Product Name

  • Name

    Imiquimod

  • EINECS 619-387-8
  • CAS No. 99011-02-6
  • Article Data25
  • CAS DataBase
  • Density 1.28 g/cm3
  • Solubility Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol.
  • Melting Point 292-294 °C
  • Formula C14H16N4
  • Boiling Point 456.7 °C at 760 mmHg
  • Molecular Weight 240.308
  • Flash Point 230 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance White to off white crystalline powder
  • Safety 26-45-36/37/39-27
  • Risk Codes 25-36/37/38
  • Molecular Structure Molecular Structure of 99011-02-6 (Imiquimod)
  • Hazard Symbols ToxicT, IrritantXi
  • Synonyms Aldara;4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline;1H-Imidazo(4,5-c)quinolin-4-amine, 1-(2-methylpropyl)-;
  • PSA 56.73000
  • LogP 3.40390

Synthetic route

4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline
201030-96-8

4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Product distribution / selectivity; Heating / reflux;98%
Stage #1: 4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 20℃;
Stage #3: With ammonia In water at 20℃; Product distribution / selectivity;		98%
4-chloro-1H-imidazo[4,5-c]-quinoline
132206-92-9

4-chloro-1H-imidazo[4,5-c]-quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In dimethyl sulfoxide for 0.5h;
Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In dimethyl sulfoxide at 105℃; for 2h;
Stage #3: With hydrogenchloride In water; dimethyl sulfoxide pH=8; Product distribution / selectivity;		98%
N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide

N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ethylenediamine In water at 70 - 95℃; for 4h;91.8%
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide With hydrazine In water at 70℃;
Stage #2: With 2,4,4-trimethylpentan-1-ol In water at 94 - 95℃; for 5h;
Stage #3: In methanol; water at 60℃; for 0.25h; Heating / reflux;		63.3%
4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; water In methanol Product distribution / selectivity;90%
5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile
960254-02-8

5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium amide In toluene at 20 - 100℃; for 2h;90%
4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: 4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate In methanol; water at 75℃; for 0.5h;
Stage #2: With ammonia In water		89.7%
With ammonia; water In methanol Product distribution / selectivity;89.7%
4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; water In methanol Product distribution / selectivity;88%
4-iodo-1-isobutyl-1H-imidazo-[4,5-c]-quinoline
896106-15-3

4-iodo-1-isobutyl-1H-imidazo-[4,5-c]-quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia In methanol at 150 - 155℃; Autoclave (ca. 20 kg pressure);86%
With ammonia In methanol at 150 - 155℃; under 14711.4 Torr; Product distribution / selectivity; Autoclave;86%
4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
99010-64-7

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia In dimethyl sulfoxide at 20 - 150℃; under 1875.19 - 3750.38 Torr; for 6 - 12h; Product distribution / selectivity;85.7%
With ammonia at 150℃; for 7h;82%
With ammonia; formamide at 145℃; for 20 - 25h; Product distribution / selectivity;78%
imiquimod hydrochloride

imiquimod hydrochloride

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: imiquimod hydrochloride With sodium hydrogensulfide; pyrographite In water at 85 - 90℃; for 0.333333h;
Stage #2: With ammonium hydroxide In water at 20 - 80℃; Purification / work up;		80.5%
With sodium hydroxide In water at 20℃; for 0.5h; Product distribution / selectivity;
1-Isobutyl-2-methylsulfanyl-1H-imidazo[4,5-c]quinolin-4-ylamine
177212-77-0

1-Isobutyl-2-methylsulfanyl-1H-imidazo[4,5-c]quinolin-4-ylamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 0.5h; Heating;80%
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide
99010-63-6

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; chloroformic acid ethyl ester In dichloromethane; water at 0 - 20℃; for 1h; Cooling with methanol-ice bath;76%
With ammonium hydroxide; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 0.25h;71%
Multi-step reaction with 2 steps
1: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
2: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: CH2Cl2 / 0.25 h / Heating
2: NaOMe / methanol / 2 h / Heating
View Scheme
4-bromo-1H-imidazo[4,5-c]quinoline

4-bromo-1H-imidazo[4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In ISOPROPYLAMIDE for 0.5h;
Stage #2: 4-bromo-1H-imidazo[4,5-c]quinoline In ISOPROPYLAMIDE at 140℃; for 2h; Product distribution / selectivity;		75.4%
N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine

N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With hydrogenchloride; zinc In ethanol; water at 20℃; for 1h; Product distribution / selectivity;70%
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine With hydrogenchloride; zinc In ethanol; water at 20℃; for 1h;
Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Product distribution / selectivity;		70%
1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine
1040136-68-2

1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine With sulfuric acid; water In dimethyl sulfoxide at 140℃; for 20h;
Stage #2: With sodium hydroxide; water In dimethyl sulfoxide at 20 - 60℃; for 2h; pH=10 - 11; Product distribution / selectivity;		70%
Stage #1: 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine In dimethyl sulfoxide at 140 - 150℃; for 9h;
Stage #2: With sodium hydroxide; water In dimethyl sulfoxide at 20 - 60℃; for 2h; pH=10 - 11; Product distribution / selectivity;
4-chloro-1H-imidazo[4,5-c]-quinoline
132206-92-9

4-chloro-1H-imidazo[4,5-c]-quinoline

A

1-isobutyl-1H-imidazo[4,5-c]quinoline-4-formamide

1-isobutyl-1H-imidazo[4,5-c]quinoline-4-formamide

B

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In ISOPROPYLAMIDE for 0.5h;
Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In ISOPROPYLAMIDE at 120℃; for 1h; Product distribution / selectivity;		A 54%
B 39%
N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
144660-62-8

N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Heating;
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
99010-24-9

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: peracetic acid / ethanol / 2.5 h / 60 °C
2: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
3: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: peracetic acid / ethanol / 2.5 h / 60 °C
2: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: peracetic acid / ethanol / 2.5 h / 60 °C
2: CH2Cl2 / 0.25 h / Heating
3: NaOMe / methanol / 2 h / Heating
View Scheme
3-Amino-4-(2-methylpropylamino)-quinoline
99010-09-0

3-Amino-4-(2-methylpropylamino)-quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1 h / Heating
2: peracetic acid / ethanol / 2.5 h / 60 °C
3: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
4: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 3 steps
1: 1 h / Heating
2: peracetic acid / ethanol / 2.5 h / 60 °C
3: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 1 h / Heating
2: peracetic acid / ethanol / 2.5 h / 60 °C
3: CH2Cl2 / 0.25 h / Heating
4: NaOMe / methanol / 2 h / Heating
View Scheme
N-(2-methylpropyl)-3-nitro-4-quinolinamine
99009-85-5

N-(2-methylpropyl)-3-nitro-4-quinolinamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
2: 1 h / Heating
3: peracetic acid / ethanol / 2.5 h / 60 °C
4: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
5: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 4 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
2: 1 h / Heating
3: peracetic acid / ethanol / 2.5 h / 60 °C
4: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
2: 1 h / Heating
3: peracetic acid / ethanol / 2.5 h / 60 °C
4: CH2Cl2 / 0.25 h / Heating
5: NaOMe / methanol / 2 h / Heating
View Scheme
2-chloro-N4-(2-methylpropyl)quinoline-3,4-diamine
133860-76-1

2-chloro-N4-(2-methylpropyl)quinoline-3,4-diamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 61 percent / toluene / 1.5 h / Heating
2: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
2-chloro-N4-(2-methylpropyl)-3-nitroquinoline-4-amine
133860-75-0

2-chloro-N4-(2-methylpropyl)-3-nitroquinoline-4-amine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr
2: 61 percent / toluene / 1.5 h / Heating
3: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
quinolin-4-ol
611-36-9

quinolin-4-ol

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C
2: SOCl2; DMF / CH2Cl2 / 3 h / Heating
3: Et3N / CH2Cl2 / 0.25 h / Heating
4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
5: 1 h / Heating
6: peracetic acid / ethanol / 2.5 h / 60 °C
7: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
8: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 7 steps
1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C
2: SOCl2; DMF / CH2Cl2 / 3 h / Heating
3: Et3N / CH2Cl2 / 0.25 h / Heating
4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
5: 1 h / Heating
6: peracetic acid / ethanol / 2.5 h / 60 °C
7: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C
2: SOCl2; DMF / CH2Cl2 / 3 h / Heating
3: Et3N / CH2Cl2 / 0.25 h / Heating
4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
5: 1 h / Heating
6: peracetic acid / ethanol / 2.5 h / 60 °C
7: CH2Cl2 / 0.25 h / Heating
8: NaOMe / methanol / 2 h / Heating
View Scheme
4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one
15151-57-2

4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: POCl3; Et3N / toluene / 4 h / 80 - 90 °C
2: 17.8 g / Et3N / CH2Cl2 / 0.5 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr
4: 61 percent / toluene / 1.5 h / Heating
5: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
3-nitro-quinolin-4-ol
50332-66-6

3-nitro-quinolin-4-ol

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: SOCl2; DMF / CH2Cl2 / 3 h / Heating
2: Et3N / CH2Cl2 / 0.25 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
4: 1 h / Heating
5: peracetic acid / ethanol / 2.5 h / 60 °C
6: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
7: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 6 steps
1: SOCl2; DMF / CH2Cl2 / 3 h / Heating
2: Et3N / CH2Cl2 / 0.25 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
4: 1 h / Heating
5: peracetic acid / ethanol / 2.5 h / 60 °C
6: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: SOCl2; DMF / CH2Cl2 / 3 h / Heating
2: Et3N / CH2Cl2 / 0.25 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
4: 1 h / Heating
5: peracetic acid / ethanol / 2.5 h / 60 °C
6: CH2Cl2 / 0.25 h / Heating
7: NaOMe / methanol / 2 h / Heating
View Scheme
4-chloro-3-nitroquinoline
39061-97-7

4-chloro-3-nitroquinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 0.25 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
3: 1 h / Heating
4: peracetic acid / ethanol / 2.5 h / 60 °C
5: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
6: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2 / 0.25 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
3: 1 h / Heating
4: peracetic acid / ethanol / 2.5 h / 60 °C
5: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 0.25 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
3: 1 h / Heating
4: peracetic acid / ethanol / 2.5 h / 60 °C
5: CH2Cl2 / 0.25 h / Heating
6: NaOMe / methanol / 2 h / Heating
View Scheme
2,4-dichloro-3-nitroquinoline
132521-66-5

2,4-dichloro-3-nitroquinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 17.8 g / Et3N / CH2Cl2 / 0.5 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr
3: 61 percent / toluene / 1.5 h / Heating
4: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: PdCl2(PPh3)2, K2CO3, Et4N(1+)Cl(1-) / dimethylformamide / 2 h / 110 °C
2: 10percent aq. NaOH / dioxane / 12 h / Heating
3: Et3N, DPPA / benzene / 1 h / 50 °C
4: 1,2-dichloro-benzene / 1 h / Heating
5: 88 percent / POCl3 / 1 h / Heating
6: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C
7: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating
View Scheme
1-isobuty-1H-limidazole
16245-89-9

1-isobuty-1H-limidazole

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT, 12 h
2: 83 percent / NBS / CCl4 / 1 h / Ambient temperature
3: 98 percent / Pd(PPh3)4, aq. Na2CO3 / toluene; ethanol / 4 h / 110 °C
4: 98 percent / NBS / CCl4 / 1 h
5: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 1 h, 2.) Et2O, hexane, RT, 12 h
6: 46 percent / Et3N, PPh3, CCl4 / acetonitrile / 1.) RT, 1 h, 2.) reflux, 3 h
7: 62 percent / 1,2-dichloro-benzene / 8 h / Heating
8: 41 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 4 h / Heating
9: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C
10: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating
View Scheme
maleic acid
110-16-7

maleic acid

imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

Conditions
ConditionsYield
In methanol; water at 74℃; Heating / reflux;91%
imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

Conditions
ConditionsYield
With maleic acid In methanol; water at 74℃; for 0.5h;91%
oxalic acid
144-62-7

oxalic acid

imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 160℃; for 0.5h;90%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 160℃; for 0.5h;89%
N-t-butyloxycarbonyl-N-methylglycine anhydride
70533-97-0

N-t-butyloxycarbonyl-N-methylglycine anhydride

imiqimod
99011-02-6

imiqimod

tert-butoxycarbonyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-sarcosine

tert-butoxycarbonyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-sarcosine

Conditions
ConditionsYield
With triethylamine for 8h; Reflux;87.5%
With triethylamine In ethyl acetate for 2h; Reflux;87.5%
imiqimod
99011-02-6

imiqimod

C14H14(2)H2N4

C14H14(2)H2N4

Conditions
ConditionsYield
With deuterium In N,N-dimethyl acetamide under 1500.15 Torr; for 24h; Glovebox; Heating;80%
imiqimod
99011-02-6

imiqimod

benzyl alcohol
100-51-6

benzyl alcohol

N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
415726-68-0

N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Conditions
ConditionsYield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 140℃; for 18h; Sealed tube;72%
5-bromo-2,3-dihydrobenzo[b]furan
66826-78-6

5-bromo-2,3-dihydrobenzo[b]furan

imiqimod
99011-02-6

imiqimod

C22H22N4O

C22H22N4O

Conditions
ConditionsYield
With copper(l) iodide; N,N'-dibenzylethanediamide; potassium tert-butylate In tert-butyl alcohol at 100℃; for 24h; Molecular sieve; Schlenk technique; Inert atmosphere;43%
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
1188307-60-9

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

imiqimod
99011-02-6

imiqimod

C36H39N5O14

C36H39N5O14

Conditions
ConditionsYield
Stage #1: imiqimod With N-ethyl-N,N-diisopropylamine In ethyl acetate for 0.333333h; Microwave irradiation;
Stage #2: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate In ethyl acetate at 87℃; for 0.75h; Microwave irradiation;		40%
Stage #1: imiqimod With N-ethyl-N,N-diisopropylamine In ethyl acetate Microwave irradiation;
Stage #2: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate In ethyl acetate at 87℃; for 0.75h; Microwave irradiation;		40%
imiqimod
99011-02-6

imiqimod

ethane-1,2-diyl bis(4-nitrophenyl carbonate)

ethane-1,2-diyl bis(4-nitrophenyl carbonate)

2-(4-nitrophenyl carbonate)ethyl (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)carbamate

2-(4-nitrophenyl carbonate)ethyl (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)carbamate

Conditions
ConditionsYield
In tetrahydrofuran at 90℃; under 750.075 Torr; for 0.833333h; Microwave irradiation; Sealed tube;39%
2-(2-nitrophenyl)propyl chloroformate
179691-31-7

2-(2-nitrophenyl)propyl chloroformate

imiqimod
99011-02-6

imiqimod

C24H25N5O4

C24H25N5O4

Conditions
ConditionsYield
In 1,4-dioxane at 10 - 50℃; for 6h;38%
C42H76N2O15

C42H76N2O15

imiqimod
99011-02-6

imiqimod

C56H90N6O14

C56H90N6O14

Conditions
ConditionsYield
With HATU In dichloromethane at 20℃;35%
imiqimod
99011-02-6

imiqimod

8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
723281-26-3

8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Conditions
ConditionsYield
With bromine; acetic acid at 20℃; for 18h;26%
Stage #1: imiqimod With bromine In acetic acid for 24h;
Stage #2: With sodium carbonate In water for 18h;
With N-Bromosuccinimide In chloroform at 20 - 50℃; for 1.83333h; Heating / reflux;

Imiquimod Chemical Properties

Molecular Structure of Imiquimod (CAS NO.99011-02-6):

IUPAC Name: 1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine 
Empirical Formula: C14H16N4
Molecular Weight: 240.3036
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 33.95 Å2
Index of Refraction: 1.681
Molar Refractivity: 71.02 cm3
Molar Volume: 187.7 cm3
Surface Tension: 48.8 dyne/cm
Density: 1.28 g/cm3
Flash Point: 230 °C
Enthalpy of Vaporization: 71.67 kJ/mol
Boiling Point: 456.7 °C at 760 mmHg
Vapour Pressure: 1.58E-08 mmHg at 25°C
Melting point: 292-294°C
Stability: Incompatible with strong oxidizing agents
InChl
InChI=1/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
Smiles
c12c3c(nc(c1ncn2CC(C)C)N)cccc3
Product Categories: Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals

Imiquimod History

  The original FDA approval was on February 27, 1997, FDA Application No. (NDA) 020723, by 3M.

Imiquimod Uses

  Imiquimod (CAS NO.99011-02-6) is a prescription medication that acts as an immune response modifier. Imiquimod is approved to treat actinic keratosis, superficial basal cell carcinoma, and external genital warts. It has also been tested for treatment of molluscum contagiosum, vulvar intraepithelial neoplasia, common warts that have proven difficult to treat and vaginal intraepithelial neoplasia.Outstanding cosmetic result has resulted from the treatment of both large superficial basal cell carcinoma and squamous cell carcinoma in-situ, but the morbidity and discomfort of the treatment can be severe. Focal recurrence of tumor has been seen after imiquimod treatment, but appear to be amenable to surgical excision.

  Imiquimod can also cause subclinical lesions to become visible. This unmasking effect is felt to be of clinical benefit as lesions that may have otherwise have been missed are being treated. Photographs of actinic keratosis and basal cell carcinomas before, during and after treatment show the unmasking of subclinical disease.

Imiquimod Safety Profile

Safety Information about Imiquimod (CAS NO.99011-02-6):
Hazard Codes: ToxicT,IrritantXi
Risk Statements: 25-36/37/38
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-45-36/37/39-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2811 6.1/PG 3
Adverse side effects have been reported, in some cases serious and systemic, resulting in the revision of warning labels.

Imiquimod Specification

  Imiquimod , with CAS number of 99011-02-6, can be called 4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline ; 1H-Imidazo(4,5-c)quinolin-4-amine, 1-(2-methylpropyl)- ; 1H-Imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)- . It is a white to off white crystalline powder.

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