Ethyl p-methylbenzenesulfonate

HCID 6638

Basic information

CAS
80-40-0
Standard SMILES
CCOS(=O)(=O)c1ccc(C)cc1
InChIKey
VRZVPALEJCLXPR-UHFFFAOYSA-N
Molecular formula
C9H12O3S
Average molar mass
200.26 g/mol
Monoisotopic mass
200.05071524

Names & identifiers

Preferred name
Ethyl p-methylbenzenesulfonate
IUPAC
ethyl 4-methylbenzenesulfonate
English name
Ethyl p-toluenesulfonate
Molecular formula
C9H12O3S
Molecular weight
200.25

Names & synonyms

Ethyl p-toluenesulfonate80-40-0Ethyl 4-methylbenzenesulfonateEthyl tosylateEthyl p-tosylateETHYL P-METHYLBENZENESULFONATEBenzenesulfonic acid, 4-methyl-, ethyl esterEthyl p-TSp-Toluenesulfonic acid, ethyl esterEthyl-p-toluenesulfonateEthyl PTSEthyl 4-toluenesulfonate
Show more names
Ethyl para-toluenesulfonateMittel AEP4-METHYLBENZENESULFONIC ACID, ETHYL ESTERethylpts
p-Toluolsulfonsaeure aethyl esterNSC 8887toluene-4-sulfonic acid ethyl esterEthyl p-methyl benzenesulfonateCCRIS 10284-Methylbenzenesulfonic acid ethyl esterHSDB 5235EINECS 201-276-7

Database identifiers

CAS
80-40-0
PubChem CID
6638
DTXSID
DTXSID2058833
UNII
2160N0YURF
EC Number
201-276-7
Nikkaji
J3.853I

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
51.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Benzenesulfonic Acid Derivatives
SpringerMaterials PropertiesDiamagnetic susceptibility
LogPLog kow = 1.81
Density1.17
Color/Form · 2 items

MONOCLINIC CRYSTALS

MONOCLINIC PRISMS FROM ACETIC ACID, ETHYL ACETATE

Solubility · 2 items

INSOL IN WATER; SOL IN ALC, ETHER, HOT ACETIC ACID

SOL IN HOT ETHYL ACETATE

Physicochemical properties

Melting point
29 · 29-33 °C(lit.)
Boiling point
158 · 158-162 °C10 mm Hg(lit.)
Density
1.174 g/mL · 1.174 g/mL at 25 °C(lit.)
vapor pressure
0.6 hPa · 0.6 hPa (14 °C)
refractive index
20 · n20/D 1.511(lit.)
Flash point
316 °F · 316 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.6% (1 of 169) of reports.

Danger

H301 (65.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 169 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzenesulfonic acid, 4-methyl-, ethyl ester

Benzenesulfonic acid, 4-methyl-, ethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryAn irritant; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 3 (65.1%)

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

Non-Human Toxicity Excerpts · 4 items

MUTAGENICITY: MUTATION RESEARCH 87: 211 (1981). DNA REPAIR-DEFICIENT BACTERIAL TESTS: POSITIVE.

65 MG/KG ADMIN SC TO BD RATS WEEKLY FOR 50 WK; 3/11 DEVELOPED LOCAL SARCOMAS AFTER 600 DAYS. /FROM TABLE/

Several direct acting mutagens were tested for mutagenic activity in adult Drosophila melanogaster when administered in feeding or as an injected dose. An inhibitor or cytochrome p450, 1-phenylimidazole, administered at concentrations of 2.5, 4 and 10 mmol, was not mutagenic in Drosophila. Methyl-p-toluenesulfonate applied orally was a weak mutagen. When administered simultaneously with 1-phenylimidazole, a concentration dependent increase was noted in mutagenic activity of methyl-p-toluenesulfonate. Following injection, mutagenesis by methyl-p-toluenesulfonate was considerable. Ethyl-p-toluenesulfonate demonstrated marginal mutagenesis in Drosophila when orally applied but was decidedly mutagenic on injection. Simultaneous treatment with 4 mmol 1-phenylimidazole and 1 mmole of ethyl-p-toluenesulfonate did not alter mutagenesis nor did treatment with diethylmaleate (glutathione depletion). Combined treatment with 2 mmol ethyl-p-toluenesulfonate and 2 mmol 1-phenylimidazole produced a statistically significant increase in mutagenesis. /It was concluded/ that weak mutagenesis by p-toluenesulfonates after feeding experiments compared to considerable effects after injection suggests metabolic deactivation in the gut.

The cancerogenic activity of 12 direct alkylating substances was tested in 535 BD rats. Local sarcomas were produced by the subcutaneous injections once a week of p-toluene sulfonic acid methylester. Only a jew tumors were observed following treatment with p-toluene sulfonic acid ethylester and p-toluenesulfonic acid butylester were not cancerogenic.

Safety data

F
21
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
XT6825000
ridadr
UN2811

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as plasticizer for cellulose acetate and as an ethylating agent; [Hawley]

PLASTICIZER FOR CELLULOSE ACETATE; ETHYLATING AGENT

General Manufacturing InformationBenzenesulfonic acid, 4-methyl-, ethyl ester: ACTIVE
Applications · 4 items

UsesEthyl p-toluenesulfonate was used to develop an extraction method for methyl and ethyl esters of various sulfonic acids in active pharmaceutical ingredients using solid-phase micro extraction coupled to GC/MS in the selected ion monitoring mode. It was used in a study to develop a fast and accurate method for determination of residues of some common alkylating agents employed in drug synthesis by in situ derivatization-headspace-gas chromatography-mass spectrometry.

UsesEthyl p-toluenesulfonate can be used in the manufacture of organic synthesis, and also can be used as intermediate of methylation reagent and sensitive material. It also is flexibilizer of cellulose acetate.

UsesFor ethylation.

General DescriptionEthyl p-toluenesulfonate (EPTS), used as a potent alkylating agent in the modern pharmaceutical industry, is classified as a potential genotoxic impurity. It is an alkyl sulfonate formed by the reaction of ethanol with p-toluenesulfonic acid during the production of active pharmaceutical ingredients. Because EPTS has the ability to alkylate DNA, it may pose risks such as carcinogenicity and teratogenicity; therefore, its content must be strictly controlled[1].

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Related reactions

39 records

Compound notes

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