2-CHLOROETHYL P-TOLUENESULFONATE Chemical Properties

Melting point:

157-161℃

Boiling point:

153 °C0.3 mm Hg(lit.)

Density 

1.294 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.529(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless to yellow

BRN 

1968816

CAS DataBase Reference

80-41-1(CAS DataBase Reference)

EPA Substance Registry System

Ethanol, 2-chloro-, 4-methylbenzenesulfonate (80-41-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

23-36/37/39-24/25

RIDADR 

2810

WGK Germany 

3

RTECS 

XT6475000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29055900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-CHLOROETHYL P-TOLUENESULFONATE Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO YELLOW LIQUID

Uses

2-Chloroethyl 4-methylbenzenesulfonate is a useful reactant for the synthesis of triphenylethanamine derivatives, and fluorinated carbazole derivatives.

Uses

2-Chloroethyl p-toluenesulfonate was used to develop method for the determination of a variety of hydrophobic aromatic sulfonates by micellar electrokinetic chromatography.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 5783, 1988 DOI: 10.1021/jo00259a035

Synthesis

General procedure for the synthesis of p-toluenesulfonic acid-β-chloroethyl ester from p-toluenesulfonyl chloride and 2-chloroethanol: 1. 180mL of dichloromethane (DCM) was added to a 1L round bottom flask (RBF) to which p-toluenesulfonyl chloride (172g, 0.884mol) and pyridine (59g, 0.75mol) were added, and the flask was cooled in an ice bath for about 5 minutes. 2. 2-chloroethanol (40.3 g, 0.496 mol) was added slowly, then the flask was removed from the ice bath and stirred at room temperature (r.t.) for 15 hours. 3. The reaction mixture was poured into a 1 L dispensing funnel and washed sequentially twice with a mixture of 300 mL of water plus 50 mL of pyridine, and then washed with 300 mL of water plus 75 mL of aqueous hydrochloric acid 36% wt (the aqueous phase was discarded after each wash). 4. The solvent was removed under reduced pressure to afford analytically pure p-toluenesulfonic acid-β-chloroethyl ester (1) as a pale yellow, thick, syrupy product (116 g, 0.494 mol, 100% yield). 1H NMR data: δ= 7.81 (d, 2H, aromatic, interstitial with CH3, J = 8.3 Hz), 7.37 (d, 2H, aromatic, adjacent to CH3, J = 8.3 Hz), 4.23 (t, OCH2, J = 5.9 Hz), 3.66 (t, CH2Cl, J = 5.9 Hz), 2.46 (s, CH3).

References

[1] Patent: WO2009/52148, 2009, A1. Location in patent: Page/Page column 29
[2] Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 3, p. 147 - 153
[3] Patent: WO2010/3048, 2010, A1. Location in patent: Page/Page column 87-88
[4] Synthesis, 1993, # 11, p. 1141 - 1144
[5] Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5136 - 5142

2-CHLOROETHYL P-TOLUENESULFONATE(80-41-1)Related Product Information

• Methyl benzenesulfonate
• 2-Chloroethanol
• Sodium methanesulfinate
• p-Toluenethiol
• Methyl toluenesulfonate
• 2-CHLOROETHYL P-TOLUENESULFONATE
• p-Toluenesulfonic acid
• BENZENESULFINIC ACID
• Ethyl methanesulfonate
• AMMONIUM METHANESULFONATE
• Methyl methanesulfonate
• Sulfur dioxide
• Ethyl p-toluenesulfonate
• Ethyl benzenesulphonate
• P-TOLUENESULFINIC ACID
• Thiophenol
• METHYL BENZENESULFINATE
• Benzenesulfonic acid