[ CAS No. 1075-35-0 ] {[proInfo.proName]}

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2D 3D

Structure of 1075-35-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1075-35-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1075-35-0 ]

SDS Specification

Alternatived Products of [ 1075-35-0 ]

Product Details of [ 1075-35-0 ]

CAS No. :	1075-35-0	MDL No. :	MFCD00005619
Formula :	C₉H₈ClN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	WUVWAXJXPRYUME-UHFFFAOYSA-N
M.W :	165.62	Pubchem ID :	70636
Synonyms :

Calculated chemistry of [ 1075-35-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.27
TPSA :	15.79 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	3.08
Log Po/w (WLOGP) :	3.13
Log Po/w (MLOGP) :	2.46
Log Po/w (SILICOS-IT) :	3.63
Consensus Log Po/w :	2.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.064 mg/ml ; 0.000387 mol/l
Class :	Soluble
Log S (Ali) :	-3.08
Solubility :	0.138 mg/ml ; 0.000834 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.28
Solubility :	0.00873 mg/ml ; 0.0000527 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 1075-35-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1075-35-0 ]

* 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 [ 1075-35-0 ]
Downstream synthetic route of [ 1075-35-0 ]

[ 1075-35-0 ] Synthesis Path-Upstream 1~1

1
[ 1075-35-0 ]
[ 124-38-9 ]
[ 21296-93-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10476 - 10480[2] Angew. Chem., 2014, vol. 126, # 39, p. 10644 - 10648,5

[ 1075-35-0 ] Synthesis Path-Downstream 1~12

1
[ 1075-35-0 ]
[ 33513-42-7 ]
[ 57335-86-1 ]

Yield	Reaction Conditions	Operation in experiment
99%		0.96 g of POCl3 was added drop wise to a solution of 2-methyl-5-chloroindole (1.0 g) in 20 mL of DMF), at 10 C. The mixture was stirred at 50 C. for 1 hr, cooled and diluted with saturated NaHCO3. The suspension was heated at 60 C. for 15 min, cooled, and the precipitates of 2-methyl-5-chloroindole-3-carboxaldehyde were filtered.Yield 1.14 g (99%). An analytical sample was crystallized from EtOH.
92%		General procedure: POCl3 (1.73 mL, 18.6 mmol) was slowly added dropwise into stirred and ice-cooled DMF (5.0 mL). The reaction mixture was stirred at 1-5 C for 20 min, then a solution of corresponding substituted 2-methylindole 6 (15.5 mmol) in DMF (5.0 mL) was slowly added. The resulting reaction mixture was slowly warmed to 35 C and kept at this temperature for 40 min. It was then allowed to cool down to room temperature. To this mixture, ice (~10 g) was added followed by 5 M NaOH solution (31 mL, 155 mmol). The reaction mixture was heated at 95 C for 30 min, and then it was allowed to cool down to room temperature. To this mixture, ice (~10 g) was again added, and the resulting reaction mixture was stirred for 30 min. The desired product was collected by filtration and washed several times with water.

Reference： [1]Patent: US2010/168417,2010,A1 .Location in patent: Page/Page column 30
[2]Tetrahedron Letters,2018,vol. 59,p. 1014 - 1018
[3]Chemistry - A European Journal,2016,vol. 22,p. 12637 - 12640
[4]European Journal of Medicinal Chemistry,1989,vol. 24,p. 145 - 154
[5]Green Chemistry,2019,vol. 21,p. 968 - 972
[6]Organic Letters,2021,vol. 23,p. 6515 - 6519
[7]Tetrahedron Letters,2021,vol. 82

2
[ 1075-35-0 ]
[ 79-04-9 ]
[ 620603-92-1 ]

Reference： [1]Pharmaceuticals,2021,vol. 14
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 543 - 552

3
[ 1075-35-0 ]
[ 14204-27-4 ]
5-chloro-2-methyl-3-(phenylthio)-1H-indole [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 565 - 568

4
[ 124064-21-7 ]
[ 1075-35-0 ]
[ 479422-23-6 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 135 - 158

5
[ 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

6
[ 1075-35-0 ]
[ 113100-81-5 ]
[ 683813-23-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylsilane; trifluoroacetic acid; In dichloromethane;	To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (0.86 g, 5.2 mmol) and 4-(3-Oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired product in 94% (1.67 g) yield.
94%	With triethylsilane; trifluoroacetic acid; In dichloromethane;	To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (0.86 g, 5.2 mmol) and 4-(3-oxo-propyl)- benzoic acid methyl ester (1.Og, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired product (1.67g) in 94% yield.
94%	With triethylsilane; trifluoroacetic acid; In dichloromethane;	To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (0.86 g, 5.2 mmol) and 4-(3-oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired product in 94% (1.67 g) yield.

Reference： [1]Patent: US2004/82785,2004,A1 .Location in patent: Page 16
[2]Patent: WO2006/128142,2006,A2 .Location in patent: Page/Page column 34
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 3388 - 3413
[4]Patent: US2008/9485,2008,A1 .Location in patent: Page/Page column 19
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 135 - 158

7
[ 1075-35-0 ]
[ 124064-22-8 ]
[ 872674-58-3 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 135 - 158

8
[ 1075-35-0 ]
[ 25015-63-8 ]
5-chloro-2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 15552 - 15553

9
[ 1075-35-0 ]
[ 936243-76-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3248 - 3265

10
C₁₄H₁₁ClF₃NO₄ [ No CAS ]
[ 1075-35-0 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7721 - 7725

11
[ 1075-35-0 ]
[ 93749-47-4 ]
[ 479422-23-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylsilane; trifluoroacetic acid; In dichloromethane; water; at 20℃; for 48h;	To the above product (1.0 eq) and 5-chloro-2-methyl indole (1.0 eq) in CH2Cl2 (0.12 M) was added triethylsilane (3.0 eq) followed by trifluoroacetic acid (3.0 eq). After being stirred overnight at room temperature, added water and trifluroacetic acid (1.0 eq) to the reaction mixture, stirred at room temperature for two days, diluted with CH2Cl2, washed with 1N NaOH, water, brine, dried over sodium sulfate. Trituration of the material with CH2Cl2 and hexanes afforded the C3 alkylated indole in 92% yield
92%		To the above product (1.0 eq) and 5-chloro-2-methyl indole (1.0 eq) in CH2CI2 (0.12 M) was added triethylsilane (3.0 eq) followed by trifluoroacetic acid (3.0 eq). After being stirred overnight at room temperature, water and trifluroacetic acid (1.0 eq) were added to the reaction mixture, which was stirred at room temperature for two days, diluted with CH2CI2, washed with 1N NaOH, water, and brine, and dried over sodium sulfate. Trituration of the material with CH2CI2 and hexanes afforded the C3 alkylated indole in 92% yield
92%	With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20℃;	To the above product (1.0 eq) and 5-chloro-2-methyl indole (1.0 eq) in CH2Cl2 (0.12 M) was added triethylsilane (3.0 eq) followed by trifluoroacetic acid (3.0 eq). After being stirred overnight at room temperature, added water and trifluroacetic acid (1.0 eq) to the reaction mixture, stirred at room temperature for two days, diluted with CH2Cl2, washed with 1N NaOH, water, brine, dried over sodium sulfate. Trituration of the material with CH2Cl2 and hexanes afforded the C3 alkylated indole in 92% yield

Reference： [1]Patent: US2004/82785,2004,A1 .Location in patent: Page 10
[2]Patent: WO2006/128142,2006,A2 .Location in patent: Page/Page column 25
[3]Patent: US2008/9485,2008,A1 .Location in patent: Page/Page column 12
[4]Tetrahedron,2008,vol. 64,p. 7871 - 7876

12
[ 1075-35-0 ]
5-chloro-3-iodo-2-methyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; p-Chlorothiophenol; In ethanol; for 1.16667h;	A solution of iodine (14 g) was added dropwise over 10 mins to a solution of the 5-chloro- 2-methyl indole (8.3 g) and 4-chlorothiophenol [(8] g) in ethanol (250 ml) and stirred for 1 hour. The mixture was concentrated in vacuo and the residue was treated with diethyl ether to give the sub-title compound as an off white solid (9.9 g) MS: APCI (+ve): 291 [M+H] [+]

Reference： [1]Patent: WO2003/101981,2003,A1 .Location in patent: Page 45

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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Ghs Precautionary Statements

Precautionary Statements-General
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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.
P220	Keep/Store away from clothing/combustible materials.
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
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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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.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
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.
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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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H223	Flammable aerosol
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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
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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
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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
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H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
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H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
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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

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[ CAS No. 1075-35-0 ] {[proInfo.proName]}

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