| Identification | More | [Name]
Tosyl chloride | [CAS]
98-59-9 | [Synonyms]
4-METHYLBENZENESULFONYL CHLORIDE
4-METHYLBENZENESULPHONYL CHLORIDE
4-toluene sulfochloride
4-TOLUENESULFONYL CHLORIDE
4-Toluolsulfonyl chloride
AKOS BBS-00004428
PARA TOLUENE SULFONYL CHLORIDE
P-TOLUENESULFOCHLORIDE
P-TOLUENESULFONYL CHLORIDE
P-TOLUENESULPHONYL CHLORIDE
p-tosyl chloride
PTSC
TOLUENE-4-SULFONYL CHLORIDE
TOS-CL
TOSYL CHLORIDE
4-methyl-benzenesulfonylchlorid
4-toluenesulfonicacid,chloride
4-Tosyl chloride
Benzenesulfonylchloride,4-methyl-
m-methylbenzenesulfonylchloride | [EINECS(EC#)]
202-684-8 | [Molecular Formula]
C7H7ClO2S | [MDL Number]
MFCD00007450 | [Molecular Weight]
190.65 | [MOL File]
98-59-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White to yellow solid | [Melting point ]
65-69 °C(lit.)
| [Boiling point ]
134 °C10 mm Hg(lit.)
| [density ]
1,006 g/cm3 | [vapor pressure ]
1 mm Hg ( 88 °C)
| [RTECS ]
DB8929000 | [Fp ]
128 °C
| [storage temp. ]
Store at RT. | [solubility ]
methylene chloride: 0.2 g/mL, clear
| [form ]
Crystalline Powder | [color ]
White | [Stability:]
Stable. Substances to be avoided include strong bases and strong oxidizing agents and water. Moisture sensitive. | [Water Solubility ]
hydrolyses | [Sensitive ]
Moisture Sensitive | [Merck ]
14,9534 | [BRN ]
607898 | [Contact allergens]
Tosyl chloride is used mainly in the preparation of
chemical derivatives in the pharmaceutical, plastics,
and organic chemical industries. | [InChIKey]
YYROPELSRYBVMQ-UHFFFAOYSA-N | [CAS DataBase Reference]
98-59-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzenesulfonyl chloride, 4-methyl-(98-59-9) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
98-59-9(EPA Substance) |
| Hazard Information | Back Directory | [Uses]
It can be used for organic synthesis, for example: dyes, saccharin,etc.
| [General Description]
A white to gray powdered solid with a distinctive odor. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Used to make other chemicals. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. | [Fire Hazard]
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. | [Preparation]
Tosyl chloride is a by-product from the production of ortho-toluenesulfonyl chloride (a precursor for the synthesis of the common food additive and catalyst saccharin), via the chlorosulfonation of toluene:
CH3C6H5+ SO2Cl2→ CH3C6H4SO2Cl + HCl | [Flammability and Explosibility]
Nonflammable | [Purification Methods]
Material that has been standing for a long time contains tosic acid and HCl and has m ca 65-68o. It is purified by dissolving (10g) in the minimum volume of CHCl3 (ca 25mL) filtered, and diluted with five volumes (i.e. 125mL) of pet ether (b 30-60o) to precipitate impurities. The solution is filtered, clarified with charcoal and concentrated to 40mL by evaporation. Further evaporation to a very small volume gives 7g of white crystals which are analytically pure, m 67.5-68.5o. (The insoluble material is largely tosic acid and has m 101-104o.) [Pelletier Chem Ind (London) 1034 1953.] It also crystallises from toluene/pet ether in the cold, from pet ether (b 40-60o) or *benzene. Its solution in diethyl ether has been washed with aqueous 10% NaOH until colourless, then dried (Na2SO4) and crystallised by cooling in powdered Dry-ice. It has also been purified by dissolving in *benzene, washing with aqueous 5% NaOH , then dried with K2CO3 or MgSO4, and distilled under reduced pressure and can be sublimed at high vacuum [Ebel Chem Ber 60 20861927]. [Beilstein 11 IV 375.] |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R29:Contact with water liberates toxic gas. | [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) .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
1
| [F ]
9-21 | [Hazard Note ]
Corrosive | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29049020 | [Hazardous Substances Data]
98-59-9(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 4680 mg/kg |
| Questions And Answer | Back Directory | [Reaction]
Tosyl chloride is called "TsCl", with strong nucleophilicity and substitution reaction with nucleophilic reagent. For example, reaction with the alcohol into the ester:
ROH + TsCl-Py → ROTs + Py + HCl-, reaction with amine and hydrazine respectively to generate the sulfonamide and sulfonyl hydrazide:
| [Chemical Properties]
White flaky crystal. melting point is 71 ℃. Boiling point is 151.6 ℃ (1.67kPa), 145-146 ℃ (2.0kPa). Soluble in alcohol, ether and benzene, insoluble in water.
| [Usage]
1.Tosyl chloride is an intermediate for disperse dyes, azoic dyes, acid dyes. Also used in the production of drugs homosulfanilamide.
2. Used for the analysis Reagents, but also for organic synthesis, dye preparation and molecule rearrangement in the hormone synthesis.
3. Used for organic synthesis, sulfa drugs and as pesticide intermediates. | [Production method]
Toluene chlorosulfonation production into o-toluenesulfonyl chloride, at the same time p-toluenesulfonyl chloride is also generated. The filter cake was separated from the o-toluenesulfonyl chloride, refined to obtain p-toluenesulfonyl chloride.
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