[ CAS No. 367-25-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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Quality Control of [ 367-25-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 367-25-9 ]

SDS Specification

Alternatived Products of [ 367-25-9 ]

Product Details of [ 367-25-9 ]

CAS No. :	367-25-9	MDL No. :	MFCD00007648
Formula :	C₆H₅F₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CEPCPXLLFXPZGW-UHFFFAOYSA-N
M.W :	129.11	Pubchem ID :	9709
Synonyms :

Safety of [ 367-25-9 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P305+P351+P338-P311	UN#:	2810
Hazard Statements:	H227-H302+H312-H315-H319-H331-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 367-25-9 ]

* 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 [ 367-25-9 ]
Downstream synthetic route of [ 367-25-9 ]

[ 367-25-9 ] Synthesis Path-Upstream 1~3

1
[ 367-25-9 ]
[ 36556-56-6 ]

Yield	Reaction Conditions	Operation in experiment
0.44 mol	With N-chloro-succinimide In dichloromethane at 10℃; for 2 h; Reflux	0.5 mol (1.0 eq) of 2,4-difluoroaniline and 200 ml of dichloromethane were charged into a reaction flask,Stir to dissolve all,Control the internal temperature of 10 ~ 15 in 5 batches into 0.55mol (1.1eq) NCS,Feeding finished,Heated to reflux 2h,In the control,Raw material reaction is complete,Add 10percent dilute hydrochloric acid to the bottle to adjust the pH to 6-7,The organic phase is separated,Washed,Rotate to dryness to give 0.44 mol (0.88 eq) of 2,4-difluoro-5-chloroaniline.0.44 mol of 2,4-difluoro-5-chloroaniline was charged into 1.5 mol (3 eq) of 25percent dilute sulfuric acid,Stirring 0.5h,And then into which 0.75mol (1.5eq) times of sodium phosphite,Control the internal temperature of 30 ~ 35 drop 0.5mol (1eq) sodium nitrite aqueous solution,Dripping finished control kettle temperature rise per hour 4 ~ 5 ,The program temperature,Kettle temperature rose to 60 ,Insulation stirring 2h,Static stratification,The organic phase is washed with water again,For steam distillation,The distilled product was separated from the distillation column by distillation of 3,5-difluorochlorobenzene 0.41 mol (0.82 eq)Purity 99.8percent.

Reference： [1] Patent: CN106986741, 2017, A, . Location in patent: Paragraph 0017; 0018; 0019; 0020; 0021; 0022

2
[ 367-25-9 ]
[ 1421372-66-8 ]

Reference： [1] Patent: CN107793413, 2018, A,

3
[ 367-25-9 ]
[ 1421373-65-0 ]

Reference： [1] Patent: CN107793413, 2018, A,

[ 367-25-9 ] Synthesis Path-Downstream 1~9

1
[ 320-72-9 ]
[ 367-25-9 ]
[ 80033-99-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 305 - 312

2
[ 367-25-9 ]
[ 181765-85-5 ]
[ 741281-04-9 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 5737 - 5750

3
[ 367-25-9 ]
[ 367-34-0 ]
[ 3862-73-5 ]

Reference： [1]Journal of Fluorine Chemistry,2005,vol. 126,p. 661 - 667

4
[ 367-25-9 ]
[ 2267-99-4 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 94,95, 97

5
[ 3240-35-5 ]
[ 367-25-9 ]
2,4-difluoro-N-(4-sulfamoylbenzylidene)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		75(i) 2,4-Difluoro-N-(4-sulfamoylbenzylidene)aniline Following a procedure similar to that described in Example 1(i), but using 4-sulfamoylbenzaldehyde and 2,4-difluoroaniline as starting materials, the title compound was obtained as a white powder (yield 47%). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) δ ppm: 8.79 (1H, singlet); 8.12 (2H, doublet, J=8 Hz); 7.97 (2H, doublet, J=8 Hz); 7.58-7.34 (4H, multiplet); 7.21-7.13 (1H, multiplet).

Reference： [1]Patent: US5908858,1999,A

6
[ 36556-48-6 ]
[ 2613-34-5 ]
[ 367-25-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide;palladium; In hydrogenchloride; methanol; water;	Example 7 88 ml of methanol, 44 ml of water, 0.2 g of palladium-on-charcoal containing 10% Pd and 0.04 mol of <strong>[2613-34-5]3-chloro-2,4-difluoroaniline</strong> are charged to the same reactor as that of Example 6. A hydrogen pressure is introduced in the reactor, which is heated to 90 C. The hydrogen pressure is kept constant at 1.9*106 Pa absolute at 90 C. During the reaction, sodium hydroxide is added in proportion as hydrochloric acid is given off until an amount is reached which is comparable with that used for a corresponding amount of chlorodifluoroaniline in Example 6. After a period of 3 hours, the degree of conversion of the <strong>[2613-34-5]3-chloro-2,4-difluoroaniline</strong> is 100% and the 2,4-difluoroaniline yield is 99%. The remainder of the conversion product (1%) is composed of 4-fluoroaniline and of traces of aniline.

Reference： [1]Patent: US5856577,1999,A

7
[ 29745-44-6 ]
[ 137640-84-7 ]
[ 367-25-9 ]
N-(2,4-difluorophenyl)-2-(3-α,α,α-trifluoromethylphenoxy)-6-pyridinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In thionyl chloride; dichloromethane;	EXAMPLE 24 Preparation of N-(2,4-difluorophenyl)-2-(3-alpha,alpha,alpha-trifluoromethylphenoxy)-6-pyridinecarboxamide 6-(3-alpha,alpha,alpha-Trifluoromethylphenoxy)picolinic acid (7.1 g) in thionyl chloride (50 ml) was refluxed for 1 hour. The excess thionyl chloride was evaporated in vacuo and dichloromethane added to the residual picolinoyl chloride. A solution of 2,4-difluoroaniline (3.3 g) and triethylamine (2.6 g) in dichloromethane (50 ml) was then added dropwise with stirring at ambient temperature. After stirring a further 1 hour, the reaction mixture was washed with water, dried over anhydrous magnesium sulphate and the dichloromethane evaporated. The residue was purified on a silica gel column using dichloromethane as eluant to give the title compound (6.9 g) as a white solid of melting point 110-111 C. m/e Theory: Found 394:394
	With triethylamine; In thionyl chloride; dichloromethane;	Example 24 Preparation of N-(2,4-difluorophenyl)-2-(3-alpha,alpha,alpha-trifluoromethylphenoxy)-6-pyridinecarboxamide 6-(3-alpha,alpha,alpha-Trifluoromethylphenoxy)picolinic acid (7.1g) in thionyl chloride (50ml) was refluxed for 1 hour. The excess thionyl chloride was evaporated in vacuo and dichloromethane added to the residual picolinoyl chloride. A solution of 2,4-difluoroaniline (3.3g) and triethylamine (2.6g) in dichloromethane (50ml) was then added dropwise with stirring at ambient temperature. After stirring a further 1 hour, the reaction mixture was washed with water, dried over anhydrous magnesium sulphate and the dichloromethane evaporated. The residue was purified on a silica gel column using dichloromethane as eluant to give the title compound (6.9g) as a white solid of melting point 110-111C.

Reference： [1]Patent: US5294597,1994,A
[2]Patent: EP447004,1991,A2

8
[ 367-25-9 ]
[ 27398-39-6 ]
[ 931105-81-6 ]

Yield	Reaction Conditions	Operation in experiment
53%		Example 41; 3-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)pyrazine-2-carboxamide, bis(trifluoroacetic acid) salt; A) 3-Chloro-N-(2,4-difluorophenyl)pyrazine-2-carboxamide; To a mixture of <strong>[27398-39-6]3-chloropyrazine-2-carboxylic acid</strong> (Tyger Scientific, 500 mg, 3.15 mmol) in methylene chloride (30 mL) and DMF (0.1 mL) was added oxalyl chloride (593 mg, 4.7 mmol). After stirring 30 min the reaction mixture was concentrated in vacuo. The residue was taken up in acetonitrile (12 mL) and was treated with triethylamine (920 mg, 9.1 mmol) and 2,4-difluoroaniline (430 mg, 3.3 mmol) and stirred 30 min. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried over anhydrous MgSO4, and then concentrated in vacuo. The resulting solid was recrystallized (ethyl acetate/hexanes) to give the amide (455 mg, 53percent) as a solid. MS(ESI+) m/z 270 (M+H)+.

Reference： [1]Patent: US2007/78140,2007,A1 .Location in patent: Page/Page column 47-48

9
[ 367-25-9 ]
[ 103361-99-5 ]

Reference： [1]Patent: CN107459495,2017,A

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Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Passerini Reaction ? Petasis Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

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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.
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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.
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[ CAS No. 367-25-9 ] {[proInfo.proName]}

Quality Control of [ 367-25-9 ]

Related Doc. of [ 367-25-9 ]

Product Details of [ 367-25-9 ]

Safety of [ 367-25-9 ]

Application In Synthesis of [ 367-25-9 ]

[ 367-25-9 ] Synthesis Path-Upstream 1~3

[ 367-25-9 ] Synthesis Path-Downstream 1~9

Technical Information

Related Functional Groups of [ 367-25-9 ]

Fluorinated Building Blocks

Aryls

Amines

Precautionary Statements-General

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Storage

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Health hazards

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Inquiry

Related Functional Groups of
[ 367-25-9 ]