91-94-1

Usage

Uses

Used in the Production of Azo Dyes and Pigments:
3,3'-Dichlorobenzidine is used as an intermediate in the manufacture of azo dyes and pigments for printing inks, textiles, paints, plastics, and crayons. Its chemical structure allows it to react with other compounds to form a wide range of colored products with various shades and properties.
Used in the Production of Yellow and Red Pigments:
3,3'-Dichlorobenzidine is used as a key ingredient in the production of yellow and red pigments for the printing ink, textile, paper, paint, rubber, plastic, and related industries. These pigments are valued for their color strength, stability, and resistance to various environmental factors.
Used as a Curing Agent for Isocyanate-Terminated Polymers and Resins:
3,3'-Dichlorobenzidine is used as a curing agent for isocyanate-terminated polymers and resins. Its ability to react with isocyanate groups allows it to cross-link and cure these polymers, resulting in improved mechanical properties and durability.
Used as a Rubber Compounding Ingredient:
3,3'-Dichlorobenzidine is used as a rubber compounding ingredient, where it helps to improve the physical and chemical properties of rubber products. Its presence in rubber compounds can enhance the rubber's resistance to heat, oxidation, and other forms of degradation.
Used for Analytical Determination of Gold:
3,3'-Dichlorobenzidine is used in analytical chemistry for the determination of gold. Its chemical properties allow it to form complexes with gold ions, which can be measured and used to determine the concentration of gold in a sample.
Formerly Used as a Chemical Intermediate for Direct Red 61 Dye:
3,3'-Dichlorobenzidine was formerly used as a chemical intermediate for the production of Direct Red 61 dye. This dye was used in various applications, including textiles and paper, but has since been replaced by other, more environmentally friendly dyes.

Air & Water Reactions

Insoluble in water.

Health Hazard

3,3'-Dichlorobenzidine (DCB) is carcinogenic in several animal species.

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.

Carcinogenicity

Studies in several test systems have shown DCB to be genotoxic in vitro and in vivo and suggest that this effect most likely mediates the carcinogenicity of the chemical. In vitro, DCB has induced sister chromatid exchanges, unscheduled DNA synthesis, and positive responses in bacterial Salmonella assays; in vivo DCB induced micronuclei in polychromatic erythrocytes in male mice and fetuses. Because of demonstrated potent carcinogenicity in multiple animal species, evidence of genotoxicity, and structural relationship to the known bladder carcinogen benzidine, DCB should be regarded as a probable human carcinogen and exposure by any route should be avoided. 3,3￠-Dichlorobenzidene has no threshold limit value (TLV) exposure limit and is classified as an A3, confirmed animal carcinogen with unknown relevance to humans, and a notation for skin absorption.

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.

InChI:InChI=1/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2

Upstream product

• 88-73-3 2-Chloronitrobenzene 
• 7647-01-0 hydrogenchloride 
• 782-74-1 1,2-bis(2-chlorophenyl)hydrazine 
• 1310-73-2 sodium hydroxide 
• 97-36-9 m-acetoacetoxylidide 
• 4433-79-8 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene 
• 2415-85-2 3-oxo-N-(p-tolyl)butanamide 
• 112-57-2 N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine 
• 64-17-5 ethanol 
• 7334-33-0 2,2'-dichloroazobenzene 
• 613-35-4 N,N'-Diacetylbenzidin 

Downstream Products

• 35958-51-1 N,N'-diacetyl-3,3'-dichlorobenzidine 
• 72732-23-1 N-acetyl-3,3'-dichlorobenzidine 
• 98275-06-0 4.4'-Di-(4-nonyloxy-benzylidenamino)-3.3'-dichlor-biphenyl 
• 13497-54-6 4,4'-Dihydroxy-3,3'-dichlorobiphenyl 
• 858811-38-8 N,N'-(3,5,3',5'-tetrachloro-biphenyl-4,4'-diyl)-bis-benzenesulfonamide 
• 37989-84-7 3,3'-dichloro-4,4'-dinitro-biphenyl 
• 782-74-1 1,2-bis(2-chlorophenyl)hydrazine 
• 124236-34-6 C₃₆H₃₃Cl₃N₆O₆ 
• 97794-07-5 C_.I_. pigment yellow 12 
• 3520-72-7 pigment orange 13 
• 49744-39-0 3,3'-dichloro-biphenyl-4,4'-bisdiazonium; chloride 
• 5102-83-0 pigment yellow 13 

Relevant academic research and scientific papers

Production process of 3, 3'-dichlorobenzidine hydrochloride

The invention relates to a production process of 3, 3'-dichlorobenzidine hydrochloride, which belongs to the field of organic chemical industry, and is characterized in that o-nitrochlorobenzene is used as a main raw material to carry out catalytic hydrogenation reduction reaction, the obtained reduction product is rectified, and then the rectified target product 2, 2-dichlorohydroazobenzene is subjected to transposition and separation to obtain the 3, 3'-dichlorobenzidine hydrochloride. According to the method, zero emission of waste acid in production of 3, 3'-dichlorobenzidine is realized, waste acid pollution is completely eradicated, the key problem restricting production of 3, 3-dichlorobenzidine is solved, the byproduct 2-chloroaniline is realized, the economic benefit is improved, in addition, the production procedures are greatly reduced, the production efficiency is improved, and the energy consumption is reduced.

Surface-active compounds based on modified castor oil fatty substances

The demands on the properties of pigments, in particular in the fields of emulsion paints and printing inks, which constantly become more specific have made it necessary to develop selective and environmentally friendly dispersing, emulsifying and coupling auxiliaries. The compounds according to the invention are esterification and/or arylation products prepared from natural or modified castor oil or ricinoleic acids, which products are alkoxylated and, if desired, linked by esterification with dicarboxylic acids to give recurring structural units. If desired, the terminal hydroxyl groups of these modified alkoxylates of castor oil fatty substances have been esterified with fatty acids, aromatic carboxylic acids and/or resin acids and any free hydroxyl groups which may be present have preferably been reacted with dicarboxylic acids and sulfite to give the corresponding monoesters containing anionic radicals. The compounds according to the invention are suitable for a wide range of applications in the field of surface-active agents, for example in the preparation of azo pigments, emulsion paints and printing inks, for improving the coloristic and rheological properties. The compounds according to the invention are particularly compatible with the environment owing to their biodegradability.

Basic azo dyestuffs of the 3-cyano-2,4,6-triamino pyridine series

The new basic azo dyestuffs of the formula STR1 wherein the symbols have the meaning given in the description, are suitable for dyeing synthetic and naturally occurring substrates which can be dyed with basic dyestuffs.

Pigment compositions for solvent and water-based ink systems and the methods for producing them

This invention is an azo pigment composition containing a water insoluble metal salt of a water soluble polymer; a method of preparing said composition and ink compositions prepared from said azo pigment compositions.

Azo pigment compositions and process for their preparation

This invention is that of an azo pigment composition containing about 1 to 10 percent by weight of a nonionic alkyl polyglycoside dispersing agent. The polyglycosides useful in the invention have the general formulae: wherein: M is an oxygen, sulfur, nitrogen phosphorous or silicon atom; n is an integer from 8 to 18, preferably 8 to 11 and X represents the number average degree of polymerization having a numerical value from about 1 to about 2. These azo pigment compositions are prepared by conducting the azo pigment coupling reaction in the presence of said alkyl polyglycoside. The resulting pigment exhibit superior application properties in water based ink systems.

Dispersant-containing disazo pigment composition

A disazo pigment composition which can provide a printing ink having excellent fluidity, gloss and storage stability, and which contains: a disazo pigment obtained by a coupling reaction between a tetrazo compound of dihalogenobenzidine and acetoacetanilides, and a reaction product from a coupling reaction between an acetoacetylation product and a tetrazo compound of dihalogenobenzidine.

3,3'-Dichloro-4,4-diaminodiphenyl sulfonic acids

The invention provides compounds having the formula I or II STR1 and their salts and hydrates, having high value as intermediates for dyestuff additives for pigment compositions and as intermediates for metal-containing pigments.

Aryloxy p-benzidine compounds

There are provided substituted p-benzidines of the formula STR1 wherein Ar is phenyl or phenoxyphenyl.

Triazinyl reactive dyestuffs in which triazinyl group is further substituted with a beta-chloroethylsulfonyl- or vinylsulfonylbutyrylamino moiety

Reactive dyes of the formula STR1 in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthrone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C1-4 -alkyl, X is a substituent which is detachable as an anion, B is a radical of the formula STR2 R1 and R2, independently of each other, are hydrogen or substituted or unsubstituted C1-4 -alkyl or phenyl, A is a substituted or unsubstituted aliphatic or aromatic bridge member, Y is a --CO--Z or --SO2 --Z radical, Z is an aliphatic, aromatic or heterocyclic reactive radical, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and in high dyeing yield produce dyeings and prints having good fastness properties.