[ CAS No. 1037298-24-0 ]

Name: 1037298-24-0|2-Amino-5-chloro-4-iodophenol|95%
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SKU: A261773
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Quality Control of [ 1037298-24-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1037298-24-0 ]

SDS Specification

Alternatived Products of [ 1037298-24-0 ]

Product Details of [ 1037298-24-0 ]

CAS No. :	1037298-24-0	MDL No. :	MFCD27978469
Formula :	C₆H₅ClINO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SHJLQMPWDJBRDG-UHFFFAOYSA-N
M.W :	269.47 g/mol	Pubchem ID :	92135481
Synonyms :

Calculated chemistry of [ 1037298-24-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.6
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.46
Log Po/w (XLOGP3) :	2.16
Log Po/w (WLOGP) :	2.24
Log Po/w (MLOGP) :	2.33
Log Po/w (SILICOS-IT) :	2.27
Consensus Log Po/w :	2.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.32
Solubility :	0.13 mg/ml ; 0.000484 mol/l
Class :	Soluble
Log S (Ali) :	-2.76
Solubility :	0.464 mg/ml ; 0.00172 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.03
Solubility :	0.251 mg/ml ; 0.000933 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.0

Safety of [ 1037298-24-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1037298-24-0 ]

* 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.

Downstream synthetic route of [ 1037298-24-0 ]

[ 1037298-24-0 ] Synthesis Path-Downstream 1~10

1
[ 1037298-24-0 ]
[ 1629270-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C 3: methanol; sodium cyanoborohydride / toluene
	Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C

Reference： [1]Current Patent Assignee: ARAXES PHARMA LLC - US2014/288045, 2014, A1
[2]Current Patent Assignee: ARAXES PHARMA LLC - WO2016/44772, 2016, A1

2
[ 1037298-24-0 ]
[ 1629270-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C 3: methanol; sodium cyanoborohydride / toluene 4: water; lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C
	Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 60 °C

Reference： [1]Current Patent Assignee: ARAXES PHARMA LLC - US2014/288045, 2014, A1
[2]Current Patent Assignee: ARAXES PHARMA LLC - WO2016/44772, 2016, A1

3
[ 1037298-24-0 ]
[ 1629267-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C 3: methanol; sodium cyanoborohydride / toluene 4: water; lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 5: potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
	Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 60 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: ARAXES PHARMA LLC - US2014/288045, 2014, A1
[2]Current Patent Assignee: ARAXES PHARMA LLC - WO2016/44772, 2016, A1

4
[ 1037298-24-0 ]
[ 1629267-96-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / methanol; toluene / 2 h / 20 °C 3.1: methanol; sodium cyanoborohydride / toluene 4.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 5.1: chloroformic acid ethyl ester; 4-methyl-morpholine / tetrahydrofuran / 0.75 h / -10 °C 5.2: 0.5 h / -10 - 20 °C
	Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 60 °C 4.1: chloroformic acid ethyl ester; 4-methyl-morpholine / tetrahydrofuran / 0.75 h / -10 °C 4.2: 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: ARAXES PHARMA LLC - US2014/288045, 2014, A1
[2]Current Patent Assignee: ARAXES PHARMA LLC - WO2016/44772, 2016, A1

5
[ 1037298-24-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C

Reference： [1]Current Patent Assignee: ARAXES PHARMA LLC - US2014/288045, 2014, A1

6
[ 1037298-24-0 ]
[ 23719-80-4 ]
[ 1629270-05-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In tetrahydrofuran for 15h; Inert atmosphere; Reflux;	44 2-Amino-5-chloro-4-cyclopropylphenol Example 44 2-Amino-5-chloro-4-cyclopropylphenol To a mixture of 2-amino-5-chloro-4-iodophenol (500 mg, 1.9 mmol), PdCl2(dppf) (136 mg, 0.19 mmol) in THF (10 mL) under argon at RT, cyclopropylmagnesium bromide (16 mL, 11.4 mmol, 0.7 M in THF) was added and the mixture was stirred at reflux for 15 h. The mixture was allowed to cool to RT, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (10-20% ethyl acetate/hexanes) to afford the desired product (220 mg, 63% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.27 (s, 1H), 6.62 (s, 1H), 6.22 (s, 1H), 4.53 (s, 2H), 1.89-1.93 (m, 1H), 0.83-0.87 (m, 2H), 0.46-0.49 (m, 2H).
63%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 15h; Inert atmosphere; Reflux;	56 2-Amino-S -chloro-4-cyclopropylphenol To a mixture of 2-amino-S-chloro-4-iodophenol (500 mg, 1.9 mmol), PdC12(dppf) (136 mg, 0.19 mmol) in THF (10 mL) under argon at RT, cyclopropylmagnesium bromide (16 mL, 11.4 mmol, 0.7 M in THF) was added and the mixture was stirred at reflux for 15 h. The mixture was allowed to cool to RT, and partitioned between ethyl acetate and water. The organic layer was washed with brine,dried over Na2504 and concentrated. The residue was purified by flash column chromatography on silica gel (10-20% ethyl acetate / hexanes) to afford the desired product (220 mg, 63% yield) as a brown solid. ‘H NMR (400 MHz, DMSO-d6) ö: 9.27 (s, 1H), 6.62 (s, 1H), 6.22 (s, 1H), 4.53(s, 2H), 1.89-1.93 (m, 1H), 0.83-0.87 (m, 2H), 0.46-0.49 (m, 2H).

Reference： [1]Current Patent Assignee: ARAXES PHARMA LLC - US2014/288045, 2014, A1 Location in patent: Paragraph 0643
[2]Current Patent Assignee: ARAXES PHARMA LLC - WO2016/44772, 2016, A1 Location in patent: Paragraph 333

7
[ 6627-53-8 ]
[ 1037298-24-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trifluoromethanesulfonic acid anhydride; sulfuric acid; N-iodo-succinimide / 400 min / 20 °C 2: iron; ammonium chloride / ethanol; water; tetrahydrofuran / 2 h / 70 °C 3: boron tribromide / dichloromethane / 3 h / 20 °C / Cooling with ice

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP4067343, 2022, A1

8
[ 1508278-48-5 ]
[ 1037298-24-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iron; ammonium chloride / ethanol; water; tetrahydrofuran / 2 h / 70 °C 2: boron tribromide / dichloromethane / 3 h / 20 °C / Cooling with ice

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP4067343, 2022, A1

9
[ 1508278-49-6 ]
[ 1037298-24-0 ]

Yield	Reaction Conditions	Operation in experiment
257 mg	With boron tribromide In dichloromethane at 20℃; Cooling with ice;	2.3 (Step 3) 2-Amino-5-chloro-4-iodophenol A solution of 4-chloro-5-iodo-2-methoxyaniline (400 mg) obtained in the preceding step 2 in dichloromethane (4.0 mL) was cooled in an ice bath, and boron tribromide (1 M solution in dichloromethane, 2.8 mL) was added thereto. The mixture was warmed to room temperature and stirred for 3 hours. Water and chloroform were added to the reaction mixture, and then, the mixture was neutralized with an aqueous sodium hydroxide solution, followed by extraction with chloroform/methanol (5/1). The organic layer was washed with water and saturated saline and dried over sodium sulfate, then the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (hexane:ethyl acetate) to obtain the title compound (257 mg) .

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP4067343, 2022, A1 Location in patent: Paragraph 0210; 0212

10
[ 1011460-68-6 ]
[ 1037298-24-0 ]
[ 2648340-01-4 ]

Yield	Reaction Conditions	Operation in experiment
4 mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 100℃;	57.1 (Step 1) 2-Amino-5-chloro-4-(1-(trifluoromethyl)vinyl)phenol To a solution of 2-amino-5-chloro-4-iodophenol (50 mg) obtained in Production Example 2 in 1,4-dioxane (1 mL), 4,4,6-trimethyl-2-(1-(trifluoromethyl)vinyl)-1,3,2-dioxaborinane (91.5 mg), Pd(PPh3)4 (32 mg), and a 2 M aqueous sodium carbonate solution (186 µL) were added, and the mixture was stirred overnight at 100°C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with saturated saline. The resultant product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to obtain the title compound (4.0 mg) .
4 mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 100℃;	57.1 (Step 1) 2-Amino-5-chloro-4-(1-(trifluoromethyl)vinyl)phenol To a solution of 2-amino-5-chloro-4-iodophenol (50 mg) obtained in Production Example 2 in 1,4-dioxane (1 mL), 4,4,6-trimethyl-2-(1-(trifluoromethyl)vinyl)-1,3,2-dioxaborinane (91.5 mg), Pd(PPh3)4 (32 mg), and a 2 M aqueous sodium carbonate solution (186 µL) were added, and the mixture was stirred overnight at 100°C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with saturated saline. The resultant product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to obtain the title compound (4.0 mg) .

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP4067343, 2022, A1 Location in patent: Paragraph 0388
[2]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP4067343, 2022, A1 Location in patent: Paragraph 0388

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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.
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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.
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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.
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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:
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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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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
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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. 1037298-24-0 ]

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[ 1037298-24-0 ] Synthesis Path-Downstream 1~10

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Aryls

Chlorides

Amines

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[ 1037298-24-0 ]