| Identification | More | [Name]
Methyl p-toluenesulfonate | [CAS]
80-48-8 | [Synonyms]
4-methylbenzenesulfonic acid methyl ester
4-TOLUENESULFONATE METHYL ESTER
4-TOLUENESULFONIC ACID METHYL ESTER
8-METHOXYPYRENE-1,3-6-TRISULFONIC ACID TRISODIM SALT
LABOTEST-BB LT00782089
METHYL 4-TOLUENESULFONATE
METHYL P-TOLUENESULFONATE
METHYL P-TOLUENESULPHONATE
METHYL P-TOSYLATE
METHYL TOLUENE-4-SULPHONATE
METHYL TOSYLATE
MPTS
MPTS, TRISODIUM SALT
P-TOLUENESULFONIC ACID METHYL ESTER
PTS1
TRISODIUM-8-METHOXYPYRENE-1,3,6-SULFONATE
TRISODIUM 8-METHOXYPYRENE-1,3,6-TRISULFONATE
4-methyl-benzenesulfonicacimethylester
Benzenesulfonicacid,4-methyl-,methylester
Methyl 4-methylbenzenesulfonate | [EINECS(EC#)]
201-283-5 | [Molecular Formula]
C8H10O3S | [MDL Number]
MFCD00008417 | [Molecular Weight]
186.23 | [MOL File]
80-48-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellow low melting solid | [Melting point ]
25-28 °C(lit.)
| [Boiling point ]
144-145 °C5 mm Hg(lit.)
| [density ]
1.234 g/mL at 25 °C(lit.)
| [vapor density ]
6.45 (vs air)
| [vapor pressure ]
1 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.5172(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid or Low Melting Solid | [color ]
White to yellow | [Water Solubility ]
Insoluble | [Sensitive ]
Moisture Sensitive | [BRN ]
609209 | [LogP]
1.88 at 25℃ | [CAS DataBase Reference]
80-48-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzenesulfonic acid, 4-methyl-, methyl ester(80-48-8) | [EPA Substance Registry System]
80-48-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R34:Causes burns.
R43:May cause sensitization by skin contact.
R40:Limited evidence of a carcinogenic effect.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S24:Avoid contact with skin . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
XT7000000
| [F ]
21 | [Autoignition Temperature]
896 °F | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29051900 | [Safety Profile]
Poison by ingestion and
subcutaneous routes. An eye and severe skin
irritant. A vesicant and skin sensitizer.
Questionable carcinogen with experimental
tumorigenic data. When heated to
decomposition it emits toxic fumes of SOx. | [Hazardous Substances Data]
80-48-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 341 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Tosyl chloride-->4-methylbenzenediazonium tetrafluoroborate-->Tetrabutylammonium 4-toluenesulfonate-->[Hydroxy(tosyloxy)iodo]benzene-->4-Toluenesulfonyl bromide-->2,2,2-TRIFLUOROETHYL METHYL ETHER-->DIMETHYLZINC-->Trimethyl orthoacetate | [Preparation Products]
1,3,3-Trimethyl-2-methyleneindoline-->5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE-->2,5-diphenylthiazole-->3,5-Bis(2-cyanoprop-2-yl)toluene-->1-methyl-4-[(4-methylphenyl)sulfonyloxymethoxysulfonyl]benzene-->2-NONYNE-->METHYL FLUORIDE-->METHYL 3,5-DIMETHYLBENZOATE-->2-CHLORO-1-METHYLPYRIDINIUM P-TOLUENESULFONATE-->ETHYL METHYL ETHER-->3,6-diamino-2,7,10-trimethylacridinium chloride-->Basic Orange 5 |
| Hazard Information | Back Directory | [Hazard]
Toxic by ingestion and inhalation, strongirritant to skin and eyes. | [Chemical Properties]
white to slightly yellow low melting solid | [Uses]
Methyl p-Toluenesulfonate can be used in the manufacture of dyes and organic synthesis, and also is the raw materials of methylation.
| [Preparation]
Methyl p-toluenesulfonate was synthesized by the reaction of p-toluenesulfonyl chloride with methanol. Mix p-toluenesulfonyl chloride and methanol, slowly add 25% sodium hydroxide solution, control the temperature below 25 °C, stop adding alkali when the pH is 9, continue stirring for 2 hours, and leave overnight. The lower layer of reactant was taken, the upper layer was extracted with benzene, the extract was recovered with benzene and then combined with the lower layer, washed with water and 5% potassium carbonate solution in turn, dried and distilled under reduced pressure to obtain the finished product of methyl p-toluenesulfonate. | [Synthesis Reference(s)]
Chemical and Pharmaceutical Bulletin, 29, p. 623, 1981 DOI: 10.1248/cpb.29.623
Synthetic Communications, 15, p. 1057, 1985 DOI: 10.1080/00397918508076842 | [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. | [Purification Methods]
The ester is purified by distillation in vacuo and could be crystallised from pet ether or Et2O/pet ether at low temperature. It is a powerful methylating agent, is TOXIC andis a skin irritant, so it is better to purify it by repeated distillation. [IR: Schreiber Anal Chem 21 1168 1949, Buehler et al. J Org Chem 2 167 1937, Roos et al. Org Synth Coll Vol I 145 1948, Beilstein 11 IV 247.] |
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