Name: 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE
SKU: 77500-04-0

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Pharmaceutical (13)
Others (4)
Organic Chemicals (4)

Basic Information

Molecular Structure:
CAS No.:	77500-04-0
Name:	2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE
Article Data:	5

Formula:	C₁₁H₁₁N₅
Molecular Weight:	213.242
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;
Density:	1.47 g/cm³
Melting Point:	> 300 °C
Boiling Point:	458.4 °C at 760mmHg
Flash Point:	231 °C
Hazard Symbols:	T
PSA:	69.62000
LogP:	1.98830

Synthetic route

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

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

Conditions

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

: 506-68-3
bromocyane

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

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

: 506-68-3
bromocyane

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

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

Conditions

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

: 367-31-7
4-fluoro-1,2-phenylenediamine

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) hydrogen / 1.) Raney nickel / 1.) ethanol, RT View Scheme

: 364-78-3
2-nitro-4-fluoroaniline

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

Conditions

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

: 107095-02-3
N4-methyl-3-nitro-1,2,4-benzenetriamine

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

Conditions

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

: 96601-02-4
7-fluoro-2-methylquinoxaline

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 16 h / 179 - 180 °C 3: 1.) H2 / 1.) Ni View Scheme

: 96600-57-6
7-methylamino-2-methylquinoxaline

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

Conditions

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

: 1831-88-5
7-chloro-2-methylquinoxaline

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 3: 1.) H2 / 1.) Ni View Scheme

: 108905-67-5
3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline

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

Conditions

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

Raw Materials

364-78-3

506-68-3

615-71-4

Downstream Products

113638-78-1

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Chemistry

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

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.

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.

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) .

Safety Profile

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

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 .