88-06-2 Usage
Description
2,4,6-Trichlorophenol is a colorless to yellow solid that has a strong phenol-like smell. It decomposes at elevated temperatures when heated to produce corrosive and toxic fumes including chlorine and hydrogen chloride. It is soluble in organic solvents and partially soluble in water.
Previously, it was used in the manufacture of other chemicals. Moreover, it was also used as an antiseptic, a pesticide for leather, wood, and preservation of glue as well as an anti-mildew treatment. Nevertheless, the production of 2,4,6-Trichlorophenol was discontinued in America in the 1980s.
Health Effects
Human beings may be exposed to 2,4,6-Trichlorophenol via inhalation and can cause altered pulmonary functions, respiratory effects, and pulmonary lesions. Moreover, 2,4,6-trichlorophenol can irritate the lungs and throat causing coughing and wheezing. In animal models, ingestion of 2,4,6-trichlorophenol caused an increase in occurrences of leukemia, lymphoma, and liver cancer. As such, 2,4,6-Trichlorophenol might be a carcinogenic in humans.
Contact can severely burn and irritate the eyes and skin with possible eye damage. Elevated exposures may cause weakness, restlessness, rapid breathing, shaking, tremors, coma, seizures, or even death.
Extreme exposure to 2,4,6-trichlorophenol can have devastating effect on a developing fetus. Other long-term effect to repeated exposure may cause bronchitis with shortness of breath.
Chemical Properties
Yellow flakes; strong phenolic odor. Soluble in
acetone, alcohol, and ether; insoluble in water. Nonflammable.
Physical properties
Colorless needles or yellow solid with a strong, phenolic, musty or rotten vegetable-type odor. At
40 °C, the lowest concentration at which an odor was detected was 380 μg/L. At 25 °C, the lowest
concentration at which a taste was detected was >12 μg/L (Young et al., 1996).
Uses
Different sources of media describe the Uses of 88-06-2 differently. You can refer to the following data:
1. Wood preservative; disinfectant; fungicide,
herbicide, defoliant.
2. 2,4,6-Trichlorophenol is used as a broad range pesticide against insects, fungi, vegetation and bacteria. It has become a common environmental contaminant and probable human carcinogen.
3. Fungicide, herbicide, defoliant.
Definition
ChEBI: A trichlorophenol with phenolic substituents on positions 2, 4 and 6.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2,4,6-Trichlorophenol is incompatible with acid chlorides, acid anhydrides and oxidizing agents. 2,4,6-Trichlorophenol can be converted to the sodium salt by reaction with sodium carbonate. Forms ethers, esters and salts by reaction with metals and amines. Undergoes substitution reactions such as nitration, alkylation, acetylation and halogenation. Can be hydrolyzed by reaction with bases at elevated temperatures and pressures. Reacts with alkalis at high temperatures .
Health Hazard
In experimental animals, 2,4,6-
trichlorophenol causes toxic effects to the liver
and hematologic system and cancer. There is
no reliable information regarding exposure and
toxic effects in humans.
Fire Hazard
Literature sources indicate that 2,4,6-Trichlorophenol is nonflammable.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic data. Poison
by intraperitoneal route. Moderately toxic by
ingestion and skin contact. A skin and
severe eye irritant. Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits toxic fumes of Cl-. Used as a
germicide and preservative. See also
CHLOROPHENOLS.
Carcinogenicity
2,4,6-Trichlorophenol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental fate
Biological. In activated sludge, only 0.3% mineralized to carbon dioxide after 5 d (Freitag et al.,
1985). In anaerobic sludge, 2,4,6-trichlorophenol degraded to 4-chlorophenol (Mikesell and Boyd,
1985). When 2,4,6-trichlorophenol was statically incubated in the dark at 25 °C with yeast extract
and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was
observed. At concentrations of 5 and 10 mg/L, 96 and 97% biodegradation, respectively, were
observed after 7 d (Tabak et al., 1981).
Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ
= 365 nm) converted 2,4,6-trinitrophenol to carbon dioxide at a significant rate (Matthews, 1986).
A carbon dioxide yield of 65.8% was achieved when 2,4,6-trichlorophenol adsorbed on silica gel
was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. An aqueous solution containing chloramine reacted with 2,4,6-trichlorophenol
to yield the following intermediate products after 2 h at 25 °C: 2,6-dichloro-1,4-
benzoquinone-4-(N-chloro)imine and 4,6-dichloro-1,2-benzoquinone-2-(N-chloro)imine (Maeda et
al., 1987).
Purification Methods
Crystallise the phenol from *benzene, EtOH or EtOH/water. [Beilstein 6 IV 1005.]
Check Digit Verification of cas no
The CAS Registry Mumber 88-06-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 88-06:
(4*8)+(3*8)+(2*0)+(1*6)=62
62 % 10 = 2
So 88-06-2 is a valid CAS Registry Number.
88-06-2Relevant articles and documents
Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/01/04)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
Efficient demethylation of aromatic methyl ethers with HCl in water
Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.
supporting information, p. 1995 - 2009 (2021/03/26)
A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.
Kinetic studies on 2,6-lutidine catalyzed peroxyoxalate chemiluminescence in organic and aqueous medium: Evidence for general base catalysis
Augusto, Felipe A.,Bartoloni, Fernando H.,Cabello, Maidileyvis C.,dos Santos, Ana Paula F.,Baader, Wilhelm J.
, (2019/07/31)
The peroxyoxalate reaction, base catalyzed perhydrolysis of activated aromatic oxalate esters in the presence of chemiluminescence activators, has widespread analytical and bioanalytical applications and is one of the most efficient chemiluminescence transformations known. We report here a kinetic study on this reaction using 2,6-lutidine as catalyst in organic (1,2-dimethoxyethane) and aqueous medium. In both media, experimental conditions can be designed which lead to reproducible results important for analytical applications. Observed rate constants (determined by observing the light emission intensity as well as absorbance variation due to phenol releases) show dependence on both the 2,6-lutidine and the hydrogen peroxide concentration, indicating their participation in the rate-limiting step of the transformation. The rate constants obtained from these kinetic studies proved to be at least one order of magnitude higher in water than in 1,2-dimethoxyethane as solvent. Kinetic experiments designed to distinguish between three different types of catalysis (nucleophilic, specific base and general base catalysis) clearly indicate that the role of 2,6-lutidine in this reaction is as general base catalyst in water as well as most likely in organic medium.
