[ CAS No. 172595-66-3 ] {[proInfo.proName]}

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Quality Control of [ 172595-66-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 172595-66-3 ]

CAS No. :	172595-66-3	MDL No. :
Formula :	C₁₂H₁₂ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	237.68	Pubchem ID :	-
Synonyms :

Safety of [ 172595-66-3 ]

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Application In Synthesis of [ 172595-66-3 ]

* 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.

Downstream synthetic route of [ 172595-66-3 ]

[ 172595-66-3 ] Synthesis Path-Downstream 1~2

1
[ 1075-35-0 ]
[ 96-32-2 ]
[ 172595-66-3 ]

Yield	Reaction Conditions	Operation in experiment
63%		To a 250 mL round bottom flask under an atmosphere of nitrogen was added <strong>[1075-35-0]5-chloro-2-methylindole</strong> (5.0 g, 30.2 mmol, 1.0 equiv) and 100 mL THF. The resulting solution was cooled to -78 C. in a dry ice/acetone bath, and n-butyllithium (21 mL of 1.51M solution, 31.72 mmol, 1.05 equiv) was added dropwise over 30 minutes. This was allowed to stir at -78 C. for 30 minutes, at which point zinc chloride (4.12 g, 30.2 mmol, 1.0 equiv) was added as a solution in 5 mL THF dropwise. The resulting mixture was allowed to warm to room temperature. Methyl bromoacetate (2.78 mL, 30.2 mmol, 1.0 equiv) was then added and the reaction allowed to stir fro 24 hours. The reaction mixture was then poured into 500 mL saturated aqueous ammonium chloride and extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with water and brine and dried over MgSO4. Filtration and concentration in vacuo gave the crude material which was purified by silica gel chromatography to give the desired product as a yellow oil (4.53 g, 63%). 1H NMR (400 MHz, CHLOROFORM-d) δ 2.35 (s, 3H) 3.64 (s, 2H) 3.68 (s, 3H) 6.99-7.07 (m, 1H) 7.09-7.14 (m, 1H) 7.46 (d, J=2.0 Hz, 1H) 7.95 (br. s., 1H).

Reference： [1]Patent: US2011/105509,2011,A1 .Location in patent: Page/Page column 41; 42; 43
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 5088 - 5109
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 135 - 158
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 8859 - 8874

2
[ 172595-66-3 ]
[ 19017-52-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: methyl 2-(5-chloro-2-methyl-1H-indol-3-yl)acetate With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water	84.2 To a 250 mL round bottom flask was added intermediate 114, methyl 2-(5-chloro-2-methyl-1H-indol-3-yl)acetate (4.53 g, 19.07 mmol, 1.0 equiv) and 50 mL THF. To this was added a solution of Lithium hydroxide (2.28 g, 95.37 mmol, 5.0 equiv) in 25 mL water. To the resulting biphasic mixture was added methanol dropwise until a single layer formed. The resulting solution was stirred for 2 hours at room temperature. It was then poured into 1.2 N HCl(aq) and the aqueous layer was extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with water and brine and dried over magnesium sulfate. Filtration and removal of solvent in vacuo gave the desired product (3.59 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H) 3.56 (s, 2H) 6.98 (dd, J=8.5, 2.1 Hz, 1H) 7.25 (d, J=8.6 Hz, 1H) 7.40 (d, J=2.0 Hz, 1H) 11.05 (s, 1H) 12.12 (s, 1H).
84%	With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h;
	With lithium hydroxide In 1,4-dioxane; water for 1.5h;

Reference： [1]Current Patent Assignee: PFIZER INC - US2011/105509, 2011, A1 Location in patent: Page/Page column 42; 43
[2]Location in patent: experimental part Kaila, Neelu; Huang, Adrian; Moretto, Alessandro; Follows, Bruce; Janz, Kristin; Lowe, Michael; Thomason, Jennifer; Mansour, Tarek S.; Hubeau, Cedric; Page, Karen; Morgan, Paul; Fish, Susan; Xu, Xin; Williams, Cara; Saiah, Eddine [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5088 - 5109]
[3]De Vita, Elena; Schüler, Peter; Lovell, Scott; Lohbeck, Jasmin; Kullmann, Sven; Rabinovich, Eitan; Sananes, Amiram; Heßling, Bernd; Hamon, Veronique; Papo, Niv; Hess, Jochen; Tate, Edward W.; Gunkel, Nikolas; Miller, Aubry K. [Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8859 - 8874]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
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P273	Avoid release to the environment.
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P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
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P321
P322
P330	Rinse mouth.
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P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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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:
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P353	Rinse skin with water/shower.
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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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.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P411
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P413
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P422
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P411 + P235	Keep cool.
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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
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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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
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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
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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. 172595-66-3 ] {[proInfo.proName]}

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[ 172595-66-3 ] Synthesis Path-Downstream 1~2

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