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6804-07-5

Basic Information
CAS No.: 6804-07-5
Name: Carbadox
Article Data: 10
Molecular Structure:
Molecular Structure of 6804-07-5 (Carbadox)
Formula: C11H10 N4 O4
Molecular Weight: 262.225
Synonyms: Carbazicacid, 3-(2-quinoxalinylmethylene)-, methyl ester, N,N'-dioxide (7CI); Carbazicacid, 3-(2-quinoxalinylmethylene)-, methyl ester, N1,N4-dioxide (8CI);Hydrazinecarboxylic acid, (2-quinoxalinylmethylene)-, methyl ester,N,N'-dioxide; Hydrazinecarboxylic acid,[(1,4-dioxido-2-quinoxalinyl)methylene]-, methyl ester (9CI); 2-Formylquinoxaline-1,4-dioxidecarbomethoxyhydrazone; Carbadox; Fortigro; GS 6244; Getroxel; Mecadox; Methyl3-(2-quinoxalinylmethylene)carbazate N1,N4-dioxide;Quinoxaline-2-carbomethoxyhydrazone 1,4-dioxide
EINECS: 229-879-0
Density: 1.447g/cm3
Melting Point: 239-240 ºC
Boiling Point: 405.47°C (rough estimate)
Flash Point: 18°(64°F)
Solubility: Soluble in 1N NaOH (50 mg/ml), and water (partly).
Hazard Symbols:
Risk Codes: R45;R11;R22   
Safety: Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
PSA: 101.61000
LogP: 1.77760
Synthetic route
6804-07-5

methyl 3-(2-quinoxalinylmethylene)carbazate N1,N4-dioxide

desoxycarbadox

Conditions
ConditionsYield
With sodium dithionite; acetic acid at 26 - 33℃; for 1h;
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    Carbadox Basic information Product Name: Carbadox Synonyms: 2-formylquinoxaline1,4-dioxidecarbomethoxyhydrazone;3-(2-chinoxalinylmethylen-1,4-dioxid)methylkarbazat;

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Chemistry

Molecular Structure of Carbadox (CAS NO.6804-07-5):

EINECS: 229-879-0
IUPAC Name: Methyl N-[(E)-(1-hydroxy-4-oxidoquinoxalin-4-ium-2-ylidene)methyl]iminocarbamate 
Molecular Formula: C11H10N4O4
Molecular Weight: 262.221500 g/mol
XLogP3-AA: 0.3
H-Bond Donor: 1
H-Bond Acceptor: 6
Canonical SMILES: COC(=O)N=NC=C1C=[N+](C2=CC=CC=C2N1O)[O-]
Isomeric SMILES: COC(=O)N=N/C=C/1\C=[N+](C2=CC=CC=C2N1O)[O-]
InChI: InChI=1S/C11H10N4O4/c1-19-11(16)13-12-6-8-7-14(17)9-4-2-3-5-10(9)15(8)18/h2-7,18H,1H3/b8-6+,13-12?
InChIKey: BPMVRAQIQQEBLN-OBPBNMOMSA-N
Index of Refraction: 1.647
Molar Refractivity: 65.92 cm3
Molar Volume: 181.2 cm3
Surface Tension: 60.7 dyne/cm
Density: 1.44 g/cm3
Melting Point: 239-240 °C
Water Solubility: 1755 mg/L at 25 °C
Storage Temp.: 2-8 °C

History

In early 2004, Carbadox was banned by the Canadian government as a livestock feed additive and for human consumption and also banned by the European Union at any level. It is approved in the United States for use in swine for up to 42 days before slaughter.

Toxicity Data With Reference

1.    

dns-hmn:oth 50 mg/L

    JTEHD6    Journal of Toxicology and Environmental Health. 10 (1982),143.
2.    

mnt-mus-orl 100 mg/kg

    MUREAV    Mutation Research. 144 (1985),81.
3.    

orl-rat LD50:850 mg/kg

    CKFRAY    Ceskoslovenska Farmacie. 30 (1981),26.
4.    

orl-mus LD50:2810 mg/kg

    CKFRAY    Ceskoslovenska Farmacie. 30 (1981),26.

Safety Profile

Safety Information of Carbadox (CAS NO.6804-07-5):
Hazard Codes: F Extremely,T Toxic
Risk Statements: 45-11-22
R45:May cause cancer
R11:Highly flammable
R22:Harmful if swallowed
Safety Statements: 53-45
S53:Avoid exposure - obtain special instructions before use
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 1325 4.1/PG 2
WGK Germany: 3
RTECS: FE2779000
Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Specification

  Carbadox with CAS Registry Number of 6804-07-5 is yellow crystalline solid. When heated to decomposition, it yields Carbon monoxide , Carbon dioxide , and Nitrogen oxides. Carbadox is also known as Carbadox [USAN:INN:BAN] ; 2-Formylquinoxaline 1,4-dioxide carbomethoxyhydrazone ; 3-(2-Chinoxalinylmethylen-1,4-dioxid)methylkarbazat ; 3-(2-Chinoxalinylmethylen-1,4-dioxid)methylkarbazat [Czech] ; CCRIS 3002 ; Carbadoxum ; Carbadoxum [INN-Latin] ; Fortigro ; GS 6244 ; Getroxel ; HSDB 7028 ; Hydrazinecarboxylic acid (2-quinoxalinylmethylene)-, methyl ester N(sup 1),N(sup 4)-dioxide ; Karbadox ; Karbadox [Czech] ; Mecadox ; Methyl 3-(2-quinoxalinylmethylene)carbazate N(sup 1),N(sup 4)-dioxide ; Methyl 3-(2-quinoxalinylmethylene)carbazate-N1,N4-dioxide ; UNII-M2X04R2E2Y ; Carbazic acid, 3-(2-quinoxalinylmethylene)-, methyl ester, N(sup 1),N(sup 4)-dioxide ; Hydrazinecarboxylic acid, (2-quinoxalinylmethylene)-, methyl ester N(sup 1),N(sup 4)-dioxide ; Hydrazinecarboxylic acid, (2-quinoxalinylmethylene)-, methyl ester, N,N'-dioxide (9CI) . It is used as antimicrobial to prevent and treat dysentery in swine and to maintain weight gain during periods of stress. It is also used as pharmaceutical excipient, feed additive.