[ CAS No. 2916-68-9 ] {[proInfo.proName]}

Name: 2916-68-9|2-(Trimethylsilyl)ethanol|98%
Brand: Ambeed
SKU: A398015
Price: 18.0 USD
Availability: InStock
Rating: 98 (30 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 2916-68-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2916-68-9 ]

Product Details of [ 2916-68-9 ]

CAS No. :	2916-68-9	MDL No. :	MFCD00002825
Formula :	C₅H₁₄OSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZNGINKJHQQQORD-UHFFFAOYSA-N
M.W :	118.25	Pubchem ID :	18013
Synonyms :

Calculated chemistry of [ 2916-68-9 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.18
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	1.32
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	-0.49
Consensus Log Po/w :	1.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.54
Solubility :	3.43 mg/ml ; 0.029 mol/l
Class :	Very soluble
Log S (Ali) :	-1.78
Solubility :	1.96 mg/ml ; 0.0165 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.33
Solubility :	5.54 mg/ml ; 0.0469 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.56

Safety of [ 2916-68-9 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501	UN#:	1987
Hazard Statements:	H225	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2916-68-9 ]

* 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.

Upstream synthesis route of [ 2916-68-9 ]
Downstream synthetic route of [ 2916-68-9 ]

[ 2916-68-9 ] Synthesis Path-Upstream 1~6

1
[ 2916-68-9 ]
[ 1663-67-8 ]
[ 18457-04-0 ]

Reference： [1] Patent: US4584133, 1986, A,
[2] Patent: US4443373, 1984, A,

2
[ 50-00-0 ]
[ 2916-68-9 ]
[ 76513-69-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	at 0℃; for 0.5 h;	Practical Example 1; 13.5 g (0.45 mol) of paraformaldehyde and 125.0 g (1.15 mol) of chlorotrimethylsilane were introduced into a 300-mL four-neck flask fitted with a thermometer and stirrer. 54.4 g (0.46 mol) of 2-trimethylsilylethanol was added dropwise over 30 minutes while stirring and cooling with an ice bath. After warming the reaction mixture to room temperature, the pressure was reduced to 100 mmHg using an aspirator, and the hydrogen chloride was removed. The low boiling fraction was distilled off, and additional vacuum distillation was carried out to provide 34.0 g of 2-(trimethylsilyl)ethoxymethyl chloride. The2-(trimethylsilyl)ethoxymethyl chloride product had a purity of 76percent, and the yield was 33percent.; Practical Example 2; 6.0 g (0.2 mol) of paraformaldehyde and 108.6 g (1 mol) of chlorotrimethylsilane were introduced into a 200-mL four-neck flask fitted with a thermometer and stirrer. 23.7 g (0.2 mol) of 2-trimethylsilylethanol was added dropwise over 30 minutes while stirring and cooling with an ice bath. After warming the reaction mixture to room temperature, the pressure was reduced to 100 mm Hg using an aspirator, and the hydrogen chloride was removed. After then adding 5 drops of diisopropylethylamine, the low boiling fraction was distilled off, and additional vacuum distillation was carried out to provide 22.9 g of 2-(trimethylsilyl)ethoxymethyl chloride. The purity of the obtained 2-(trimethylsiIyl)ethoxymethyl chloride was very high, i.e., 98percent, and the yield was 68percent.

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, p. 5719
[2] Tetrahedron Letters, 1980, vol. 21, # 35, p. 3343 - 3346
[3] Helvetica Chimica Acta, 1988, vol. 71, p. 957 - 963
[4] Patent: WO2006/40964, 2006, A1, . Location in patent: Page/Page column 6; 7
[5] Bulletin de la Societe Chimique de France, 1986, # 2, p. 245 - 252
[6] Patent: WO2006/40964, 2006, A1, . Location in patent: Page/Page column 7

3
[ 2916-68-9 ]
[ 7693-46-1 ]
[ 80149-80-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 7, p. 735 - 738
[2] Journal of Organic Chemistry, 1983, vol. 48, # 9, p. 1539 - 1541
[3] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 608 - 612
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 2181 - 2186
[5] Patent: WO2018/149419, 2018, A1, . Location in patent: Paragraph 001255

4
[ 74124-79-1 ]
[ 2916-68-9 ]
[ 78269-85-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In acetonitrile at 20℃; for 3 h;	Compound 41; TEA (21.9 mL, 155.6 mmol, 3.0 eq.) was added to 2-trimethylsilanyl- ethanol (7.4 mL, 51.88 mmol, 1.0 eq.) in 260 mL MeCN, followed by di- succinimidyl carbonate (20 g, 1.5 eq.). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and extracted using EtOAc/ saturated NaHCO₃. The organic layer was concentrated after dried over Na₂SO₄. Ether (100 mL) was added to the residue to form a precipitate. The precipitate was filtered and dried to give Compound 41 as a white solid (11.1 g, 84percent). ¹H NMR (300 MHz, CDCl₃): δ 4.42 (t, 3 H), 2.82 (s, 4 H), 1.16 (t, 2 H), 0.1 (s, 9 H).
82%	With triethylamine In acetonitrile at 25℃; for 16 h;	Example 5; methyl (l-l- ( {2- [ (2, 36)-3-amino-2-hydroxy-4-phenylbutyl]-2- benzylhydrazino} carbonyl)-2, 2-dimethylpropylcarbamate; Example 5A; 1- (f [2- (trimethylsilyl) ethoxy] carbonyl} oxy)-2, 5-pyrrolidinedione; Trimethylsilylethanol (7.4 mL, 52 mmol) was dissolved in acetonitrile (260 mL) and treated with disuccinimoyl carbonate (20 g, 1.5 equivalents) and triethylamine (33 mL, 3 equivalents) at 25°C for 16h. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was triturated with ether to form a solid which was filtered and dried to give 11.12 g (82percent) of the title compound.
82%	With triethylamine In acetonitrile	EXAMPLE 5A 1-([2-(trimethylsilyl)ethoxy]carbonyl}oxy)-2,5-pyrrolidinedione Trimethylsilylethanol (7.4 mL, 52 mmol) was dissolved in acetonitrile (260 mL) and treated with disuccinimoyl carbonate (20 g, 1.5 equivalents) and triethylamine (33 mL, 3 equivalents) at 25° C. for 16 h. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was triturated with ether to form a solid which was filtered and dried to give 11.12 g (82percent) of the title compound.

Reference： [1] Patent: WO2008/11117, 2008, A2, . Location in patent: Page/Page column 491
[2] Patent: WO2005/61487, 2005, A1, . Location in patent: Page/Page column 115
[3] Patent: US2005/159469, 2005, A1, . Location in patent: Page/Page column 59

5
[ 2916-68-9 ]
[ 32315-10-9 ]
[ 78269-85-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In tetrahydrofuran	Example 43 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate To a solution of triphosgene (25 g, 0.5 eq.) in THF (200 mL) was added dropwise a mixture of 2-(trimethylsilyl)ethanol (20 g, 1 eq.) and TEA (25 mL, 1.1 eq.) in THF at 0° C. After being stirred at rt for 2 hr, a solution of HOSu (1 eq.) in THF (50 mL) was added into the reaction mixture at 0° C. The resulting mixture was stirred overnight. The resulted solid was removed away by filtration under reduced pressure. The filtrate was treated by chromatographic column on silica gel eluted by CH₂Cl₂. The collected fractions was condensed to 10 mL of volume and poured into pure hexanes. The precipitated solid 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate was collected in 78percent yield by filtration under reduced pressure. ¹H NMR (400 M) 4.4 (d, 2H), 2.9 (s, 4H), 2.2 (d, 2H), 0.1 (s, 1H); ¹³C NMR 172, 154, 74, 28, 19, 0.

Reference： [1] Patent: US2010/105607, 2010, A1,

6
[ 2916-68-9 ]
[ 78269-85-9 ]

Reference： [1] Synthesis, 1987, # 4, p. 346 - 349
[2] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 564 - 570

[ 2916-68-9 ] Synthesis Path-Downstream 1~88

1
[ 13322-90-2 ]
[ 2916-68-9 ]
[ 81336-83-6 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 4603 - 4606

2
[ 1119-72-8 ]
[ 2916-68-9 ]
[ 84397-12-6 ]

Reference： [1]Helvetica Chimica Acta,1982,vol. 65,p. 1412 - 1417
[2]Helvetica Chimica Acta,1986,vol. 69,p. 718 - 725

3
[ 2916-68-9 ]
[ 2389-45-9 ]
[ 89121-14-2 ]

Yield	Reaction Conditions	Operation in experiment
98.2%		6-benzyloxycarbonylamino-2-tert-butoxycarbonyl-L-amino-hexanoic acid (1.9g), DMAP (62mg), and 2-trimethylsilylethanol (720iL) are dissolved in 25mL DCM, and then the mixture is cool to 0 C. After stirring at 0 C for 5mm, reaction mixture is added DCC (1.40g) at 0 C, and the resulting slurry is kept at 0 C and stirring for 15mm. Then reaction mixture is warmed to room temperature and kept stirring for 24 hours. The solution is filtered to remove formed N,N? -Dicyclohexylurea from reaction. The filtrate is then concentrated under reduced pressure, to generate an off-white viscous oil as crude product. The crude product is subjected to silica gel flash chromatography (5 -20% ethyl acetate in hexanes) to yield a colorless viscous liquid compound 14 (2.36, 98.2%). Rf = 0.63 (30% ethyl acetate/hexanes). 1H-NMR (400MHz, CDC13) (ppm): 7.30-7.38 (C1620H, m, 5H), 5.09 (C14H, s, 2H), 4.81 (C8H, br, s, 1H), 4.23 (C5H, t, J= 8.64Hz, 2H), 3.19 (C12H, q, J= 6.38Hz, 2H) 1.79 (C9H, br, m, 2H), 1.48-1.62 (C10 11H, br, m, 3H), 1.43 (C4H, s, 9H), 1.35 (C10H, br, m, 1H), 1.00 (C6H, t, J= 8.68Hz, 2H), 0.04 (C7H, s, 9H). 13C-NMR (600MHz, CDC13) i5 (ppm): 173.07(C1), 156.65 (C13), 155.69 (C2), 136.80 (C15), 128.72, 128.34, 128.30 (C1620), 80.05 (C3), 66.84 (C14), 63.95 (C5), 53.47 (C8), 40.90 (C12), 33.71(C9), 29.56 (C10), 28.53 (C4), 22.60 (C11), 17.59 (C6), -1.31 (C7). HRMS (ESI) mlz calculated for C24T-L10N2O6Si+H 481.2734, found 481.2728. Formula is confirmed as C24H40N2O6Si.

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1305 - 1309
[2]Patent: WO2016/81522,2016,A1 .Location in patent: Paragraph 00286; 00298

4
[ 2916-68-9 ]
[ 13737-36-5 ]
[ 119549-48-3 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 2003 - 2006

5
[ 2916-68-9 ]
[ 17191-43-4 ]
[ 144876-64-2 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 8471 - 8490

6
[ 2916-68-9 ]
[ 84624-27-1 ]
[ 134020-67-0 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 2535 - 2542

7
[ 2916-68-9 ]
[ 65635-85-0 ]
[ 129919-93-3 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 7659 - 7672
[2]Journal of Organic Chemistry,1994,vol. 59,p. 5192 - 5205

8
[ 2916-68-9 ]
[ 142855-80-9 ]
[ 151132-67-1 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 4493 - 4496

9
[ 2916-68-9 ]
[ 220400-04-4 ]
[ 158686-44-3 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 4206 - 4210
[2]Beilstein Journal of Organic Chemistry,2010,vol. 6

10
[ 2916-68-9 ]
[ 16108-03-5 ]
[ 135998-71-9 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 4763 - 4774

11
[ 2916-68-9 ]
[ 7693-46-1 ]
[ 80149-80-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine; for 18h;	2-trimethylsilylethanol (25.1 mmol, 3.0 g) was reacted with p-nitrophenyl chloroformate (27.6 mmol, 5.74 g) in pyridine (60 mmol, 4.9 ml) for 18 hours, then concentrated and purified by column chromatography using silicon dioxide gel, eluting with 20 % ethyl acetate in petroleum ether to afford 4-nitrophenyl 2-(trimethylsilyl)ethyl carbonate (5.89 g, 82 % yield).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 735 - 738
[2]Journal of Organic Chemistry,1983,vol. 48,p. 1539 - 1541
[3]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 608 - 612
[4]Patent: WO2019/40104,2019,A2 .Location in patent: Paragraph 00229; 00230
[5]Journal of the Chemical Society. Perkin transactions I,1986,p. 2181 - 2186
[6]Patent: WO2018/149419,2018,A1 .Location in patent: Paragraph 001255

12
[ 2916-68-9 ]
[ 1069-08-5 ]
[ 162554-41-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 421 - 426
[2]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 1077 - 1088

13
[ 2916-68-9 ]
[ 64263-84-9 ]
(S)-3-Benzyloxy-2-(tert-butoxycarbonyl-methyl-amino)-propionic acid 2-trimethylsilanyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine; dmap; dicyclohexyl-carbodiimide In dichloromethane

Reference： [1]Kim, Hong Yong; Stein, Karin; Toogood, Peter L. [Chemical Communications, 1996, # 14, p. 1683 - 1684]

14
[ 2916-68-9 ]
[ 3972-36-9 ]
[ 182247-47-8 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6169 - 6172

15
[ 2916-68-9 ]
[ 6970-83-8 ]
[ 81616-17-3 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7096 - 7097

16
[ 2916-68-9 ]
[ 14618-78-1 ]
[ 196939-50-1 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 9662 - 9671

17
[ 2916-68-9 ]
[ 13574-13-5 ]
[ 172694-24-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine; dicyclohexyl-carbodiimide In acetonitrile for 18h; Ambient temperature;
90%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
84%	Stage #1: Boc-Glu(OBzl)-OH With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: 2-(Trimethylsilyl)ethanol at 20℃; for 19h;

Stage #1: Boc-Glu(OBzl)-OH With 1,1'-carbonyldiimidazole In dichloromethane Stage #2: 2-(Trimethylsilyl)ethanol

Reference： [1]Pacofsky, Gregory J.; Lackey, Karen; Alligood, Krystal J.; Berman, Judd; Charifson, Paul S.; Crosby, Renae M.; Dorsey Jr., George F.; Feldman, Paul L.; Gilmer, Tona M.; Hummel, Conrad W.; Jordan, Steven R.; Mohr, Christopher; Shewchuk, Lisa M.; Sternbach, Daniel D.; Rodriguez, Marc [Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1894 - 1908]
[2]Bertuzzi, Diego L.; Braga, Carolyne B.; Ornelas, Catia; Perli, Gabriel [New Journal of Chemistry, 2020, vol. 44, # 12, p. 4694 - 4703]
[3]Figliola, Carlotta; Marchal, Estelle; Groves, Brandon R.; Thompson, Alison [RSC Advances, 2019, vol. 9, # 25, p. 14078 - 14092]
[4]Khan, Najat S.; Riggle, Brittany A.; Seward, Garry K.; Bai, Yubin; Dmochowski, Ivan J. [Bioconjugate Chemistry, 2015, vol. 26, # 1, p. 101 - 109]

18
[ 2916-68-9 ]
[ 16966-09-9 ]
[ 65903-67-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1601 - 1606

19
[ 2916-68-9 ]
[ 166663-25-8 ]
[ 185425-57-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1863 - 1868

20
[ 85920-63-4 ]
[ 2916-68-9 ]
[ 17165-45-6 ]

Reference： [1]Synthesis,1999,p. 1951 - 1960

21
[ 2916-68-9 ]
[ 59486-73-6 ]
[ 235083-21-3 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 8415 - 8426

22
[ 2916-68-9 ]
[ 119-24-4 ]
[ 530-62-1 ]
[ 292045-48-8 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 1455 - 1460
[2]Journal of Organic Chemistry,2000,vol. 65,p. 5016 - 5021
[3]RSC Advances,2019,vol. 9,p. 14078 - 14092

23
[ 2916-68-9 ]
[ 4668-42-2 ]
[ 213473-96-2 ]

Reference： [1]Monatshefte fur Chemie,2000,vol. 131,p. 879 - 888

24
[ 2916-68-9 ]
[ 21040-45-9 ]
(1E)-3-(2-trimethylsilylethoxy)-1-phenylpropene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With diethylzinc In tetrahydrofuran; hexane at 25℃; for 2h;

Reference： [1]Kim, Hahn; Lee, Chulbom [Organic Letters, 2002, vol. 4, # 24, p. 4369 - 4371]

25
[ 2916-68-9 ]
[ 34897-61-5 ]
[ 357958-50-0 ]

Reference： [1]Synthesis,2002,p. 2616 - 2626

26
[ 2916-68-9 ]
[ 2848-01-3 ]
3-diphenylphosphanyl-propanoic acid 2-trimethylsilanyl-ethyl ester [ No CAS ]

Reference： [1]Synlett,2003,p. 473 - 476

27
[ 2916-68-9 ]
[ 226924-21-6 ]
[ 594838-53-6 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 4421 - 4432

28
[ 2916-68-9 ]
[ 68322-84-9 ]
[2-(2-bromo-4-trifluoromethyl-phenoxy)-ethyl]-trimethyl-silane [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4683 - 4685

29
[ 2916-68-9 ]
[ 33863-76-2 ]
[2-(3-bromo-5-chloro-phenoxy)-ethyl]-trimethyl-silane [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4683 - 4685

30
[ 2916-68-9 ]
[ 47173-80-8 ]
(R)-3-benzyloxy-2-tert-butoxycarbonylamino-propionic acid (2-trimethylsilanyl)ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 20h;Cooling with ice;	To a 25 mL round bottom flask was added Boc-D-Ser(OBn)-OH (4.00 g, 12.6 mmol), 2-(trimethylsilyl)ethanol (3.20 g, 27.1 mmol, 2 equiv), and dichloromethane (3.4 mL, 0.25 M). The solution was cooled in an ice bath for 20 min then dicyclohexylcarbodiimide (5.60 g, 27.1 mmol, 2 equiv) was added followed by 4-(dimethylamino)pyridine (1.59 g, 13.5 mmol, 1 equiv). The reaction was allowed to warm to room temperature overnight (20 h). The reaction was washed sequentially with 1 N HCl, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography (1:4 EtOAc/Hex) yielding the product as a clear oil.

Reference： [1]Organic Letters,2011,vol. 13,p. 4216 - 4219
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2241 - 2245
[3]Patent: US2016/222430,2016,A1 .Location in patent: Paragraph 0207; 0208

31
[ 2916-68-9 ]
[ 7021-11-6 ]
[ 638214-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 20℃; for 18h;	Intermediate 54 2- (Trimethylsilyl)ethyl 4-(4-hydroxyphenyl)butanoate. To a stirred solution of 2- (trimethylsilyl)ethanol (0.56 mL, 3.91 mmol) in THF (1 mL) at rt under nitrogen, was added 4-DMAP (113 mg, 0.92 mmol) followed by EDC (177 mg, 0.92 mmol).After about 1 minute Et3N (170 muL, 1.22 mmol) was added, drop-wise followed by <strong>[7021-11-6]4-(4-hydroxyphenyl)butanoic acid</strong> (150 mg, 0.83 mmol) in THF (4 mL) and the mixture stirred at rt for 18 hours. The mixture was then partitioned between Et2O (25 mL) and aqueous HCl (2M, 30 mL) and the layers separated. The aqueous layer was re-extracted with Et2O (20 mL) and the combined organic layer washed with brine (50 mL), dried (MgSO4) and concentrated under vacuum to give a'chalk-white' milky oil. Purification by SPE (silica, 5 g Cartridge) eluting with cyclohexane : EtOAc (gradient 25:1 to 1:2) afforded the title compound (55mg). LC/MS: m/z 298.2 [M+NH4]+, Rt 3.63 min.

Reference： [1]Patent: WO2004/315,2003,A1 .Location in patent: Page 46

32
[ 74124-79-1 ]
[ 2916-68-9 ]
[ 78269-85-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In acetonitrile; at 20℃; for 3h;	Compound 41; TEA (21.9 mL, 155.6 mmol, 3.0 eq.) was added to 2-trimethylsilanyl- ethanol (7.4 mL, 51.88 mmol, 1.0 eq.) in 260 mL MeCN, followed by di- succinimidyl carbonate (20 g, 1.5 eq.). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and extracted using EtOAc/ saturated NaHCO3. The organic layer was concentrated after dried over Na2SO4. Ether (100 mL) was added to the residue to form a precipitate. The precipitate was filtered and dried to give Compound 41 as a white solid (11.1 g, 84%). 1H NMR (300 MHz, CDCl3): delta 4.42 (t, 3 H), 2.82 (s, 4 H), 1.16 (t, 2 H), 0.1 (s, 9 H).
82%	With triethylamine; In acetonitrile; at 25℃; for 16h;	Example 5; methyl (l-l- ( {2- [ (2, 36)-3-amino-2-hydroxy-4-phenylbutyl]-2- benzylhydrazino} carbonyl)-2, 2-dimethylpropylcarbamate; Example 5A; 1- (f [2- (trimethylsilyl) ethoxy] carbonyl} oxy)-2, 5-pyrrolidinedione; Trimethylsilylethanol (7.4 mL, 52 mmol) was dissolved in acetonitrile (260 mL) and treated with disuccinimoyl carbonate (20 g, 1.5 equivalents) and triethylamine (33 mL, 3 equivalents) at 25C for 16h. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was triturated with ether to form a solid which was filtered and dried to give 11.12 g (82%) of the title compound.
82%	With triethylamine; In acetonitrile;	EXAMPLE 5A 1-([2-(trimethylsilyl)ethoxy]carbonyl}oxy)-2,5-pyrrolidinedione Trimethylsilylethanol (7.4 mL, 52 mmol) was dissolved in acetonitrile (260 mL) and treated with disuccinimoyl carbonate (20 g, 1.5 equivalents) and triethylamine (33 mL, 3 equivalents) at 25 C. for 16 h. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was triturated with ether to form a solid which was filtered and dried to give 11.12 g (82%) of the title compound.

With triethylamine; In acetonitrile; at 20℃;

To a solution of compound 16 (22.2 mL, 0.156 mol, 1.0 eq) in CH3CN (780 mL) was added Et3N (65.7 mL, 0.468 mol, 3.0 eq) and compound 17 (60 g, 0.234 mmol, 1.5 eq) at room temperature and stirred for overnight. After completion, concentrated and EA (500 mL) was added, washed with saturated NaHCCh (200 mL), NaCl (200 mL*3), dried over Na2S04. Filtered and concentrated to give yellow liquid (18, 54.2 g, crude) which was used into next step without purification.

Reference： [1]Patent: WO2008/11117,2008,A2 .Location in patent: Page/Page column 491
[2]Patent: WO2005/61487,2005,A1 .Location in patent: Page/Page column 115
[3]Patent: US2005/159469,2005,A1 .Location in patent: Page/Page column 59
[4]Patent: WO2019/118878,2019,A1 .Location in patent: Page/Page column 57

33
[ 2916-68-9 ]
[ 16205-98-4 ]
[ 861859-00-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	<strong>[16205-98-4]3-oxo-cyclohexanecarboxylic acid</strong> (2.00 g, 14.1 mmol), 2-trimethylsilylethanol (2.5 ml, 17.4 mmol), 4-dimethylaminopyridine (148 mg, 1.21 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.44 g, 17.9 mmol) in methylene chloride (14 ml) was stirred for 18 h. The solution was diluted with 10% aqueous hydrochloric acid and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to yield 3.41 g (100% yield) of <strong>[16205-98-4]3-oxo-cyclohexanecarboxylic acid</strong> 2-trimethylsilanyl-ethyl ester as a clear oil.1H NMR (300 MHz, CDCI3) 8 4.16 (m, 2H), 2.75 (m, 1H), 2.55 (d, J=7.9 Hz,2H), 2.36 (m, 2H), 2.08 (m, 2H), 1.82 (m, 2H), 0.98 (m, 2H), 0.04 (s, 9H).
100%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	A solution of <strong>[16205-98-4]3-oxo-cyclohexanecarboxylic acid</strong> (2.00 g, 14.1 mmol), 2- trimethylsilylethanol (2.5 mL, 17.4 mmol), 4-dimethylaminopyridine (148 mg, 1.21 mmol), and 1- (3-dimethylaminopropyl)-3-ethyicarbodiimide hydrochloride (3.44 g, 17.9 mmol) in methylene chloride (14 mL) was stirred for 18 h. The solution was diluted with 10% aqueous hydrochloric acid and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to yield 3.41 g (100% yield) of <strong>[16205-98-4]3-oxo-cyclohexanecarboxylic acid</strong> 2- trimethylsilanyl-ethyl ester as a clear oil. 1H NMR (300 MHz, CDCI3) 6 4.16 (m, 2H), 2.75 (m, 1H), 2.55 (d, J=7.9 Hz, 2H), 2.36 (m, 2H), 2.08 (m, 2H), 1.82 (m, 2H), 0.98 (m, 2H), 0.04 (s, 9H).
100%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In Dichlorodifluoromethane; for 18h;	A solution of <strong>[16205-98-4]3-oxo-cyclohexanecarboxylic acid</strong> (2.00 g, 14.1 mmoi), 2- trimethylsilylethanol (2.5 mL, 17.4 mmol), 4-dimethylaminopyridine (148 mg, 1.21 mmol), and 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.44 g, 17. 9 mmol) in methylene chloride (14 mL) was stirred for 18 h. The solution was diluted with 10% aqueous hydrochloric acid and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to yield 3.41 g (100% yield) of 3-oxo- cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a clear oil. 1H NMR (300 MHz, CDCI3) ; a 4.16 (m, 2H), 2.75 (m, 1H), 2.55 (d, J=7.9 Hz, 2H), 2.36 (m, 2H), 2. 08 (m, 2H), 1.82 (m, 2H), 0.98 (m, 2H), 0.04 (s, 9H).

Reference： [1]Patent: WO2006/10095,2006,A2 .Location in patent: Page/Page column 95-96
[2]Patent: WO2005/70407,2005,A1 .Location in patent: Page/Page column 300-301
[3]Patent: WO2005/87215,2005,A1 .Location in patent: Page/Page column 341

34
[ 2916-68-9 ]
[ 56663-76-4 ]
[ 880652-50-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; at 18 - 22℃; for 16.0h;	b) Compound 6.4; A solution of acid 6.3 (8.00 g, 71.3 mmol), 2-(trimethylsilyl)ethanol (10.2 mL, 71.3 mmol), Et3N (20.9 mL, 150 mmol) and TBTU (29.8 g, 92.8 mmol) in DMF (120 mL) was stirred at room temperature for 16 h. The reaction mixture was diluted with Et2O and the resulting solution was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 95/5) to afford the compound 6.4 (10.8 g, 71percent yield) as a clear oil.
69%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	A round-bottom flask was charged with <strong>[56663-76-4]2,2-dimethylbut-3-ynoic acid</strong> (1.00 g, 8.93 mmol, 1.00 equiv), 2-(trimethylsilyl)ethan-1-ol (1.05 g, 8.93 mmol, 1.00 equiv), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (3.72 g, 11.6 mmol, 1.30 equiv), TEA (1.81 g, 17.9 mmol, 2.00 equiv), and DMF (10 mL). The resulting solution was stirred overnight at room temperature. The reaction mixture was diluted with ethyl ether (30 mL), and the resulting solution was washed with water (130 mL) and brine (120 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 1.30 g (69percent yield) of 2-(trimethylsilyl)ethyl 2,2-dimethylbut-3-ynoate as yellow oil. 1H NMR (300 MHz, Chloroform-d) delta 4.28-4.22 (m, 2H), 2.27 (s, 1H), 1.50 (s, 6H), 1.08-1.02 (m, 2H), 0.07 (s, 9H).

Reference： [1]Patent: US2006/69261,2006,A1 .Location in patent: Page/Page column 22
[2]Patent: US2018/134674,2018,A1 .Location in patent: Paragraph 0527

35
[ 7311-64-0 ]
[ 2916-68-9 ]
2-(trimethylsilyl)ethyl 3-bromo-2-thiophenecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; triethylamine; In 1,1-dichloroethane; dichloromethane;	Step A. A solution of <strong>[7311-64-0]3-bromothiophene-2-carboxylic acid</strong> (1 mmol) and SOCl2 (3 mmol) in 1 mL of dichloroethane was heated at 80 C. for 20 h and then the solvents evaporated. The residue was dissolved in 2 mL CH2Cl2 and mixed with triethylamine (3 mmol) and 2-(trimethylsilyl)ethanol (1.3 mmol) at rt for 12 h. Extractive isolation provided 2-(trimethylsilyl)ethyl 3-bromo-2-thiophenecarboxylate as an oil.

Reference： [1]Patent: US2002/40014,2002,A1

36
1-(3-dimethylaminopropyl-3-ethyl carbodiimide hydrochloride) [ No CAS ]
[ 2916-68-9 ]
[ 124700-40-9 ]
trimethylsilanylethyl 2-fluoro-4-iodobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In hexane; dichloromethane; ethyl acetate;	Trimethylsilanylethyl 2-fluoro-4-iodobenzoate (Compound D) To a solution of 115.5 mg (0.4 mmol) of <strong>[124700-40-9]2-fluoro-4-iodobenzoic acid</strong> (Compound B) in 10 mL of dichloromethane (under a blanket of argon) was added 91.5 mg (0.5 mmol) of 1-(3-dimethylaminopropyl-3-ethyl carbodiimide hydrochloride) and 53 mg (0.4 mmol) of 4-dimethylaminopyridine. To this reaction mixture was added 0.16 ml (132 mg, 1.1 mmol) of 2-trimethylsilylethanol and the resultant mixture was allowed to stir at ambient temperature for 23 hours. The reaction mixture was extracted between ethyl ether and water and the layers were separated. The aqueous phase was washed with ethyl ether (2*50 mL) and the organic phases were combined. The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to a clear, colorless oil. Purification by flash chromatography (silica, 3% ethyl acetate in hexane) gave the title compound as a clear, colorless oil. PMR (CDCl3): delta 0.07 (9H, s), 1.13 (2H, dd, J=8.5, 10.3 Hz), 4.42 (2H, q, J=8.5, 10.3 Hz), 7.50-7.70 (3H, m).

Reference： [1]Patent: US5919970,1999,A

37
[ 2916-68-9 ]
[ 821-38-5 ]
[ 196405-77-3 ]

Yield	Reaction Conditions	Operation in experiment
47%		EXAMPLE 56 (1) Mono-[2-(trimethylsilanyl)ethyl] tetradecanedioate (62) Tetradecanedioic acid (4.90 g, 19.0 mmol) was converted to the ester with 2-(trimethylsilyl)ethanol (2.25 g, 19.0 mmol) under N,N-dimethylaminopyridine and 1,3-dicyclohexylcarbodiimide in the same manner as the example 54 (1) to give the compound 62 (2.80 g, 47%). Mp 51-52 C. PMR (CDCl3): deltaH0.04 (9 H, s, (CH3)3 Si),0.98 (2 H, m, CH2 Si), 1.28 (16 H, bs, --CH2 --), 1.63 (4 H, bm, --CH2 --), 2.27 and 2.31 (each 2 H, t, 7.2 Hz, --CH2 CO--), and 4.15 (2 H, m, CH2 O). Elementary analysis (for C19 H38 O4 Si) Calcd.: C, 63.64% H, 10.68% Found: C, 63.65% H, 10.59%

Reference： [1]Patent: US6054591,2000,A

38
[ 321-50-6 ]
[ 2916-68-9 ]
2-(trimethylsilyl)ethyl 4-fluoroanthranilate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In di-isopropyl ether;	EXAMPLE 20 7-Fluoro-1H-3,1-benzoxazine-2,4-dione (2.0 g), sodium hydroxide (0.05 g) and 2-(trimethylsilyl)ethanol (1.31 g) were heated together at 100 for 30 minutes until effervescence ceased. After cooling, the residue was suspended in diisopropyl ether, then filtered and evaporated. The residue was recrystallized from petroleum ether to give 2-(trimethylsilyl)ethyl 4-fluoroanthranilate, mp 43-44. (Compound 20).

Reference： [1]Patent: US5093364,1992,A

39
[ 2916-68-9 ]
[ 89380-77-8 ]
[ 929278-65-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With diethylazodicarboxylate; In dichloromethane; at 0 - 20℃; for 5h;	To a slurry of polymer-supported triphenylphosphine (179.0 g, 2.2 mmol/g, 393.8 mmol) in dichloromethane (1 L) was added 2-(trimethylsilyl)ethanol (56.0 ml_, 393.8 mmol) and <strong>[89380-77-8]methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate</strong> (20.0 g, 98.4 mmol), which may be prepared in a manner analogous to the literature procedure (Barker, J.M.; Huddleston, P.R.; Wood, M. L.; Burkitt, S.A. Journal of Chemical Research (Miniprint)2QW , 1001-1022). The mixture was cooled to 0 C and diethylazodicarboxylate (62.0 ml_, 393.8 mmol) was added dropwise via addition funnel. The reaction mixture was stirred at room temperature for 5 h and then was filtered through a fritted funnel and concentrated onto silica gel. Purification by column chromatography provided 29.7 g (99%) of the title compound. 1H NMR (400 MHz, DMSO-cfe): delta 8.17 (s, 1 H), 4.30 (t, 2H, J= 8.2 Hz), 3.76 (s, 3H), 1.07 (t, 2H, J= 8.4 Hz), 0.04 (s, 9 H).

Reference： [1]Patent: WO2007/30366,2007,A1 .Location in patent: Page/Page column 93

40
[ 2916-68-9 ]
[ 471-53-4 ]
18-β-glycyrrhetic acid 2-trimethylsilanyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With pyridine; 2-chloro-1,3-dimethylimidazolinium chloride; at 20.0℃; for 16.0h;	18-beta-Glycyrrhetic acid 2-trimethylsilanyl-ethyl ester 2-(Trimethylsilyl)ethanol (0.86 mL, 6.0 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.85 g, 5.4 mmol) were added to a solution of 18-beta-glycyrrhetic acid (1.26 g, 2.7 mmol) in pyridine (8 mL). After stirring for 16 h at r.t., the solution was poured over water and extracted with CH2Cl2. Organics were washed with 1N HCl and brine, dried (MgSO4), and concentrated in vacuo. Purification by silica gel chromatography (20% EtOAc/hexanes) gave 1.24 g (81%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): delta 5.66 (s, 1H), 4.11-4.23 (m, 2H), 3.20-3.26 (m, 1H), 2.76-2.82 (m, 1H), 2.34 (s, 1H), 0.68-2.14 (m, 42H), 0.05 (s, 9H). MS (ES) [m+H] calculated for C35H58O4Si 571; found 571.

Reference： [1]Patent: US7235672,2007,B1 .Location in patent: Page/Page column 10; 23

41
[ 2916-68-9 ]
[ 60031-08-5 ]
[ 939024-46-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; diisopropyl-carbodiimide; In N,N-dimethyl-formamide;	To a solution of acid (570 mg, 3.24 ramol), TMS ethanol (1.86 mL, 12.9 mmol), DMAP (198 mg, 1.62 mmol) in 16.2 mL of DMF was added DIC (0.602 mL, 3.89 mmol). The resulting solution was stirred overnight. The crude reaction mixture was then transferred to a seperatory funnel containing EtOAc, and water. The water layer was washed 3 X with EtOAc, the organic layers were combined, dried with MgSO4, filtered and concentrated to yield an oil. The crude oil residue was purified with the Biotage MPLC (grad: 100% Hex to 80/20 Hex/EtOAc) to afford the title compound (718 mg; 80% yield).

Reference： [1]Patent: WO2007/61930,2007,A1 .Location in patent: Page/Page column 65

42
[ 432025-97-3 ]
[ 2916-68-9 ]
1,3--(trimethylsilyl)ethoxy]carbonyl}-5-ethynylbenzene [ No CAS ]

Reference： [1]Photochemistry and Photobiology,2007,vol. 83,p. 1513 - 1528

43
[ 2916-68-9 ]
[ 68325-15-5 ]
[ 945989-08-2 ]

Yield	Reaction Conditions	Operation in experiment
81.7%		Step B: Preparation of 3-(2-(trimethylsilyl)ethoxy)<strong>[68325-15-5]isonicotinonitrile</strong>: A flask was charged with 2-(trimethylsilyl)ethanol (1.02 g, 8.66 mmol) and added THF (20 mL). Sodium hydride (0.219 g, 8.66 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. 3-Chloro<strong>[68325-15-5]isonicotinonitrile</strong> (1.00 g, 7.22 mmol) was added, and the reaction mixture was stirred at ambient temperature for 1 hour and then at 50 0C overnight. A saturated solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate, dried and concentrated to give the desired product (1.30 g, 81.7% yield) as light brown semi solid material.

Reference： [1]Patent: WO2008/91770,2008,A1 .Location in patent: Page/Page column 32

44
[ 2916-68-9 ]
[ 22621-41-6 ]
[ 1065010-05-0 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 13110 - 13119

45
[ 2916-68-9 ]
[ 53554-29-3 ]
[ 866884-82-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5472 - 5477

46
[ 2916-68-9 ]
[ 13726-67-5 ]
[ 123836-70-4 ]

Reference： [1]Synthesis,2009,p. 809 - 814

47
[ 2916-68-9 ]
[ 136083-57-3 ]
[ 1149729-35-0 ]

Reference： [1]Synthesis,2009,p. 809 - 814

48
[ 2916-68-9 ]
[ 104091-09-0 ]
[ 1149729-36-1 ]

Reference： [1]Synthesis,2009,p. 809 - 814

49
[ 2916-68-9 ]
[ 13280-60-9 ]
[ 1055310-30-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3959 - 3962
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4825 - 4828
[3]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2669 - 2672

50
[ 144163-65-5 ]
[ 2916-68-9 ]
(2-thiazol-2-ylethyl)carbamic acid 2-trimethylsilanylethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Suspend <strong>[144163-65-5]3-thiazol-2-yl-propionic acid</strong> (650 mg, 4.14 mmol) in toluene (20 mL) under nitrogen. Add triethylamine (580 AL, 4.14 mmol) followed by diphenyl phosphoryl azide (1.14 g, 4.14 mmol). Heat the reaction mixture at 80C for 2 hours then add trimethylsilyl ethanol (1.2 mL, 8.28 mmol) and heat the solution an additional hour at 80C. Cool to 30C overnight. Concentrate the mixture, basify with 10% sodium hydroxide, and extract with ethyl acetate (2 x 100 mL). Wash the organic phase with brine (100 mL), dry over sodium sulfate, filter, and concentrate. Perform flash chromatography on silica gel eluting with 1: 1 hexane/ethyl acetate to afford 570 mg of (2- thiazol-2-yl-ethyl) carbamic acid 2-trimethylsilanyl-ethyl ester as a yellow OIL. H NMR (CDC13) 6 7. 71 (d, J= 3 Hz, 1H), 7.23 (d, J= 3 Hz, 1H), 5.30 (br s, 1H), 4.02-4. 21 (m, 2H), 3.58-3. 70 (m, 2H), 3.19-3. 29 (m, 2H), 0.95-1. 06 (m, 2H), 0.05 (s, 9H).

Reference： [1]Patent: WO2005/9941,2005,A1 .Location in patent: Page 32-33

51
[ 2916-68-9 ]
[ 14389-86-7 ]
[ 850913-48-3 ]

Yield	Reaction Conditions	Operation in experiment
85%		[2-(Benzvloxv)-phenvl1-carbamic acid 2-trimethvlsilanyl-ethvl ester 2-(Benzyloxy) benzoic acid (5.064g, 22. 2mmol), diphenylphosphoryl azide (7.2mL, 33. 4mmol, 1.5eq) and triethylamine (4.6mL, 33. 4mmol, 1.5eq) were heated in toluene (44mL, 0.5M) at 80C for 30 minutes. Trimethylsilyl ethanol (6.4mL, 44. 4mmol) was added and heating was continued for 24 hours (complete after 1 hr). Upon cooling, the mixture was diluted with ethyl acetate and washed sequentially with 2M HCI and saturated sodium bicarbonate, dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica gel with iso-hexane containing ethyl acetate (1-3%) to yield the title compound (6.440g, 85%) as a colourless oil. 'H NMR (CDCI3) 8H : 0.00 (9H, s), 0.94-1. 05 (2H, m), 4.13-4. 27 (2H, m), 5.04 (2H, s), 6.81- 6.97 (3H, m), 7.15 (1H, s), 7.25-7. 41 (5H, m), 8.06 (1H, br).

Reference： [1]Patent: WO2005/37786,2005,A1 .Location in patent: Page/Page column 30

52
[ 2916-68-9 ]
[ 42417-65-2 ]
[ 1226972-82-2 ]

Reference： [1]Synlett,2010,p. 399 - 402

53
[ 2916-68-9 ]
[ 32315-10-9 ]
[ 78269-85-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In tetrahydrofuran;	Example 43 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate To a solution of triphosgene (25 g, 0.5 eq.) in THF (200 mL) was added dropwise a mixture of 2-(trimethylsilyl)ethanol (20 g, 1 eq.) and TEA (25 mL, 1.1 eq.) in THF at 0 C. After being stirred at rt for 2 hr, a solution of HOSu (1 eq.) in THF (50 mL) was added into the reaction mixture at 0 C. The resulting mixture was stirred overnight. The resulted solid was removed away by filtration under reduced pressure. The filtrate was treated by chromatographic column on silica gel eluted by CH2Cl2. The collected fractions was condensed to 10 mL of volume and poured into pure hexanes. The precipitated solid 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate was collected in 78% yield by filtration under reduced pressure. 1H NMR (400 M) 4.4 (d, 2H), 2.9 (s, 4H), 2.2 (d, 2H), 0.1 (s, 1H); 13C NMR 172, 154, 74, 28, 19, 0.

Reference： [1]Patent: US2010/105607,2010,A1

54
[ 2916-68-9 ]
[ 86060-82-4 ]
2-(trimethylsilyl)ethyl N2-(9-fluorenylmethoxycarbonyl)-N6-(benzyloxycarbonyl)-L-lysinate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3012 - 3019

55
[ 2916-68-9 ]
[ 32315-10-9 ]
[ 50492-22-3 ]
[ 1253040-30-0 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5325 - 5327

56
[ 2916-68-9 ]
[ 20099-90-5 ]
[ 1187761-12-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 4h;	Example 28.Synthesis of 2-((trimethyl)silyl)ethyl 4-(2-(bromo)acetyl)benzoate.DMAP (0.01 g, 0.12 mmol), DCC (0.14 g, 0.68 mmol) and 2-trimethylsilylethanol (0.11 mL, 0.80 mmol) were added to a solution of 4-(2-(bromo)acetyl)benzoic acid (0.15 g, 0.62 mmol) in CH2Cl2 (5 mL) at 0°C.The mixture was stirred at room temperature for 4 hours, and then concentrated under reduced pressure.The residue was purified by flash chromatography with hexane-EtOAc (3:1) as an eluent (yield: 47percent).mp 60-61°C. 1H NMR (300 MHz, CDCl3) delta 0.02 (s, 9H), 1.05-1.11 (m, 2H), 4.35-4.41 (m, 4H), 7.95 (d, J = 9.0 Hz, 1 H), 8.07 (d, J = 8.7 Hz, 1 H).13C NMR (75.5 MHz, CDCl3) delta -1.5, 17.3, 30.6, 63.9, 128.7, 129.7, 135.1, 137.1, 165.5, 190.7. HRMS (EI) calculated for C14H19BrO3Si (M+): 342.0286, experimental: 342.0206.

Reference： [1]Patent: EP2292587,2011,A1 .Location in patent: Page/Page column 25-26

57
[ 2916-68-9 ]
[ 4387-36-4 ]
2-(2-trimethylsilanylethoxy)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 110℃; for 14h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol percent), 1,10-phenanthroline (20percent mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110°C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5338 - 5341

58
[ 2916-68-9 ]
[ 69113-59-3 ]
[ 1338215-30-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 110℃; for 14h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol %), 1,10-phenanthroline (20% mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5338 - 5341

59
[ 2916-68-9 ]
[ 3032-81-3 ]
[ 1338215-37-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 110℃; for 14h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol percent), 1,10-phenanthroline (20percent mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110°C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5338 - 5341

60
[ 2916-68-9 ]
[ 202982-67-0 ]
[ 1338215-43-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 110℃; for 14h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol %), 1,10-phenanthroline (20% mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5338 - 5341

61
[ 2916-68-9 ]
[ 66256-28-8 ]
[ 1338215-44-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In toluene at 110℃; for 14h; Inert atmosphere; Sealed tube;	General procedure for coupling reaction General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol %), 1,10-phenanthroline (20% mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110°C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

Reference： [1]Dibakar, Mullick; Prakash, Anjanappa; Selvakumar, Kumaravel; Ruckmani, Kandasamy; Sivakumar, Manickam [Tetrahedron Letters, 2011, vol. 52, # 41, p. 5338 - 5341]

62
[ 2916-68-9 ]
[ 82565-68-2 ]
C₂₉H₃₂INO₄Si [ No CAS ]

Reference： [1]Synthesis,2011,p. 3255 - 3260

63
[ 2916-68-9 ]
[ 1015070-56-0 ]
[ 201230-82-2 ]
[ 1235382-35-0 ]

Yield	Reaction Conditions	Operation in experiment
85.4%	With N-ethyl-N,N-diisopropylamine;1,3-bis-(diphenylphosphino)propane; palladium dichloride; at 60.0℃; for 8h;carbon monoxide atmosphere;	<strong>[1015070-56-0]6-Bromo-4-hydroxyisoquinoline</strong> (15.7 g, 70.0 mmol) produced in Example 15 (15a) was dissolved in dimethylformamide (100 mL), to which 2-trimethylsilylethanol (100 mL), diisopropylethylamine (27.1 g, 210 mmol), 1,3-bis(diphenylphosphino)propane (8.57 g, 21.0 mmol), and palladium chloride (3.72 g, 21.0 mmol) were then added, followed by stirring at 60C for eight hours under a carbon monoxide atmosphere. The solvent was distilled off under reduced pressure. Water was added to the residue thus obtained, and the resulting mixture was extracted with dichloromethane. The resulting organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography((a mixed solvent of hexane : ethyl acetate - 1 : 1) : methanol, 100 : 0 - 70 : 30, V/V) to give the desired title compound (17.3 g, yield 85.4%). 1H-NMR (CDCl3 delta: 0. 11 (9H, s), 1.11-1.24 (2H, m), 4.46-4.55 (2H, m), 8.02 (1H, d, J = 8.4 Hz), 8.24 (1H, d, J = 8.4 Hz), 8.38 (1H, s), 8.87 (1H, s), 9.09 (1H, s).

Reference： [1]Patent: EP2380878,2011,A1 .Location in patent: Page/Page column 30; 31

64
[ 2916-68-9 ]
[ 132388-69-3 ]
[ 1391105-22-8 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 13244 - 13247

65
[ 2916-68-9 ]
[ 132388-69-3 ]
C₂₉H₃₆N₂O₃Si [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 13244 - 13247

66
[ 2916-68-9 ]
[ 858230-84-9 ]
[ 917-61-3 ]
[ 1425783-56-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1394 - 1397

67
[ 1006-99-1 ]
[ 2916-68-9 ]
[ 917-61-3 ]
[ 1425783-54-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; triethylamine In toluene at 110℃; for 16h; Inert atmosphere;

Reference： [1]Vinogradova, Ekaterina V.; Park, Nathaniel H.; Fors, Brett P.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 6, p. 1394 - 1397]

68
[ 6214-35-3 ]
[ 2916-68-9 ]
C₈H₁₅IO₂Si [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6757 - 6761
Angew. Chem.,2013,vol. 125,p. 6889 - 6893

69
[ 1198-14-7 ]
[ 2916-68-9 ]
[ 1586038-78-9 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 566 - 571
[2]Chemical Communications,2015,vol. 51,p. 15458 - 15461

70
[ 2916-68-9 ]
[ 63648-73-7 ]
bis[2-(trimethylsilyl)ethyl] (2R)-2-[N-(benzyloxycarbonyl)amino]pentane-1,5-dioate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 7328 - 7334
Angew. Chem.,2014,vol. 53-126,p. 7456 - 7462

71
[ 2916-68-9 ]
[ 144120-53-6 ]
C₂₇H₃₃NO₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;	Compounds 25 (500 mg, 1. 26 mmol) dissolve in DMF (10 mL), 2-trimethylsilylethanol (0. 43 mL, 1. 89 mmol), HATU (718 mg, 1. 89 mmol) and n-methylmorpholine (0. 21 mL, 1. 89 mmol) added. After the solution was stirred at room temperature overnight, add water and extracted with ethyl acetate. Extracts and washed with water and brine, dried over anhydrous magnesium sulfate. Distilled under reduced pressure solvent, residue-silicagelchromatofie (hexane / ethyl acetate) purified as colorless-clad materials, compounds 27 (294 mg, 25%).

Reference： [1]Patent: JP2016/27001,2016,A .Location in patent: Paragraph 0133; 0134

72
[ 2916-68-9 ]
[ 144120-53-6 ]
C₂₄H₄₁NO₆Si [ No CAS ]

Reference： [1]Patent: JP2016/27001,2016,A

73
[ 2916-68-9 ]
[ 616-76-2 ]
C₁₃H₁₈O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h;Inert atmosphere;	10226] After <strong>[616-76-2]5-formylsalicylic acid</strong> (2 g, 12.03 8 mmol) was dissolved in DMF at 0 C. under nitrogen atmosphere, 2-(tri- methylsilyl)ethanol (1.72 mE, 12.038 mmol) and dimethylaminopyridine (DMAP, 147 mg, 1.204 mmol), and dicyclohexylcarbodiimide (DCC, 2.5 g, 12.038 mmol) were added thereto. The mixture was stirred at room temperature for 12 hours. Afier the reaction was completed, ethylacetate (100 mE) and distilled water (100 mE) were added thereto. The organic layer obtained as described above was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to colunm chromatography, thereby obtaining Compound 2a (1.6 g, 50%).10227] ?HNMR (400 MHz, CDC13) oe 11.38 (s, 1H), 9.77 (s, 1H), 7.48 (d, J=8.4 Hz, 1H), 6.61 (dd, J=8.4, 2.0 Hz, 1H), 6.53 (d, J=2.0 Hz, 1H), 5.36-5.25 (m, 4H), 4.23 (m, 1H), 3.73 (s, 1H), 2.06 (s, 9H).
50%	With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h;Inert atmosphere;	<strong>[616-76-2]5-formylsalicylic acid</strong> (2g, 12.03 8mmol) was dissolved in DMF at 0C under nitrogen atmosphere, and then 2-(trimethylsilyl)ethanol (1.72mL, 12.03 8mmol) and dimethylaminopyridine (DMAP, 147mg, 1 .2O4mmol), and dicyclohexylcarbodiimide (DCC, 2.5g, 12.03 8mmol) were added thereto. The mixture was stirred at room temperature for 12 hours. After the reaction was completed, ethylacetate (lOOmL) and distilled water (lOOmL) were added thereto. The organic layer obtained as described above was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subj ected to column chromatography, thereby obtaining Compound 2a(1.6g, 50%).?HNMR(400MHz, CDC13) 11.38 (s, 1H), 9.77 (s, 1H), 7.48 (d, , J 8.4Hz, 1H), 6.61 (dd, J= 8.4, 2.0Hz, 1H), 6.53 (d, , J= 2.0Hz, 1H), 5.365.25 (m, 4H), 4.23 (m, 1H), 3.73 (s, 1H), 2.06 (s, 9H)

Reference： [1]Patent: US2016/184451,2016,A1 .Location in patent: Paragraph 0226; 0227
[2]Patent: WO2017/51249,2017,A1 .Location in patent: Page/Page column 33; 34

74
[ 2916-68-9 ]
[ 62234-37-1 ]
[ 1383778-38-8 ]
2-(trimethylsilyl)ethyl 3-[N₂-acetyl-N₆-(tert-butoxycarbonyl)-L-lysyl]amino}-D-alaninate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was obtained by coupling of 3-amino-N-[(benzyloxy)carbonyl]-D-alanine and 2,5- dioxopyrrolidin-1-yl N2-acetyl-N6-(tert-butoxycarbonyl)-L-lysinate in DMF in the presence of N,N10 diisopropylethylamine, followed by coupling of the carboxylic acid group with 2-(trimethylsilyl)ethanolin acetonitrile in the presence of pyridine and 1 ,3-dicyclohexylcarbodiimide and subsequent deprotection of the benzyloxycarbonyl group by hydrogenation in methanol in presence of 10% Pd/C at room temperature for 2 h.LC-MS (Method 1): R1 = 0.70 mm; MS (ESIpos): m/z = 475 (M+H)+

Reference： [1]Patent: WO2016/207090,2016,A2 .Location in patent: Page/Page column 287

75
[ 2916-68-9 ]
[ 149910-98-5 ]
[ 13939-06-5 ]
2-(trimethylsilyl)ethyl isochroman-7-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 180 - 201

76
[ 3284-51-3 ]
[ 2916-68-9 ]
2-(trimethylsilyl)ethyl 5-methyl-1H-pyrrole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium tert-butylate; at 110℃; for 5h;	General procedure: Ethyl pyrrole-2-carboxylate (278 mg, 2.0 mmol) was added to 2-(trimethylsilyl)ethanol (2.0 mL), followed by KOtBu (24 mg, 0.2mmol). The mixture was then heated to 110 C and stirred for 5 h. After completion, the mixture was diluted with H2O (100 mL) and extracted with EtOAc (3 × 35 mL), the combined extracts were washed with brine (30 mL) and dried over Na2SO4. Removal of the solvent andpurification by column chromatography (hexanes/EtOAc, 20:1) gave the product as a white solid (270 mg, 64%); mp 67-68 C.IR: 3311, 2954, 1679, 1555, 1414, 1316, 1168, 1127, 1031, 963, 837,744 cm-1.1H NMR (400 MHz, CDCl3): delta = 9.30 (br s, 1 H, H-1), 6.96-6.94 (m, 1 H,H-3), 6.91-6.89 (m, 1 H, H-5), 6.26-6.24 (m, 1 H, H-4), 4.39-4.35 (m,2 H, O-CH2), 1.12-1.07 (m, 2 H, Si-CH2), 0.07 (s, 9 H, Si-CH3).13C NMR (100 MHz, CDCl3): delta = 161.4, 123.1, 122.6, 114.9, 110.3, 62.5,17.4, -1.4. HRMS (ESI): m/z [M + Na]+ calcd for C10H17NO2SiNa: 234.0921; found: 234.0912.

Reference： [1]Synthesis,2017,vol. 49,p. 2544 - 2544

77
[ 2916-68-9 ]
[ 1975-51-5 ]
2-(trimethylsilyl)ethyl 2-methyl-4-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75 g		A) 2-(Trimethylsilyl)ethyl 2-methyl-4-nitrobenzoate 4-Dimethylaminopyridine (67.4 g) and WSC hydrochloride (95.46 g) were added to a mixture of <strong>[1975-51-5]2-methyl-4-nitrobenzoic acid</strong> (50 g) and dichloromethane (600 mL) at room temperature, followed by stirring at room temperature for 30 minutes. 2-(Trimethylsilyl)ethanol (58.79 g) was then added thereto at room temperature, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to obtain the title compound (75 g). 1H NMR (400 MHz, CDCl3) delta 0.08 (9H, s), 1.13-1.17 (2H, m), 2.68 (3H, s), 4.41-4.45 (2H, m), 7.95 (1H, d, J=8.7 Hz), 8.05-8.08 (1H, m), 8.10 (1H, s).

Reference： [1]Patent: US2017/349605,2017,A1 .Location in patent: Paragraph 0624; 0625

78
[ 2916-68-9 ]
[ 4651-67-6 ]
3α-hydroxy-7-oxo-5β-cholanoic acid trimethylsilylethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.1%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0℃; for 16h;	3alpha-Hydroxy-7-oxo-5beta-cholanoic acid (39.0 g, 100 mmol),2-(trimethylsilyl)ethanol (14.2 g,120mmol)Dissolved 5gDMAP150mml of dichloromethane,Freeze and cool to 0 C,A solution of DCC (dicyclohexylcarbodiimide) (26.8 g, 130 mmol) in dichloromethane was slowly added dropwise.After the dropwise addition, the reaction was incubated at 0C for 16 hours.After filtration, the filtrate was concentrated under reduced pressure to give 3alpha-hydroxy-7-oxo-5beta-cholanoic acid-trimethylsilylethyl ester (47.7 g, yield 97.1%).

Reference： [1]Patent: CN107383139,2017,A .Location in patent: Paragraph 0088

79
[ 2916-68-9 ]
[ 2420-87-3 ]
C₂₆H₃₄O₈Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
171 g	With 4-butanolide; dmap; triethylamine; at 20℃; for 24h;	In a 3 L of a flask equipped with a stirrer and a thermometer were charged 100 g (340 mmol) of 3,3?,4,4?-biphenyltetracarboxylic dianhydride (s-BPDA), 68.8 g (680 mmol) of triethylamine, 41.5 g (340 mmol) of N,N-dimethyl-4-aminopyridine and 400 g of gamma-butyrolactone, then, 80.4 g (680 mmol) of 2-(trimethylsilyl)ethanol (Rs-1) was added dropwise to the mixture while stirring at room temperature, and the resulting mixture was stirred under room temperature for 24 hours. Thereafter, under ice-cooling, 408 g of 10% aqueous hydrochloric acid solution was added dropwise to stop the reaction. To the reaction mixture was added 800 g of 4-methyl-2-pentanone, and the organic layer was collected by separation and washed with 600 g of water six times. The solvent of the obtained organic layer was distilled off to obtain 171 g of the tetracarboxylic acid diester compound (X-1) having the following structure.

Reference： [1]Patent: US2018/120702,2018,A1 .Location in patent: Paragraph 0246

80
[ 2916-68-9 ]
[ 3177-24-0 ]
C₁₀H₁₄ClN₃OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.4%		Under nitrogen atmosphere, 2-(trimethylsilyl)ethanol (2.5 mL, 17.3 mmol) was dissolved in tetrahydrofuran (25 mL). Under ice cooling, sodium hydride (60percent oil dispersion, 506 mg, 12.6 mmol) was added to the solution. The mixture was stirred at room temperature for 1 hour. Under ice cooling, the tetrahydrofuran solution (5 mL) of the compound 28 (2.0 g, 11.5 mmol) was added dropwise to the mixture. The mixture was stirred at room temperature for 5.5 hours. A 2 mol/L aqueous solution of hydrochloric acid was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed by brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (hexane-ethyl acetate) to give the compound 29 (1.07 g, yield 36.4percent). 1H-NMR (CDCl3) delta: 0.11 (s, 9H), 1.18-1.26 (m, 2H), 4.63-4.67 (m, 2H), 8.59 (s, 1H).

Reference： [1]Patent: EP3287443,2018,A1 .Location in patent: Paragraph 0620; 0621

81
[ 2916-68-9 ]
[ 2389-60-8 ]
2-(trimethylsilyl)ethyl N6-(tert-butoxycarbonyl)-L-lysinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		To a solution of N-benzyloxycarbonyl-N"-tert-butyloxycarbonyl-L-lysine 23 (667 mg, 1.75 mmol), ECD (673 mg,3.51 mmol), and 4-(dimethylamino)pyridine (DMAP, 175 mg, 1.43 mmol) in CH2Cl2 (8.9 mL),2-(trimethylsilyl)ethanol (380 L, 310 mg, 2.62 mmol) was added and the mixture was stirred atroom temperature for 25 h. It was then washed with sat. NaHCO3 (3 30 mL), brine (3 30 mL),and water (60 mL). The organic layer was dried over Na2SO4 and the solvent was removed underreduced pressure. The resultant crude product was purified by column chromatography (6:4, petroleumether-CH2Cl2) to give the N-protected lysine ester as a colourless oil (653 mg, 77%). This material(600 mg, 1.25 mmol) was dissolved in MeOH (2 mL), Pd/C (10%, 190 mg, 0.179 mmol) was added andthe mixture was stirred under a hydrogen atmosphere (1 bar) at room temperature for 3 h. It was thenfiltered over celiterTM, the residue was washed with MeOH and the solvent of the combined filtrateswas removed under reduced pressure to give 24 as a colourless oil (422 mg, 99%, 77% over 2 stepsfrom 23). 1H NMR (300 MHz, CD2Cl4, 100 C): delta[ppm] = 4.53-4.44 (m, 1H, N"H), 4.26-4.20 (m, 2H,H-10), 3.39-3.35 (m, 1H, H-2), 3.14-3.07 (m, 2H, H-6), 1.80-1.68 (m, 1H, H-3a), 1.59-1.39 (m, 5H, H-3b,H-4, H-5), 1.45 (s, 9H, Boc-CH3), 1.05-1.00 (m, 2H, H-20), 0.08 (s, 9H, Si(CH3)3). 13C-NMR (75 MHz,CD2Cl4, 100 C): delta[ppm] = 175.38 (C-1), 155.57 (Boc-C=O), 78.67 (Boc-C), 62.70 (C-10), 54.33 (C-2), 40.48(C-6), 34.25 (C-3), 29.64 (C-5), 28.23 (Boc-CH3), 22.71 (C-4), 17.34 (C-20), -1.77 (Si(CH3)3). MS (ESI+):m/z = 347.2 [M + H]+. HRMS (ESI+): calcd.: 347.2361 [M + H]+, found: 347.2364. IR (ATR): n [cm-1] =3372, 2952, 2364, 1713, 1520, 1365, 1250, 1171, 838. Optical rotation: [alpha]D25 = +5.5 (c = 0.58, CHCl3).TLC: Rf (95:5, CH2Cl2-MeOH) = 0.80.

Reference： [1]Molecules,2018,vol. 23

82
[ 2018-66-8 ]
[ 2916-68-9 ]
[ 65903-62-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 14h;Inert atmosphere;	To a solution ofN-benzyloxycarbonyl-L-leucine 30 (10.0 g, 37.8 mmol) in CH2Cl2 (385 mL), EDC (9.21 g, 48 mmol),DMAP (922 mg, 7.55 mmol), and 2-(trimethylsilyl)ethanol (6.87 mL, 5.67 g, 48.0 mmol) were added andthe mixture was stirred at room temperature for 14 h. It was then washed with HCl (1 M, 3 600 mL),sat. NaHCO3 (3 600 mL), and brine (3 600 mL). The organic layer was dried over NaSO4 and thesolvent was removed under reduced pressure. N-benzyloxycarbonyl-L-leucine trimethylsilylethylester was isolated after column chromatography as a colourless oil (11.8 g, 86%). To a solution ofthis material (366 mg, 1.00 mmol) in MeOH (40 mL), TFA (80 L, 0.12 g, 1.0 mmol) and Pd/C (10%,146 mg, 0.130 mmol) were added and the mixture was stirred under hydrogen atmosphere (1 bar) atroom temperature for 4 h. It was then filtered over celite and the residue was washed with MeOH.The solvent of the combined filtrates was removed under reduced pressure to give 28 as a colourlesssolid (345 mg, quant., 86% over 2 steps from 30). 1H NMR (300 MHz, CDCl3): delta[ppm] = 4.29-4.23(m, 2H, H-10), 3.90 (dd, J = 7.0, 7.0 Hz, 1H, H-2), 1.87-1.73 (m, 3H, H-3, H-4), 1.05-0.99 (m, 2H, H-20),0.97 (d, J = 6.1 Hz, 3H, H-5), 0.95 (d, J = 6.1 Hz, 3H, H-5), 0.04 (s, 9H, Si(CH3)3). 13C NMR (75 MHz,CDCl3): delta[ppm] = 170.12 (C-1), 162.73-161.77 (m, TFA-COO), 116.32-114.45 (m, TFA-CF3), 65.12 (C-10),51.54 (C-2), 39.61 (C-3), 24.29 (C-4), 22.09 (C-5), 21.74 (C-5), 17.19 (C-20), 1.68 (Si(CH3)3). 19F NMR(282 MHz, CDCl3): delta[ppm] = 75.98 (TFA-CF3). MS (ESI+): m/z = 232.2 [M TFA]+. HRMS (ESI+):calcd.: 232.1727 [M TFA]+, found: 232.1724. IR (ATR): n [cm-1] = 1733, 1665, 1250, 1201, 1174, 1137,1042, 930, 834. Optical rotation: [alpha]D25 = 3.6 (c = 1.0, CHCl3). m.p. = 85 C. TLC: Rf (9:1, petroleumether:EtOAc) = 0.76.

Reference： [1]Molecules,2018,vol. 23

83
[ 874-61-3 ]
[ 2916-68-9 ]
[ 945843-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃;	To a solution of (10.0 g, 70.3 mmol) in tetrahydrofuran (250 mL) were added 2- (trimethylsilyl)ethanol (11.0 g, 93.0 mmol), Ni -((ethylimino)methylene)-N3 ,N3 - dimethylpropane-1,3-diamine hydrochloride (20.0 g, 104 mmol) and N,Ndimethylpyridin-4-amine (15.5 g, 127 mmol) at room temperature. After stirredovernight, the mixture was concentrated to give a residue, which was diluted with water(50 mL), extracted by ethyl acetate (150 mL) twice. The combined organic layers werewashed by 2 M hydrochloride aqueous solution (150 mL), brine (150 mL), dried overNa2 SO4(), filtered and concentrated to afford the desired product (14.1 g, 90 % purity,74 % yield) as light yellow oil. ?H NIVIR (300 1VIFIz, CDC13) 4.25 - 4.19 (m, 2H), 2.79-2.68 (m, 1H), 2.56-2.45 (m, 2H), 2.41 -2.31 (m, 2H), 2.27-2.17 (m, 2H), 2.08 - 1.97(m, 2H), 1.05 - 0.98 (m, 2H), 0.07 (s, 9H).

Reference： [1]Patent: WO2019/1420,2019,A1 .Location in patent: Page/Page column 86

84
[ 2916-68-9 ]
[ 117997-81-6 ]
C₂₂H₃₅NO₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 96%		Synthesis of N-(t-Butoxycarbonyl)-α-[2-(trimethylsilyl)ethyoxy]-γ-benzyl-L-glutamate 14 After a CH2Cl2 solution of N-(t-butoxycarbonyl)-γ-benzyl-L-glutamic acid, Compound 13 (˜5.0 g, 14.8 mmol) and carbonyldiimidazole (CDI) (˜2.64 g, 16.3 mmol) was stirred at room temperature one hour, 2-(trimethylsilyl)ethanol (˜1.93 g, 16.3 mmol) was added, and the reaction mixture was further stirred at room temperature overnight (20 hours). The reaction solution was then washed with an aqueous NaCl solution, dried over Na2SO4, and the solvent removed under reduced pressure. Purification by Biotage flash chromatography (EtOAc/Hexane) gave the desired Compound 14 as a colorless liquid (˜6.2 g, 14.2 mmol, ˜96% isolated yield). Proton NMR confirmed the product structure.

Reference： [1]Patent: US10736969,2020,B2 .Location in patent: Page/Page column 31; 32

85
[ 2916-68-9 ]
[ 4998-07-6 ]
2-(trimethylsilyl)ethyl 4,5-dimethoxy-2-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	methyl 4, 5 -dim eth oxy-2-propwlam ido ben u te (4) General procedure: To a solution of 3 (50 mg. 0.24 mmol) in dry CH2CI2 (10 mL) was added propiolic aci (0.022 mL, 0.36 mraol) and N, JV’ -dicyciohexyiearbodiimide (73 mg, 0.36 mmol) in dry CH2CI2 (5 mL) dropwise in an ice-bath. The resulting solution was stirred under N? for 2 h. T he reaction mixture was suspended in H2O (50 mL) and then extracted with CH2CI2 (3 x 50 L). The combined organic layer was dried over MgSC , filtered and concentrated in vacuo. The mixture was filtered and washed with EtOAc/-hexane ~ 1:1 (10 mL). The residue was purified by silica gel chromatography (EtOAc/n-hexane ^ 1 :5) to afford 4 (57 mg, 91%). *H NMR (500 MHz, CDCb) d 11.56 (s, 1 H), 8.31 (s, 1 H), 7.44 (s, 1 H), 3.93 (s, 3H), 3.90 (s, 3H), 3.87 (s, 3H), 2.92 (s, 1H).

Reference： [1]Current Patent Assignee: ACADEMIA SINICA; SHIH MING CHE - WO2021/113062, 2021, A1 Location in patent: Page/Page column 7-9

86
[ 2916-68-9 ]
[ 201230-82-2 ]
[ 4119-41-9 ]
C₁₅H₂₄O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With RuHClPNP<SUP>iPr</SUP>(CO); caesium carbonate In toluene at 90℃; for 12h; chemoselective reaction;

Reference： [1]Ai, Han-Jun; Wu, Xiao-Feng; Yuan, Yang [Chemical Science, 2022, vol. 13, # 8, p. 2481 - 2486]

87
[ 288-32-4 ]
[ 38496-18-3 ]
[ 12628-74-9 ]
[ 2916-68-9 ]
[ 19230-27-4 ]
Pd(dppt)Cl₂ [ No CAS ]
[ 13292-87-0 ]
[ 36476-78-5 ]
[ 87768-27-2 ]
[ 18162-48-6 ]
[ 620595-02-0 ]
[ 74-88-4 ]
[ 57-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; dmap; trifluoromethylsulfonic anhydride; N,N,N-tributylbutan-1-aminium fluoride; anhydrous potassium acetate; palladium diacetate; trifluoroacetic acid; trimethylamine	3 Example 3 Example 3 Chemical Synthesis of Protected PD6 Prodrug Comprising Cholesterol Chemical synthesis of a protected PD6 prodrug comprising cholesterol is synthesized using the following protocol. First, Intermediate 1: 2,6-dichloro-3-carboxypyridine was treated with trimethylsilylethanol in THF followed by reduction with borane dimethylsulfide complex. Then, Intermediate 2: Intermediate 1 was treated with Dess-Martin Reagent. Then, Intermediate 3: 4-hydroxy-2,3-dihydro-1H-inden-2-one was treated with imidazole and tert-Butyldimethylsilyl chloride in DCM. Then, Intermediate 4: Intermediate 3 was treated with R(+)-2-methyl-CBS-oxaborolidine and borane dimethylsulfide in toluene. Then, Intermediate 5: Intermediate 4 was combined with Intermediate 2, palladium acetate, tBuXPHos, and cesium carbonate in toluene top. Then, Intermediate 6: Intermediate 5 was treated with TBAF in THF at -78° C. for 15 minutes followed by triflic anhydride, trimethylamine, and DMAP in DCM at room temperature. Then, Intermediate 7: Intermediate 6 was treated with B2Pin2, Pd-dppt and potassium acetate in dioxane. Then, Intermediate 8: Intermediate 7 was treated with 1,3-dibromo-2-chlorobenzene, Pd(dppt)Cl2, and Potassium acetate. Then, Intermediate 9: Intermediate 8 was treated with Palau-CI and 20% TFA in DCM/DMF. Then, Intermediate 10: Intermediate 9 was treated with cesium fluoride in DMF at 60 C followed by methyl iodide and potassium carbonate. Then, Intermediate 11: Intermediate 10 was treated with 4,4,5,5-tetramethyl-2-(4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-1,3,2-dioxaborolane and palladium triphenylphosphine. Then, Intermediate 12: Intermediate 11 was treated with 3-azetidine carboxylic acid, potassium acetate, and triacetoxysodium borohydride. Then, Intermediate 13: The ketal in intermediate 12 was hydrolyzed to the aldehyde with HCl in dioxane, then the aldehyde was converted with s-aminomethylpyrrolidin-2-one, potassium acetate, and sodium triacetoxyborohydride. Then, Intermediate 14: Intermediate 13 was converted the BOC derivative by treatment with BOO anhydride, followed by EDC mediated esterification with cholesterol, then removal of the BOC group with HCl in dioxane to yield the final PD6 Prodrug. ().

Reference： [1]Current Patent Assignee: NAMMI THERAPEUTICS - US2022/80051, 2022, A1

88
[ 288-32-4 ]
[ 38496-18-3 ]
[ 12628-74-9 ]
[ 2916-68-9 ]
[ 19230-27-4 ]
Pd(dppt)Cl₂ [ No CAS ]
[ 13292-87-0 ]
[ 36476-78-5 ]
[ 87768-27-2 ]
[ 18162-48-6 ]
[ 620595-02-0 ]
[ 74-88-4 ]
1,2-Dipalmitoyl-sn-glycero-3-phosphoglycerol, sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; dmap; trifluoromethylsulfonic anhydride; N,N,N-tributylbutan-1-aminium fluoride; anhydrous potassium acetate; palladium diacetate; trifluoroacetic acid; trimethylamine	4 Example 4 Example 4 Chemical Synthesis of Protected PD6 Prodrug Comprising DPPG Chemical synthesis of a protected PD6 Prodrug comprising DPPG is synthesized using the following protocol. First, Intermediate 1: 2,6-dichloro-3-carboxypyridine was treated with trimethylsilylethanol in THF followed by reduction with borane dimethylsulfide complex. Then, Intermediate 2: Intermediate 1 was treated with Dess-Martin Reagent. Then, Intermediate 3: 4-hydroxy-2,3-dihydro-1H-inden-2-one was treated with imidazole and tert-Butyldimethylsilyl chloride in DCM. Then, Intermediate 4: Intermediate 3 was treated with R(+)-2-methyl-CBS-oxaborolidine and borane dimethylsulfide in toluene. Then, Intermediate 5: Intermediate 4 was combined with Intermediate 2, palladium acetate, tBuXPHos, and cesium carbonate in toluene top. Then, Intermediate 6: Intermediate 5 was treated with TBAF in THF at -78° C. for 15 minutes followed by triflic anhydride, trimethylamine, and DMAP in DCM at room temperature. Then, Intermediate 7: Intermediate 6 was treated with B2Pin2, Pd-dppt and potassium acetate in dioxane. Then, Intermediate 8: Intermediate 7 was treated with 1,3-dibromo-2-chlorobenzene, Pd(dppt)Cl2, and Potassium acetate. Then, Intermediate 9: Intermediate 8 was treated with Palau-CI and 20% TFA in DCM/DMF. Then, Intermediate 10: Intermediate 9 was treated with cesium fluoride in DMF at 60 C followed by methyl iodide and potassium carbonate. Then, Intermediate 11: Intermediate 10 was treated with 4,4,5,5-tetramethyl-2-(4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-1,3,2-dioxaborolane and palladium triphenylphosphine. Then, Intermediate 12: Intermediate 11 was treated with 3-azetidine carboxylic acid, potassium acetate, and triacetoxysodium borohydride. Then, Intermediate 13: The ketal in intermediate 12 was hydrolyzed to the aldehyde with HCl in dioxane, then the aldehyde was converted with s-aminomethylpyrrolidin-2-one, potassium acetate, and sodium triacetoxyborohydride. Then, Intermediate 14: Intermediate 13 was converted the BOC derivative by treatment with BOC anhydride, followed by EDC mediated esterification with DPPG, then removal of the BOC group with HCl in dioxane to yield the final PD6 Prodrug. ().

Reference： [1]Current Patent Assignee: NAMMI THERAPEUTICS - US2022/80051, 2022, A1

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H250	Catches fire spontaneously if exposed to air
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2916-68-9 ] {[proInfo.proName]}

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[ 2916-68-9 ] Synthesis Path-Upstream 1~6

[ 2916-68-9 ] Synthesis Path-Downstream 1~88

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