2,4-Diaminoazobenzene
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2,4-Diaminoazobenzene
structure -
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CAS No:
495-54-5
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Formula:
C12H12N4
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Chemical Name:
2,4-Diaminoazobenzene
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Synonyms:
1,3-Benzenediamine,4-(2-phenyldiazenyl)-;C.I. Solvent Orange 3;1,3-Benzenediamine,4-(phenylazo)-;4-(2-Phenyldiazenyl)-1,3-benzenediamine;Chrysoidine Base;Chrysoidine Base A;Chrysoidine Base B;Chrysoidine G Base;Chrysoidine J Base;Chrysoidine Y Base;Chrysoidine Y Base New;Chrysoidine YD Base;Fat Brown GG;Grasan Chrysoidine;Waxoline Orange Y;4-(Phenylazo)-1,3-phenylenediamine;Azobenzene-2,4-diamine;2,4-Diaminoazobenzene;Solvent Orange 3;Neptune Orange Base 206;C.I. 11270:1;NSC 3273;89961-16-0
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CAS No:
2,4-Diaminoazobenzene Basic Attributes
212.25
212.25
207-803-7
IP3X2567YP
3273
DTXSID4043856
REDDISH-BROWN CRYSTALLINE POWDER|Red-brown powder|Burgundy crystalline powder
Characteristics
76.8
4.42880
DryPowder, WetSolid
1.23 g/cm3
118-118.5 DEG C
2262 deg C
214.8ºC
1.65
In water = 20 mg/l; in ethanol = 9 mg/l; in methyl Cellosolve = 20 mg/l
1.13E-07mmHg at 25°C
GIVES YELLOW SOLN IN CONCN SULFURIC ACID, ORANGE SOLN IN DIL SULFURIC ACID, AND IN NITRIC ACID|Unstable to excessive heat in solution preparation
Safety Information
S24/25
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P391, P405, P501
H302
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P391, P405, and P501|Danger|P201, P202, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P332+P313, P333+P313, P362, P363, P405, and P501
Toxicity
C.I. Solvent Orange 3's production and use as a dye for cotton, silk, leather, plastics, wood and as a biological stain(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 840(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(3), indicates that C.I. Solvent Orange 3 will have low mobility in soil(SRC). As C.I. Solvent Orange 3 may act as an ionic compound in the environment, volatilization of this compound will not be important from soil surfaces(4,SRC). This compound may be susceptible to biodegradation under anaerobic conditions(SRC); environmental microorganisms were able to metabolize C.I. Solvent Orange 3 under anaerobic conditions, forming aromatic amines(5).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 840(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(1), indicates that C.I. Solvent Orange 3 may adsorb to suspended solids and sediment in water(SRC). As C.I. Solvent Orange 3 may act as an ionic compound, volatilization from water surfaces is not expected(3,SRC). According to a classification scheme(4), an estimated BCF value of 114(1,SRC), from the measured water solubility(2), suggests that bioconcentration in aquatic organisms is high(SRC). This compound may be susceptible to biodegradation under anaerobic conditions; environmental microorganisms were able to metabolize C.I. Solvent Orange 3 under anaerobic conditions, forming aromatic amines(5).|ATMOSPHERIC FATE: The ionic nature of C.I. Solvent Orange 3 makes this compound essentially non-volatile(1,SRC).
An estimated BCF value of 114 was calculated for C.I. solvent Orange 3(SRC), using a measured water solubility(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is high(SRC).
The Koc of C.I. Solvent Orange 3 is estimated as approximately 840(SRC), using a measured water solubility of 20 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that C.I. Solvent Orange 3 has low mobility in soil(SRC). Due to the ionic nature of the dye, the retention of C.I. Solvent Orange 3 by ion-exchange processes(4,SRC), particularly on clay surfaces and adsorption at mineral surfaces such as geothite(5,SRC), may slow down or prevent leaching(SRC).
Since C.I. Solvent Orange 3 may act as an ionic compound in the environment, volatilization from water and moist soil surfaces will not be important(1,SRC).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,040 workers (2,690 of these are female) are potentially exposed to C.I. Solvent Orange 3 in the US(1). Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where C.I. Solvent Orange 3 is produced or used(SRC). The general population will be exposed to C.I. Solvent Orange 3 via dermal contact with products containing this compound(SRC).
Drug Information
WHEN CHRYSOIDINE WAS FED TO MICE, ONLY VERY SMALL AMOUNTS (23.8 MICROMOLES/KG PROTEIN AFTER 7 DAYS) WERE FOUND BOUND TO LIVER PROTEINS.
A case control study in West Yorkshire (England, UK) was used to investigate possible risks of bladder cancer among those fishermen who used azo-based dyestuffs to stain maggots or who purchased ready colored maggots. No risks were found, although the confidence limits of the estimates are wide. These data refer to exposures over 10 yr ago and it is possible that recent changes in fishing practice, if they have occurred, are not yet assessable due to the long mean latency seen in bladder cancer when exposure to carcinogens is not great. The general use of these substances is not proposed to be without hazard, rather no risk is associated with the study group and the chemicals under study apparently are not a major cause of bladder cancer.
C.I. Basic Orange 2
2,4-Diaminoazobenzene Use and Manufacturing
HOFMANN, BER 10, 213 (1877); MAXIMOFF, US PATENT 2,053,095 (1935 TO AZODAL CO).|m-Phenylenediamine + benzenediazonium chloride (azo coupling)
Dyeing silk and cotton.Biological stain.
Dyes
< 25,000 lb|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1981) PROBABLY GREATER THAN 9.08X10+6 GRAMS
ESSENTIALLY 100% AS A DYE
Synthetic dye and pigment manufacturing|1,3-Benzenediamine, 4-(2-phenyldiazenyl)-: ACTIVE|Cationic orange dye with a monoazo chromophore
CHEMICAL MONITORING OF URINE FROM WORKERS POTENTIALLY EXPOSED TO BENZIDINE-DERIVED AZO DYES WAS DETERMINED BY COLORIMETRIC AND GAS CHROMATOGRAPHIC METHODS.
Computed Properties
Molecular Weight:212.25
XLogP3:2.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:212.106196400
Monoisotopic Mass:212.106196400
Topological Polar Surface Area:76.8
Heavy Atom Count:16
Complexity:235
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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