[ CAS No. 16732-65-3 ] {[proInfo.proName]}

Name: 16732-65-3|6-Bromo-1H-indole-2-carboxylic acid|96%
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SKU: A122895
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3d Animation Molecule Structure of 16732-65-3

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Quality Control of [ 16732-65-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16732-65-3 ]

SDS Specification

Alternatived Products of [ 16732-65-3 ]

Product Details of [ 16732-65-3 ]

CAS No. :	16732-65-3	MDL No. :	MFCD02664469
Formula :	C₉H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SVBVYRYROZWKNJ-UHFFFAOYSA-N
M.W :	240.05	Pubchem ID :	4011696
Synonyms :

Calculated chemistry of [ 16732-65-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.96
TPSA :	53.09 Å²

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) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.46
Log Po/w (XLOGP3) :	3.0
Log Po/w (WLOGP) :	2.63
Log Po/w (MLOGP) :	1.8
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.29

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.66
Solubility :	0.052 mg/ml ; 0.000216 mol/l
Class :	Soluble
Log S (Ali) :	-3.78
Solubility :	0.0399 mg/ml ; 0.000166 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.52
Solubility :	0.0732 mg/ml ; 0.000305 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 16732-65-3 ]

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 [ 16732-65-3 ]

* 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.

Upstream synthesis route of [ 16732-65-3 ]
Downstream synthetic route of [ 16732-65-3 ]

[ 16732-65-3 ] Synthesis Path-Upstream 1~7

1
[ 16732-65-3 ]
[ 5318-27-4 ]

Reference： [1] Chemische Berichte, 1955, vol. 88, p. 370,373

2
[ 16732-65-3 ]
[ 52415-29-9 ]

Reference： [1] Liebigs Annalen der Chemie, 1985, vol. 1985, # 4, p. 785 - 793
[2] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4911 - 4914
[3] Chemische Berichte, 1955, vol. 88, p. 370,373

3
[ 103858-53-3 ]
[ 16732-65-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 19, p. 3957 - 3960
[2] Patent: WO2018/53267, 2018, A1, . Location in patent: Page/Page column 90; 91

4
[ 99365-39-6 ]
[ 16732-65-3 ]

Reference： [1] Journal of the Chemical Society, 1954, p. 3403,3406
[2] Chemische Berichte, 1955, vol. 88, p. 370,373
[3] Journal of the Chemical Society, 1954, p. 3403,3406

5
[ 16732-65-3 ]
[ 64-17-5 ]
[ 103858-53-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	Reflux	To a suspension of 6-bromo-1H-indole-2-carboxylic acid (5.0 g, 20.8 mmol) in MeOH (100 mL) was added SOCl2 (2.26 mL, 31 mmol) very slowly. The mixture was heated under reflux until TLC analysis showed no starting material was left. Solvent was removed under reduced pressure and the crude product was collected as a brown powder (5.52 g, 99percent yield) after drying. It was used for next step reaction without purification. MS: Calcd for C11H11BrNO2 265.99 and 267.99 [M-H-], found 265.95 and 267.95 [M-H-].

Reference： [1] Patent: WO2018/165611, 2018, A1, . Location in patent: Page/Page column 198-199
[2] Patent: EP3339305, 2018, A1, . Location in patent: Paragraph 0133; 0134

6
[ 16732-65-3 ]
[ 103858-53-3 ]

Reference： [1] Gazzetta Chimica Italiana, 1958, vol. 88, p. 1147,1153, 1159
[2] Chemische Berichte, 1955, vol. 88, p. 370,373

7
[ 16732-65-3 ]
[ 923197-75-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4 h; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃;	To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlH₄ (1.0 M in THF, 4.20 mL, 4.20 mmol) dropwise at 0° C. The reaction mixture was stirred for 4 h while warming to room temperature. The reaction was quenched with water and 15percent aqueous NaOH at 0° C. to form a precipitate which was filtered through Celite. The filtrate was extracted with EtOAc (3*). The extracts were dried over Na₂SO₄, filtered and concentrated under reduced pressure to give the title compound (696 mg, 73percent) as a yellow solid: ¹H NMR (500 MHz, CDCl₃) δ 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0, 1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H).

Reference： [1] Liebigs Annalen der Chemie, 1986, # 3, p. 438 - 455
[2] Patent: US2012/157469, 2012, A1, . Location in patent: Page/Page column 28-29
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377

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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.
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.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
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.
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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:
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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.
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Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; In methanol; at 60℃; for 3h;	TDI01249-1-a (2 g, 8.33 mmol) and methanol (20 mL) were added to a 100 mL flask, thionyl chloride (1.98 g16.66 mmol) was added, and then the reaction was performed at 60C for 3 hours. Thin layer chromatography (petroleumether : ethyl acetate=10:1) indicated the reaction was complete. The reaction solution was concentrated to give a crudeproduct, and the crude product was dissolved in dichloromethane (100 mL). The dichloromethane phase was washedwith a saturated aqueous solution of sodium hydrogen carbonate twice (50 ml for each time). The dichloromethanephase was then washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtainTDI01249-1-b (2.149 g, brown solid, yield: 100%).1H NMR (400 MHz, CDCl3) delta 7.59 (s, 1H), 7.54 (d, J = 8.5 Hz, 1H), 7.25 (d, J = 8.6 Hz, 1H), 7.18 (s, 1H), 3.96 (s, 3H).
100%	With thionyl chloride; at 60℃; for 3h;	TDI01249-1-a (2 g, 8.33 mmol) and methanol (20 mL) were added to a 100 mL flask, thionyl chloride (1.98 g, 16.66 mmol) was added, and then the reaction was performed at 60C for 3 hours. Thin layer chromatography (petroleum ether : ethyl acetate=10:1) indicated the reaction was complete. The reaction solution was concentrated to give a crude product, and the crude product was dissolved in dichloromethane (100 mL). The dichloromethane phase was washed with a saturated aqueous solution of sodium hydrogen carbonate twice (50 ml for each time). The dichloromethane phase was then washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain TDI01249-1-b (2.149 g, brown solid, yield: 100%). 1H NMR (400 MHz, CDCl3) delta 7.59 (s, 1H), 7.54 (d, J = 8.5 Hz, 1H), 7.25 (d, J = 8.6 Hz, 1H), 7.18 (s, 1H), 3.96 (s, 3H).
90%	With thionyl chloride; for 2h;Reflux;	Into a 2000-mL 3-necked round-bottom flask was placed a solution of 6-bromo-1 H-indole-2- carboxylic acid 1 (100 g, 417 mmol) in methanol (1000 mL). This was followed by the addition of thionyl chloride (100 g, 840 mmol) dropwise with stirring. The resulting solution was heated to reflux for 2 h. The reaction mixture was cooled to rt and a precipitate was formed. The solids were collected by filtration, washing with methanol, and dried in an oven under reduced pressure, giving 2 (95 g, 90%) as a white solid.

90%	With thionyl chloride; for 2h;Reflux;	2. B Synthesis of X038 Succinate Ester Into a 2000-mL 3-necked round-bottom flask was placed a solution of <strong>[16732-65-3]6-bromo-1H-indole-2-carboxylic acid</strong> 1 (100 g, 417 mmol) in methanol (1000 mL). This was followed by the addition of thionyl chloride (100 g, 840 mmol) dropwise with stirring. The resulting solution was heated to reflux for 2 h. The reaction mixture was cooled to rt and a precipitate was formed. The solids were collected by filtration, washing with methanol, and dried in an oven under reduced pressure, giving 2 (95 g, 90%) as a white solid.
86%	With sulfuric acid; at 0 - 80℃; for 12h;	To the stirred solution of 6-bromo- lH-indole-2-carboxylic acid (la, 5.0 g, 20.83 mmol) in methanol (50.0 mL), sulphuric acid (9 mL, 1.8 vol) was added at 0 C. The reaction mixture was stirred at 80 C for 12 h. After completion of reaction, the reaction mixture was quenched with ice and precipitated solid was filtered and washed with water (100 mL x 2). The compound obtained was dried under vacuum. The crude was purified by CombiFlash using 40 g RediSep and 10% ethyl acetate in hexane as eluent to afford methyl -6-bromo-lH-indole-2-carboxylate as white solid (2a). Yield: 4.5 g (86%). MS (ESI): 252.99 m/z found 253.99 [M+H]+1.
58%	With sulfuric acid;Reflux;	6-Bromo-1H-indole-2-carboxylic acid (1.0 g, 4.17 mmol) was dissolved in methanol (100 mL), and it was treated with catalytic amount of concentrated sulfuric acid. The mixture was refluxed overnight. After removal of solvent, it was diluted with ethyl acetate. The organic layer was washed with 10% NaOH and brine, and it was dried over Na2S04.The organic layer was concentrated under reduced pressure, and the residue was purified on an ISCOchromatograph (0-50% ethyl acetate/hexane) to give product as a pink solid (612 mg, 58%); 'H NMR (300 MHz) (CDCh) d 9.01 (bs, 1H), 7.59 (s, 1H), 7.55 (d, J= 9 Hz, 1H), 7.28-7.24 (m, 1H), 7.19 (s, 1H), 3.96 (s, 3H).
	With thionyl chloride;Reflux;	To a suspension of <strong>[16732-65-3]6-bromo-1H-indole-2-carboxylic acid</strong> (5.0 g, 20.8 mmol) in MeOH (100 mL) was added SOCl2 (2.26 mL, 31 mmol) very slowly. The mixture was heated under reflux until TLC showed no starting material left. Solvent was removed under reduced pressure and the crude product was collected as a brown powder (5.2 g, 98% yield) after drying. It was used for next step reaction without purification.1H NMR (300 MHz, CDCl3) delta 8.88 (br, 1H), 7.59 (s, 1H), 7.55 (d, J = 6 Hz, 1H), 7.25 (m, 1H), 7.19 (s, 1H), 3.96 (s, 3H).

Yield	Reaction Conditions	Operation in experiment
95.5%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 50℃; for 1h;	General procedure: TDI01243-1 (1.0 g, 4.17 mmol) and N,N-dimethylformamide (10 mL) were successively added to a 50 mL single neck flask, HATU (2.38 g, 5.0 mmol) and DIEA (1.72 mL, 10.43 mmol) were cautiously added under stirring, and the reaction was performed in an oil bath at 50 C for 1 h. After the reaction was complete, the reaction solution was slowly poured into water (20 mL) under stirring. A large amount of solid precipitated, and was filtered after being stirred for 30 min. The solid was washed with water as well as a mixed solvent of petroleum ether and ethyl acetate (v/v = 20/1) for several times, to afford TDI01243-2 (1.26 g, grey-yellow solid, yield: 95.5%). 1H NMR (400 MHz, DMSO-d6) delta 12.08 (s, 1H), 10.83 (s, 1H), 9.56 (s, 1H), 9.10 (d, J = 5.9 Hz, 1H), 8.12 (dd, J = 5.5, 2.2 Hz, 1H), 7.73 (d, J = 8.5 Hz, 1H), 7.66 (s, 1H), 7.54 (s, 1H), 7.25 (d, J = 8.5 Hz, 1H). MS m/z (ESI): 317.0 [M+H].
1.17 g	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	Compound TDI01209-4 (1 g, 4.167 mmol) and <strong>[20744-39-2]4-aminopyridazine</strong> (475 mg, 4.999 mmol) were dissolved inN,N-dimethylformamide (40 mL), HATU (1.586 g, 4.167 mmol) and diisopropylethylamine (1.612 g, 12.501 mmol) wereadded, and the reaction was performed at room temperature for 16 h. After completion of the reaction, water (50 mL)was added, and a large amount of solid precipitated, and was filtered after being stirred for 30min to afford compoundTDI01209-5 (1.17 g, yellow solid, yield: 88.9%). MS m/z (ESI): 316.9 [M+H].

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

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride;Reflux;	To a suspension of 6-bromo-1H-indole-2-carboxylic acid (5.0 g, 20.8 mmol) in MeOH (100 mL) was added SOCl2 (2.26 mL, 31 mmol) very slowly. The mixture was heated under reflux until TLC analysis showed no starting material was left. Solvent was removed under reduced pressure and the crude product was collected as a brown powder (5.52 g, 99% yield) after drying. It was used for next step reaction without purification. MS: Calcd for C11H11BrNO2 265.99 and 267.99 [M-H-], found 265.95 and 267.95 [M-H-].
	With sulfuric acid; at 0 - 100℃; for 2h;	6-Bromo-1H-indole-2-carboxylic acid 13a (5.00g, 20.8mmol) was dissolved in 75mL of absolute ethanol and cooled down to 0C, 12.5mL 98% of concentrated sulfuric acid was slowly added, the reaction solution was heated to 100C and was reacted for 2 hours. The reaction solution was slowly poured into an ice-water mixture (200mL), the newly obtained mixture was extracted with ethyl acetate (50mL*3). The combined organic phases were washed with saturated brine (250mL) then saturated sodium carbonate solution (250mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude ethyl 6-bromo-1H-indole-2-carboxylate 13b (5.58g, light red solid), the product was subjected to the next step of reaction without purification. MS m / z (ESI): 269.9 [M + 1]

[ CAS No. 16732-65-3 ] {[proInfo.proName]}

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[ 16732-65-3 ] Synthesis Path-Upstream 1~7

[ 16732-65-3 ] Synthesis Path-Downstream 1~88

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