ChemicalBook > CAS DataBase List > (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate

(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate

Product Name
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
CAS No.
23735-43-5
Chemical Name
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
Synonyms
(S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate;(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE;Travoprost Impurity 51;(S)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE;L-α,β-Isopropylideneglycerol-γ-tosylate;(S)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE;(S)-3-Toxyloxy-1,2-propanediol acetonide;2,3-ISOPROPYLIDENE-SN-GLYCEROL 1-TOSYLATE;(S)-1-O-tosyl-2,3-O-isopropylideneglycerol;(2S)-1-O-Tosyl-2-O,3-O-isopropylideneglycerol
CBNumber
CB6164890
Molecular Formula
C13H18O5S
Formula Weight
286.34
MOL File
23735-43-5.mol
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(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate Property

Melting point:
29-31 °C
alpha 
4.2 º (c=10, abs.alcohol)
Boiling point:
398.71°C (rough estimate)
Density 
1.208 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.506(lit.)
Flash point:
>230 °F
storage temp. 
Inert atmosphere,2-8°C
form 
powder to lump to clear liquid
color 
White or Colorless to Light yellow
optical activity
[α]26/D +7.5°, c = 2% in DMF
BRN 
89799
InChI
InChI=1/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3/t11-/s3
InChIKey
SRKDUHUULIWXFT-LBPXTSNRNA-N
SMILES
C1(C=CC(C)=CC=1)S(=O)(=O)OC[C@@H]1COC(C)(C)O1 |&1:12,r|
CAS DataBase Reference
23735-43-5(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
F 
10-21
HS Code 
29329990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
337420
Product name
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate
Purity
97%
Packaging
1g
Price
$171
Updated
2023/01/07
Sigma-Aldrich
Product number
337420
Product name
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate
Purity
97%
Packaging
5g
Price
$304
Updated
2023/01/07
TCI Chemical
Product number
D2550
Product name
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
Purity
>98.0%(GC)
Packaging
1g
Price
$198
Updated
2025/07/31
TCI Chemical
Product number
D2550
Product name
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
Purity
>98.0%(GC)
Packaging
5g
Price
$645
Updated
2025/07/31
TRC
Product number
D469555
Product name
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
Packaging
1g
Price
$115
Updated
2021/12/16
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(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate has been used as a reactant for the synthesis of 16-(3-trifluoromethyl)phenoxy PGF2α analog travoprost (T715600) which has potent topical ocular activity. (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate has also been used for the preparation of p38 mitogen activated protein (MAP) kinase inhibitors.

Synthesis

98-59-9

14347-78-5

23735-43-5

The general procedure for the synthesis of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate from p-toluenesulfonyl chloride and (R)-(-)-glycerol acetonide was carried out as follows: in accordance with the methodology used for the preparation of (R)-(-)-20a, (R)-(-)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolan-1,3-dioxolan (19b) ( 2.50 g) was converted to (S)-(+)-3-toluenesulfonyloxy-1,2-propanediol acetone compound 20b (5.23 g, 98% yield, 99.2% ee). [α]D20 +4.5 (c 1.0, EtOH) (literature value [α]D25 +4.7 (c 1.0, EtOH)).IR, NMR, and HRMS spectroscopic data were in complete agreement with the (R)-(-)-20a enantiomer.

References

[1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1719 - 1723
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213
[3] Tetrahedron, 2013, vol. 69, # 5, p. 1634 - 1648
[4] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6304 - 6311
[5] Journal of the Chemical Society, Chemical Communications, 1984, # 6, p. 349 - 350

(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate Suppliers

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View Lastest Price from (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate 23735-43-5
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000KGS
Release date
2025-02-19

23735-43-5, (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonateRelated Search:

ETHANE Dimethyl sulfoxide Methanol Xylene Dimethyl sulfate Dimethyl phthalate Sulfanilic acid N,N-Dimethylformamide Calcium dobesilate Amlodipine Besylate p-Toluenesulfonic acid Dimethyl ether Dodecylbenzenesulphonic acid Benzenesulfonic acid Linear alkyl benzenesulphonate Dimethyl carbonate Dimethyl fumarate Dacthal

  • (S)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE
  • (S)-(+)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
  • (S)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
  • (S)-(+)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENSULFONATE
  • (S)-(+)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
  • (S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL-4-METHYLBENZENESULFONATE
  • (S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
  • 2,3-ISOPROPYLIDENE-SN-GLYCEROL 1-TOSYLATE
  • 2,2-DIMETHYL-4(S)-4-(P-TOLYLSULFONYL)METHYL-1,3-DIOXALANE
  • 1,3-DIOXOLANE-4-METHANOL, 2,2-DIMETHYL-, 4-METHYLBENZENESULFONATE, (4S)-
  • L-α,β-Isopropylideneglycerol-γ-tosylate
  • (S)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulphonate
  • (S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOLUENE-4-SULFONATE
  • (S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE
  • (S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFONATE
  • (S)-1,2-O-ISOPROPYLIDENEGLYCEROL-3-TOLUENESULFONATE
  • (S)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE
  • (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
  • (S)-3-Toxyloxy-1,2-propanediol acetonide
  • (s)-2,2-dimethyl-1,3-dioxolane-4-methyl p-toluenesulfonate
  • (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol 4-toluenesulfo
  • 2,3-Isopropylidene-sn-glycerol 1-tosylate, (S)-2,2-Dimethyl-1,3-dioxolane-4-methyl p-toluenesulfonate, L-α,β-Isopropylideneglycerol-γ-tosylate
  • 2,3-Isopropylidene-sn-glycerol 1-tosylate, L-α,β-Isopropylideneglycerol-γ-tosylate
  • (2S)-1-O-Tosyl-2-O,3-O-isopropylideneglycerol
  • 4-Methylbenzenesulfonic acid (S)-2,2-dimethyl-1,3-dioxolane-4α-ylmethyl ester
  • p-Toluenesulfonic acid [(S)-2,2-dimethyl-1,3-dioxolane-4α-yl]methyl ester
  • p-Toluenesulfonic acid [S,(+)]-2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester
  • p-Toluenesulfonic acid [S,(+)]-2,2-dimethyl-1,3-dioxolane-4-ylmethyl ester
  • (S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate,97%
  • L-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL-GAMMA-TOSYLATE
  • L-(+)-1,2-ISOPROPYLIDENEGLYCEROL 3-(P-TOLUENESULFONATE)
  • (4S)-2,2-dimethyl-4-(4-toluenesulphonyloxymethyl)-1,3-dioxolane
  • (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethylp-Toluenesulfonate&gt
  • 1,3-Dioxolane-4-methanol, 2,2-dimethyl-, 4-(4-methylbenzenesulfonate), (4S)-
  • Travoprost Impurity 51
  • (S)-(2,2-dimethyl-1,3-dioxalan-4-yl)methyl-4-methylbenzenesulfonate
  • (S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-tolue...
  • (S)-1-O-tosyl-2,3-O-isopropylideneglycerol
  • (<i>S</i>)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl <i>p</i>-toluenesulfonate
  • 23735-43-5
  • Asymmetric Synthesis
  • Organic Building Blocks
  • Protected Alcohols
  • Dioxolanes
  • Chiral Building Blocks
  • Dioxanes & Dioxolanes
  • Glycidyl Compounds, etc. (Chiral)
  • chiral
  • Chiral Building Blocks
  • Dioxanes & Dioxolanes
  • Dioxolanes
  • Glycidyl Compounds, etc. (Chiral)
  • Synthetic Organic Chemistry
  • ADVANCED INT.