L(-)-10-Camphorsulfonyl chloride Chemical Properties

Melting point:

66-68 °C(lit.)

alpha 

-33 º (c=3, chloroform)

Boiling point:

349.4±15.0 °C(Predicted)

Density 

1.331±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Acetone, Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

color 

White

optical activity

[α]18/D 33°, c = 3 in chloroform

Water Solubility 

Decomposes

Sensitive 

Moisture Sensitive

BRN 

3205975

InChI

InChI=1S/C10H15ClO3S/c1-9(2)7-3-4-10(9,8(12)5-7)6-15(11,13)14/h7H,3-6H2,1-2H3/t7-,10-/m0/s1

InChIKey

BGABKEVTHIJBIW-UHFFFAOYSA-N

SMILES

[C@@]12(CS(Cl)(=O)=O)C(C)(C)[C@@]([H])(CC1)CC2=O

CAS DataBase Reference

39262-22-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-21

HazardClass 

8

PackingGroup 

II

HS Code 

29147090

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Skin Corr. 1B

MSDS

• Language:English Provider:(1R)-Camphor-10-sulfonic acid chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L(-)-10-Camphorsulfonyl chloride Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

A chiral derivative of Camphor.

Uses

L(-)-10-Camphorsulfonyl chloride is a useful synthetic intermediate,it is used for asymmetric hydroxylation.

Synthesis

In the dry 250 mL round bottom flask with magnetic stirrer, reflux condenser tube and drying tube, add sulfoxide, cooled to 0 ?? with an ice water bath, under stirring in batches to add camphorsulfonic acid synthesized by the above method, reacted at 0 ?? for 1h, withdraw the ice bath, so that the natural warming, and then reacted at room temperature for another 2h, microthermal to the solution until clarified, the tail gas is absorbed by a 10% solution of sodium hydroxide. At the end of the reaction, the excess sulfoxide chloride was evaporated under reduced pressure, and the reactants were poured into crushed ice with rapid stirring, quickly filtered, washed with ice water and dried under vacuum to obtain a white powdery solid. After petroleum ether recrystallization to get the product levocamphor-10-sulfonyl chloride.

Purification Methods

If free from OH bands in the IR, then recrystallise it from Et2O or pet ether; otherwise treat it with SOCl2 at 50o for 30minutes, evaporate, dry the residue over KOH in a vacuum and recrystallise it. The (±)-acid chloride has m 85o [Bartlett & Knox Org Synth 45 14 1965]. Itis characterised as the amide (prisms from EtOH) m 132o, [ ] 17 (+) and (-) 1.5o (EtOH). On repeated recrystallisation from EtOH the anilide has m 120.5-121o, [] 25 +76o (c 1, CHCl3). [Read & Storey J Chem Soc 2761 1930, Sutherland & Shriner J Am Chem Soc 58 62 1936, Halterman et al. J Am Chem Soc 109 8105 1987, Bartlet & Knox Org Synth 45 55 1945, Beilstein 11 IV 650.]

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