2-chlorophenol

95-57-8

Organic synthesis. 
Intermediate in the manufacture of higher
chlorophenols and phenolic resins. 
Also  used in a process for
extracting sulfur and nitrogen compounds from coal.

Colourless liquid.

Characteristic, medicinal. 
Unpleasant, penetrating.

Odour threshold, water: 0.005 ppm at 20 °C and 0.001 ppm at 60
°C. 0.00033 mg/l at 30 °C and 0.0025 mg/l at 60 °C. 0.002 mg/l
was the geometric mean of odour threshold responses of panel
members at 25 °C (Sax 1986).

The threshold for taste in water at 40 °C was 0.05 ppm
(Sax 1986).

128.56

Half-lives for evaporation of 2-chlorophenol from stirred and
static water at a depth of 0.38 cm at 23.8 °C were 1.35 and
1.60 hours, respectively (Chiou et al. 1980).

Using the estimated Henry's law constant, a half-life of 73
days was estimated for evaporation from a river 1 m deep,
flowing a 1 m/sec with a wind velocity of 3 m/sec (Lyman et al 
1982).

Koc: sediments, fine 4890; coarse 3990; clay loam soil 51.1
(Isaacson & Frink 1984) (Boyd 1982).

Adsorption to the organo-clay Bentone 24 has been shown to be
pH sensitive for 2-chlorophenol. 2-Chlorophenol was 76.6 %
adsorbed by Bentone 24 in aqueous solution at pH 7.8 and 15 %
adsorbed by Bentonen 18c at pH 7.6 (Miller & Faust 1973).

Using the water solubility and the log octanol/water partition
coefficient, Koc's of 16 and 352 were estimated, respectively
(Lyman et al. 1982).

18.46 % (air), 77.44 % (water), 4.11 % (sediment).

Soluble in alcohol, ether, and aqueous sodium hydroxide. 
Very
soluble in water.

The estimated vapor phase half-life in the atmosphere as a
result of addition of ozone to the aromatic ring is 1.96 days
(GEMS 1986).

2-Chlorophenol (4.46x10-5 mol) reacted with 1 mL NO in 1 liter
air for 5 hours to give the 4- and 6-nitro-2-chlorophenol
adducts in 36 % and 30 % yields, respectively (Kanno & Nojima 
1979).

The photolysis should be affected by pH, as demostrated by the
fact that the quantum yields for the disappearance of the
undissociated form was 10 times less than that for the
dissociated form when 2-chlorophenol was irradiated at 296 nm
in aqueous solution at pH 8-13; the main product of photolysis
from the undissociated form was pyrocatecol and
cyclopentadienic acid from the dissociated form (Boule et al 
1982).

Microbial decomposition in soils was studied using the shake
culture method. 
The medium was sterilized and had a pH of 7.2.
2-chlorophenol was added to a final concentration of 0.050
mg/ml and 4 g of freshly sampled soil was added to 100 ml of
medium as an inoculum. 
Temperature was 30 °C and cultures were
aerated on the shaker. 
Two soil types were used: Mardin silt
loam and Dunkirk silt loam. 
UV spectrophotometry was used to
measure persistence. 
Time required for the complete
disapperance in Dunkirk and Mardin soils was 14 and 47 days,
respectively. 
Information that it was microbial decomposition
was tested (positive) by use of sodium azide treated samples. -

Manometric analysis of different genera of soil bacteria for
co-oxidation fo phenol and 2-chlorophenol indicated that three
Norcardia strains, three Pseudomonad strains, a Bacillus
strain, and Mycobacterium coeliacum were capable of
co-oxidation. 
Oxidation was to either 3- or 4-chlorocatechol
(Sax 1986).

AEROBIC DEGRADATION IN SOIL
Maximum adsorption wavelength: 275 nm
NON-STERILE SOIL
Minimum time for >70% decrease: 0.50 - 1.00 d
% decomposition at the termination of the experiment:1.5d, 100%
STERILE SOIL
% decomposition at the termination of the experiment:  40d, 67%
(Baker et al. 1980)

ANAEROBIC DEGRADATION IN SOIL
Maximum adsorption wavelength: 275 nm
NON-STERILE SOIL
Minimum time for >70% decrease: 10 - 24 d
% decomposition at the termination of the experiment:  80d, 78%
STERILE SOIL
Minimum time for >70% decrease: 24 - 80 d
% decomposition at the termination of the experiment:  80d, 82%
(Baker et al. 1980)

Degradation by Pseudomonas: 200 mg/l at 30°C:
                parent: 100% ring disruption in 52 hr
                mutant: 100% ring disruption in 26 hr
                (Verschueren 1983)   

Decomposition rate in soil suspensions: 14 days for complete
disappearance (Verschueren 1983).

Decomposition period by a soil microflora: >64 days
(Verschueren 1983).

Decomposition of 2-chlorophenol in soils was studied by making
a solution of 1 g 2-chlorophenol in 4 l of tap water and
buffers and then allowing it to percolate through Rothamsted
soil. 66 % disappeared in 10 days. 
Further additions of
compound to the system showed rates of disappearance nearly
twice that of the initial rate. 
When tested against sterilized
soil the disappearance was found to have twice the rate in
unsterilized soil over a period of 7 days. 0.1 % sodium azide
added to solutions showed no significant effects. 
Pretreatment
with phenol showed no significant change. -  
Found as an
intermediate in degradation of 2,4-D by two Pseudomonas
strains. 
The proposed pathway of degradation was from
2-chlorophenol to 3-chlorocatechol to alpha-chloromuconic acid
(Sax 1986).

In activated sludge with an initial concentration of 100 mg/l,
100 % ring degradation was noted in 3 days and 100 % chloride
ion development was noted in 4 days. -  
The persistence of
2-chlorophenol in polluted river water and dilute sewage was
examined at 20 °C. 
At an initial concentration of 1 mg/l added
to a usual dilution of domestic sewage, removal was not noted
over the 20 - 30 days period of observation, presumed to be due
to lack of microorganisms capable of attacking the chemical. 
At
the same concentration in polluted river water, dissipation was
in 15 - 23 days. 
Addition of seed considerably enhanced
dissipation. 
Results of this indicate removal by specialized
microflora (Sax 1986).

Biodegradation:
0% by BOD
period: 14d
substance: 100 mg/l
sludge: 30 mg/l
(MITI 1992)

Biodegradtion should be an important fate process with complete
removal reported in 13 and 36 days in die-away tests using two
raw river waters and 15 days in acclimated river water (Howard 
1989).

Half-lives unacclimated anerobic sewage sludge were: 1 week (3
or 10 ppm), 2 weeks (30 ppm), 8 weeks (97 ppm) and 33 weeks
(285 ppm); lag time was <1 week for all concn tested (Hrudey 
et al. 1987).

Dogs excreted 87 % of administered 2-chlorophenol as conjugated
of sulfate and glucuronic acid. 
Rabbits also apparently
conjugate 2-chlorophenol, derived from chlorobenzene exposure,
in the same fashion (Sax 1986).

The metabolic fate of 2-chlorophenol in tomato plants included
glycoside formation. 
Beta-o-chlorophenylgentiobioside was
isolated from the roots. 
No evidence for the formation of this
glycoside in shoots was found (Sax 1986).

Inhibition on degradation of glucose by Pseudomonas fluorescens
at: 30 mg/l, and E. coli at: 400 mg/l (Verschueren 1983).

BCF: bluegill sunfish 214; goldfish 7.1 (Barrows et al. 1980)
(Kobayashi et al. 1979).

Using the water solubility and the log octanol/water partion
coefficient, BCF's of 1.9 and 25 were estimated, respectively
(Lyman et al. 1982).

The inhibition of oxidative phosphorylation by 50 % was shown
at a concentration of 0.000520 M in rat liver mitochondria.

Measurement was via oxygen consumption using polarographic
techniques. -  2-MCP produced reversible inhibition of etiolated
pea brei (a finely divided tissue suspension) catalase, and of
crystalline beef liver catalase in vitro at a level of 
0.00004 M (Sax 1986).

Toxic by skin absorption, inhalation or ingestion. 
Strong
tissue irritant. 
When heated to decomposition, highly toxic
fumes may be emitted.

LDLo, scu, frog, 400 mg/kg (Sax 1986).

The effect of 2-chlorophenol on respiration of activated sludge
was studied using Wanburg techniques and GLC analysis. 
The
inoculum was a mixture from 2 treatment plants that had been
exposed to continuous incoming phenol in the range of 0.01 -
0.35 mg/l for 12 months. 
At concentrations of 1 mg/l, 100 %
degradation was noted after 3 hours, 97 % degradation was seen
after 6 hours at initial concentration of 10 mg/l, and only 20
% degradation after 6 hours with an initial concentration of
100 mg/l. 98 % recovery was noted with the analysis, indicating
little adsorption onto particulate matter (Sax 1986).

Photosynthetic suspression in Chlorella pyrenoidosa (as
measured by O2 production via a modified Warburg apparatus) was
88 % and 74 %, as compared with the control, at concentrations 
of 100 and 500 mg/l, respectively. 
The concentration at which
no substantial toxicity occurred was 10 mg/l. 
The tests were
performed under steady-state conditions, algal density was 1.0
g/l (dry wt), 25 °C, aerated (with 5 % CO2 in air) for a period 
of 72 hours with constant illumination (Sax 1986).

Tetrahymena pyriformis; EC50, grw, 67.97 mg/l, 2 days
(Schultz 1987).

More toxic than meta or para isomers (Sax 1986).