Product Name

  • Name

    2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE

  • EINECS
  • CAS No. 77500-04-0
  • Article Data5
  • CAS DataBase
  • Density 1.47 g/cm3
  • Solubility
  • Melting Point > 300 °C
  • Formula C11H11N5
  • Boiling Point 458.4 °C at 760mmHg
  • Molecular Weight 213.242
  • Flash Point 231 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 77500-04-0 (2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE)
  • Hazard Symbols ToxicT
  • Synonyms 3H-Imidazo(4,5-f)quinoxaline, 2-amino-3,8-dimethyl-;3,8-Dimethyl-3H-imidazo(4,5-f)quinoxalin-2-amine;8-Methyl-IQX;2-Amino-3,8-dimethyl-3H-imidazo(4,5-f)quinoxaline;3H-Imidazo[4,5-f]quinoxalin-2-amine,3,8- dimethyl-;8-MeIQX;3H-Imidazo(4,5-f)quinoxalin-2-amine, 3,8-dimethyl-;MeIQx;3,8-DIMETHYL-3H-IMIDAZO(4,5-f) QUINOXALIN-2-AMINE;2-AMINO-3,8-DIMETHYL-3H-IMIDAZO(4,5-f) QUINOXALINE;
  • PSA 69.62000
  • LogP 1.98830

Synthetic route

2-(N-benzylamino)-3,8-dimethylimidazo<4,5-f>quinoxaline
138336-27-3

2-(N-benzylamino)-3,8-dimethylimidazo<4,5-f>quinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 96h; Heating;72%
bromocyane
506-68-3

bromocyane

3,N6-Dimethyl-quinoxaline-5,6-diamine
92116-67-1

3,N6-Dimethyl-quinoxaline-5,6-diamine

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

bromocyane
506-68-3

bromocyane

2-methyl-7-methylamino-8-nitroquinoxaline
78411-55-9

2-methyl-7-methylamino-8-nitroquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
With hydrogen; nickel 1.) ethanol, RT; Yield given. Multistep reaction;
With hydrogen; nickel Multistep reaction;
4-fluoro-1,2-phenylenediamine
367-31-7

4-fluoro-1,2-phenylenediamine

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 1.) hydrogen / 1.) Raney nickel / 1.) ethanol, RT
View Scheme
2-nitro-4-fluoroaniline
364-78-3

2-nitro-4-fluoroaniline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen / Raney nickel / ethanol / Ambient temperature
3: 1.) hydrogen / 1.) Raney nickel / 1.) ethanol, RT
View Scheme
N4-methyl-3-nitro-1,2,4-benzenetriamine
107095-02-3

N4-methyl-3-nitro-1,2,4-benzenetriamine

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 1.) H2 / 1.) Ni
View Scheme
7-fluoro-2-methylquinoxaline
96601-02-4

7-fluoro-2-methylquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 16 h / 179 - 180 °C
3: 1.) H2 / 1.) Ni
View Scheme
7-methylamino-2-methylquinoxaline
96600-57-6

7-methylamino-2-methylquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 1.) H2 / 1.) Ni
View Scheme
7-chloro-2-methylquinoxaline
1831-88-5

7-chloro-2-methylquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
3: 1.) H2 / 1.) Ni
View Scheme
3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline
108905-67-5

3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 51.1 percent / aq. KMnO4, glacial acetic acid / 0.75 h / Ambient temperature
2: 88 percent / 45 h / 140 - 150 °C
3: 72 percent / ammonium formate / 10percent Pd/C / methanol / 96 h / Heating
View Scheme
3,8-dimethyl-2-(methylsulfonyl)imidazo<4,5-f>quinoxaline
138336-21-7

3,8-dimethyl-2-(methylsulfonyl)imidazo<4,5-f>quinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / 45 h / 140 - 150 °C
2: 72 percent / ammonium formate / 10percent Pd/C / methanol / 96 h / Heating
View Scheme
3-methyl-6-aminoquinoxaline
4236-41-3

3-methyl-6-aminoquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: C5H5N
2: HNO3, AcOH
3: H2SO4
4: NaH
5: 1.) Fe-HCl, 2.) base
View Scheme
6-amino-3-methyl-5-nitroquinoxaline
78411-54-8

6-amino-3-methyl-5-nitroquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaH
2: 1.) Fe-HCl, 2.) base
View Scheme
2-methyl-7-methylamino-8-nitroquinoxaline
78411-55-9

2-methyl-7-methylamino-8-nitroquinoxaline

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Fe-HCl, 2.) base
View Scheme
4-Methyl-N-(3-methyl-quinoxalin-6-yl)-benzenesulfonamide
78411-52-6

4-Methyl-N-(3-methyl-quinoxalin-6-yl)-benzenesulfonamide

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: HNO3, AcOH
2: H2SO4
3: NaH
4: 1.) Fe-HCl, 2.) base
View Scheme
4-Methyl-N-(3-methyl-5-nitro-quinoxalin-6-yl)-benzenesulfonamide
78411-53-7

4-Methyl-N-(3-methyl-5-nitro-quinoxalin-6-yl)-benzenesulfonamide

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2SO4
2: NaH
3: 1.) Fe-HCl, 2.) base
View Scheme
benzene-1,2,4-triamine
615-71-4

benzene-1,2,4-triamine

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
2: C5H5N
3: HNO3, AcOH
4: H2SO4
5: NaH
6: 1.) Fe-HCl, 2.) base
View Scheme
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

O6-benzyl-8-bromo-3′,5′-O-bis(tert-butyldimethylsilyl)-N2-dimethoxytrityl-2′-deoxyguanosine
479408-23-6

O6-benzyl-8-bromo-3′,5′-O-bis(tert-butyldimethylsilyl)-N2-dimethoxytrityl-2′-deoxyguanosine

6-benzyloxy-N2-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-9H-purine-2,8-diamine
661465-21-0

6-benzyloxy-N2-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-9H-purine-2,8-diamine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 6h; Buchwald-Hartwig arylamination reaction;97%
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

Trimethylenediamine
109-76-2

Trimethylenediamine

2-N-aminopropyl-MeIQx
113638-78-1

2-N-aminopropyl-MeIQx

Conditions
ConditionsYield
at 175℃; for 168h;68%
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

A

IQx-8-CHO

IQx-8-CHO

B

IQx-8-COOH

IQx-8-COOH

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane for 5h; Heating;A 30%
B 60%
With selenium(IV) oxide In 1,4-dioxane for 5h; Heating;A 60%
B 30%
With selenium(IV) oxide In 1,4-dioxane for 5h; Reflux;A 30%
B 60%
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

8-CH2OH-IQX

8-CH2OH-IQX

Conditions
ConditionsYield
With liver S-9 protein from rats pretreated with PCB; NAD; NADPH; glucose 6-phosphate dehydrogenase at 37℃; for 3h; pH=7.6; Dehydrogenation;
With selenium(IV) oxide
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

A

8-CH2OH-IQX

8-CH2OH-IQX

B

IQx-8-CHO

IQx-8-CHO

Conditions
ConditionsYield
Stage #1: 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline With selenium(IV) oxide In 1,4-dioxane for 5h; Heating;
Stage #2: With sodium cyanoborohydride In dimethyl sulfoxide at 37℃; for 1h;
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

2-amino-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-1,9-dihydro-purin-6-one

2-amino-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-1,9-dihydro-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / tris(dibenzylideneacetone)dipalladium; 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene; Cs2CO3 / toluene / 6 h / 100 °C
2: CCl3COOH / methanol; CH2Cl2
3: H2 / Pd / tetrahydrofuran
View Scheme
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-9H-purine-2,8-diamine
896719-54-3

6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-9H-purine-2,8-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / tris(dibenzylideneacetone)dipalladium; 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene; Cs2CO3 / toluene / 6 h / 100 °C
2: CCl3COOH / methanol; CH2Cl2
View Scheme
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

N2-(2'-deoxyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline

N2-(2'-deoxyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97 percent / tris(dibenzylideneacetone)dipalladium; 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene; Cs2CO3 / toluene / 6 h / 100 °C
2: CCl3COOH / methanol; CH2Cl2
3: H2 / Pd / tetrahydrofuran
4: triethylammine trihydrogenfluoride complex / tetrahydrofuran
View Scheme
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

4-Amino-N-[3-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-propyl]-benzamide
113638-85-0

4-Amino-N-[3-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-propyl]-benzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / 168 h / 175 °C
2: pyridine / 2 h / Ambient temperature
3: H2 / 10percent Pd/C / ethanol
View Scheme
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

N-[3-(3,8-Dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-propyl]-4-nitro-benzamide
113638-79-2

N-[3-(3,8-Dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-propyl]-4-nitro-benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / 168 h / 175 °C
2: pyridine / 2 h / Ambient temperature
View Scheme
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

A

8-CH2OH-IQX

8-CH2OH-IQX

B

IQx-8-COOH

IQx-8-COOH

Conditions
ConditionsYield
Stage #1: 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline With selenium(IV) oxide In 1,4-dioxane for 5h; Reflux;
Stage #2: With sodium cyanoborohydride In 1,4-dioxane at 37℃; for 1h;
2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

N2-(3,8-dimethylimidazo[4,5-f]quinoxalin-2-yl)sulfamic acid

N2-(3,8-dimethylimidazo[4,5-f]quinoxalin-2-yl)sulfamic acid

Conditions
ConditionsYield
With pyridine; chlorosulfonic acid
L-serin
56-45-1

L-serin

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline
77500-04-0

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline

C14H16N6O2

C14H16N6O2

Conditions
ConditionsYield
at 200℃;

2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline Chemical Properties

Empirical Formula: C11H11N5
Molecular Weight: 213.2385 g/mol
Index of Refraction: 1.776 
Melting point: > 300 °C
Density: 1.47 g/cm3 
Melting Point: > 300 °C
Flash Point: 231 °C
Enthalpy of Vaporization: 71.87 kJ/mol
Boiling Point: 458.4 °C at 760 mmHg
Vapour Pressure: 1.38E-08 mmHg at 25 °C
Structure of 2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline (CAS NO.77500-04-0):
             
IUPAC Name: 3,8-Dimethylimidazo[4,5-f]quinoxalin-2-amine 
XLogP3: 1
H-Bond Donor: 1
H-Bond Acceptor: 4
Tautomer Count: 4
Exact Mass: 213.101445
MonoIsotopic Mass: 213.101445
Topological Polar Surface Area: 69.6
Heavy Atom Count: 16 
Canonical SMILES: CC1=CN=C2C=CC3=C(C2=N1)N=C(N3C)N
InChI: InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)
InChIKey: DVCCCQNKIYNAKB-UHFFFAOYSA-N
Product Categories of 2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline (CAS NO.77500-04-0): Heterocyclic Compounds; Mutagenesis Research Chemicals

2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline Uses

 2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline (CAS NO.77500-04-0) has been used for diet meat mutagen heterocyclic amine colorectal adenoma recurrence.

2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline Toxicity Data With Reference

1.    

mma-sat 5 ng/plate

     MUREAV    Mutation Research. 144 (1985),131.
2.    

slt-dmg-orl 100 ng/kg

     JJCREP    Japanese Journal of Cancer Research (Gann). 76 (1985),468.
3.    

msc-ham:ovr 300 mg/L

     MUTAEX    Mutagenesis. 2 (1987),483.

2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline Consensus Reports

IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 56 (1993),p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 56 (1993),p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 40 (1986),p. 283.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human No Adequate Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 40 (1986),p. 283.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 56 (1993),p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ToxicT
RTECS: NJ5925500
Hazard Note: Toxic

2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline Specification

 2-Amino-3,8-dimethylimidazo(4,5-f)quinoxaline also can be called 2-Amino-3,8-dimethyl-3H-imidazo(4,5-f)quinoxaline ; 3,8-Dimethyl-3H-imidazo(4,5-f)quinoxalin-2-amine ; 8-MeIQX ; 8-Methyl-IQX ; BRN 4188271 ; CCRIS 2536 .

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