[ CAS No. 55142-85-3 ] {[proInfo.proName]}

Name: 55142-85-3|5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine|96%
Brand: Ambeed
SKU: A269629
Rating: 95 (32 reviews)

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 55142-85-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 55142-85-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55142-85-3 ]

SDS Specification

Alternatived Products of [ 55142-85-3 ]

Product Details of [ 55142-85-3 ]

CAS No. :	55142-85-3	MDL No. :	MFCD00661081
Formula :	C₁₄H₁₄ClNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PHWBOXQYWZNQIN-UHFFFAOYSA-N
M.W :	263.79	Pubchem ID :	5472
Synonyms :	PCR 5332	Chemical Name :	5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Calculated chemistry of [ 55142-85-3 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.29
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	78.06
TPSA :	31.48 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.97
Log Po/w (XLOGP3) :	3.63
Log Po/w (WLOGP) :	3.28
Log Po/w (MLOGP) :	3.51
Log Po/w (SILICOS-IT) :	5.03
Consensus Log Po/w :	3.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.11
Solubility :	0.0205 mg/ml ; 0.0000778 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.98
Solubility :	0.0277 mg/ml ; 0.000105 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.37
Solubility :	0.00112 mg/ml ; 0.00000424 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.5

Safety of [ 55142-85-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 55142-85-3 ]

* 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 [ 55142-85-3 ]
Downstream synthetic route of [ 55142-85-3 ]

[ 55142-85-3 ] Synthesis Path-Upstream 1~12

1
[ 865187-82-2 ]
[ 89-97-4 ]
[ 55142-85-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 5℃; for 5 h; Heating / reflux	Example 24: Synthesis of 5-[(2-chlorophenyl) methyl] -4,5, 6,7- tetrahydrothieno [3,2-c] pyridine (compound of formula la; Ticlopidine); At below 5 °C, 5. 0 g of 2- (2-bromoethyl)-3-bromomethylthiophene obtained in Example 7 was dissolved in 50 mL of acetonitrile, and added thereto was a solution obtained by dissolving 2.7 g of 2-chlorobenzylamine and 6.8 g of diisopropylethylamine in 25 mL of acetonitrile. The resulting mixture was refluxed for 5 hours, and concentrated by evaporation under reduced pressure. The residue was dissolved in 100 mL of ethyl acetate, and washed twice with 70 mL portions of water. The organic layer was washed with 50 mL of saturated sodium chloride aqueous solution and concentrated under reduced pressure. The dark yellow colored oily residue thus obtained was subjected to a silica gel column chromatography (eluent, n-hexane: ethyl acetate = 5 : 1) to obtain 3.6 g (yield of 78percent) of the title compound as a yellowish oil. 'H-NMR (CDC13, ppm) : 6 2.87-2. 91 (m, 4H), 3.66 (s, 2H), 3.85 (s, 2H), 6.73 (d, 1H, J = 5.0 Hz), 7.09 (d, 1H, J = 0.5 Hz), 7.19-7. 29 (m, 2H), 7.35-7. 42 (m, 1H), 7. 52-7. 61 (m, 1H).

Reference： [1] Patent: WO2005/87779, 2005, A1, . Location in patent: Page/Page column 22-23

2
[ 50-00-0 ]
[ 54903-50-3 ]
[ 694-80-4 ]
[ 55142-85-3 ]

Reference： [1] Molecules, 2010, vol. 15, # 11, p. 8144 - 8155

3
[ 54903-50-3 ]
[ 611-19-8 ]
[ 55142-85-3 ]

Reference： [1] European Journal of Medicinal Chemistry, 1974, vol. 9, # 5, p. 483 - 486
[2] Patent: US4906756, 1990, A,
[3] Patent: US4997945, 1991, A,
[4] Patent: EP522956, 1993, A2,

4
[ 128988-10-3 ]
[ 55142-85-3 ]

Reference： [1] Patent: US4965359, 1990, A,

5
[ 79714-07-1 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274

6
[ 79714-11-7 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274
[2] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274

7
[ 88720-42-7 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274
[2] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274

8
[ 79714-00-4 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274
[2] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274

9
[ 79714-04-8 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1981, vol. 16, # 8, p. 1271 - 1274

10
[ 41661-47-6 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1991, vol. 32, # 9, p. 1777 - 1780

11
[ 611-19-8 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1991, vol. 32, # 9, p. 1777 - 1780

12
[ 135576-51-1 ]
[ 55142-85-3 ]

Reference： [1] Heterocycles, 1991, vol. 32, # 9, p. 1777 - 1780

[ 55142-85-3 ] Synthesis Path-Downstream 1~79

1
[ 55142-85-3 ]
[ 73099-83-9 ]

Reference： [1]Heterocycles,1979,vol. 12,p. 1479 - 1482

2
[ 54903-50-3 ]
[ 611-19-8 ]
[ 55142-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; toluene;	3C. Ticlopidine Free Base To a suspension of sodium hydride (0.42 g, 8.6 mmole) in THF (5.0 ml) is added a solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1.0 g, 7.2 mmole), prepared, for example, as described in Example 3B, in THF (10 ml). The mixture is stirred under a nitrogen atmosphere at room temperature for 30 minutes and o-chlorobenzyl chloride (1.74 g, 10.8 mmole) is added. After stirring at room temperature for 90 minutes, toluene (15 ml) is added and the mixture is heated to reflux for 15 to 20 hours. Disappearance of starting material is confirmed by TLC. The mixture is then cooled to room temperature and acidified with 40 ml 1N hydrochloric acid. The organic layer is separated. The aqueous layer is extracted with 50 ml of toluene. The aqueous layer is then separated and basified with dilute aqueous sodium hydroxide to pH 13-14. The product is extracted into methylene chloride (340 ml). The methylene chloride extracts are washed (150 ml water) and (1*50 ml salt solution) then dried over anhydrous magnesium sulfate and concentrated to give the desired product. Following the above procedure, there was obtained 1.5 g (80%) of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (ticlopidine free base) as a light yellow oil. NMR (CDCl3) delta: 7.7-7.15 (m, 4H), 7.05 (d, 1H), 6.65 (d, 1H), 3.8 (s, 2H), 3.6 (s, 2H), 2.85 (br.s, 4H).
	In tetrahydrofuran; toluene;	A-3. Ticlopidine Free Base To a suspension of sodium hydride (0.42 g, 8.6 mmole) in THF (5.0 ml) is added a solution of 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (1.0 g, 7.2 mmole), prepared, for example, as described in Example A-2, in THF (10 ml). The mixture is stirred under a nitrogen atmosphere at room temperature for 30 minutes and o-chlorobenzyl chloride (1.74 g, 10.8 mmole) is added. After stirring at room temperature for 90 minutes, toluene (15 ml) is added and the mixture is heated to reflux for 15 to 20 hours. Disappearance of starting material is confirmed by TLC. The mixture is then cooled to room temperature and acidified with 40 ml 1N hydrochloric acid. The organic layer is separated. The aqueous layer is extracted with 50 ml of toluene. The aqueous layer is then separated and basified with dilute aqueous sodium hydroxide to pH 13-14. The product is extracted into methylene chloride (340 ml). The methylene chloride extracts are washed (150 ml water) and 1*50 ml salt solution) then dried over anhydrous magnesium sulfate and concentrated to give the desired product. Following the above procedure, there is obtained 1.5 g (80%) of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (ticlopidine free base) as a light yellow oil. Reported NMR (CDCl3) w: 7.7-7.15 (m,4H), 7.05 (d,1H), 6.65 (d,1H), 3.8 (s,2H), 3.6 (s,2H), 2.85 (br.s,4H).
		f. contacting 4,5,6,7-tetrahydrothieno[3,2-c]pyridine with sodium hydride followed by o-chlorobenzyl chloride to give 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, and

Reference： [1]European Journal of Medicinal Chemistry,1974,vol. 9,p. 483 - 486
[2]Patent: US4906756,1990,A
[3]Patent: US4997945,1991,A
[4]Patent: EP522956,1993,A2

3
[ 55142-85-3 ]
[ 79-03-8 ]
[ 90997-36-7 ]
[ 90997-27-6 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

4
[ 79714-07-1 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1271 - 1274

5
5-(2-Chloro-benzyl)-hexahydro-thieno[3,2-c]pyridine-3,7a-diol [ No CAS ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 1777 - 1780

6
[ 55142-85-3 ]
[ 75-07-0 ]
[ 90997-23-2 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

7
[ 55142-85-3 ]
[ 123-38-6 ]
[ 90997-24-3 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

8
[ 55142-85-3 ]
[ 75-36-5 ]
[ 90997-25-4 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

9
[ 55142-85-3 ]
[ 141-75-3 ]
[ 90997-29-8 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

10
[ 55142-85-3 ]
[ 2528-61-2 ]
[ 90997-31-2 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

Yield	Reaction Conditions	Operation in experiment
64%		4. Preparation of 5-(2-chloro-benzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 15 g (0.052 mole) of the compound obtained in (3), 100 ml water and 5 ml of a 35% aqueous formaldehyde solution (0.58 mole) are heated at 90 C. during 15 minutes, after which 2N hydrochloric acid (100 ml) is added thereto and the resulting mixture is heated at 90 C. during 1.5 hour. After cooling, a slight precipitate is removed by filtration. The aqueous phase is made alkaline with 2N NaOH and is then extracted with 350 ml diisopropyl ether. The organic phase is washed with water, dried over sodium sulfate and concentrated, to give 11.32 g of a light orange oil. This oil is then dissolved in isopropyl ether and, after addition of dry HCl, gives 10 g of a hydrochloride precipitate which is purified by recrystallization from boiling absolute ethanol (Yield: 64%).
		(d) Production of 5-[2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]-pyridine 0.97 g (3.68 mmol) of 1-[(2-chlorophenyl)methyl]-3-(2-propenyl)-4-piperidine was dissolved, under argon, in 10 ml of methylene chloride and cooled to -60 to -70 C. Then 0.86 g (7.39 mmol) of trifluoroacetic acid in 2.5 ml of methylene chloride was instilled within 5 minutes. Then ozone was introduced until the solution showed a greenish blue color. The excess ozone was removed with nitrogen. Then a solution of 0.28 g (4.37 mmol) of dimethyl sulfide in 2.5 ml of methylene chloride was instilled within 5 minutes. After 5 minute stirring at -60 to 70 C., it was warmed to 0 C. 5 ml of methanol and then, within 5 minutes, a solution of 3.39 g (12.88 mmol) of tin tetrachloride in 5 ml of methylene chloride was added to this solution (exothermic). Introduction of hydrogen chloride began at 0 C., 5 minutes later the introduction of hydrogen sulfide began. The introduction was ended after 6 hours and stirring was continued for 10 hours. The reaction mixture was concentrated by evaporation. 75 ml of water, 75 ml of ether and sodium carbonate were added to the residue, until the pH of the mixture was about 9. The organic phase was separated, dried with magnesium sulfate and concentrated by evaporation. The yield was 0.903 g of 5-[2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]-pyridine, which equals 73 percent. Data concerning the compound was: 1 H-NMR: (CDCl3, 300 MHz) delta in ppm; 7.54, d, J=7.5 Hz, 1H; 7.36, d, J=7.5 Hz, 1H; 7.20, q, J=7.5 Hz, 2H; 7.06, d, J=5 Hz, 1H; 6.70, d, J=5 Hz, 1H; 3.83, s, 2H; 3.64, s, 2H; 2.88, m, 4H
		(d) Production of 5-[(2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]-pyridine 13.50 g (51.2 mmol) of 1-[(2-chlorophenyl)methyl]-3-(2-propenyl)-4-piperidine was placed under argon in 220 ml of methylene chloride and cooled to -60 C. Then 11.93 g (102.4 mmol) of trifluoroacetic acid in 30 ml of methylene chloride was added. Then the introduction of ozone began (251 of O2 /h/0.6 A). As soon as the solution became greenish (excess the feeding of ozone (30 minutes) was stopped. N2 was passed through the solution for 15 minutes to drive out the excess ozone (solution became yellowish). Then 3.94 g (61.4 mmol) of dimethyl sulfide in 30 ml of methylene chloride was instilled in 10 minutes. It was stirred for 5 minutes more at 60 C. and then cooled with ice water to 0 C. Then 170 ml of methanol and in 20 minutes a solution of 34.31 g of titanium tetrachloride in 56 ml of methylene chloride were added. Then HCl gas and 5 minutes later H2 S gas was introduced (yellow precipitate after a few minutes). The introduction of HCl and H2 S were stopped after 3.5 hours. The flask was closed and allowed to stand overnight at room temperature. The reaction mixture was completely concentrated by evaporation. 200 ml of ether plus 200 ml of 1n HCl were added to the residue. 10.3 g (75 percent) of the subtitle product (noted above) was obtained as brownish oil from the organic phase. The crude product was dissolved in 250 ml of ether and then treated at 0 C. with HCl gas to produce the hydrochloride. 10.25 g (66 percent) of the subtitle compound (noted above) was obtained as hydrochloride. For the compound, the melting point (Mp) was 208 to 211 C.

		Also, among the compounds represented by formula (5) and salts thereof, examples of preferred compounds include the following: ... 5-(alpha-methoxycarbonyl-2-chlorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine, 2-acetoxy-5-(alpha-methoxycarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c] pyridine, 5-(alpha-methoxycarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c ]pyridine, 2-acetoxy-5-(alpha-methoxycarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c] pyridine, 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (nonproprietary name: ticlopidine; available as ticlopidine hydrochloride), 5-(alpha-methoxycarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (nonproprietary name: cropidogrel; available as clopidogrel sulfate), 5-(alpha-methoxycarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, 5-(alpha-cyclopropylcarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno [3,2-c]pyridin e, ...
		Also, among the compounds represented by formula (5) and salts thereof, examples of preferred compounds include the following: ... 5-(alpha-methoxycarbonyl-2-chlorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine, 2-acetoxy-5-(alpha-methoxycarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, 5-(alpha-methoxycarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine, 2-acetoxy-5-(alpha-methoxycarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (nonproprietary name: ticlopidine; available as ticlopidine hydrochloride),
		non-steroidal antiinflamatories;ticlopidine;heparin;warfarin;

12
[ 34846-44-1 ]
sodium-compound of ethane-1,1,2-tricarboxylic acid triethyl ester [ No CAS ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1271 - 1274
[2]Heterocycles,1981,vol. 16,p. 1271 - 1274
[3]Heterocycles,1981,vol. 16,p. 1271 - 1274
[4]Heterocycles,1981,vol. 16,p. 1271 - 1274

13
[ 55142-85-3 ]
[ 90997-53-8 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247
[2]Heterocycles,1984,vol. 22,p. 1235 - 1247

14
[ 55142-85-3 ]
[ 90997-52-7 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

15
[ 55142-85-3 ]
[ 90997-45-8 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

16
[ 55142-85-3 ]
[ 90997-43-6 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

17
[ 55142-85-3 ]
[ 90997-62-9 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

18
[ 55142-85-3 ]
[ 90997-37-8 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

19
[ 55142-85-3 ]
[ 90997-67-4 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

20
[ 55142-85-3 ]
[ 344583-79-5 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

21
[ 55142-85-3 ]
[ 344600-31-3 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

22
[ 55142-85-3 ]
[ 90997-46-9 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

23
[ 55142-85-3 ]
[ 90997-48-1 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

24
[ 55142-85-3 ]
[ 90997-49-2 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

25
[ 55142-85-3 ]
[ 90997-47-0 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

26
[ 55142-85-3 ]
[ 754142-54-6 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

27
[ 55142-85-3 ]
[ 752940-59-3 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

28
[ 55142-85-3 ]
[ 121347-24-8 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

29
[ 55142-85-3 ]
[ 90997-41-4 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

30
[ 55142-85-3 ]
[ 756433-18-8 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

31
[ 55142-85-3 ]
[ 742017-20-5 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

32
[ 55142-85-3 ]
[ 90997-42-5 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

33
[ 55142-85-3 ]
[ 790615-52-0 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

34
[ 55142-85-3 ]
[ 90997-56-1 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247
[2]Heterocycles,1984,vol. 22,p. 1235 - 1247

35
[ 55142-85-3 ]
[ 90997-54-9 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

36
[ 55142-85-3 ]
(2-Butyl-thieno[3,2-c]pyridin-3-yl)-(3,5-dibromo-4-hydroxy-phenyl)-methanone [ No CAS ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

37
[ 55142-85-3 ]
5-(2-Chloro-benzyl)-2-heptyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine [ No CAS ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

38
[ 55142-85-3 ]
[ 90997-65-2 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

39
[ 55142-85-3 ]
[ 90997-63-0 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

40
[ 55142-85-3 ]
[ 90997-58-3 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247
[2]Heterocycles,1984,vol. 22,p. 1235 - 1247

41
[ 55142-85-3 ]
[ 741209-49-4 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

42
[ 55142-85-3 ]
[2-Butyl-5-(2-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-3-yl]-(4-hydroxy-phenyl)-methanone [ No CAS ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

43
[ 55142-85-3 ]
[ 749805-59-2 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

44
[ 55142-85-3 ]
[ 91019-57-7 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

45
[ 55142-85-3 ]
[ 90997-70-9 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

46
[ 55142-85-3 ]
[ 90997-72-1 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1235 - 1247

47
[ 79714-11-7 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1271 - 1274
[2]Heterocycles,1981,vol. 16,p. 1271 - 1274

48
[ 88720-42-7 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1271 - 1274
[2]Heterocycles,1981,vol. 16,p. 1271 - 1274

49
[ 79714-00-4 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1271 - 1274
[2]Heterocycles,1981,vol. 16,p. 1271 - 1274

50
[ 79714-04-8 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1271 - 1274

51
[ 41661-47-6 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 1777 - 1780

52
[ 611-19-8 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 1777 - 1780

53
[ 135576-51-1 ]
[ 55142-85-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 1777 - 1780

54
[ 865187-82-2 ]
[ 89-97-4 ]
[ 55142-85-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 5℃; for 5h;Heating / reflux;	Example 24: Synthesis of 5-[(2-chlorophenyl) methyl] -4,5, 6,7- tetrahydrothieno [3,2-c] pyridine (compound of formula la; Ticlopidine); At below 5 C, 5. 0 g of 2- (2-bromoethyl)-3-bromomethylthiophene obtained in Example 7 was dissolved in 50 mL of acetonitrile, and added thereto was a solution obtained by dissolving 2.7 g of 2-chlorobenzylamine and 6.8 g of diisopropylethylamine in 25 mL of acetonitrile. The resulting mixture was refluxed for 5 hours, and concentrated by evaporation under reduced pressure. The residue was dissolved in 100 mL of ethyl acetate, and washed twice with 70 mL portions of water. The organic layer was washed with 50 mL of saturated sodium chloride aqueous solution and concentrated under reduced pressure. The dark yellow colored oily residue thus obtained was subjected to a silica gel column chromatography (eluent, n-hexane: ethyl acetate = 5 : 1) to obtain 3.6 g (yield of 78%) of the title compound as a yellowish oil. 'H-NMR (CDC13, ppm) : 6 2.87-2. 91 (m, 4H), 3.66 (s, 2H), 3.85 (s, 2H), 6.73 (d, 1H, J = 5.0 Hz), 7.09 (d, 1H, J = 0.5 Hz), 7.19-7. 29 (m, 2H), 7.35-7. 42 (m, 1H), 7. 52-7. 61 (m, 1H).

Reference： [1]Patent: WO2005/87779,2005,A1 .Location in patent: Page/Page column 22-23

55
[ 55142-85-3 ]
[ 688-74-4 ]
[ 83427-51-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With n-butyllithium; dihydrogen peroxide; oxalic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; acetone;	a) 5-(2-chlorobenzyl)-5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one formula II: Z=S; m=1; n=2; R=CH2 (2-ClC6 H4)). 79 cm3 of a 12% solution of butyllithium in hexane (0.147 mole) are introduced dropwise into a solution, cooled to -20 C., of 32.6 g (0.123 mole) of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3, 2-c]pyridine in 320 cm3 of tetrahydrofuran. When the addition is complete, the lithium derivative precipitates and the temperature is allowed to return to 0 C. 15 cm3 of hexamethylphosphoric triamide (HMPT) are then added: the precipitate becomes deep red. The temperature is lowered to -40 C. and a solution of tributyl borate (39.8 cm3 =0.147 mole) in 40 cm3 of anhydrous tetrahydrofuran is added dropwise in the course of half an hour. The precipitate disappears and the reaction medium becomes light yellow. The temperature is maintained at -40 C. for half an hour then brought to 10 C. and maintained for 2 hours at this temperature. 33 cm3 (0.291 mole) of 30% hydrogen peroxide are added dropwise while the temperature of the medium is maintained below 30 C. A copious precipitate is formed during the addition. Stirring is maintained for 1 hour at room temperature. The reaction medium is poured into water, the product is extracted with 3*200 cm3 of ethyl ether and the organic phases are dried over sodium sulphate and concentrated under vacuum at a temperature below 40 C. The residual liquid is chromatographed on a silica column (eluent: cyclohexane/ethyl acetate, 6:4) to remove the remaining HMPT. After evaporation to dryness, the residue is treated with one molar equivalent of oxalic acid in acetone, and the light yellow crystals formed are filtered off. On recrystallization in ethanol, beige-coloured crystals of oxalate are obtained. yield: 52%, m.p. 170 C. Base: m.p. 73-74.5 C. (ethanol) NMR (CDCl3) 7.1-7.6(m,4H); 6.2(s,1H); 4.2-4.7(m,1H); 3.9(s,2H); 1.5-4.2(m,6H).
52%	With n-butyllithium; dihydrogen peroxide; oxalic acid; In tetrahydrofuran; hexane; cyclohexane; ethyl acetate; acetone;	EXAMPLE 1 5-(o-Chlorobenzyl)-5,6,7,7a-tetrahydro-4H-thieno-[3,2-c]pyridin-2-one; formula (I), R=2-Cl-C6 H4; R'=H; n=1; derivative No. 1 79 cc. of a 12% solution of butyl lithium in hexane (0.147 mol) are added dropwise to a solution, cooled to -20 C., of 32.6 g. (0.123 mol) 5-(o-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine in 320 cc. tetrahydrofuran (THF). At the end of the addition, the lithium derivative (III) precipitates and the temperature is allowed to return to 0 C. 15 cc. Hexamethylphosphotriamide (HMPT), previously dried over a 4 A molecular sieve, are then added. The precipitate becomes dark red. The temperature is lowered to -40 C. and a solution of 39.8 cc. (0.147 mol) tributyl borate in 40 cc. anhydrous tetrahydrofuran is added dropwise in the course of half an hour. The precipitate disappears and the reaction mixture becomes light yellow. The temperature is kept at -40 C. for half an hour and then returned to 10 C. for 2 hours. 33 cc. (0.291 mol) 30% hydrogen peroxide are added dropwise, whilst keeping the temperature of the reaction mixture below 30 C., an intense precipitate forming during the addition. Stirring is continued for 1 hour at ambient temperature. The reaction mixture is then poured into water and extracted with 3*200 cc. diethyl ether and the organic phases are dried over anhydrous sodium sulphate and concentrated in vacuo at a temperature below 40 C. The remaining liquid is chromatographed over a silica column (using a 6/4 v/v cyclohexane/ethyl acetate mixture) to remove residual HMPT. After evaporation of the solution obtained, the residue is treated with a molar equivalent of oxalic acid in acetone, the light yellow crystals formed being filtered off. Upon recrystallisation from ethanol, beige crystals of the oxalate are obtained; yield 52% of theory; m.p. 170 C.; IR(KBr): nuCO: 1660 cm-1 (broad).

Reference： [1]Patent: US5190938,1993,A
[2]Patent: US4515951,1985,A

56
[ 128988-10-3 ]
[ 55142-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tin(IV) chloride; sodium carbonate; In chloroform; water;	(e) Production of 5-[2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]-pyridine 1.35 g (5.13 mmol) of tin tetrachloride was placed in 10 ml of chloroform. Then 0.39 g (1.47 mmol) of 1-[(2-chlorophenyl)methyl]-4-oxo-3-piperidine acetaldehyde, dissolved in 15 mol of chloroform, was added to it. After cooling to -15 C., introduction of hydrogen chloride and introduction of hydrogen sulfide began. The introduction ended after 6 hours. It was stirred for 10 hours at room temperature. The reaction mixture was concentrated by evaporation. 30 ml of water, 30 ml of ether and 1.5 g of sodium carbonate (pH 8-9) were added. The organic phases was separated, dried on magnesium sulfate and concentrated by evaporation. The yield was 0.27 g of 5-[(2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]-pyridine, which equals 70 percent. Data concerning the compound was: 1 H-NMR: (CDCl3, 300 MHz) delta in ppm; 7.54, d, J=7.5 Hz, 1H; 7.36, d, J=7.5 Hz, 1H; 7.20, q, J=7.5 Hz, 2H; 7.06, d, J=5 Hz, 1H; 6.70, d, J=5 Hz, 1H; 3.83, s, 2H; 3.64, s, 2H; 2.88, m, 4H

Reference： [1]Patent: US4965359,1990,A

Yield	Reaction Conditions	Operation in experiment
90%		A mixture of 168 g of 2-thienylcarboxaldehyde and 12.9 g of isopropyl chloroacetate is then introduced over 30 minutes. The solution is stirred for 25 minutes at this temperature and 257 g of an aqueous solution of sodium hydroxide at a concentration of 35% are then added over 30 minutes. The mixture is stirred at 50 C. for 2 hours, is cooled to 25 C. and 161.5 g of hydroxylamine hydrochloride dissolved in 200 ml of water are then introduced over 30 minutes. The mixture is kept stirred for 30 minutes and is then added to 1.5 l of water and 1.5 l of dichloromethane. It is extracted with twice 1 l of dichloromethane, the organic phases are combined and are dried over sodium sulphate. After filtration and evaporation of the solvents 191 g of crystalline 2-thienylacetaldoxime are obtained. Yield: 90% M.P. 92 C. 1 H NMR spectrum (DMSO-d6) (300 MHz)delta=3.68 ppm [2H,d,CH2 (Z)]; 3.84 ppm [2H,d,CH2 (E)]; 6.62-6.91 ppm [3H,m, aromatic protons]; 7.37 ppm [1H,t,C(H)=N]; 10.71 ppm [H,s,OH(Z)]; 11.1 ppm [1H,s,OH(E)]. The following examples illustrate the preparation of ticlopidine and of clopidogrel.

58
[ 55142-85-3 ]
[ 68559-55-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium permanganate; In acetone;	EXAMPLE 1 4-Oxo-5-o.chlorobenzyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (Derivative n1) To a stirred solution of 5-o.chlorobenzyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (6.5 g; 24.6 mmoles) in acetone (250 ml) heated at 40 C., is added portionwise finely powdered potassium permanganate (15.59 g; 98.6 mmoles). The reaction causes the refluxing of the solvent. On completion of the addition, the reaction mixture is maintained at 40 C. for a further 30 minutes, after which it is cooled and filtered through a silica bed. The filtrate is evaporated to dryness, and the resulting solid material is recrystallized from diisopropyl ether, to give white crystals, M.p.=60 C. (Yield: 55%).

Reference： [1]Patent: US4193997,1980,A

59
[ 55142-85-3 ]
[ 68-12-2 ]
[ 1056463-57-0 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 1041 - 1048

60
[ 55142-85-3 ]
[ 762-42-5 ]
[ 1056463-59-2 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 1041 - 1048

61
[ 55142-85-3 ]
[ 762-42-5 ]
[ 1056463-60-5 ]
[ 1056463-61-6 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 1041 - 1048

62
[ 50-00-0 ]
[ 54903-50-3 ]
[ 694-80-4 ]
[ 55142-85-3 ]

Reference： [1]Molecules,2010,vol. 15,p. 8144 - 8155

63
[ 55142-85-3 ]
C₂₃H₂₄ClNO₄S [ No CAS ]

Reference： [1]Drug Metabolism and Disposition,2014,vol. 42,p. 141 - 152

64
[ 55142-85-3 ]
[ 83427-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	With glucose-6-phosphate dehydrogenase; alpha-D-glucose 6-phosphate; cytochrome P450 2C19; NADP; magnesium chloride; In aq. phosphate buffer; at 37℃;pH 7.4;Enzymatic reaction;	The incubation mixture consisted of 0.2 mg/ml pooled microsomes or 20 pmol/ml recombinant CYP, <strong>[55142-85-3]ticlopidine</strong> (2 and 20 mM), andan NADPH-generating system (1.3 mM beta-nicotinamide adenine dinucleotidephosphate, 3.3 mM glucose 6-phosphate, 3.3 mM MgCl2, and 1.0 U/ml glucose-6-phosphate dehydrogenase) in a total volume of 100 mL phosphate buffer (0.1 M, pH 7.4). The reaction was initiated by the addition of theNADPH-generating system and continued in a water bath at 37C for 10 minutes. The reaction was terminated by the addition of the same volume of acetonitrile-containing internal standard (1 mM of 2-oxo-clopidogrel). After centrifugation at 16,000g for 5 minutes, a 2-mL aliquot of the supernatant was injected directly into the LC-MS/MS system.

Reference： [1]Drug Metabolism and Disposition,2014,vol. 42,p. 141 - 152

65
[ 617-86-7 ]
[ 55142-85-3 ]
5-(2-chlorobenzyl)-2-(triethylsilyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium tert-butylate; In tetrahydrofuran; at 45℃; for 48h;Inert atmosphere; Glovebox;	The reaction was conducted according to the General Procedure by heating KOt- Bu (11.2 mg, 0.1 mmol, 20 mol%), <strong>[55142-85-3]ticlopidine</strong> (132.5 mg, 0.5 mmol, 1 equiv), Et3SiH (243 muL, 1.5 mmol, 3 equiv), and 0.5 mL of THF at 45 C for 48 h. The desired product 13a (107.7 mg, 57% yield) was obtained as a colorless oil after purification by silica gel flash chromatography (gradient elution, 5?10% Et2O in hexanes). Rf = 0.4 (10% Et2O in hexanes); 1H NMR (500 MHz, CDCl3) delta 7.56 (dd, J = 7.5, 1.8 Hz, 1H), 7.37 (dd, J = 7.8, 1.5 Hz, 1 H), 7.25 (td, J = 7.4, 1.5 Hz, 1H), 7.20 (td, J = 7.6, 1.9 Hz, 1 H), 6.86 (s, 1H), 3.84 (s, 2H), 3.67 (d, J = 1.6 Hz, 2H), 2.94 (t, J = 5.9 Hz, 2H), 2.87 (t, J = 5.4 Hz, 2H), 1.02- 0.98 (m, 9H), 0.80- 0.74 (m, 6H); 13C NMR (125 MHz, CDCl3) delta 139.2, 136.5, 135.6, 134.4, 134.0, 133.2, 130.8, 129.6, 128.3, 126.8, 58.7, 53.3, 51.0, 26.1, 7.5, 4.6. IR (Neat Film, NaCl) 2952, 2908, 2873, 2805, 2763, 1462, 1443, 1413, 1375, 1360, 1347, 1303, 1289, 1234, 1169, 1125, 1106, 1047, 1032, 1018, 991, 907, 835, 752 cm-1; HRMS (MM: ESI-APCI+) calc?d for C20H29ClNSSi [M+H]+: 378.1473, found 378.1480.

Reference： [1]Nature,2015,vol. 518,p. 80 - 84
[2]Patent: WO2016/22624,2016,A1 .Location in patent: Paragraph 0389; 0390

66
[ 55142-85-3 ]
[ 542-91-6 ]
5-(2-chlorobenzyl)-2-(diethylsilyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]

Reference： [1]Nature,2015,vol. 518,p. 80 - 84

67
[ 55142-85-3 ]
[ 766-77-8 ]
5-(2-chlorobenzyl)-2-(dimethyl(phenyl)silyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium tert-butylate; In tetrahydrofuran; at 45℃; for 108h;Inert atmosphere; Glovebox;	The reaction was conducted according to the General Procedure by heating KOt- Bu (11.2 mg, 0.1 mmol, 20 mol%), <strong>[55142-85-3]ticlopidine</strong> (134.5 mg, 0.5 mmol, 1 equiv), PhMe2SiH (230 muL, 1.5 mmol, 3 equiv), and 0.5 mL of THF at 45 C for 108 h. Product 13c (135.4 mg, 68% yield) was obtained as a colorless oil after purification by silica gel flash chromatography (3% Et2O in hexanes). Rf = 0.3 (10% Et2O in hexanes); 1H NMR (500 MHz, CDCl3) delta 7.58- 7.52 (m, 3H), 7.39- 7.34 (m, 4H), 7.25- 7.18 (m, 2H), 6.87 (s, 1H), 3.82 (s, 2H), 3.64 (t, J = 1.7 Hz, 2H), 2.95- 2.92 (m, 2H), 2.88- 2.84 (m, 2H), 0.56 (s, 6H); 13C NMR (125 MHz, CDCl3) delta 140.1, 138.2, 136.4, 135.9, 135.2, 134.4, 134.1, 133.9, 130.8, 129.6, 129.4, 128.3, 128.0, 126.8, 58.6, 53.2, 50.9, 26.1, -1.1. IR (Neat Film, NaCl) 3067, 2953, 2918, 2806, 2764, 1652, 1471, 1446, 1427, 1361, 1248, 1169, 1109, 1033, 990, 907, 832, 810, 777, 753 cm-1; HRMS (MM: ESI-APCI+) calc?d for C22H25ClNSSi [M+H]+: 398.1160, found 398.1152.

Reference： [1]Nature,2015,vol. 518,p. 80 - 84
[2]Patent: WO2016/22624,2016,A1 .Location in patent: Paragraph 0394; 0395

68
[ 55142-85-3 ]
[ 542-91-6 ]
5-(2-chlorobenzyl)-2-(diethylsilyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]
bis(5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)diethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%; 18%	With potassium tert-butylate; In tetrahydrofuran; at 45℃; for 108h;Inert atmosphere; Glovebox;	The reaction was conducted according to the General Procedure by heating KOt- Bu (11.2 mg, 0.1 mmol, 20 mol%), <strong>[55142-85-3]ticlopidine</strong> (134.5 mg, 0.5 mmol, 1 equiv), Et2SiH2 (194 muL, 1.5 mmol, 3 equiv), and 0.5 mL of THF at 45 C for 108 h. Products 13b (97.9 mg, 56% yield) and SI-13b (27.3 mg, 18% yield) were obtained after purification by silica gel flash chromatography (gradient elution, 5?50% Et2O in hexanes).

Reference： [1]Patent: WO2016/22624,2016,A1 .Location in patent: Paragraph 0391

69
[ 55142-85-3 ]
[ 124-38-9 ]
C₁₅H₁₄ClNO₂S [ No CAS ]

Reference： [1]Nature Chemistry,2017,vol. 9,p. 453 - 456

70
[ 55142-85-3 ]
[ 3412-44-0 ]
(E)-5-(2-chlorobenzyl)-2-(1,3-diphenylallyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 15248 - 15252
Angew. Chem.,2018,vol. 130,p. 15468 - 15472,5

71
[ 55142-85-3 ]
C₁₄H₁₃⁽²⁾HClNS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With water-d2; silver; In dimethyl sulfoxide; at 40℃; for 12h;	Silver reagent (0.3 mmol), phosphine ligand (0.3 mmol), deuterated water (0.4 g, 20 mmol), <strong>[55142-85-3]ticlopidine</strong> (0.26 g, 1 mmol) and dimethyl sulfoxide (5mL) were added to a 10 mL three-necked flask. After reacting at 40 C for 12 hours, the reaction was quenched by the addition of saturated ammonium chloride solution, the mixture was extracted with dichloromethane, the organic phase was combined, the organic solvent was concentrated, and the product was further purified by column chromatography to obtain deuterated <strong>[55142-85-3]ticlopidine</strong>, yield 95 %. Deuterium substitution rate of 91%.

Reference： [1]Organic Letters,2019,vol. 21,p. 6745 - 6749
[2]Patent: CN110156766,2019,A .Location in patent: Paragraph 0015

72
[ 623-26-7 ]
[ 55142-85-3 ]
[ 2585660-74-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With thiobenzoic acid; potassium phosphate In N,N-dimethyl acetamide at 20℃; for 6h; Irradiation;

Reference： [1]Kobayashi, Fumihisa; Fujita, Masashi; Ide, Takafumi; Ito, Yuta; Yamashita, Kenji; Egami, Hiromichi; Hamashima, Yoshitaka [ACS Catalysis, 2021, vol. 11, # 1, p. 82 - 87]

73
[ 100-48-1 ]
[ 55142-85-3 ]
[ 2585660-75-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With thiobenzoic acid; potassium phosphate In N,N-dimethyl acetamide at 20℃; for 6h; Irradiation;

Reference： [1]Kobayashi, Fumihisa; Fujita, Masashi; Ide, Takafumi; Ito, Yuta; Yamashita, Kenji; Egami, Hiromichi; Hamashima, Yoshitaka [ACS Catalysis, 2021, vol. 11, # 1, p. 82 - 87]

74
[ 55142-85-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
89%	With deuteromethanol; silver carbonate at 50 - 80℃;

Reference： [1]Tlahuext-Aca, Adrian; Hartwig, John F. [ACS Catalysis, 2021, vol. 11, # 3, p. 1119 - 1127]

75
[ CAS Unavailable ]
[ 55142-85-3 ]
[ 444728-11-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With 2-Picolinic acid; iron(III) chloride; tert-Butyl peroxybenzoate; 18-crown-6 ether In acetonitrile at 50℃; for 48h;

Reference： [1]Yilmaz, Ozgur; Dengiz, Cagatay; Emmert, Marion H. [Journal of Organic Chemistry, 2021, vol. 86, # 3, p. 2489 - 2498]

76
[ 54903-50-3 ]
[ 873-32-5 ]
[ 55142-85-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With nickel trifluoromethanesulfonate; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 100℃; for 16h;

Reference： [1]Chandrashekhar, Vishwas G.; Baumann, Wolfgang; Beller, Matthias; Jagadeesh, Rajenahally V. [Science, 2022, vol. 376, # 6600, p. 1433 - 1441]

77
[ 611-17-6 ]
[ 28783-41-7 ]
[ 55142-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20℃; Inert atmosphere;

Reference： [1]Gunasekera, Disni; Mahajan, Jyoti P.; Wanzi, Yanick; Rodrigo, Sachini; Liu, Wei; Tan, Ting; Luo, Long [Journal of the American Chemical Society, 2022, vol. 144, # 22, p. 9874 - 9882]

78
[ 623-26-7 ]
[ 55142-85-3 ]
[ 2585660-74-6 ]
[ 2785342-31-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 26% 2: 10%	With anhydrous Sodium acetate; lithium perchlorate In N,N-dimethyl acetamide at 20℃; for 48h; Schlenk technique; Inert atmosphere; Electrochemical reaction;

79
[ 55142-85-3 ]
[ 4559-70-0 ]
[ 2839626-94-5 ]

Yield	Reaction Conditions	Operation in experiment
51 %	With hyper-crosslinked porous organic polymers constructed by Friedel-Crafts alkylation reaction of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene with formaldehyde dimethyl acetal; air In water at 20℃; Irradiation;

Reference： [1]Zhu, Shan-Shan; Zuo, Lin; Liu, Yan; Yu, Bing [Green Chemistry, 2022, vol. 51]

Same Skeleton Products

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[ 55142-85-3 ]

A218498[ 53885-35-1 ]

5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride

Reason: Free-salt

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P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 55142-85-3 ] {[proInfo.proName]}

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Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 55142-85-3 ]

[ 55142-85-3 ] Synthesis Path-Upstream 1~12

[ 55142-85-3 ] Synthesis Path-Downstream 1~79

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Precautionary Statements-General

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