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
Show more names
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
- Formal charge
- 0
- Complexity
- 232
Experimental & physicochemical properties
Color/Form
MONOCLINIC CRYSTALS
MONOCLINIC PRISMS FROM ACETIC ACID, ETHYL ACETATE
Solubility
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
- storage temp.
- 2 · 2-8°C
- solubility
- 1.24 g/l · 1.24g/l
- form
- Liquid After Melting
- color
- Clear colorless to pale brown
- Water Solubility
- Insoluble
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,3858
- BRN
- 611213 · 611213
- InChI
- 1S/C9H12O3S/c1-3-12-13(10,11)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3
- InChIKey
- VRZVPALEJCLXPR-UHFFFAOYSA-N
- SMILES
- CCOS(=O)(=O)c1ccc(C)cc1
- CAS DataBase Reference
- 80 · 80-40-0(CAS DataBase Reference)
- FDA UNII
- 2160 N0YURF · 2160N0YURF
- NIST Chemistry Reference
- 4 · Benzenesulfonic acid, 4-methyl-, ethyl ester(80-40-0)
- EPA Substance Registry System
- 4 · Benzenesulfonic acid, 4-methyl-, ethyl ester (80-40-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-40-22
- Safety Statements
- 26 · 26-45-36/37/39
- RIDADR
- 2811 · UN2811
- WGK Germany
- 3 · 3
- RTECS
- 6825000 · XT6825000
- F
- 21 · 21
- Autoignition Temperature
- 500 °C · 500 °C
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29041000 · 29041000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 80 · 80-40-0(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
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
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.
Safety & protection
Disposal Methods
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
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
- hs_code
- 29041000
- risk_code
- 36/37/38-40-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-45-36/37/39
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Autoignition Temperature
- 500 °C
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 80-40-0(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as plasticizer for cellulose acetate and as an ethylating agent; [Hawley]
PLASTICIZER FOR CELLULOSE ACETATE; ETHYLATING AGENT
Applications
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].
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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