21286-54-4

Basic information

• Product Name: D(+)-10-Camphorsulfonyl chloride
• Synonyms: (+)-Camphor-10-sulfonyl chloride, (1S)-Camphor-10-sulfonic acid chloride;Bicyclo[2.2.1]heptane-1-methanesulfonyl chloride, 7,7-dimethyl-2-oxo-;D-2-Oxobornane-10-sulfonyl chloride;(1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfochloride;[1S,4R,(+)]-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonic acid chloride;D(+)-10-Camphorsulfonyl chloride,97%;D(+)-1-CaMphorsulfonyl chloride;D(+)-10-CaMphorsulfonyl chloride, 97% 5GR
• CAS NO: 21286-54-4
• Molecular Formula: C₁₀H₁₅ClO₃S
• Molecular Weight: 250.74
• EINECS: 244-314-8
• Product Categories: chiral;Chiral Reagents;Bicyclic Monoterpenes;Biochemistry;for Resolution of Alcohols & Thiols;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Terpenes;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfonyl Chlorides;Pharmaceutical Intermediates
• Mol File: 21286-54-4.mol
• Article Data: 51

Chemical Properties

• Melting Point: 67-68 °C
• Boiling Point: 349.4 °C at 760 mmHg
• Flash Point: 165.1 °C
• Appearance: Off-white to beige/Crystalline Powder
• Density: 1.2078 (estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 32 ° (C=1, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Sensitive: Moisture Sensitive
• BRN: 3205974
• CAS DataBase Reference: D(+)-10-Camphorsulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: D(+)-10-Camphorsulfonyl chloride(21286-54-4)
• EPA Substance Registry System: D(+)-10-Camphorsulfonyl chloride(21286-54-4)

Safety Data

• Hazard Codes: C
• 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
• Hazardous Substances Data: 21286-54-4(Hazardous Substances Data)

Usage

Description

D(+)-10-Camphorsulfonyl chloride is a chiral derivative of camphor, which is a white to light yellow crystalline powder. It is a valuable synthetic intermediate in various chemical reactions.

Uses

Used in Chemical Synthesis:
D(+)-10-Camphorsulfonyl chloride is used as a synthetic intermediate for asymmetric hydroxylation, a key reaction in the synthesis of enantiomerically pure compounds. Its chiral nature allows for the selective formation of specific enantiomers, which is crucial in the development of pharmaceuticals and other chiral molecules.
Used in Chiral Derivatives:
As a chiral derivative of camphor, D(+)-10-Camphorsulfonyl chloride is utilized in the preparation of other chiral compounds and intermediates. Its unique structural features make it a versatile building block in the synthesis of various biologically active molecules and specialty chemicals.

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.]

InChI:InChI=1/C10H15ClO3S/c1-9(2)6-4-5-10(9,3)8(12)7(6)15(11,13)14/h6-7H,4-5H2,1-3H3

Upstream product

• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 61380-66-3 (1S)-(+)-10-camphorsulfonic acid 
• 77541-94-7 ω-D-camphorsulfinic acid 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 76-26-6 [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid 
• 61380-66-3 [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid 
• 35963-20-3 (R)-10-camphorsulfonic acid 

Downstream Products

• 132757-64-3 N-(2-pyridyl)camphor-10-sulfonamide 
• 132757-64-3 (1R)-2-oxo-bornane-10-sulfonic acid-[2]pyridylamide 
• 62319-13-5 (1S,4R)-methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonate 
• 40248-67-7 4-nitrophenyl ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate 
• 111032-38-3 (1S)-2-oxo-bornane-10-sulfonic acid p-tolyl ester 
• 108293-34-1 (1S)-2-oxo-bornane-10-sulfonic acid-((1S)-neomenthyl ester) 
• 108293-34-1 (1S)-2-oxo-bornane-10-sulfonic acid l-menthyl ester 
• 159650-89-2 (+)-(S)-2-sec-butylphenol 
• 36383-18-3 (-)-(R)-2-sec-butylphenol 
• 108293-34-1 (1S)-2-oxo-bornane-10-sulfonic acid-((1R)-menthyl ester) 

Relevant articles and documents

Synthesis and characterization of camphorsulfonyl acetate of cellulose

Novel cellulose derivatives were prepared from reacting (1R)-(+)-camphor-10-sulfonic chloride (CSC) with cellulose acetate (CA) in acetone and triethylamine. The reaction conditions, including reaction time and reactant molar ratios, were optimized. The structure of the products was confirmed by means of 1H NMR, 13C NMR, FT-IR and elementary analysis. The techniques were also used to determine the degree of the substitution of camphorsulfonyl groups (DSCS). The data calculated from 1H NMR, 13C NMR, percent grafting (G%) and elementary analysis coincided with those from chemical analysis. Compared to cellulose acetate, the cellulose derivatives exhibited decreased thermal stability, improved solubility in organic solvents and enhanced enantioselectivity towards tyrosine isomers. The solubility and enantioselectivity increased with increasing degrees of camphorsulfonyl substitution.

Modeling of the Diels-Alder reaction enantioselectivity by quantum mechanics and molecular mechanics

The enantioselectivity of the Diels-Alder reaction between (E)-3-(4-nitrophenyl)-1-(pyridin-3-yl)prop-2-en-1-one and cyclopenta-1,3-diene in the chiral ionic liquids 3-butyl-1-methylimidazolium (S)-camphorsulfonate and (S)-1-methyl-3-(pyrrolidin-2-ylmethyl)- imidazolium tosylate or upon chiral promotion with chiral oxazaborolidine was modeled by molecular and quantum mechanics and then experimentally studied; computations were in good agreement with the experimental data, resulting in no stereoselectivity with a chiral ionic liquid used as a co-solvent and prominent stereoselectivity upon chiral promotion.

Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides

A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated.

New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections

Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components. The produced compounds exhibited high activity against the vaccinia virus (an enveloped virus belonging to the poxvirus family), which was combined with low cytotoxicity. Some compounds had a selectivity index higher than that of the reference drug cidofovir; the highest SI = 1123 was exhibited by 1-adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene moiety. The produced compounds demonstrated inhibitory activity against other orthopoxviruses: cowpox virus (SI = 30-406) and ectromelia virus (mousepox virus, SI = 39-707). This journal is

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.