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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
Pricing and availability is not currently available.

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.[1] Kinetics of reactions of methyl p-toluenesulfonate with N,N-dimethylaniline has been investigated.[2] It participates in selective 1-substitution reaction of tetrazole.[3]

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)
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
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
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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