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4,4'-bis(dimethylamino)benzhydrol
119-58-4

4,4'-bis(dimethylamino)benzhydrol

bis(4-dimethylaminophenyl)(3-guaiazulenyl)methane
1562305-68-3

bis(4-dimethylaminophenyl)(3-guaiazulenyl)methane

Conditions
ConditionsYield
With o-benzenedisulfonimide In neat (no solvent) at 30℃; for 5.5h; Friedel-Crafts Alkylation;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethanone
846-34-4

2,2,2-trifluoro-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethanone

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2.3h;94%
In dichloromethane

Guaiazulene Chemical Properties

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

Guaiazulene Toxicity Data With Reference

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.

Guaiazulene Consensus Reports

Reported in EPA TSCA Inventory.

Guaiazulene Safety Profile

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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