[ CAS No. 206559-36-6 ] {[proInfo.proName]}

Name: 206559-36-6|3-Benzyloxyphenylisothiocyanate|97%
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3d Animation Molecule Structure of 206559-36-6

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Quality Control of [ 206559-36-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 206559-36-6 ]

SDS Specification

Alternatived Products of [ 206559-36-6 ]

Product Details of [ 206559-36-6 ]

CAS No. :	206559-36-6	MDL No. :	MFCD00060374
Formula :	C₁₄H₁₁NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QJLFNDXMZQJMDL-UHFFFAOYSA-N
M.W :	241.31	Pubchem ID :	561446
Synonyms :

Calculated chemistry of [ 206559-36-6 ]

Physicochemical Properties

Num. heavy atoms :	17
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 :	72.11
TPSA :	53.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.05
Log Po/w (XLOGP3) :	5.19
Log Po/w (WLOGP) :	3.85
Log Po/w (MLOGP) :	4.37
Log Po/w (SILICOS-IT) :	5.03
Consensus Log Po/w :	4.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.86
Solubility :	0.0033 mg/ml ; 0.0000137 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.06
Solubility :	0.000208 mg/ml ; 0.000000863 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.26
Solubility :	0.00132 mg/ml ; 0.00000546 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.3

Safety of [ 206559-36-6 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P261-P273-P280-P305+P351+P338-P310	UN#:	2923
Hazard Statements:	H331-H302-H312-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 206559-36-6 ]

* 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 [ 206559-36-6 ]
Downstream synthetic route of [ 206559-36-6 ]

[ 206559-36-6 ] Synthesis Path-Upstream 1~1

1
[ 1484-26-0 ]
[ 6160-65-2 ]
[ 206559-36-6 ]

Reference： [1] Patent: WO2005/7601, 2005, A2, . Location in patent: Page/Page column 35-36

[ 206559-36-6 ] Synthesis Path-Downstream 1~8

1
[ 206559-36-6 ]
[ 959938-92-2 ]
methyl [trans-4-(4-[(5-[3-(benzyloxy)phenyl]amino}-1,3,4-oxadiazol-2-yl)carbonyl]amino}-3-nitrophenyl)cyclohexyl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		Intermediate 21 : Methyl fcralpha«s-4-(4-([(5-{f3-(benzyloxy)phenyI1amino\|-l,3,4- oxadiazol-2-yl)carbonilamino}-3-nitrophenvi)cyclohexyllacetate; l-(Benzyloxy)-3-isothiocyanatobenzene (290 mg, 1.2 mmol) was added in one portion to a stirred solution of methyl [/ralpha«5-4-(4-[hydrazino(oxo)acetyl]amino}-3- nitrophenyl)cyclohexyl]acetate (Intermediate lvi, 378 mg, 1.0 mmol) in DMA (5 mL) and the reaction mixture was stirred at ambient temperature for 4 h. EDCI (288 mg, 1.5 mmol) was added in one portion and the reaction mixture was heated in a microwave at 80C for 10 mins. Water (15 mL) was added and the mixture was filtered to leave a solid, which was washed with water to give the title compound as a solid (470mg, 80%). 'H NMR deltal.Odelta-l^l (2H, m), 1.46-1.6 (2H, m), 1.73-1.9 (5H, m), 2.27 (2H, d), 2.6-2.7(IH, m), 3.61 (3H, s), 5.12 (2H, s), 6.76 (IH, dd), 7.17 (IH, dd), 7.25-7.5 (7H, m), 7.7 (IH, dd), 7.92-8.05 (2H, m), 11.05 (IH, s), 11.4 (IH, s); MS m/e MH+ SSO.

Reference： [1]Patent: WO2007/141517,2007,A1 .Location in patent: Page/Page column 59

3
[ 1484-26-0 ]
[ 6160-65-2 ]
[ 206559-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃;	EXAMPLE 1. PREPARATION OF 1- (3-BENZYLOXY) PHENYLTHIOUREA (Compound 1); 1. I 02N X 1. 2. 1. TCD ., base >, I Compound 1 [0114] 3-Nitrophenol (X) is converted to ether (Y) by sequential treatment with sodium hydride and benzylbromide. Reduction of the aniline with tin chloride provides aniline (Z). In certain circumstances the reduction may be accomplished using a hydrogen/Pd catalyst system when the substituent on the aryl group does not include an aryl group. [0115] The final product, Compound 1 is obtained by treatment of Z with thiocarbonyl di- imidazole followed by ammonia. 3-Benzyloxyaniline (5 g, 25 mmol) is added dropwise over a one minute period to 4.94 g (27.6 mmol) thiocabonyl di-imidazole in methylene chloride (150 ml). The resulting mixture is stirred at room temperature overnight. An additional 400 mg thiocarbonyl di- imidazole (TCDI) is added and the reaction is continued for 2 hours more. The reaction is diluted with hexane and filtered through silica. Concentration provides 5.1 g of the desired 3- benzyloxyphenyl isothiocyanate. [0116] A portion of this isothiocyanate (50 mg, 0.21 mmol) in 1 ml methylene chloride is mixed with 0.5 ml of 2 M ammonia in methanol. After 30 minutes the reaction is concentrated to provide Compound 1 in quantitative yield. [0117] Alternatively thiocarbonyl di-imidazole (1.1 mmol, 196 mg) is added to a solution of 3-benzyloxyaniline (1 mmol, 199 mg) in dichloromethane (5 mL). The reaction is stirred at room temperature until the aniline is consumed, about 1 hour. A solution of methanolic ammonia (2 M, 2 mL) is added and the stirring continued for 2 hours. Solvent is evaporated and the residue purified by chromatography on silica gel to give 150 mg of (3-benzyloxyphenyl) thiourea. [0118] NMR (CDCI3) D : 5.08 (s, 2H), 6.03 (brs, 2H), 6.8 (M, 2H), 6.93 (m, 1H), 7. 3- 7. 47 (M, 6H), 7.82 (brs, 1H). MS (APCI) : M++1 = 259.

Reference： [1]Patent: WO2005/7601,2005,A2 .Location in patent: Page/Page column 35-36

4
[ 206559-36-6 ]
[ 117174-83-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia; In methanol; dichloromethane; for 0.5h;Product distribution / selectivity;	EXAMPLE 1. PREPARATION OF 1- (3-BENZYLOXY) PHENYLTHIOUREA (Compound 1); 1. I 02N X 1. 2. 1. TCD ., base >, I Compound 1 [0114] 3-Nitrophenol (X) is converted to ether (Y) by sequential treatment with sodium hydride and benzylbromide. Reduction of the aniline with tin chloride provides aniline (Z). In certain circumstances the reduction may be accomplished using a hydrogen/Pd catalyst system when the substituent on the aryl group does not include an aryl group. [0115] The final product, Compound 1 is obtained by treatment of Z with thiocarbonyl di- imidazole followed by ammonia. 3-Benzyloxyaniline (5 g, 25 mmol) is added dropwise over a one minute period to 4.94 g (27.6 mmol) thiocabonyl di-imidazole in methylene chloride (150 ml). The resulting mixture is stirred at room temperature overnight. An additional 400 mg thiocarbonyl di- imidazole (TCDI) is added and the reaction is continued for 2 hours more. The reaction is diluted with hexane and filtered through silica. Concentration provides 5.1 g of the desired 3- benzyloxyphenyl isothiocyanate. [0116] A portion of this isothiocyanate (50 mg, 0.21 mmol) in 1 ml methylene chloride is mixed with 0.5 ml of 2 M ammonia in methanol. After 30 minutes the reaction is concentrated to provide Compound 1 in quantitative yield. [0117] Alternatively thiocarbonyl di-imidazole (1.1 mmol, 196 mg) is added to a solution of 3-benzyloxyaniline (1 mmol, 199 mg) in dichloromethane (5 mL). The reaction is stirred at room temperature until the aniline is consumed, about 1 hour. A solution of methanolic ammonia (2 M, 2 mL) is added and the stirring continued for 2 hours. Solvent is evaporated and the residue purified by chromatography on silica gel to give 150 mg of (3-benzyloxyphenyl) thiourea. [0118] NMR (CDCI3) D : 5.08 (s, 2H), 6.03 (brs, 2H), 6.8 (M, 2H), 6.93 (m, 1H), 7. 3- 7. 47 (M, 6H), 7.82 (brs, 1H). MS (APCI) : M++1 = 259.

Reference： [1]Patent: WO2005/7601,2005,A2 .Location in patent: Page/Page column 35-36

5
[ 206559-36-6 ]
C₂₄H₂₆ClN₂Pol [ No CAS ]
C₃₈H₃₇ClN₃OPolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 4h;	Step b): General procedure for the preparation of the N-(3-amino-propyl)-N'-(benzyloxyphenyl)thiourea resins; A 0.24 M solution of benzyloxyphenyl isothiocyanate in dichloromethane (4.5 ml; 6 eq.) is added to a reactor containing the 1,3-propane-diamine resin (180 umol; 1 eq.). The suspension is stirred for 4 hours at room temperature. The resin is then washed with dichloromethane (3x5 ml) and N-methylpyrrolidone (NMP; 3x5 ml). The resin is stored as a suspension in NMP (1 ml) and then used in the following reaction.

Reference： [1]Patent: WO2006/10422,2006,A1 .Location in patent: Page/Page column 20

6
[ 206559-36-6 ]
[ 892491-52-0 ]
5-[3-(benzyloxy)phenyl]amino}-N-(6-morpholin-4-ylpyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3873 - 3878

7
[ 206559-36-6 ]
[ 32315-10-9 ]
C₁₅H₁₁F₄NO₂ [ No CAS ]

Reference： [1]Nature,2019,vol. 573,p. 102 - 107

8
[ 206559-36-6 ]
C₂₃H₁₈F₃NO₂ [ No CAS ]

Reference： [1]Nature,2019,vol. 573,p. 102 - 107

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P222	Do not allow contact with air.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P262	Do not get in eyes, on skin, or on clothing.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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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. 206559-36-6 ] {[proInfo.proName]}

Quality Control of [ 206559-36-6 ]

Related Doc. of [ 206559-36-6 ]

Product Details of [ 206559-36-6 ]

Calculated chemistry of [ 206559-36-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 206559-36-6 ]

Application In Synthesis of [ 206559-36-6 ]

[ 206559-36-6 ] Synthesis Path-Upstream 1~1

[ 206559-36-6 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 206559-36-6 ]

Aryls

Ethers

Isocyanates and Isothiocyanates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 206559-36-6 ]