[ CAS No. 6575-05-9 ] {[proInfo.proName]}

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Quality Control of [ 6575-05-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6575-05-9 ]

SDS Specification

Alternatived Products of [ 6575-05-9 ]

Product Details of [ 6575-05-9 ]

CAS No. :	6575-05-9	MDL No. :	MFCD00052711
Formula :	C₇H₂Cl₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PGODHCIOIPODFE-UHFFFAOYSA-N
M.W :	206.46	Pubchem ID :	522179
Synonyms :		Chemical Name :	2,4,6-Trichlorobenzonitrile

Calculated chemistry of [ 6575-05-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.19
TPSA :	23.79 ?2

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) :	-5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	3.52
Log Po/w (WLOGP) :	3.52
Log Po/w (MLOGP) :	3.2
Log Po/w (SILICOS-IT) :	3.72
Consensus Log Po/w :	3.2

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.74
Solubility :	0.0375 mg/ml ; 0.000181 mol/l
Class :	Soluble
Log S (Ali) :	-3.7
Solubility :	0.0409 mg/ml ; 0.000198 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.34
Solubility :	0.0095 mg/ml ; 0.000046 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.71

Safety of [ 6575-05-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6575-05-9 ]

* 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 [ 6575-05-9 ]
Downstream synthetic route of [ 6575-05-9 ]

[ 6575-05-9 ] Synthesis Path-Upstream 1~6

1
[ 6324-50-1 ]
[ 557-21-1 ]
[ 6575-05-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 85℃;	Add l-iodo-2,4,6-trichlorobenzene (1500 mg, 4.88 mmol), zinc cyanide (345 mg, 2.94 mmol) and tetrakis(triphenylphosphine)palladium(0) (282 mg, 0.244 mmol) to anhydrous DMF (30 mL). Heat to 85 ⁰C overnight. Cool to room temperature, dilute with toluene, wash with 2 N ammonium hydroxide (3x) and saturated aqueous sodium chloride and concentrate. Purify by silica gel chromatography, eluting with EPO <DP n="75"/>hexanes/dichloromethane to give 2,4,6-trichlorobenzonitrile (850 mg, 84percent): ¹HNMR (400 MHz, CDCl₃) δ 7.76 (s, IH), 7.65 (s, IH).

Reference： [1] Patent: WO2006/44454, 2006, A1, . Location in patent: Page/Page column 73-74

2
[ 22241-21-0 ]
[ 6575-05-9 ]

Reference： [1] Chinese Chemical Letters, 2011, vol. 22, # 7, p. 815 - 818

3
[ 23400-04-6 ]
[ 6575-05-9 ]

Reference： [1] Journal of the American Chemical Society, 1940, vol. 62, p. 1432,1434

4
[ 74-96-4 ]
[ 106-94-5 ]
[ 6575-05-9 ]

Reference： [1] Patent: US4530797, 1985, A,

5
[ 634-93-5 ]
[ 6575-05-9 ]

Reference： [1] Chemische Berichte, 1894, vol. 27, p. 3151

6
[ 62-53-3 ]
[ 6575-05-9 ]

Reference： [1] Chemische Berichte, 1894, vol. 27, p. 3151

[ 6575-05-9 ] Synthesis Path-Downstream 1~19

1
[ 6575-05-9 ]
[ 50-43-1 ]

Reference： [1]Chemische Berichte,1894,vol. 27,p. 3151
[2]Journal of the American Chemical Society,1932,vol. 54,p. 4380,4382

2
[ 6575-05-9 ]
[ 23400-04-6 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1902,vol. 21,p. 384

3
[ 6575-05-9 ]
[ 101084-06-4 ]

Yield	Reaction Conditions	Operation in experiment
	With borane-THF; In tetrahydrofuran; at 40℃; for 2h;	A.2.26 Synthesis of (2,4,6-trichlorophenyl)methanamine To a solution of <strong>[6575-05-9]2,4,6-trichlorobenzonitrile</strong> (0.69 mmol) in 2 mL THF was added a solution of BH3 (2.77 mmol, 1 M in THF). The reaction mixture was heated to 40C for 2 h and then cooled to RT. 1 mL MeOH was added and the mixture was stirred at RT for 30 min. Water was added, the mixture was basified with 1 M NaOH solution and extracted twice with EtOAc. The combined organic layers were dried over MgS04 and concentrated in vacuo to give the desired product as slightly yellow oil. LC-MS (C): tR = 0.51 min; [M+H]+: 210.13.
		To a solution of <strong>[6575-05-9]2,4,6-trichlorobenzonitrile</strong> (0.69 mmol) in 2 mL THF was added a solution of BH3 (2.77 mmol, 1M in THF). The reaction mixture was heated to 40 C. for 2 h and then cooled to RT. 1 mL MeOH was added and the mixture was stirred at RT for 30 min. Water was added, the mixture was basified with 1M NaOH solution and extracted twice with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as slightly yellow oil. LC-MS (C): tR=0.51 min; [M+H]+: 210.13.

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1936,vol. <2> 146,p. 88,102
[2]Patent: WO2013/108227,2013,A1 .Location in patent: Page/Page column 65
[3]Patent: US2015/25075,2015,A1 .Location in patent: Paragraph 0402; 0403

4
[ 23400-04-6 ]
[ 6575-05-9 ]

Reference： [1]Journal of the American Chemical Society,1940,vol. 62,p. 1432,1434

5
[ 6575-05-9 ]
[ 873-32-5 ]
[ 1194-65-6 ]
[ 100-47-0 ]
[ 6574-98-7 ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 4809 - 4820

6
[ 6575-05-9 ]
2,4,6-trichloro-<i>N</i>-hydroxy-benzamidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 601 - 615

7
[ 6575-05-9 ]
C₁₈H₁₁Cl₃N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 601 - 615

8
[ 6575-05-9 ]
[ 4136-95-2 ]

Reference： [1]Journal of the American Chemical Society,1932,vol. 54,p. 4380,4382

9
[ 6575-05-9 ]
[ 65305-79-5 ]

Reference： [1]Journal of the American Chemical Society,1932,vol. 54,p. 4380,4382

10
[ 6575-05-9 ]
2,2-dichloro-1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1932,vol. 54,p. 4380,4382

11
[ 62-53-3 ]
[ 6575-05-9 ]

Reference： [1]Chemische Berichte,1894,vol. 27,p. 3151

12
[ 6324-50-1 ]
[ 557-21-1 ]
[ 6575-05-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 85℃;	Add l-iodo-2,4,6-trichlorobenzene (1500 mg, 4.88 mmol), zinc cyanide (345 mg, 2.94 mmol) and tetrakis(triphenylphosphine)palladium(0) (282 mg, 0.244 mmol) to anhydrous DMF (30 mL). Heat to 85 0C overnight. Cool to room temperature, dilute with toluene, wash with 2 N ammonium hydroxide (3x) and saturated aqueous sodium chloride and concentrate. Purify by silica gel chromatography, eluting with EPO <DP n="75"/>hexanes/dichloromethane to give 2,4,6-trichlorobenzonitrile (850 mg, 84%): 1HNMR (400 MHz, CDCl3) delta 7.76 (s, IH), 7.65 (s, IH).

Reference： [1]Patent: WO2006/44454,2006,A1 .Location in patent: Page/Page column 73-74

13
[ 6575-05-9 ]
[ 24473-00-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With formic acid; nickel-aluminum alloy; water; at 100℃; for 4h;	Add <strong>[6575-05-9]2,4,6-trichlorobenzonitrile</strong> (206 mg, 1.0 mmol) to 96% formic acid (5 niL, 96%) and water (1 mL). Add nichol/aluminum alloy (206 mg) to the mixture. Heat at 100 0C for 4 hours. Dilute with ethyl acetate and filter through Celite. Extract the filtrate with. N sodium hydroxide and saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate to give 2,4,6-trichlorobenzaldehyde (195 mg, 93%). 1H NMR (400 MHz, CDCl3) delta 10.36 (s, IH), 7.99 (s,lH), 7.61 (s, IH).

Reference： [1]Patent: WO2006/44454,2006,A1 .Location in patent: Page/Page column 74

14
[ 74-96-4 ]
[ 106-94-5 ]
[ 6575-05-9 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 13 Example 1 was repeated except that the reaction temperature was changed to 355 C. and 2,6-dichlorotoluene containing 2% of ethyl bromide was replaced by 2,4,6-trichlorotoluene containing 2% of n-propyl bromide which was fed at a rate of 50.5 g per hour. 2,4,6-trichlorobenzonitrile was obtained in an amount of 40.7 g per hour. The quantity of unreacted 2,4,6-trichlorotoluene was 4.8 g. Conversion was 90.3%, yield was 77.9%, and selectivity was 86.3%.

Reference： [1]Patent: US4530797,1985,A

15
[ 6575-05-9 ]
[ 39895-55-1 ]
[ 1039766-00-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dimethylaluminum chloride; In hexane; toluene; at 20 - 150℃; for 0.533333h;Microwave irradiation;	EXAMPLE 57; N-[1-[4-(1,1-Dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-2-(2,4,6-trichlorophenyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 57a) 3-[4-(1,1-Dimethylethyl)phenyl]methyl}-6-hydroxy-2-(2,4,6-trichlorophenyl)-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.408 g, 2.50 mmol), <strong>[6575-05-9]2,4,6-trichlorobenzonitrile</strong> (0.619 g, 3.00 mmol) and toluene (3 mL) at room temperature. After 2 min at room temperature, the mixture was stirred in a microwave reactor at 150 C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.60 g, 10.0 mmol), 2-methoxyethanol (15 mL) and 4.37 M sodium methoxide in methanol (2.30 mL, 10.0 mmol) were added and the mixture refluxed under nitrogen for 8 h. After cooling, the mixture was poured into water (150 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.551 g, 50%) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.88 (s, 2 H) 5.59 (s, 1 H) 6.79-6.85 (m, 2 H) 7.18-7.25 (m, 2 H) 7.84 (s, 2 H) 11.94 (br. s., 1 H).

Reference： [1]Patent: US2008/171756,2008,A1 .Location in patent: Page/Page column 38

16
[ 22241-21-0 ]
[ 6575-05-9 ]

Reference： [1]Chinese Chemical Letters,2011,vol. 22,p. 815 - 818

17
[ 6575-05-9 ]
3-[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-2-(2,4,6-trichlorophenyl)-4(3H)-pyrimidinone [ No CAS ]

Reference： [1]Patent: US2008/171756,2008,A1

18
[ 6575-05-9 ]
C₂₆H₂₆Cl₃N₃O₅ [ No CAS ]

Reference： [1]Patent: US2008/171756,2008,A1

19
[ 6575-05-9 ]
N-[1-[4-(1,1-dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-2-(2,4,6-trichlorophenyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine disodium salt [ No CAS ]

Reference： [1]Patent: US2008/171756,2008,A1

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction ? Vilsmeier-Haack Reaction

Historical Records

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[ 6575-05-9 ]

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Ghs Precautionary Statements

Precautionary Statements-General
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P220	Keep/Store away from clothing/combustible materials.
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P222	Do not allow contact with air.
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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

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[ CAS No. 6575-05-9 ] {[proInfo.proName]}

Quality Control of [ 6575-05-9 ]

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Product Details of [ 6575-05-9 ]

Calculated chemistry of [ 6575-05-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6575-05-9 ]

Application In Synthesis of [ 6575-05-9 ]

[ 6575-05-9 ] Synthesis Path-Upstream 1~6

[ 6575-05-9 ] Synthesis Path-Downstream 1~19

Technical Information

Related Functional Groups of [ 6575-05-9 ]

Aryls

Chlorides

Nitriles

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Prevention

Response

Storage

Disposal

Physical hazards

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Environmental hazards

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[ 6575-05-9 ]