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3,3'-Dichlorobenzidine

3,3'-Dichlorobenzidine
3,3'-Dichlorobenzidine structure
CAS No.
91-94-1
Chemical Name:
3,3'-Dichlorobenzidine
Synonyms
ci23060;c.i.23060;CCRIS 220;C.I. 23060;curithanec126;3.3'-Dichlorob;Curithane C 126;Dichlorobenzidine;rcrawastenumberu073;WLN: ZR BG DR DZ CG
CBNumber:
CB5178304
Molecular Formula:
C12H10Cl2N2
Formula Weight:
253.13
MOL File:
91-94-1.mol

3,3'-Dichlorobenzidine Properties

Melting point:
132.5°C
Boiling point:
398.89°C (rough estimate)
Density 
1.3171 (rough estimate)
vapor pressure 
4.2 x 10-7 at 25 °C (estimated, Howard, 1989)
refractive index 
1.6400 (estimate)
Flash point:
10 °C
storage temp. 
2-8°C
solubility 
Soluble in ethanol, benzene, and glacial acetic acid (Windholz et al., 1983)
form 
neat
Henry's Law Constant
4.5 x 10-8 atm?m3/mol at 25 °C (estimated, Howard, 1989)
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
HUWXDEQWWKGHRV-UHFFFAOYSA-N
CAS DataBase Reference
91-94-1(CAS DataBase Reference)
NIST Chemistry Reference
[1,1'-Biphenyl]-4,4'-diamine, 3,3'-dichloro-(91-94-1)
EPA Substance Registry System
[1,1'-Biphenyl]- 4,4'-diamine, 3,3'-dichloro-(91-94-1)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T,N,F
Risk Statements  45-21-43-50/53-52/53-39/23/24/25-23/24/25-11-51/53
Safety Statements  53-45-60-61-36/37-16-7
RIDADR  UN 3077 9/PG 3
WGK Germany  3
RTECS  DD0550000
HazardClass  IRRITANT
HS Code  29215900
Hazardous Substances Data 91-94-1(Hazardous Substances Data)
Toxicity Acute oral LD50 for rats as free base or dihydrochloride are 7,070 and 3,820, respectively (Gerade and Gerade, 1974).
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H312 Harmful in contact with skin Acute toxicity,dermal Category 4 Warning P280,P302+P352, P312, P322, P363,P501
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H350 May cause cancer Carcinogenicity Category 1A, 1B Danger
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
H412 Harmful to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 3 P273, P501
Precautionary statements:
P201 Obtain special instructions before use.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P501 Dispose of contents/container to..…

3,3'-Dichlorobenzidine price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 48029 3,3′-Dichlorobenzidine solution certified reference material, 2000 μg/mL in methanol 91-94-1 48029 $37.6 2018-11-23 Buy
Sigma-Aldrich 48525 3,3′-Dichlorobenzidine analytical standard 91-94-1 48525 $70 2018-11-23 Buy

3,3'-Dichlorobenzidine Chemical Properties,Uses,Production

Chemical Properties

colourless to white crystalline solid

Chemical Properties

3,3’-Dichlorobenzidine is a gray or purple crystalline solid.

Physical properties

Colorless to grayish-purple needles or crystals with a mild or pungent odor

Uses

Intermediate in the manufacture of azo dyes and pigments for printing inks, textiles, paints, plastics, and crayons; curing agent for isocyanate-terminated polymers and resins; rubber compounding ingredient; analytical determination of gold; formerly used as chemical intermediate for direct red 61 dye.

General Description

Gray to purple crystalline powder. Insoluble in water. Very toxic. Used in the dye industry, curing agent for isocyanate terminated resins.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl and NOx.

Potential Exposure

A halide-and amine-substituted aromatic compound used in the dye industry, curing agent for isocyanate terminated resins. The major uses of dichlorobenzidine are in the manufacture of pigments for printing ink, textiles, plastics, and crayons and as a curing agent for solid urethane plastics. There are no substitutes for many of its uses. Additional groups that may be at risk include workers in the printing or graphic arts professions handling the 3,3’-DCB-based azo pigments. 3,3’-DCB may be present as an impurity in the pigments, and there is some evidence that 3,3’-DCB may be metabolically liberated from the azo pigment

Source

Synthesized from o-chloronitrobenzene in the presence of NaOH and zinc dust (Shriner et al., 1978).

Environmental Fate

Biological. In activated sludge, 2.7% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Sikka et al. (1978) reported 3,3′-dichlorobenzidine is resistant to degradation by indigenous aquatic microbial communities in a 4-wk period. Under aerobic and anaerobic conditions, 3,3′-dichlorobenzidine is mineralized very slowly (Boyd et al., 1984; Chung and Boyd, 1987). Nyman et al. (1997a) studied the transformation of 3,3′-dichlorobenzidine under laboratory controlled conditions at 20 °C. Wet sediment (50 g) and water (150 mL) from Lake Macatawa, Holland, MI were placed in glass serum bottles and purged with nitrogen to ensure anaerobic conditions to which 3,3′-dichlorobenzidine was added. The bottles were incubated in the dark at 20 °C for 12 months. Soil and water samples were retrieved periodically for transformation product identification using HPLC. The investigators identified 3-chlorobenzidine as a transient metabolite from the biological transformation of 3,3′-dichlorobenzidine. 3-Chlorobenzidine rapidly dechlorinated forming the end product benzidine.
Photolytic. An aqueous solution subjected to UV radiation caused a rapid degradation (half-life <10 min) to monochlorobenzidine, benzidine, and several unidentified, brightly-colored, waterinsoluble chromophores (Banerjee et al., 1978). In a similar experiment, 3,3′-dichlorobenzidine in an aqueous solution was subjected to radiation at λ=310 nm for approximately 15 min. During the period of irradiation, concentrations of 3,3′-dichlorobenzidine decreased rapidly. 3-Chlorobenzidine formed as a transient intermediate which underwent dechlorination forming a benzidine, a stable photoproduct. Depending upon the wavelength used, the benzidine yields ranged from 8 to 12% of the total 3-chlorobenzidine transformed (Nyman et al., 1997). A carbon dioxide yield of 41.2% was achieved when 3,3′-dichlorobenzidine adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. 3,3′-Dichlorobenzidine will not hydrolyze to any reasonable extent (Kollig, 1993).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities at were 300, 190, 120, and 73 mg/g, respectively (Dobbs and Cohen, 1980).

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Purification Methods

Crystallise the benzidine from EtOH, pet ether (m 133o) or *benzene. [Beilstein 13 H 234, 13 I 67, 13 II 106, 13 III 477, 13 IV 384.] CARCINOGEN.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Achemical base: neutralize acids to form salts plus water with an exothermic reaction. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generatedby amines in combination with strong reducing agents such as hydrides, nitrides, alkali metals, and sulfides.

Waste Disposal

Incineration (816C, 0.5 second for primary combustion; 1204C, 1.0 second for secondary combustion). The formation of elemental chlorine can be prevented through injection of steam ormethane into the combustion process. nitrogen oxides may be abated through the use of thermal or catalytic devices. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

3,3'-Dichlorobenzidine Preparation Products And Raw materials

Raw materials

Preparation Products


3,3'-Dichlorobenzidine Suppliers

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3,3'-Dichlorobenzidine Spectrum


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