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158992

Sigma-Aldrich

Methyl p-toluenesulfonate

98%

Synonym(s):

Methyl p-methylbenzenesulfonate, Methyl toluene-4-sulfonate, Methyl tosylate, Methylp-tosylate

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About This Item

Linear Formula:
CH3C6H4SO3CH3
CAS Number:
80-48-8
Molecular Weight:
186.23
Beilstein:
609209
EC Number:
201-283-5
MDL number:
MFCD00008417
UNSPSC Code:
12352100
PubChem Substance ID:
24849783
NACRES:
NA.22

vapor density

6.45 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 20 °C)

Assay

98%

form

solid

autoignition temp.

896 °F

refractive index

n20/D 1.5172 (lit.)

bp

144-145 °C/5 mmHg (lit.)

mp

25-28 °C (lit.)

density

1.234 g/mL at 25 °C (lit.)

functional group

tosylate

storage temp.

2-8°C

SMILES string

COS(=O)(=O)c1ccc(C)cc1

InChI

1S/C8H10O3S/c1-7-3-5-8(6-4-7)12(9,10)11-2/h3-6H,1-2H3

InChI key

VUQUOGPMUUJORT-UHFFFAOYSA-N

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General description

Methyl p-toluenesulfonate is sulfonate ester present as potentially genotoxic impurity in drug substances. Kinetics of reactions of methyl p-toluenesulfonate with N,N-dimethylaniline has been investigated. It participates in selective 1-substitution reaction of tetrazole.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4172V
WXBD8462V
WXBD8045V
WXBD5252V
WXBD2952V

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Secondary deuterium isotope effects.. beta.-Kinetic effects in Sn2 reactions of N, N-dimethylaniline and dimethylphenylphosphine with methyl p-toluenesulfonate, and comparison with observed and calculated vibrational frequencies.
Kaplan ED and Thornton ER.
Journal of the American Chemical Society, 89(25), 6644-6651 (1967)
The formation of tin-nitrogen bonds. V. The selective 1-substitution reaction of tetrazoles by the reaction of 5-substituted 2-(tri-n-butylstannyl) tetrazoles with methyl iodide, methyl p-toluenesulfonate, dimethyl sulfate, and ethyl bromoacetate.
Isida T, et al.
Bulletin of the Chemical Society of Japan, 46, 2176-2180 (1973)
Bryn D Monnery et al.
International journal of pharmaceutics, 521(1-2), 249-258 (2017-02-25)
The mechanism of polycation cytotoxicity and the relationship to polymer molecular weight is poorly understood. To gain an insight into this important phenomenon a range of newly synthesised uniform (near monodisperse) linear polyethylenimines, commercially available poly(l-lysine)s and two commonly used
Joachim F R Van Guyse et al.
Polymers, 13(3) (2021-02-04)
Smart or adaptive materials often utilize stimuli-responsive polymers, which undergo a phase transition in response to a given stimulus. So far, various stimuli have been used to enable the modulation of drug release profiles, cell-interactive behavior, and optical and mechanical
Lucca Trachsel et al.
ACS nano, 14(8), 10054-10067 (2020-07-07)
The physicochemical properties of cyclic polymer adsorbates are significantly influenced by the steric and conformational constraints introduced during their cyclization. These translate into a marked difference in interfacial properties between cyclic polymers and their linear counterparts when they are grafted
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