Benzylsulfonic acid

HCID 7532CAS 100-87-8

Basic information

Standard SMILES
O=S(=O)(O)Cc1ccccc1
InChIKey
NIXKBAZVOQAHGC-UHFFFAOYSA-N
Molecular formula
C7H8O3S
Average molar mass
172.2 g/mol
Monoisotopic mass
172.01941512

Overview

RN given refers to parent cpd

Names & identifiers

Preferred name
Benzylsulfonic acid
IUPAC
phenylmethanesulfonic acid

Names & synonyms

Phenylmethanesulfonic acidBENZYLSULFONIC ACIDBenzenemethanesulfonic acidToluene-alpha-sulphonic acidalpha-Toluenesulfonic acidMethanesulfonic acid, phenyl-HSDB 5339EINECS 202-897-6UNII-5BRP81V98HBRN 2208420DTXSID2059221BENZYLSULFONIC ACID [HSDB]
Show more names
4-11-00-00485 (Beilstein Handbook Reference).ALPHA.-TOLUENESULFONIC ACIDBENZYL-.ALPHA.-SULFONIC ACIDTOLUENE-.ALPHA.-SULPHONIC ACIDalphaToluenesulfonic acidRefChem:119004Methanesulfonic acid, phenylDTXCID3032462

Database identifiers

CAS
100-87-8
PubChem CID
7532
DTXSID
DTXSID2059221
ChEMBL
CHEMBL1171433
UNII
5BRP81V98H
EC Number
202-897-6
Nikkaji
J182.139C

Properties

Computed structural properties

XLogP
0.3
Topological polar surface area
62.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
CorrosivityTSA-94/30 LESS CORROSIVE TO STAINLESS STEEL THAN 75% H3PO4
Vapor Pressure0.0000034 [mmHg]
Stability/Shelf LifeTSA-94/30 WAS STABLE AGAINST CRYSTALLIZATION BELOW 50 °C

Safety & regulation

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 21(SRC), determined from a structure estimation method(2), indicates that benzylsulfonic acid is expected to have very high mobility in soil(SRC). Volatilization of benzylsulfonic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Benzylsulfonic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-6 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 21(SRC), determined from an estimation method(2), indicates that benzylsulfonic acid is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.0X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.67(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzylsulfonic acid, which has an estimated vapor pressure of 3.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant estimation method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzylsulfonic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 65 hours(SRC), calculated from its rate constant of 6.0X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase benzylsulfonic acid may be removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for benzylsulfonic acid can be estimated to be 21(SRC). According to a classification scheme(2), this estimated Koc value suggests that benzylsulfonic acid is expected to have very high mobility in soil.

Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for benzylsulfonic acid(SRC), using an estimated log Kow of -0.67(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 item

The Henry's Law constant for benzylsulfonic acid is estimated as 1.0X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that benzylsulfonic acid is expected to be essentially nonvolatile from water surfaces(2). Benzylsulfonic acid's Henry's Law constant(1) indicates that volatilization from moist soil surfaces will not occur(SRC). Benzylsulfonic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-6 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 2 items

MIXTURE OF 94% TOLUENESULFONIC ACID & 30% METHANOL (TSA-94/30) WAS LESS TOXIC THAN 75% H3PO4 IN ACUTE SKIN ABSORPTION TOXICITY, SKIN IRRITATION & EYE IRRITATION STUDIES IN RABBITS.

NO PERMANENT ILL EFFECTS WERE OBSERVED IN RATS WHICH INHALED TSA-94/30, & VAPORS WERE CONSIDERED ONLY SLIGHTLY TOXIC.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of benzylsulfonic acid with photochemically-produced hydroxyl radicals has been estimated as 6.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 65 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

PHENYLTHIO & BENZYLTHIO RADICALS WERE OXIDIZED TO DIPHENYL & DIBENZYL DISULFIDE, BENZENESULFONIC ACID, BENZENEMETHANESULFONIC ACID & SULFURIC ACID AMONG OTHERS.

INEZIN WAS METABOLIZED TO TOLUENE-ALPHA-SULFONIC ACID BY MYCELIAL CELLS OF PIRICULARIA ORYZAE.

Uses & manufacturing

Uses · 2 items

Used as a research chemical; No known commercial production in the US; [HSDB]

RESEARCH CHEMICAL

U.S. Production · 2 items

(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

Methods of ManufacturingPROBABLY BY REACTION OF HYDRAZINE HYDRATE WITH DIPHENYL METHIONATE, FOLLOWED BY DISTILLATION
General Manufacturing InformationBenzenemethanesulfonic acid: ACTIVE

Related reactions

5 records

Linked notes

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