[ CAS No. 4397-53-9 ] {[proInfo.proName]}

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Quality Control of [ 4397-53-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4397-53-9 ]

SDS Specification

Alternatived Products of [ 4397-53-9 ]

Product Details of [ 4397-53-9 ]

CAS No. :	4397-53-9	MDL No. :	MFCD00003387
Formula :	C₁₄H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	(C₆H₅)CH₂O(C₆H₄)CHO	InChI Key :	ZVTWZSXLLMNMQC-UHFFFAOYSA-N
M.W :	212.24	Pubchem ID :	78109
Synonyms :

Calculated chemistry of [ 4397-53-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.81
TPSA :	26.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.35
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	2.93
Log Po/w (MLOGP) :	2.6
Log Po/w (SILICOS-IT) :	3.57
Consensus Log Po/w :	2.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.49
Solubility :	0.068 mg/ml ; 0.00032 mol/l
Class :	Soluble
Log S (Ali) :	-3.48
Solubility :	0.0709 mg/ml ; 0.000334 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.01
Solubility :	0.00205 mg/ml ; 0.00000966 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 4397-53-9 ]

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 [ 4397-53-9 ]

* 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 [ 4397-53-9 ]
Downstream synthetic route of [ 4397-53-9 ]

[ 4397-53-9 ] Synthesis Path-Upstream 1~2

1
[ 4397-53-9 ]
[ 371-40-4 ]
[ 70627-52-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 40℃;	P-Fluoroaniline (100 g, 1.1 eq) and isopropanol (1730 ml, 10 V) were added and heated to 40 ° C. with mechanical stirring to precipitate a large amount of a pale yellow crystalline solid gradually, Stir over time and monitor until reaction is complete. The heating was stopped, the temperature was naturally lowered to room temperature while stirring, extraction and filtration were carried out, the filter cake was washed off with cold isopropanol, and after drying, a pale yellow crystalline substance SM 2 was obtained, the mass was 238 g , The yield is 95percent, and the purity is 99percent.
93.6%	Reflux; Large scale	The p-fluoroaniline (1.11kg, 10mol) and 4-benzyloxybenzaldehyde (2.12kg, 10mol) were added to 10L of toluene and refluxed. After the reaction was completed, the solvent was evaporated and the solvent was normal. n-hexane and ethyl acetate 10:1 Crystallization gave Compound 4 (2.85 kg) in 93.6percent yield.

Reference： [1] Patent: JP2016/147843, 2016, A, . Location in patent: Paragraph 0016
[2] Patent: CN107793339, 2018, A, . Location in patent: Paragraph 0021; 0023; 0031; 0038
[3] Pharmacy and Pharmacology Communications, 2000, vol. 6, # 1, p. 25 - 29
[4] Journal of Organic Chemistry, 2018,

2
[ 4397-53-9 ]
[ 403648-76-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8386 - 8395

[ 4397-53-9 ] Synthesis Path-Downstream 1~10

1
[ 4397-53-9 ]
[ 61275-22-7 ]
(S)-2-(4-Benzyloxybenzyl)amino-N-methylpropionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 579 - 590

2
[ 61439-59-6 ]
[ 4397-53-9 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 1275 - 1278

3
[ 4397-53-9 ]
[ 61439-59-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 1223 - 1227
[2]Chemical Communications,2018,vol. 54,p. 12002 - 12005

4
[ 4397-53-9 ]
[ 3171-46-8 ]
2-(4-(benzyloxy)phenyl)-4,6-dimethyl-1H-benzimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8743 - 8749

5
[ 4397-53-9 ]
[ 34800-90-3 ]
N'-[(4-benzyloxyphenyl)methylidene]-2-(naphthalen-1-yl)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; for 3h;Reflux;	General procedure: These compounds were prepared by refluxing substituted acetohydrazides 3(a-b) with 4-(benzyloxy) benzaldehyde (0.01 mol) in 20 mL of ethanol for 3 h. On cooling the reaction mixture to room temperature, a solid product appeared. The respective crude product was recrystallized using ethanol. N'-[(4-Benzyloxyphenyl)methylidene]-<strong>[34800-90-3]2-(naphthalen-1-yl)acetohydrazide</strong> (5b). The final product was obtained as a white solid with 78% yield. m.p. 182-184 C. IR (KBr): numax (cm-1), 3180 (NH), 3042 (Ar C-H), 2918 (C-H), 1661 (C=O), 1600 (C=N), 1520(C=C). 1H-NMR (400 MHz, DMSO-d6): delta ppm, 4.91 (2H, s,H-1), 5.13 (2H, s, -O-CH2), 7.07-8.21 (11H, m, Ar-H), 8.15 (1H, s, H-5), 12.43 (1H, s, H-3). 13C-NMR (100 MHz, DMSO): delta ppm, 171.01 (amide C=O, C-2), 168.80 (benzyloxyC-O), 148.62 (N=CH, C-5), (aromatic C?s), 71.01 (O-CH2), 28.75 (naphthyl-CH2, C-1). LCMS (m/z): 395 (M++1). Calcd. for C26H22N2O2: C, 79.16; H, 5.62; N, 7.10; Found: C,79.14; H, 5.64; N, 7.08 %.
78%	In ethanol; for 3h;Reflux;	General procedure: These compounds were prepared by refluxing substituted acetohydrazides 3(a-b) with 4-(benzyloxy) benzaldehyde (0.01 mol) in 20 mL of ethanol for 3 h. On cooling the reaction mixture to room temperature, a solid product appeared. The respective crude product was recrystallized using ethanol.

Reference： [1]Letters in drug design and discovery,2016,vol. 13,p. 547 - 562
[2]Letters in drug design and discovery,2016,vol. 13,p. 547 - 562

6
[ 4397-53-9 ]
[ 784-04-3 ]
C₃₀H₂₂O₂ [ No CAS ]

Reference： [1]EXCLI Journal,2017,vol. 16,p. 628 - 649

7
[ 4397-53-9 ]
[ 784-04-3 ]
C₃₀H₂₂O₂ [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2017,vol. 51,p. 564 - 575

8
[ 4397-53-9 ]
[ 784-04-3 ]
3-anthracen-9-yl-5-(4-benzyloxy-phenyl)-4,5-dihydro-1H-pyrazole [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2017,vol. 51,p. 564 - 575

9
[ 4397-53-9 ]
[ 1986-47-6 ]
(1S*,2R*)-N-(4-(benzyloxy)benzyl)-2-phenylcyclopropan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 144,p. 52 - 67

10
[ 4397-53-9 ]
[ 96145-98-1 ]
(Z)-4-(4-(benzyloxy)benzylidene)-2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	at 160℃; for 0.25h;	General procedure: 3a (141mg, 0.5mmol) and benzaldehyde (106mg, 0.75mmol) were placed in a microwave-proof glass tube and heated for 15 min at 160C in a commercial microwave apparatus. The reaction was cooled to room temperature. The reaction product was precipitated by addition of ethyl acetate and hexane, collected by filtration, and recrystallized from hexane and ethyl acetate. The title compound was obtained as an orange solid (93mg, 0.30mmol, 59%).

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2973 - 2983

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Technical Information

? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nomenclature of Ethers ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 4397-53-9 ]

Aryls

[ 1700-37-4 ]

3-Benzyloxybenzaldehyde

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[ 101093-56-5 ]

4-(Benzyloxy)-2-methylbenzaldehyde

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4-Isobutoxybenzaldehyde

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Aldehydes

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4-(Benzyloxy)-2-methylbenzaldehyde

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2-(Benzyloxy)benzaldehyde

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4-Isobutoxybenzaldehyde

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4-Propoxybenzaldehyde

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Ethers

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3-Benzyloxybenzaldehyde

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4-(Benzyloxy)-2-methylbenzaldehyde

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[ 5896-17-3 ]

2-(Benzyloxy)benzaldehyde

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4-Isobutoxybenzaldehyde

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4-Propoxybenzaldehyde

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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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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.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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H401	Toxic to aquatic life
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[ CAS No. 4397-53-9 ] {[proInfo.proName]}

Quality Control of [ 4397-53-9 ]

Related Doc. of [ 4397-53-9 ]

Product Details of [ 4397-53-9 ]

Calculated chemistry of [ 4397-53-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4397-53-9 ]

Application In Synthesis of [ 4397-53-9 ]

[ 4397-53-9 ] Synthesis Path-Upstream 1~2

[ 4397-53-9 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 4397-53-9 ]

Aryls

Aldehydes

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 4397-53-9 ]