| Identification | More | [Name]
(2R)-(-)-Glycidyl tosylate | [CAS]
113826-06-5 | [Synonyms]
2,2'-IMINOSTILBENE
(2R)-(-)-GLYCIDYL P-TOLUENESULFONATE
(2R)-GLYCIDYL TOLUENESULFONATE
(2R)-(-)-GLYCIDYL TOSYLATE
(2R)-OXIRAN-2-YLMETHYL 4-METHYLBENZENESULPHONATE
(2R)-(-)-TOLUENE-4-SULFONIC ACID 2,3-EPOXYPROPYL ESTER
5H-DIBENZ[B,F]AZEPINE
IMINOSTILBENE
LABOTEST-BB LT00440878
o,o'-iminostilbene
OXIRANEMETHANOL, 4-METHYLBENZENESULFONATE, (2R)-
P-TOLUENESULFONIC ACID (2R)-(-)-GLYCIDYL ESTER
(R)-2,3-EPOXY-1-PROPYL P-TOLUENESULFONATE
(R)-(-)-2,3-EPOXYPROPYL P-TOLUENESULFONATE
(R)-(-)-2,3-EPOXYPROPYL TOLUENE-4-SULFONATE
RARECHEM AK HZ 0050
(R)-(-)-GLYCIDYL 4-TOLUENESULFONATE
(R)-(-)-GLYCIDYL TOSYLATE
(R)-GLYCIDYL TOSYLATE
(R)-(-)-OXIRANE-2-METHANOL 4-TOLUENESULFONATE | [EINECS(EC#)]
205-970-0 | [Molecular Formula]
C10H12O4S | [MDL Number]
MFCD00010834 | [Molecular Weight]
228.26 | [MOL File]
113826-06-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
46-49 °C(lit.)
| [alpha ]
-18 º (c=2.5,CHCl3) | [Boiling point ]
340.07°C (rough estimate) | [density ]
1.3749 (rough estimate) | [refractive index ]
1.5400 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
dioxane: 50 mg/mL, clear
| [form ]
powder
| [color ]
yellow to orange
| [Optical Rotation]
-19.9° (C=1 g/100ml CHCL3) | [Water Solubility ]
decomposes | [BRN ]
3592142 | [InChI]
InChI=1/C10H12O4S/c1-8-2-4-10(5-3-8)15(11,12)14-7-9-6-13-9/h2-5,9H,6-7H2,1H3/t9-/s3 | [InChIKey]
NOQXXYIGRPAZJC-DJEYLCQNNA-N | [SMILES]
C1(=CC=C(C)C=C1)S(=O)(=O)OC[C@@H]1OC1 |&1:12,r| | [CAS DataBase Reference]
113826-06-5(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,T | [Risk Statements ]
R45:May cause cancer.
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R68:Possible risk of irreversible effects. | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S53:Avoid exposure-obtain special instruction before use . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
3
| [RTECS ]
RR0510000
| [F ]
3-10-21 | [Hazard Note ]
Irritant | [HazardClass ]
9 | [HS Code ]
29109000 |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Uses]
Protected Glycidol, (2R)-(-)-Glycidyl tosylate is used as an intermediate in the preparation of neurochemicals.
| [Synthesis]
GENERAL STEPS: Under dry conditions, p-toluenesulfonyl chloride (PTSC, 25.0 g) and (R)-oxirane-2-methanol (6.0 mL) were dissolved in anhydrous dichloromethane (DCM, 250 mL). Subsequently, triethylamine (TEA, 36.0 mL) was added slowly and dropwise at 0°C to the reaction mixture. After the reaction was stirred continuously at 0°C for 3 h, the reaction solution was concentrated by rotary evaporator. The crude product was purified by fast column chromatography (eluent: ethyl acetate/petroleum ether) to afford (R)-p-toluenesulfonic acid glycidyl ester (17.6 g) as a white solid. Yield: 85.0%; Melting point: 44-46°C; [α]D25 = +18.3 (c 1.7, acetonitrile). IR (KBr, cm-1): 1598, 1363, 1177, 969, 666, 556. 1H NMR (400 MHz, DMSO-d6) δ: 7.83 (d, J = 8.1 Hz, 2H), 7.52- 7.46 (m, 2H), 4.43 (d, J = 11.6 Hz, 1H), 3.85 (dddd, J = 7.0, 5.7, 3.7, 1.9 Hz, 1H), 3.26-3.17 (m, 1H), 2.78 (t, J = 4.6 Hz, 1H), 2.66-2.58 (m, 1H), 2.42 (s, 3H). esi -MS m/z: 251.2 [M + Na]+. | [References]
[1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8668 - 8676
[2] Chemical Communications, 2014, vol. 50, # 51, p. 6718 - 6721
[3] Organic Letters, 2012, vol. 14, # 11, p. 2834 - 2837
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3859 - 3862
[5] Angew.Chem.Int.Ed., 2014, vol. 53, p. 3859 - 3862,4 |
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