77500-04-0

Basic information

• Product Name: 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE
• Synonyms: 3H-Imidazo(4,5-F)quinoxalin-2-amine, 3,8-dimethyl-;8-Methyl-iqx;Brn 4188271;Ccris 2536;2-amino-3,8-dimethyl-3h-imidazo(4,5-f)quinoxaline;5-f)quinoxaline,2-amino-3,8-dimethyl-3h-imidazo(;MEIQX;2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE
• CAS NO: 77500-04-0
• Molecular Formula: C₁₁H₁₁N₅
• Molecular Weight: 213.24
• Product Categories: Heterocyclic Compounds;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 77500-04-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: > 300°C
• Boiling Point: 343.23°C (rough estimate)
• Flash Point: 231 °C
• Appearance: /
• Density: 1.2597 (rough estimate)
• Vapor Pressure: 1.38E-08mmHg at 25°C
• Refractive Index: 1.6880 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 2.20±0.50(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE(77500-04-0)
• EPA Substance Registry System: 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE(77500-04-0)

Safety Data

• Hazard Codes: T
• RTECS: NJ5925500
• Hazardous Substances Data: 77500-04-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 77500-04-0 differently. You can refer to the following data:
1. Diet meat mutagen heterocyclic amine colorectal adenoma recurrence.
2. Mutagen found in white meat, increasing the rate of colorectal adenomas.

Definition

ChEBI: An imidazoquinoxaline that is 3H-imidazo[4,5-f]quinoxaline substituted at positions 3 and 8 by methyl groups and at position 2 by an amino group. A mutagenic compound found in cooked beef.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Carcinogenicity

MeIQx is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals and supporting genotoxicity data.

InChI:InChI=1/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)

Synthetic route

2-(N-benzylamino)-3,8-dimethylimidazo<4,5-f>quinoxaline (138336-27-3) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 96h; Heating;	72%

bromocyane (506-68-3) + 3,N6-Dimethyl-quinoxaline-5,6-diamine (92116-67-1) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

bromocyane (506-68-3) + 2-methyl-7-methylamino-8-nitroquinoxaline (78411-55-9) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
With hydrogen; nickel 1.) ethanol, RT; Yield given. Multistep reaction;
With hydrogen; nickel Multistep reaction;

4-fluoro-1,2-phenylenediamine (367-31-7) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) H2 / 1.) Ni View Scheme

7-fluoro-2-methylquinoxaline (96601-02-4) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) H2 / 1.) Ni View Scheme

7-chloro-2-methylquinoxaline (1831-88-5) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

Conditions	Yield
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) → 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0)

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

Conditions	Yield
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) + Trimethylenediamine (109-76-2) → 2-N-aminopropyl-MeIQx (113638-78-1)

Conditions	Yield
at 175℃; for 168h;	68%

2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0) → IQx-8-CHO + IQx-8-COOH

Conditions	Yield
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) → 8-CH2OH-IQX

Conditions	Yield
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) → 8-CH2OH-IQX + IQx-8-CHO

Conditions	Yield
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-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	Yield
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) → 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)

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

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

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

Conditions	Yield
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) → 8-CH2OH-IQX + IQx-8-COOH

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

Conditions	Yield
With pyridine; chlorosulfonic acid

L-serin (56-45-1) + 2-amine-3,8-dimethylimidazo[4,5-f]quinoxaline (77500-04-0) → C14H16N6O2

Conditions	Yield
at 200℃;

Upstream product

• 78411-52-6 4-Methyl-N-(3-methyl-quinoxalin-6-yl)-benzenesulfonamide 
• 63155-04-4 4-chloro-5-methylbenzene-1,2-diamine 
• 2255-94-9 5-chloro-6-methyl-2,1,3-benzoselenadiazole 
• 149703-59-3 7-methyl-6-methylamino-5-nitroquinoxaline 
• 149703-56-0 6-methyl-5-methylamino-4-nitro-2,1,3-benzoselenadiazole 
• 147021-84-9 5-chloro-6-methyl-4-nitro-2,1,3-benzoselenadiazole 
• 506-68-3 bromocyane 
• 615-71-4 benzene-1,2,4-triamine 
• 78411-53-7 4-Methyl-N-(3-methyl-5-nitro-quinoxalin-6-yl)-benzenesulfonamide 
• 78411-55-9 2-methyl-7-methylamino-8-nitroquinoxaline 
• 78411-54-8 6-amino-3-methyl-5-nitroquinoxaline 
• 4236-41-3 3-methyl-6-aminoquinoxaline 
• 138336-21-7 3,8-dimethyl-2-(methylsulfonyl)imidazo<4,5-f>quinoxaline 
• 108905-67-5 3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline 

Downstream Products

• 113638-78-1 2-N-aminopropyl-MeIQx 
• 115781-40-3 N²-(3,8-dimethylimidazo[4,5-f]quinoxalin-2-yl)sulfamic acid 
• 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 
• 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 
• 113638-79-2 N-[3-(3,8-Dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-propyl]-4-nitro-benzamide 
• 113638-85-0 4-Amino-N-[3-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-ylamino)-propyl]-benzamide 

Relevant articles and documents

Synthesis of Mutagenic Methyl- and Phenyl-substituted 2-Amino-3H-imidazoquinoxalines via 2,1,3-Benzoselenadiazoles

2-Amino-3-methyl-3H-imidazoquinoxaline, all its derivatives with 1-4 methyl groups in positions 4, 5, 7 and 8, and 2-amino-3,5-dimethyl-7,8-diphenyl-3H-imidazoquinoxaline have been synthesized from the corresponding 6-methylamino-5-nitroquinoxalines through reduction and cyclization with cyanogen bromide.The quinoxalines were obtained from the appropriate α-dicarbonyl compounds and 4-methylamino-3-nitro-1,2-benzenediamines.The latter were prepared from 4-halo-1,2-benzenediamines via 2,1,3-benzoselenadiazoles.The 7- and 8-phenyl derivatives of 2-amino-3,5-dimethyl-3H-imidazoquinoxaline have been synthesized in a slightly different way.

Efficient synthesis of mutagenic imidazo[4,5-f] quinoxalin-2-amines via readily accessible 2,1,3-benzoselenadiazoles.

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SYNTHESIS OF 2-AMINO-3,8-DIMETHYLIMIDAZOQUINOXALINE (Me-IQx), A POTENT MUTAGEN ISOLATED FROM FRIED BEEF

A potent mutagen, 2-amino-3,8-dimethylimidazoquinoxaline (Me-IQx), isolated from fried beef and its 3,7-dimethyl derivative were synthesized from 6-amino-3-methylquinoxaline and 6-amino-2-methylquinoxaline, respectively.These compounds showed strong mutagenic activity towards Salmonella typhimurium TA98 in the presence of S9 Mix.