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Environmental fate & pathways

Adsorption / desorption

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Reference
Endpoint:
adsorption / desorption
Remarks:
adsorption
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Data is from computational model developed by USEPA
Qualifier:
according to guideline
Guideline:
other: Modeling database
Principles of method if other than guideline:
Prediction done using KOCWIN Program (v2.00)
GLP compliance:
not specified
Type of method:
other: MCI Method
Media:
soil
Specific details on test material used for the study:
- Name of the test material: α-bromo-m-toluonitrile
- IUPAC name: 3-(bromomethyl)benzonitrile
- Molecular formula: C8H6BrN
- Molecular weight: 196.046 g/mol
- Smiles: N#Cc1cc(CBr)ccc1
- Inchi: 1S/C8H6BrN/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5H2
- Substance type: Organic
- Physical state : Solid crystalline powder (Off white)
Radiolabelling:
not specified
Test temperature:
25 deg.C
Analytical monitoring:
not specified
Key result
Type:
Koc
Value:
293.5 L/kg
Temp.:
25 °C
Remarks on result:
other: Log Koc= 2.4675 (estimated by MCI method)
Transformation products:
not specified

KOCWIN Program (v2.00) Results:

==============================

SMILES : C(#N)c(cccc1CBr)c1

CHEM : Benzonitrile, 3-(bromomethyl)-

MOL FOR: C8 H6 Br1 N1

MOL WT : 196.05

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 4.864

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 3.1352

Fragment Correction(s):

1 Nitrile/Cyanide (-C#N) ............... : -0.6677

Corrected Log Koc .................................. : 2.4675

Estimated Koc: 293.5 L/kg <===========

Validity criteria fulfilled:
not specified
Conclusions:
The Soil Adsorption Coefficient i.e. Koc value of test chemical 3-(bromomethyl)benzonitrile (CAS No. 28188-41-2) was estimated using EPI suite KOCWIN Program (v2.00) as 293.5 L/kg (log Koc= 2.4675) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 3-(bromomethyl)benzonitrile has lmoderate sorption to soil and therefore have slow migration potential to ground water.
Executive summary:

The Soil Adsorption Coefficient i.e. Koc value of test chemical 3-(bromomethyl)benzonitrile (CAS No. 28188-41-2) was estimated using EPI suite KOCWIN Program (v2.00) as 293.5 L/kg (log Koc= 2.4675) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 3-(bromomethyl)benzonitrile has lmoderate sorption to soil and therefore have slow migration potential to ground water.

Description of key information

The Soil Adsorption Coefficient i.e. Koc value of test chemical 3-(bromomethyl)benzonitrile (CAS No. 28188-41-2) was estimated using EPI suite KOCWIN Program (v2.00) as 293.5 L/kg (log Koc= 2.4675) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 3-(bromomethyl)benzonitrile has lmoderate sorption to soil and therefore have slow migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:
293.5

Additional information

Various predicted data for the target compound of3-(bromomethyl)benzonitrile (CAS No. 28188-41-2)and supporting experimental weight of evidence studies for its structurally similar read across chemical were reviewed for the Adsorption end point are summarized as below.

In first weight of evidence study the Soil Adsorption Coefficient i.e. Koc value of test chemical 3-(bromomethyl)benzonitrile (CAS No. 28188-41-2) was estimated using Estimation Program Interface (EPI suite, 2017) KOCWIN Program (v2.00) as 293.5 L/kg (log Koc= 2.4675) by means of MCI method at 25 deg. C.

In another weight of evidence study the Soil Adsorption Coefficient i.e Koc value of test substance 3-(bromomethyl)benzonitrile (CAS no. 28188 -41 -2) was estimated using Adsorption Coefficient module (v12.1.0.50374) program of Advanced Chemistry Development /I-lab predictive module as Koc 456 dimensionless (log Koc= 2.6589).

 

Next weight of evidence study was done by using Sci Finder database of Ameriacn Chemical Socirty (ACS, 2017) in this study the soil adsorption co-efficient i.e.,  Koc value of test chemical 3-(bromomethyl)benzonitrile (CAS no. 28188 -41 -2) was estimated to be 391 ( log Koc =2.5921) at pH 1-10 at temperature 25 deg.C.

 

Further, by using Chemspider-ACD/Phy chem suite of Royal Society Of Chemistry (RCS, 2017) the soil adsorption co-efficient i.e., Koc value of test substance 3-(bromomethyl)benzonitrile (CAS no. 28188 -41 -2) was estimated to be 546.17 dimensionless (log Koc= 2.7373) at pH 5.5 and 7.4 and temperature 25 deg.C

 

Last predicted data study was from CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application) V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical) the adsorption coefficient i.e KOC for test substance 3-(bromomethyl)benzonitrile (CAS no. 28188 -41 -2) was estimated to be 130 L/kg (log Koc = 2.1139) .The predicted KOC result was based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 3-(bromomethyl)benzonitrile has low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

Next weight of evidence study was experimental study done for structurally similar read across chemical from authoritative database (HSDB, 2017) in this study the Koc value for read across chemical 1-(bromomethyl)-3-methylbenzene (CAS no. 620-13-3) was determined by using a structure estimation method based on molecular connectivity indices. The estimated Koc value was 710 dimensionless and log Koc is 2.8512 this log Koc value suggests that  read across chemical 1-(bromomethyl)-3-methylbenzene is expected to have moderate sorption to soil and sediment and therefore has slow migration potential to ground water.

 

Last weight of evidence study was also experimental study for another read across chemical from same source as mentioned in above study (HSDB, 2017) in this study the Koc value for read across chemical 2-phenylacetonitrile (CAS no.140-29-4) was determined by using a log Kow of 1.56 and a regression-derived equation. The estimated Koc value was 170 dimensionless and log Koc is 2.2304 this log Koc value suggests that  read across chemical 2-phenylacetonitrile is expected to have low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

On the basis of above results for target chemical 3-(bromomethyl)benzonitrile(CAS No. 28188-41-2) (from EPI suite, ACD labs, Sci Finder database, Comptox chemistry dashboard and Chemspider 2017) and for its read across chemicals (From authoritative database HSDB) it can be concluded that the log Koc value of test chemical 3-(bromomethyl)benzonitrile ranges from 2.1139 to 2.7373 indicating that the chemical 3-(bromomethyl)benzonitrile has low to moderate sorption to soil and sediment and therefore it has moderate to slow migration potential to ground water

[LogKoc: 2.4675]