[ CAS No. 90390-27-5 ]

Name: 90390-27-5|3,5-Difluorobenzylamine|98%
Brand: Ambeed
SKU: A156187
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3d Animation Molecule Structure of 90390-27-5

Structure of 90390-27-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 90390-27-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 90390-27-5 ]

SDS Specification

Alternatived Products of [ 90390-27-5 ]

Product Details of [ 90390-27-5 ]

CAS No. :	90390-27-5	MDL No. :	MFCD00061244
Formula :	C₇H₇F₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VJNGGOMRUHYAMC-UHFFFAOYSA-N
M.W :	143.13 g/mol	Pubchem ID :	145211
Synonyms :

Calculated chemistry of [ 90390-27-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	34.03
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.68
Log Po/w (XLOGP3) :	0.98
Log Po/w (WLOGP) :	2.11
Log Po/w (MLOGP) :	2.41
Log Po/w (SILICOS-IT) :	2.28
Consensus Log Po/w :	1.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.72
Solubility :	2.71 mg/ml ; 0.0189 mol/l
Class :	Very soluble
Log S (Ali) :	-1.11
Solubility :	11.0 mg/ml ; 0.0768 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.151 mg/ml ; 0.00105 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 90390-27-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H227-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 90390-27-5 ]

* 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 [ 90390-27-5 ]
Downstream synthetic route of [ 90390-27-5 ]

[ 90390-27-5 ] Synthesis Path-Upstream 1~3

1
[ 64248-63-1 ]
[ 90390-27-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With ammonia In methanol; ethyl acetate	A: 3,5-Difluorobenzylamine A solution of 3,5-difluorobenzonitrile (4 g, 28.8 mmole) in methanol saturated with ammonia (100 ml) was added to a slurry of methanol washed Raney nickel. The mixture was shaken under 50 psi hydrogen for 1.5 hours, filtered and the filtrate evaporated. The residue was dissolved in ethyl acetate and extracted with 3N HCl. The acidic solution was basified with 50percent sodium hydroxide and was extracted into ethyl acetate. The organic extract was dried (Na₂ SO₄) and concentrated to give 3.0 g (74percent) of title compound as a yellow oil which was stored under nitrogen.

Reference： [1] Organic Letters, 1999, vol. 1, # 2, p. 183 - 185
[2] Patent: US4835154, 1989, A,
[3] Patent: EP323737, 1989, A1,
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 781 - 789
[5] Patent: US4707488, 1987, A,
[6] Patent: US4761415, 1988, A,
[7] Patent: US4728741, 1988, A,
[8] Catalysis Science and Technology, 2016, vol. 6, # 13, p. 4768 - 4772

2
[ 677728-83-5 ]
[ 90390-27-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118

3
[ 100-46-9 ]
[ 90390-27-5 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 16, p. 3804 - 3809

[ 90390-27-5 ] Synthesis Path-Downstream 1~7

1
[ 1003-32-3 ]
[ 90390-27-5 ]
(3,5-Difluoro-benzyl)-[1-thiazol-5-yl-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 3701 - 3710

2
[ 90390-27-5 ]
[ 52353-35-2 ]
(3,5-difluoro-benzyl)-(2-trifluoromethyl-quinazolin-4-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran Heating;

Reference： [1]Sielecki, Thais M.; Johnson, Tricia L.; Liu, Jie; Muckelbauer, Jodi K.; Grafstrom, Robert H.; Cox, Sarah; Boylan, John; Burton, Catherine R.; Chen, Haiying; Smallwood, Angela; Chang, Chong-Hwan; Boisclair, Michael; Benfield, Pamela A.; Trainor, George L.; Seitz, Steven P. [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 9, p. 1157 - 1160]

3
[ 2985-33-3 ]
[ 90390-27-5 ]
N-(3,5-difluoro-benzyl)-2-methyl-malonamic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 18h;	1.b b) N- (3, 5-DIFLUORO-BENZYL)-2-METHYL-MALONAMIC acid ethyl ester To a solution of 2.92 g (20 mmol) methyl-malonic acid monoethyl ester in 100 ml of tetrahydrofuran 2.86 g (20 mmol) of 3, 5-difluorobenzylamine, 3.83 g (20 mmol) of N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride, 2.70 g (20 mmol) of 1- hydroxybenzotrizole hydrate and 2.58 g (20 mmol) of N, N-diisopropyl-ethylamine were added. The mixture was stirred at room temperature for 18 h. After concentration in vacuo 0.5 N HCl (50 ml) was added and the mixture was extracted with dichloromethane (three times 50 ml). The combined organic layers were extracted with 0.5 N aqueous NAHCO3 solution, dried (MGS04) and evaporated on the rotary evaporator. The residue was purified by flash chromatography (hexane/ethyl acetate = 3: 1) to yield 4.29 g (79 %) of the title compound as white crystalline solid. MS m/e (%): 272.2 (M+H+, 100).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2004/69826, 2004, A1 Location in patent: Page 19

4
[ 64269-79-0 ]
[ 90390-27-5 ]
[ 59608-97-8 ]
[ 1108653-16-2 ]

Yield	Reaction Conditions	Operation in experiment
		A 3-neck 500ml round bottle flask was charged with <strong>[59608-97-8]4-chloromethyl-thiazol-2-ylamine hydrochloride</strong> (Intermediate 1, 1 eq.) and CDI (1.05 eq.) and purged with nitrogen. <n="53"/>Anhydrous THF was added via cannula. To the resulting stirring granular suspension was added DIPEA (1.05 eq.) dropwise via addition funnel. After the addition of DIPEA was complete, the 3, 5-difluoro-benzyl amine (1.0 eq.) was added dropwise in the same manner. The reaction was quenched with DI water and the THF was removed in vacuo. The resulting orange residue was partitioned with water and DCM. The organic layer was dried with Na2SO4, filtered and solvent was removed in vacuo. The crude was purified by column chromatography (acetone/ hexanes) followed by recrystallization from iPrOAc and hexanes to afford Intermediate 107: l-(3,5-difluorobenzyl)-3-(4- chloromethyl)thiazol-2-yl)urea as a white solid.

Reference： [1]Patent: WO2009/15193,2009,A1 .Location in patent: Page/Page column 51-52

5
[ 90390-27-5 ]
[ 52833-94-0 ]
[ 1394930-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	General procedure: 2-Amino-5-bromonicotinic acid (250 mg, 1.15 mmol) was dissolved in 4 ml of DMF. The solution was cooled in an ice bath. Then to the solution were successively added HATU (460 mg, 1.21 mmol), DIPEA (210.68 mul, 1.21 mmol), (2,3-difluorophenyl)methanamine (173 mg, 1.21 mmol). The resulting solution was stirred at room temperature for 2 h and then the saturated sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate (EA). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was used in the next step without purification.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5169 - 5180

6
[ 27876-94-4 ]
[ 90390-27-5 ]
(2E,4E,6E,8E,10E,12E,14E)-N¹,N¹⁶-bis(3,5-difluorobenzyl)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenediamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃;	<strong>[27876-94-4]Crocetin</strong> GX-1 (purchased from Sigma) (0.5 mmol, 164 mg)EDCI (1.25 mmol, 239 mg),HOBt (1.25 mmol, 169 mg) in a 25 ml reaction flask.Et3N (2.5 mmol, 350 l) and 20 ml of CH2Cl2 were added under ice-cooling,Finally, 3,5-difluorobenzylamine (1.1 mmol, 130 mul) was added,The reaction was carried out at 0 C for 4 h,Followed by reaction at room temperature overnightThe products were detected by TLC and LC-MS.After confirming the reaction is complete,The reaction was stopped. The reaction solution was filtered and the solvent was removed in vacuo. 10 ml of EA was added to the solution and the solution was washed with 10 ml of 2% HCl, 5% NaHCO3 and H2O three times, and the solvent was removed in vacuo to give the crude product. The resulting crude product was separated on a silica gel column and eluted with three column volumes of CHCl3. The crude product, GX-N, was then isolated on a silica gel column and eluted with two column volumes of solvent (petroleum ether: ethyl acetate = 10: 1).N, N-dimethylformamide,And its structure was characterized by NMR.Yield: 68%.
68%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃;	<strong>[27876-94-4]Crocetin</strong> GX-1 (purchased from Sigma) (0.5 mmol, 164 mg), EDCI (1.25 mmol, 239 mg), and HOBt (1.25 mmol, 169 mg) were added in a 25 ml reaction flask. Under ice-cooling conditions, Et3N (2.5 mmol, 350 mul) and CH2Cl2 (20 ml) were added. Finally, 3,5-difluorobenzylamine (1.1 mmol, 130 mul) was added. The reaction was carried out at 0 C for 4 h followed by reaction at room temperature overnight. The products were detected by TLC and LC-MS. After confirming the reaction is complete, the reaction was stopped. The reaction solution was filtered. The solvent was removed in vacuo. 10 ml EA was added to dissolve. Washed with 2% HCl, 5% NaHCO3, H2O 10ml each 3 times. The solvent EA was finally removed in vacuo to give the crude product. The resulting crude product was separated on a silica gel column. Elution was carried out with three column volumes of CHCl3. The crude product GX-N was obtained. Then, again silica gel column separation. Elution was carried out with two column volumes of solvent (petroleum ether: ethyl acetate = 10: 1). The final products GX-N. Structure was characterized by NMR. Yield: 68%.
68%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0℃; for 4h;	<strong>[27876-94-4]Crocetin</strong> GX-1 (purchased from Sigma) (0.5 mmol, 164 mg), EDCI (1.25 mmol,239 mg), HOBt (1.25 mmol, 169 mg) in a 25 ml reaction flask.Under ice-cooling, Et3N (2.5 mmol, 350 l)And CH2Cl220ml. Finally, 3,5-difluorobenzylamine (1.1mmol, 130mul) was added and reacted at 0 C for 4h, followed by reaction at room temperature overnight.Using TCL and LC-MS test whether the product is generated, to determine the reaction is complete, stop the reaction. The reaction solution was filtered, trueRemove the solvent empty, add 10ml EA dissolved, followed by 2% HCl, 5% NaHCO3, H2O 10ml each washed three times, and finally the solvent EA was removed in vacuo to give the crude product. The crude product obtained was separated on a silica gel column and eluted with three column volumes of CHCl3. The crude GX-N product was obtained which was then separated again on a silica gel column and eluted with two column volumes of solvent (petroleum ether: ethyl acetate = 10: 1).The product GX-N was finally obtained and its structure was characterized by NMR. Yield: 68%.

Reference： [1]Patent: CN106187806,2016,A .Location in patent: Paragraph 0046; 0047; 0048
[2]Patent: CN106187949,2016,A .Location in patent: Paragraph 0046; 0047; 0048
[3]Patent: CN106431950,2017,A .Location in patent: Paragraph 0042; 0043; 0044

7
[ 90390-27-5 ]
[ 21615-34-9 ]
N-(3,5-difluorobenzyl)-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.4%	Stage #1: 3,5-difluorobenzylamine With triethylamine In toluene for 0.5h; Cooling with ice; Stage #2: 2-Methoxybenzoyl chloride In toluene at 20℃; for 1.5h;	3 Example 3 Preparation of N-(3,5difluorobenzyl)-2-methoxybenzamide (Compound A03) Dissolve 143 g (1.0 mol) of 3,5-difluorobenzylamine and 150 g of triethylamine (1.5 mol) in 1.5 L of toluene, stir for 30 minutes in an ice bath, then add 170 dissolved in 500 ml of toluene dropwise G (1.0mol) 2-methoxybenzoyl chloride, after the addition is complete, continue to stir at room temperature for 1.5 hours, add 200 ml of saturated sodium bicarbonate solution to wash, and then successively wash with 200 ml of deionized water and saturated brine, without After drying over sodium sulfate, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 245 g of the product, with a yield of 88.4%.

Reference： [1]Current Patent Assignee: NORTHWEST A&F UNIVERSITY - CN111202068, 2020, A Location in patent: Paragraph 0057-0059

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Ghs Precautionary Statements

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Code	Phrase
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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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P263	Avoid contact during pregnancy/while nursing.
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Code	Phrase
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P321
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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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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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Physical hazards
Code	Phrase
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
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
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. 90390-27-5 ]

Quality Control of [ 90390-27-5 ]

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Product Details of [ 90390-27-5 ]

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[ 90390-27-5 ] Synthesis Path-Upstream 1~3

[ 90390-27-5 ] Synthesis Path-Downstream 1~7

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Fluorinated Building Blocks

Aryls

Amines

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[ 90390-27-5 ]