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Ticlopidine hydrochloride

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Name

Ticlopidine hydrochloride

EINECS 258-837-4
CAS No. 53885-35-1 Density 1.37 g/cm3
PSA 31.48000 LogP 4.69970
Solubility Soluble in ethanol; almost soluble in water Melting Point 205°C
Formula C14H14ClNS.HCl Boiling Point 367.3 °C at 760 mmHg
Molecular Weight 300.252 Flash Point 175.9 °C
Transport Information N/A Appearance White powder
Safety 36 Risk Codes 22
Molecular Structure Molecular Structure of 53885-35-1 (Ticlopidine hydrochloride) Hazard Symbols HarmfulXn
Synonyms

Ticlopidine;Ticlopidine hydrochloride;

Article Data 14

Ticlopidine hydrochloride Synthetic route

60612-23-9

N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
In 1,3-DIOXOLANE; ethyl acetate95%
With hydrogenchloride In 1,3-dioxane; water at 90℃; for 6h; Temperature;82%
646-06-0

1,3-DIOXOLANE

60612-23-9

N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride89%
With hydrogenchloride In water at 90℃; for 6h; Temperature;82%
With hydrogenchloride In water at 90℃; for 6h; Temperature;91 g
54903-50-3

4,5,6,7-tetrahydrothieno[3,2-c]pyridine

611-19-8

1-chloro-2-(chloromethyl)benzene

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
Stage #1: 4,5,6,7-tetrahydrothieno[3,2-c]pyridine; 1-chloro-2-(chloromethyl)benzene In dichloromethane at 60℃; for 1h;
Stage #2: With hydrogenchloride In dichloromethane Reagent/catalyst; Solvent; Temperature;
87%
30433-91-1

[2-(2-thyenyl)ethyl]amine

aqueous potassium carbonate

aqueous potassium carbonate

2053-29-4

methyleneamine

611-19-8

1-chloro-2-(chloromethyl)benzene

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; formaldehyd; potassium carbonate In tetrahydrofuran; methanol; water; toluene84%
54903-50-3

4,5,6,7-tetrahydrothieno[3,2-c]pyridine

108-20-3

di-isopropyl ether

611-19-8

1-chloro-2-(chloromethyl)benzene

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate In ethanol83%

C13H14ClNS*(x)ClH

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,3-dioxane; water at 90℃; for 6h; Temperature;82%
7440-44-0

pyrographite

60612-23-9

N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
Stage #1: N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride With hydrogenchloride In 1,3-dioxane; water at 7 - 90℃; for 9h;
Stage #2: pyrographite In ethanol at 4℃; for 4h; Temperature;
82%
18997-19-8

Chloromethyl pivalate

69061-17-2

N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
In dimethyl sulfoxide51%
505-23-7

1,3 dithiane

60612-23-9

N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
In 1,2-dimethoxyethane9.4 g (62.7%)
69061-17-2

N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine

53885-35-1

ticlopidine hydrochloride

Conditions
ConditionsYield
With sodium hydroxide; methanesulfonic acid; paraformaldehyde In N-methyl-acetamide; dichloromethane

Ticlopidine hydrochloride Specification

The Ticlopidine hydrochloride, with the CAS registry number 53885-35-1 and EINECS registry number 258-837-4, has the systematic name of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (1:1). It is a kind of white solid, and belongs to the following product categories: Active Pharmaceutical Ingredients; Heterocyclic Compounds; Bases & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; Sulfur & Selenium Compounds; API's; Purinergics P2 receptor. And the molecular formula of this chemical is C14H14ClNS.HCl. What's more, it is often used as antiplatelet drug.

Physical properties about Ticlopidine hydrochloride are:  (1)ACD/LogP: 3.231; (2)ACD/LogD (pH 5.5): 1.64; (3)ACD/LogD (pH 7.4): 3.06; (4)ACD/BCF (pH 5.5): 4.28; (5)ACD/BCF (pH 7.4): 112.21; (6)ACD/KOC (pH 5.5): 34.69 ; (7)ACD/KOC (pH 7.4): 910.40; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.638; (11)Molar Refractivity: 74.44 cm3; (12)Molar Volume: 207.057 cm3; (13)Polarizability: 29.51 10-24cm3; (14)Surface Tension: 51.5359992980957 dyne/cm; (15)Density: 1.274 g/cm3; (16)Flash Point: 175.918 °C; (17)Enthalpy of Vaporization: 61.378 kJ/mol; (18)Boiling Point: 367.268 °C at 760 mmHg

Preparation of Ticlopidine hydrochloride: Add 4,5,6,7-tetrahydro thieno [3,2-c] pyridine 13.9g(0.1mol), 2-chlorobenzyl chloride 16.1g (0.1mol), triethylamine 15g(0.15mol) and acetonitrile 150ml to the reaction bulb at room temperature with stirring, recycle the acetonitrile by vacuum concentration. Add 100ml toluene and 100ml water, and the solution should be fully mixed, then the solution will separate if left to stand. Get the toluene layer, and dry it with MgSO4. After filtering, control the PH to 2 by adding chlorine hydride isopropyl alcohol solution, and keep stirring for 2 minutes, cool it down, and separate out solid. Filter again, and gives pale yellow sokid. Recrystallize with absolute ethyl alcohol, you can get the white solid, and that's your aim product. The yield is about 75%.

Ticlopidine hydrochloride can be prepared by 4,5,6,7-tetrahydro thieno [3,2-c] pyridine, 2-chlorobenzyl chloride, triethylamine and acetonitrile

You should be cautious while dealing with this chemical. It is harmful if swallowed. Therefore, you had better take the wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.Clc1ccccc1CN3Cc2c(scc2)CC3
(2)InChI: InChI=1/C14H14ClNS.ClH/c15-13-4-2-1-3-11(13)9-16-7-5-14-12(10-16)6-8-17-14;/h1-4,6,8H,5,7,9-10H2;1H
(3)InChIKey: MTKNGOHFNXIVOS-UHFFFAOYAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LD50 intraperitoneal 500mg/kg (500mg/kg)   New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 295, 1983.
mouse LD50 intravenous 55mg/kg (55mg/kg)   United States Patent Document. Vol. #4051141,
mouse LD50 oral 600mg/kg (600mg/kg)   Medical Pharmacy. Vol. 15, Pg. 272, 1981.
mouse LD50 subcutaneous 2690mg/kg (2690mg/kg)   Medical Pharmacy. Vol. 15, Pg. 272, 1981.
rat LD50 intravenous 70mg/kg (70mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981.
rat LD50 oral 1780mg/kg (1780mg/kg)   Medical Pharmacy. Vol. 15, Pg. 272, 1981.
rat LD50 subcutaneous > 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakkyoku. Pharmacy. Vol. 32, Pg. 1499, 1981.
women LDLo unreported 180mg/kg/18D- (180mg/kg) BLOOD: APLASTIC ANEMIA

LIVER: LIVER FUNCTION TESTS IMPAIRED

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Hematology. Vol. 59, Pg. 260, 1998.
women TDLo oral 49mg/kg/1W-I (49mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "JAUNDICE, CHOLESTATIC"
American Journal of Hospital Pharmacy. Vol. 51, Pg. 1821, 1994.
women TDLo oral 189mg/kg/17D- (189mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

LIVER: LIVER FUNCTION TESTS IMPAIRED
American Journal of Hospital Pharmacy. Vol. 51, Pg. 1821, 1994.
women TDLo oral 1896mg/kg/26W (1896mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "JAUNDICE, CHOLESTATIC"
Clinical Pharmacy. Vol. 12, Pg. 398, 1993.

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