[ CAS No. 634-91-3 ] {[proInfo.proName]}

Name: 634-91-3|3,4,5-Trichloroaniline|98%
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SKU: A780434
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Inaccessible (Haz class 6.1), International	USD 150+
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3d Animation Molecule Structure of 634-91-3

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Quality Control of [ 634-91-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 634-91-3 ]

SDS Specification

Alternatived Products of [ 634-91-3 ]

Product Details of [ 634-91-3 ]

CAS No. :	634-91-3	MDL No. :	MFCD00007769
Formula :	C₆H₄Cl₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XOGYQVITULCUGU-UHFFFAOYSA-N
M.W :	196.46	Pubchem ID :	12469
Synonyms :

Calculated chemistry of [ 634-91-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.88
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	3.32
Log Po/w (WLOGP) :	3.24
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	3.06
Consensus Log Po/w :	2.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.59
Solubility :	0.0501 mg/ml ; 0.000255 mol/l
Class :	Soluble
Log S (Ali) :	-3.54
Solubility :	0.0563 mg/ml ; 0.000287 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.89
Solubility :	0.0253 mg/ml ; 0.000129 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 634-91-3 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P273-P280-P301+P310-P311	UN#:	2811
Hazard Statements:	H301+H311+H331-H373-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 634-91-3 ]

* 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 [ 634-91-3 ]
Downstream synthetic route of [ 634-91-3 ]

[ 634-91-3 ] Synthesis Path-Upstream 1~4

1
[ 20098-48-0 ]
[ 634-91-3 ]

Yield	Reaction Conditions	Operation in experiment
95 %Chromat.	With carbon monoxide; water In tetrahydrofuran at 125℃; for 24 h; Inert atmosphere; Autoclave	General procedure: Into a reaction glass vial fitted with a magnetic stirring bar anda septum cap penetrated with a syringe needle was added theCo3O4/NGrC-catalyst (2 molpercent, 3 wtpercent Co-phenanthroline oncarbon, 20 mg) followed by the nitro arene (0.5 mmol), theinternal standard (hexadecane, 100 μL), THF (2 mL), and H2O(200 μL). The reaction vial was then placed into a 300 mL autoclave.The autoclave was flushed twice with nitrogen, pressurized with CO at 30 bar pressure. Finally, the autoclave was usedat 60 bar by adding nitrogen and placed into an aluminiumblock, which was preheated at 125 °C. After 24 h the autoclavewas placed into a water bath and cooled to r.t. Finally, theremaining gas was discharged, and the samples were removedfrom the autoclave, diluted with EtOAc and analyzed by GC. Todetermine the yield of isolated products, the general procedurewas scaled up by the factor of two, and no internal standard wasadded. After the reaction was completed, the catalyst was filteredoff, and the filtrate was concentrated and purified by silicagel column chromatography (n-heptane–EtOAc mixtures) togive the corresponding anilines.

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 321 - 327
[2] Anales de Quimica, 1996, vol. 92, # 2, p. 95 - 100
[3] Journal of Organic Chemistry, 1947, vol. 12, p. 275,278, 280
[4] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1948, vol. 21, p. 1152,1158[5] Chem. Zentralbl., 1949, vol. 120, p. 6193
[6] Chemische Berichte, 1894, vol. 27, p. 548
[7] Journal of the Chemical Society, 1905, vol. 87, p. 324
[8] Recueil des Travaux Chimiques des Pays-Bas, 1918, vol. 37, p. 201
[9] Chemical Communications, 2010, vol. 46, # 10, p. 1769 - 1771
[10] Chemical Communications, 2011, vol. 47, # 39, p. 10972 - 10974
[11] Synlett, 2015, vol. 26, # 3, p. 313 - 317
[12] ChemCatChem, 2018, vol. 10, # 9, p. 2009 - 2013

2
[ 21928-51-8 ]
[ 634-91-3 ]

Reference： [1] Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688

3
[ 634-91-3 ]
[ 609-19-8 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1931, vol. 50, p. 112,120

4
[ 634-91-3 ]
[ 3107-21-9 ]

Reference： [1] Acta Chimica Academiae Scientiarum Hungaricae, 1957, vol. 10, p. 227,229

[ 634-91-3 ] Synthesis Path-Downstream 1~11

1
[ 20098-48-0 ]
[ 634-91-3 ]

Yield	Reaction Conditions	Operation in experiment
95%Chromat.	With carbon monoxide; water; In tetrahydrofuran; at 125℃; under 22502.3 - 45004.5 Torr; for 24h;Inert atmosphere; Autoclave;	General procedure: Into a reaction glass vial fitted with a magnetic stirring bar anda septum cap penetrated with a syringe needle was added theCo3O4/NGrC-catalyst (2 mol%, 3 wt% Co-phenanthroline oncarbon, 20 mg) followed by the nitro arene (0.5 mmol), theinternal standard (hexadecane, 100 muL), THF (2 mL), and H2O(200 muL). The reaction vial was then placed into a 300 mL autoclave.The autoclave was flushed twice with nitrogen, pressurized with CO at 30 bar pressure. Finally, the autoclave was usedat 60 bar by adding nitrogen and placed into an aluminiumblock, which was preheated at 125 C. After 24 h the autoclavewas placed into a water bath and cooled to r.t. Finally, theremaining gas was discharged, and the samples were removedfrom the autoclave, diluted with EtOAc and analyzed by GC. Todetermine the yield of isolated products, the general procedurewas scaled up by the factor of two, and no internal standard wasadded. After the reaction was completed, the catalyst was filteredoff, and the filtrate was concentrated and purified by silicagel column chromatography (n-heptane-EtOAc mixtures) togive the corresponding anilines.

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 321 - 327
[2]ACS Catalysis,2019,p. 4302 - 4307
[3]Anales de Quimica,1996,vol. 92,p. 95 - 100
[4]Journal of Organic Chemistry,1947,vol. 12,p. 275,278, 280
[5]Zhurnal Prikladnoi Khimii,1948,vol. 21,p. 1152,1158
Chemisches Zentralblatt,1949,vol. 120,p. 6193
[6]Chemische Berichte,1894,vol. 27,p. 548
[7]Recueil des Travaux Chimiques des Pays-Bas,1918,vol. 37,p. 201
[8]Chemical Communications,2010,vol. 46,p. 1769 - 1771
[9]Chemical Communications,2011,vol. 47,p. 10972 - 10974
[10]Synlett,2015,vol. 26,p. 313 - 317
[11]ChemCatChem,2018,vol. 10,p. 2009 - 2013

2
[ 634-91-3 ]
[ 609-19-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 112,120

3
[ 634-91-3 ]
[ 3107-21-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1013 - 1018
[2]Acta Chimica Academiae Scientiarum Hungaricae,1957,vol. 10,p. 227,229

4
[ 634-91-3 ]
[ 53314-66-2 ]
[ 73627-70-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 180 - 200℃; for 14h;

Reference： [1]Kleiner, Hanss-Jerg [Liebigs Annalen der Chemie, 1980, # 2, p. 324 - 332]

5
[ 634-91-3 ]
[ 64634-61-3 ]

Yield	Reaction Conditions	Operation in experiment
		Process 1; Production of 3,4,5-trichloro-1-iodobenzene Into a suspension of 25.0 g of 3,4,5-trichloroaniline in 10 mL of acetonitrile, 25 mL of methanol and 100 mL of water, a solution of 9.7 g of sodium nitrite in 25 mL of water was dropped while stirring and ice-cooling the suspension over 20 minutes and after the completion of the dropping, the resultant mixture was stirred at 5 to 6C for 30 minutes. Next, the reaction mixture was dropped into 75 mL of an aqueous solution of 23.2 g of potassium iodide which was heated to 80C over 20 minutes and after the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 1 hour. After the completion of the reaction, 50 mL of an aqueous solution of 7.64 g of urea was added to the reaction mixture and the resultant mixture was left to be cooled down to room temperature while stirring the mixture, followed by diluting the mixture with 400 mL of ethyl acetate. Subsequently, an insoluble substance was filtered off from the mixture by Celite filtration. The organic phase was washed with 300 mL of a saturated sodium hydrogen sulfite aqueous solution and next with 200 mL of water and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluding with hexane to obtain 29.3 g of the objective substance as a light yellow crystal. Melting point: 45.0 to 46.0C 1H NMR (CDCl3, Me4Si, 300 MHz) delta 7.70 (s, 2H).

Reference： [1]Patent: EP2199287,2010,A1 .Location in patent: Page/Page column 107

6
[ 4744-50-7 ]
[ 634-91-3 ]
[ 1293923-63-3 ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: A solution of 3,4,5-trichloroaniline (1.96 g, 10 mmol) and acid anhydride (10 mmol) in glacial acetic acid (20 mL) was refluxed for 3 h. The solvent was removed under reduced pressure until the volume reached ca. 5 mL. After addition of 10 mL of acetic anhydride, the solution was refluxed again for 20 h. The solvent was removed under reduced pressure. The residue was neutralized by a solution of sodium bicarbonate (4%) until effervescence ceased. The precipitate obtained was washed with water, dried (P2O5) and recrystallized from an appropriate solvent.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 1648 - 1655

7
[ 32703-79-0 ]
[ 634-91-3 ]
[ 1293923-75-7 ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: A solution of 3,4,5-trichloroaniline (1.96 g, 10 mmol) and acid anhydride (10 mmol) in glacial acetic acid (20 mL) was refluxed for 3 h. The solvent was removed under reduced pressure until the volume reached ca. 5 mL. After addition of 10 mL of acetic anhydride, the solution was refluxed again for 20 h. The solvent was removed under reduced pressure. The residue was neutralized by a solution of sodium bicarbonate (4%) until effervescence ceased. The precipitate obtained was washed with water, dried (P2O5) and recrystallized from an appropriate solvent.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 1648 - 1655

8
[ 141573-95-7 ]
[ 634-91-3 ]
[ 1373886-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃;	The aniline compound (la to Id) (leq.) and DFMMP (1 eq.), both dissolved in an inert solvent were added to a suspension of a base (1.5 eq.) in the inert solvent at 0C. The conversion of aniline to anilide was followed by GC analyses.

Reference： [1]Patent: WO2012/55864,2012,A1 .Location in patent: Page/Page column 19-20

9
[ 634-91-3 ]
[ 86-48-6 ]
1-hydroxy-N-(3,4,5-trichlorophenyl)naphthalene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With phosphorus trichloride In chlorobenzene at 130℃; for 0.25h; Microwave irradiation;	General Procedure for Synthesis of N-(substituted phenyl)-1-hydroxynaphthalene-2-carboxamides 1-24 General procedure: 1-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the corresponding substituted aniline (5.3 mmol) were suspended in 30 mL of dry chlorobenzene. Phosphorous trichloride (2.65 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130 °C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure, the solid residue washed with 2 M HCl, and the crude product was recrystallized from aqueous ethanol. All the studied compounds are presented in Table 1.

Reference： [1]Gonec, Tomas; Kos, Jiri; Pesko, Matus; Dohanosova, Jana; Oravec, Michal; Liptaj, Tibor; Kralova, Katarina; Jampilek, Josef [Molecules, 2017, vol. 22, # 10]

10
[ 21928-51-8 ]
[ 634-91-3 ]

Reference： [1]Nature Chemistry,2017,vol. 9,p. 681 - 688

11
[ 621-82-9 ]
[ 634-91-3 ]
(2E)-3-phenyl-N-(3,4,5-trichlorophenyl)prop-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With phosphorus trichloride In chlorobenzene at 130℃; for 0.5h; Microwave irradiation;	3.1.2. Synthesis General procedure: Cinnamic acid (3.37 mM) was suspended at room temperature in dry chlorobenzene (20 mL) inside a microwave tube, where phosphorus trichloride (1.7 mM) and the corresponding aniline derivative (3.37 mM) were added dropwise. Following this step, a magnetic stirrer was added to the tube and the reaction mixture was transferred to the microwave reactor (max. 500 W) at 130 °C for 30 min, where the synthesis at elevated pressure was performed. After the mixture was cooled to 60 °C, the solvent was evaporated in vacuum. A solid residue was washed with 2M HCl, and a crude product was recrystallized, using 96% ethanol first, and then 50% ethanol [26,28].

Reference： [1]Bak, Andrzej; Devinsky, Ferdinand; Hosek, Jan; Hutta, Milan; Jampilek, Josef; Jankech, Timotej; Kos, Jiri; Kozik, Violetta; Michnova, Hana; Oravec, Michal; Smolinski, Adam; Strharsky, Tomas; Swietlicka, Aleksandra [Molecules, 2020, vol. 25, # 18]

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Physical hazards
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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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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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. 634-91-3 ] {[proInfo.proName]}

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[ 634-91-3 ] Synthesis Path-Upstream 1~4

[ 634-91-3 ] Synthesis Path-Downstream 1~11

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Aryls

Chlorides

Amines

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[ 634-91-3 ]