[ CAS No. 52465-59-5 ]

Name: 52465-59-5|2,3,6-Trichloro-5-(chloromethyl)pyridine|95%
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SKU: A653693
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{[proInfo.proName]} ,{[proInfo.pro_purity]}

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

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3d Animation Molecule Structure of 52465-59-5

Structure of 52465-59-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 52465-59-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52465-59-5 ]

SDS Specification

Alternatived Products of [ 52465-59-5 ]

Product Details of [ 52465-59-5 ]

CAS No. :	52465-59-5	MDL No. :
Formula :	C₆H₃Cl₄N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DGRWKOIUYLWSEV-UHFFFAOYSA-N
M.W :	230.91	Pubchem ID :	12257871
Synonyms :

Calculated chemistry of [ 52465-59-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.03
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	3.79
Log Po/w (WLOGP) :	3.63
Log Po/w (MLOGP) :	2.9
Log Po/w (SILICOS-IT) :	4.26
Consensus Log Po/w :	3.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.0
Solubility :	0.0233 mg/ml ; 0.000101 mol/l
Class :	Soluble
Log S (Ali) :	-3.75
Solubility :	0.0406 mg/ml ; 0.000176 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.9
Solubility :	0.0029 mg/ml ; 0.0000126 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.0

Safety of [ 52465-59-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 52465-59-5 ]

* 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 [ 52465-59-5 ]
Downstream synthetic route of [ 52465-59-5 ]

[ 52465-59-5 ] Synthesis Path-Upstream 1~4

1
[ 52465-59-5 ]
[ 54718-39-7 ]

Reference： [1] Patent: US3956340, 1976, A,

2
[ 52465-59-5 ]
[ 54718-39-7 ]

Reference： [1] Patent: US3974166, 1976, A,

3
[ 52465-59-5 ]
[ 54718-39-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 1793 - 1804

4
[ 52465-59-5 ]
[ 142266-62-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 1793 - 1804

[ 52465-59-5 ] Synthesis Path-Downstream 1~12

Yield	Reaction Conditions	Operation in experiment
	Verb. (11), POCl3;
	3,5,6-Trichlor-3-chlormethyl-5,6-dehydro-piperidin-2-on, POCl3;

2
[ 52465-59-5 ]
[ 54718-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With mercurous nitrate; nitric acid; copper(II) sulfate In sulfuric acid

Reference： [1]Laeckmann, Didier; Rogister, Françoise; Dejardin, Jean-Victor; Prosperi-Meys, Christelle; Géczy, Joseph; Delarge, Jacques; Masereel, Bernard [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 1793 - 1804]

3
[ 52465-59-5 ]
[ 54903-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2: NH₄OH

4
[ 52465-59-5 ]
[ 58584-88-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2: 81 percent / SOCl₂ / benzene; dimethylformamide / 2.5 h / Heating

5
[ 52465-59-5 ]
[ 142266-62-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2: 81 percent / SOCl₂ / benzene; dimethylformamide / 2.5 h / Heating 3: 90 percent / 10 percent NH₄OH / dioxane / 1 h / 4 °C

6
[ 52465-59-5 ]
[ 465513-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2: 81 percent / SOCl₂ / benzene; dimethylformamide / 2.5 h / Heating 3: 90 percent / 10 percent NH₄OH / dioxane / 1 h / 4 °C 4: 65 percent / 25 percent NH₄OH; NH₃ / 2 h / 130 °C 5: 90 percent / 4N NaOH / 1 h / Heating

7
[ 52465-59-5 ]
[ 465513-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2: 81 percent / SOCl₂ / benzene; dimethylformamide / 2.5 h / Heating 3: 90 percent / 10 percent NH₄OH / dioxane / 1 h / 4 °C 4: 65 percent / 25 percent NH₄OH; NH₃ / 2 h / 130 °C

8
[ 52465-59-5 ]
(2,5,6-trichloro-pyridine-3-carbonyl)guanidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2.1: CDI / dimethylformamide / 1 h / 20 °C 2.2: 12 percent / t-BuOK / dimethylformamide; dioxane / 5 h / 20 °C

9
[ 52465-59-5 ]
(2,6-diamino-5-chloro-pyridine-3-carbonyl)guanidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: HgNO₃; CuSO₄*5H₂O; HNO₃ / H₂SO₄ 2.1: 81 percent / SOCl₂ / benzene; dimethylformamide / 2.5 h / Heating 3.1: 90 percent / 10 percent NH₄OH / dioxane / 1 h / 4 °C 4.1: 65 percent / 25 percent NH₄OH; NH₃ / 2 h / 130 °C 5.1: 90 percent / 4N NaOH / 1 h / Heating 6.1: CDI / dimethylformamide / 1 h / 20 °C 6.2: 22 percent / t-BuOK / dimethylformamide; dioxane / 5 h / 20 °C

10
3,5,6-trichloro-3-chloromethyl-5,6-dehydro-piperidon-2-one [ No CAS ]
[ 41789-40-6 ]
[ 52465-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; trichlorophosphate	1 2,5,6-Trichloro-3-chloromethylpyridine (Example 6) 2,5,6-Trichloro-3-chloromethylpyridine (Example 6) 82.8 g (0.333 mol) of 3,5,6-trichloro-3-chloromethyl-5,6-dehydro-piperidon-2-one (obtained by reacting 3-chloro-3-chloromethylglutarimide with phosphorus pentachloride at a temperature of 70° - 71°C) and 400 ml (4.4 mols) of phosphorus oxychloride are heated in an autoclave at 180°C for 3 hours. Excess phosphorus oxychloride is then removed from the reaction solution on a rotary evaporator and the dark brown residue is poured onto ice. The crystals precipitated are filered off with suction, washed with water and dried overnight over diphosphorus pentoxide.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US3974166, 1976, A

11
Hg(NO₃)2 [ No CAS ]
5H₂ O [ No CAS ]
[ 52465-59-5 ]
[ 54718-39-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With CuSO4; nitric acid;	EXAMPLE 2 SPC4 115.5 g (0.50 mol) of 2,5,6-trichloro-3-chloromethylpyridine, 500 g of 97% strength sulphuric acid, 5 g of Hg(NO3)2 and 2.5 g of CuSO4. 5H2 O are introduced into a 2.5 liter sulphonation flask of the type described in Example 1, and warmed to 110C in an oil bath, whilst stirring vigorously. 150 ml (230 g) of fuming nitric acid are then added dropwise over the course of 1.5 hours. For the first 45 minutes, the reaction is not exothermic. After 50 to 60 minutes, that is to say after about 100 ml of HNO3 have been added dropwise, the reaction solution turns dark brown and the reaction becomes exothermic. As soon as the internal temperature has reached 120C, the oil bath is removed and replaced by ice water cooling, in such a way that the internal temperature does not exceed 130-140C. After completion of the addition of HNO3, the reaction solution is cooled to 40C and poured onto 800 g of ice. The acid which precipitates is filtered off, well pressed out and dried in a vacuum drying cabinet at 40C. 90 g (79.5% of theory) of crude 2,5,6-trichloronicotinic acid of melting point 164-168C are obtained. Recrystallisation of the crude product from water gives pure 2,5,6-trichloronicotinic acid in 86% yield.

Reference： [1]Patent: US3956340,1976,A

12
Hg(NO₃)2 [ No CAS ]
CuSO_4.5H₂ O [ No CAS ]
[ 52465-59-5 ]
[ 54718-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid;	2,5,6-Trichloronicotinic acid (Example 13) 115.5 g (0.5 mol) of 2,5,6-trichloro-3-chloromethylpyridine, 500 g of 97% strength sulphuric acid, 5 g of Hg(NO3)2 and 2.5 g of CuSO4.5H2 O are charged in a sulphonation flask and are heated to 110C in an oil bath with vigorous stirring. 150 ml (230 g) of fuming nitric acid are then added dropwise over the course of 1.5 hours. After about 50 to 60 minutes the reaction becomes exothermic. As soon as the internal temperature has reached 120C, the oil bath is removed and is replaced by ice water cooling of such a kind that the internal temperature does not exceed 130 - 140C. After the completion of the addition of HNO3, the reaction solution is cooled to 40C and poured onto ice. The acid precipitated is filtered off with suction, pressed well and dried in a vacuum drying cabinet at 40C. Pure 2,5,6-trichloronicotinic acid is obtained by recrystallising the crude product from water.

Reference： [1]Patent: US3974166,1976,A

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[ 52465-59-5 ]

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[ 52465-59-5 ]

Pyridines

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2,5-Dichloro-3-(chloromethyl)pyridine

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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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
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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
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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. 52465-59-5 ]

Quality Control of [ 52465-59-5 ]

Related Doc. of [ 52465-59-5 ]

Product Details of [ 52465-59-5 ]

Calculated chemistry of [ 52465-59-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 52465-59-5 ]

Application In Synthesis of [ 52465-59-5 ]

[ 52465-59-5 ] Synthesis Path-Upstream 1~4

[ 52465-59-5 ] Synthesis Path-Downstream 1~12

Related Functional Groups of [ 52465-59-5 ]

Chlorides

Related Parent Nucleus of [ 52465-59-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 52465-59-5 ]

Related Parent Nucleus of
[ 52465-59-5 ]