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2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethyl 4-methylbenzenesulfonate is a linker.

Synonyms: Tos-PEG2-O-Propargyl

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Quality Control of Tos-PEG2-O-Propargyl Purity: 97% SDS Specification

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Product Details of Tos-PEG2-O-Propargyl

CAS No. :	1119249-30-7
Formula :	C₁₄H₁₈O₅S
M.W :	298.35
SMILES Code :	C#CCOCCOCCOS(C1=CC=C(C)C=C1)(=O)=O
Synonyms :	Tos-PEG2-O-Propargyl
MDL No. :	MFCD20134051
InChI Key :	XOLBARIQCXNLPS-UHFFFAOYSA-N
Pubchem ID :	25199393

Safety of Tos-PEG2-O-Propargyl

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331-H341
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Application In Synthesis of Tos-PEG2-O-Propargyl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1119249-30-7 ]

[ 1119249-30-7 ] Synthesis Path-Downstream 1~35

1
[ 77-85-0 ]
[ 1119249-30-7 ]
[ 1119249-31-8 ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 357 - 363.

2
[ 7218-43-1 ]
[ 98-59-9 ]
[ 1119249-30-7 ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: In an oven dried REF, monopropargylate (1.0 eq)was dissolved with stirring in TRF at 0 C. Aqueous KOR (4 eq) was added to the flask in small portions immediately. After 10 minutes, tosyl chloride (1.2 eq) solution in TRF was added dropwise and stirred for 12 hours. Upon completion, reaction was quenched with aqueous ammonium chloride and extracted with DCM thrice to get crude product which was purified using silica gel column chromatography using MeORDCM as eluent. The compound 9b was prepared by general procedure 4.1.2, starting from 9a (1 g, 7 mmol), tosyl chloride (1.5 g, 8 mmol), potassium hydroxide (1.3 g, 24 mmol) in THF. The product was obtained as a pale yellow liquid (1.8 g, 6 mmol, 90%) afier purification by silica gel column chromatography using ethyl acetate/hexane as eluent, RrO.55 in 50% ethyl acetate/hexane. ‘H NMR (400 MHz, COd3): OH7.78 (d, J=8 Hz, 2H), 7.32 (d, J=8 Hz, 2H), 4.17-4.13 (m, 4H), 3.70-3.58 (m, 6H), 2.44-2.41 (m, 4H). ‘3C NMR (100 MHz, CDC13): O 144.92, 132.94,129.91, 128.04, 79.57, 77.16, 74.73, 70.59, 69.30, 69.05,68.73, 60.45, 58.48, 21.71, 21.12, 14.31. HRMS (M+Na): 321.07Mol. formula: C,4H,8055Mol. Weight: 298.08Physical appearance: pale yellow liquidYield: 90%
87%	With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃;	A solution of S3i (1.9 g, 13 mmol) in THF (30 mL) was treated with powdered sodium hydroxide (0.68 g, 17 mmol) at 0 C and toluene sulfonyl chloride (2.7 g, 14 mmol) was added. The reaction mixture was stirred allowing it to warm to room temperature overnight. The solvent was evaporated and the residue taken up in dichloromethane and washed twice with water. After drying over magnesium sulphate the solvent was evaporated and the tosylate purified by chromatography (hexane / ethyl acetate 7:1) to provide a yellow liquid (3.4 g, 87%). The intermediate (3.0 g, 10 mmol) was dissolved in acetone (40 mL) and treated with sodium iodide (3.0 g, 20 mmol). After stirring at room temperature overnight, the solvent was evaporated and the residue taken up in dichloromethane and water. The organic phase was washed with aqueoussodium thiosulfate solution and water and dried over magnesium sulfate. Concentration furnished 9-iodo-4,7-dioxa-nonyne S3 (2.2 g, 88%) as colourless liquid. 1H NMR (400 MHz, CDCI3): O 4.23 (5, 2H), 3.77 (t, 2H), 3.71 (bs, 4H), 3.28 (t, 2H), 2.45 (bs, 1H); 13C NMR (100 MHz, CDCI3): O 79.51, 74.61, 71.98,70.00, 69.05, 58.47, 2.67.
82%	With dmap; triethylamine; In dichloromethane; at 0 - 25℃; for 16h;	To a solution of 2-(2-prop-2-ynoxyethoxy)ethanol (2.00 g, 13.8 mmol, Intermediate LC), TEA (4.21 g, 41.6 mmol) and DMAP (170 mg, 1.39 mmol) in DCM (60 mL) was added 4-methylbenzenesulfonyl chloride (5.29 g, 27.7 mmol) at 0 C. The mixture was then stirred at 25 C. for 16 hours. On completion, the mixture was washed with 2.0 M aq.HCl (20 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (3.40 g, 82% yield) as light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.81 (d, J=8.4 Hz, 2H), 7.35 (m, J=8.0 Hz, 2H), 4.23-4.14 (m, 4H), 3.73-3.68 (m, 2H), 3.67-3.59 (m, 4H), 2.46 (s, 3H), 2.44 (t, J=2.4 Hz, 1H).

68%

With triethylamine; In dichloromethane; at 20℃;

Into a 250-mL round-bottom flask, was placed a solution of 2-[2-(prop-2-yn-1-yloxy)ethoxy]ethan-1-ol (1 g, 6.94 mmol, 1.00 equiv) in dichloromethane (80 mL), triethylamine (2.8 g, 27.67 mmol, 3.00 equiv), 4-dimethylaminopyridine (270 mg, 2.21 mmol, 0.30 equiv), and 4-toluenesulfonyl chloride (1.9 g, 9.97 mmol, 1.50 equiv). The resulting solution was stirred for 12 hours at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:2). The collected fractions were combined and concentrated under vacuum. This resulted in 1.4 g (68%) of 2-[2-(prop-2-yn-1-yloxy)ethoxy]ethyl 4-methylbenzene-1-sulfonate as yellow oil.

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 357 - 363.
[2]Patent: US2017/231260,2017,A1 .Location in patent: Paragraph 0141; 0142; 0398; 0399; 0400-0405.
[3]Chemistry - A European Journal,2018,vol. 24,p. 16085 - 16096.
[4]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 8113 - 8122.
[5]Patent: WO2020/204691,2020,A1 .Location in patent: Page/Page column 19; 20.
[6]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 3856; 3857.
[7]Patent: WO2021/72269,2021,A1 .Location in patent: Page/Page column 189.
[8]Journal of Medicinal Chemistry,2009,vol. 52,p. 5816 - 5825.
[9]Patent: US2019/300521,2019,A1 .Location in patent: Paragraph 0832-0833.
[10]Chemistry - A European Journal,2020,vol. 26,p. 10871 - 10881.
[11]Molecules,2022,vol. 27.

3
[ 1119249-30-7 ]
4,4-difluoro-8-(4-aminophenyl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
[ 1198404-08-8 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6383 - 6388.

4
[ 107-19-7 ]
[ 7460-82-4 ]
[ 1119249-30-7 ]

Yield	Reaction Conditions	Operation in experiment
78%		To a stirred solution of propargyl alcohol (100 mg, 1.8 mmol) in dry DMF (30 mL) was added NaH (60% in oil, 900 mg, 22 mmol) at 0 C under Ar. After stirring for 30 min at room temperature, diethylene glycol bis(p-toluenesulfonate) (2.8 g, 6.7 mmol) was added to the mixture at 0 C. The mixture was stirred for 1 h at room temperature. After quenching with sat. NH4Cl at 0 C, the resulting mixture was extracted with EtOAc (250 mL × 3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residual oil was purified by silica gel column chromatography with 20% EtOAc in hexane to obtain 1 (410 mg, 78%) as a colorless oil. 1H NMR (270 MHz, CDCl3): δ 2.43 (1H, t, J = 2.6 Hz, H-1), 2.45 (3H, s, CH3 in tosylate), 3.59-3.66 (4H, m, -OCH2CH2O-), 3.70 (2H, m, -OCH2CH2OSO2-), 4.16 (2H, m, HCCCH2O-), 4.17 (2H, m, -OCH2CH2OSO2-), 7.34 and 7.80 (each 2H, m, tosylate); HRMS (ESI-TOF, positive mode): calcd for C14H18O5SNa [M+Na]+ 321.0773, found 321.0771.
60%		250 μL (4.23 mmol) of propargyl alcohol was dissolved in 30 mL of dehydrated dimethylformamide, and 348 mg (8.7 mmol) of 60% sodium hydride was added thereto and stirred at room temperature for 30 minutes. 3.5 g (8.5 mmol) of diethylene glycol bis(p-toluene sulfonate) was added thereto while cooling with ice, thereby starting the reaction. After stirring at room temperature for 1 hour, 15 mL of a saturated aqueous solution of ammonium chloride was added thereto thereby terminating the reaction. 60 mL of water was added thereto, 3 mL of 1M hydrochloric acid was added thereto to adjust pH to be 7, and subsequently the resultant was extracted three times with 100 mL of ethyl acetate. The resultant was washed twice with 3 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and subsequently concentrated under reduced pressure thereby obtaining 3262.5 mg of a mixture of a white solid and a light yellow oily substance. The mixture was subjected to silica gel column chromatography (150 g, 3.0 cm inner diameter×35 cm length) using hexane-ethyl acetate (75:25) as an eluent thereby obtaining 753.0 mg (2.523 mmol; yield 60%) of the titled compound as a colorless clear oily substance.

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 406 - 413.
[2]Patent: US2017/290335,2017,A1 .Location in patent: Paragraph 0062; 0063.
[3]Tetrahedron Letters,2009,vol. 50,p. 6383 - 6388.

5
[ 623-05-2 ]
[ 1119249-30-7 ]
[ 1204085-28-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 8113 - 8122.

6
[ 7218-43-1 ]
[ 133-59-5 ]
[ 1119249-30-7 ]

Yield	Reaction Conditions	Operation in experiment
1.7 g (68%)		Example 12 3,6-dioxanon-8-yn-1-yl p-toluenesulfonate (12, propargyl-PEG2-OTs) 3,6-Dioxanon-8-yn-1-ol 11 (1.2 g, 8.3 mmol) and toluenesulfonyl chloride were reacted according to Example 3 to yield 1.7 g (68%) of 12 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 2.44 (t, J=2.4 Hz, 1H), 2.45 (s, 3H), 3.60-3.65 (m. 4H), 3.70 (t, J=4.8 Hz, 2H), 4.15-4.18 (m, 4H), 7.35 (d, J=8.0 Hz, 2H), 7.80 (d, J=8 Hz, 2H); 13C NMR (100.6 MHz, CDCl3): δ 21.6, 58.4, 68.7, 69.0, 69.2, 70.6, 74.6, 79.5, 128.0, 129.8, 133.1, 144.8; MS ESI (m/z): [M+H]+ calcd. for C14H19O5S, 299.09; found 299.1.

References: [1]Patent: US2010/221176,2010,A1 .

7
[ 1119249-30-7 ]
[ 108-91-8 ]
[ 1245006-69-2 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 12711 - 12716.

8
[ 1119249-30-7 ]
[ 104-94-9 ]
[ 1245006-68-1 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 12711 - 12716.

9
[ 1119249-30-7 ]
[ 62-53-3 ]
[ 1245006-67-0 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 12711 - 12716.

10
[ 1119249-30-7 ]
[ 1194396-88-7 ]
[ 1271921-22-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; at 20℃; for 1h;	To a stirred solution of 1 (2.5 g, 8.5 mmol) and 222 (1.4 g, 4.6 mmol) in THF (280 mL) was added aqueous CuSO4 (10 mg mL-1, 380 mL) and aqueous sodium ascorbate (10 mg mL-1, 340 mL) at room temperature. The mixture was stirred for 1 h before extraction with CH2Cl2 (600 mL × 3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residual oil was purified by silica gel column chromatography with 20% EtOAc in hexane to obtain Abz-E1 (2.6 g, 96%) as a pale yellow oil. 1H NMR (500 MHz, CDCl3): δ 0.68 (9H, s, t-butyl), 2.44 (3H, s, CH3 in tosylate), 3.64-3.67 (2H, m, -OCH2CH2O-), 3.69-3.72 (4H, m, -OCH2CH2OCH2CH2OSO2-), 4.18 (2H, m, -OCH2CH2OSO2-), 4.42 (1H, d, J = 8.5 Hz, HO-3), 4.62 (1H, d, J = 8.5 Hz, H-3), 4.77 (2H, s, 1,2,3-triazole-CH2O-), 7.01 (1H, s, H-1), 7.33 (2H, m, tosylate), 7.55 (2H, m, 1-phenyl), 7.78 (2H, m, tosylate), 7.83 (2H, m, 1-phenyl), 8.07 (1H, s, 1,2,3-triazole), 8.12 and 8.60 (each 1H, s, 1,2,4-triazole); 13C NMR (125 MHz, CDCl3): δ 21.6 (methyl in tosylate), 26.1 (methyl in t-butyl), 36.2 (tertiary carbon in t-butyl), 64.7, 68.7, 69.2, 69.8, and 70.7 (diethylene glycol linker), 75.6 (C3), 120.6 (C3' and C5'), 120.7 (C3 and 1,2,3-triazole), 127.6 (C1), 127.9 (tosylate), 129.8 (tosylate), 130.3 (phenyl), 132.9 (tosylate), 134.4 (phenyl), 136.6 (phenyl), 137.9 (C2), 144.9 (tosylate), 146.1 (phenyl and 1,2,3-triazole); UV λmax (MeOH) nm (ε): 271.2 (20,000); HRMS (ESI-TOF, positive mode): calcd for C29H36N6O6SNa [M+Na]+ 619.2315, found 619.2312.

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 406 - 413.

11
[ 57011-48-0 ]
[ 1119249-30-7 ]
C₁₀H₁₆N₆O₃ [ No CAS ]