[ CAS No. 1270294-05-7 ]

Name: 1270294-05-7|(R)-5,7-Difluorochroman-4-ol|97%
Brand: Ambeed
SKU: A488822
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3d Animation Molecule Structure of 1270294-05-7

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Quality Control of [ 1270294-05-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1270294-05-7 ]

SDS Specification

Alternatived Products of [ 1270294-05-7 ]

Product Details of [ 1270294-05-7 ]

CAS No. :	1270294-05-7	MDL No. :	MFCD09763634
Formula :	C₉H₈F₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HGTYMLFMXKYIQW-SSDOTTSWSA-N
M.W :	186.16	Pubchem ID :	45075740
Synonyms :

Calculated chemistry of [ 1270294-05-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.67
TPSA :	29.46 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) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	2.3
Log Po/w (MLOGP) :	1.98
Log Po/w (SILICOS-IT) :	2.63
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.2
Solubility :	1.18 mg/ml ; 0.00633 mol/l
Class :	Soluble
Log S (Ali) :	-1.59
Solubility :	4.77 mg/ml ; 0.0256 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.353 mg/ml ; 0.0019 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.58

Safety of [ 1270294-05-7 ]

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 [ 1270294-05-7 ]

* 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 [ 1270294-05-7 ]

[ 1270294-05-7 ] Synthesis Path-Downstream 1~8

1
[ 844648-22-2 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
66.5%	With dimethylsulfide borane complex; (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol In tetrahydrofuran; toluene at 20℃; for 5.5h; Inert atmosphere;	2 Preparation of (R)-5,7-difluorochroman-4-ol (5) Take a 1L three-necked flask, add anhydrous THF (66mL) and S-Me-CBS (1mol/L toluene solution, 9mL, 9mmol), protect with argon, and inject borane dimethyl sulfide complex at room temperature (10mol/L, 9.9mL, 99mmol). Dissolve 5,7-difluorochroman-4-one (16.6 g, 90 mmol) in anhydrous tetrahydrofuran (166 mL) and slowly drip into the above system. The entire dripping process lasted 5.5 hours. After dripping, let it stand overnight. The reaction solution was slowly poured into methanol cooled in an ice-water bath to generate a large number of bubbles, stirred until no obvious bubbles were generated, and concentrated to remove the solvent. Add 100 mL of ethyl acetate to dissolve, wash the organic phase with water (50 mL, 30 mL) and brine (20 mL) successively, dry over anhydrous sodium sulfate, filter, and concentrate to obtain an oil, which is placed at room temperature as a yellow solid. The chiral purity measured by chiral HPLC was 93.6%ee (OZ-H column, n-hexane/isopropanol=95/5, flow rate=1mL/min, detection wavelength 220nm). The above solid was heated and dissolved in a mixed solvent consisting of n-hexane and ethyl acetate (n-hexane/ethyl acetate=17:1), and 11.1 g of needle crystals were obtained by recrystallization, with a yield of 66.5%. [α] D20 = +141.9 (c = 1, MeOH). The chiral purity measured by chiral HPLC is >99.9%ee (OZ-H column, n-hexane/isopropanol=95/5, flow rate=1 mL/min, detection wavelength 220nm).
	Multi-step reaction with 3 steps 1: sodium tetrahydridoborate; methanol / 1 h / 0 °C 2: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 3: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C
	Multi-step reaction with 4 steps 1: sodium tetrahydridoborate; methanol / 1 h / 0 °C 2: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 4: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A Location in patent: Paragraph 0133-0138
[2]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A
[3]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A

2
[ 1270294-05-7 ]
[ 2648486-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A

3
[ 1270294-05-7 ]
[ 2648486-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3: sodium acetate / dichloromethane / 1 h
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3: sodium acetate / dichloromethane / 24 h / 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A
[2]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A

4
[ 1270294-05-7 ]
[ 942195-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3.1: sodium acetate / dichloromethane / 1 h 4.1: N-chloro-succinimide / acetonitrile / 0.58 h / 5 °C 4.2: 2 h / 20 °C
	Multi-step reaction with 4 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3.1: sodium acetate / dichloromethane / 24 h / 20 °C 4.1: N-chloro-succinimide / acetonitrile / 0.58 h / 5 °C 4.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A
[2]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A

5
[ 1369878-15-8 ]
[ 1270294-05-7 ]
[ 2648486-30-8 ]

Yield	Reaction Conditions	Operation in experiment
89.7%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 5h; Inert atmosphere; Cooling with ice;	8-9 (S)-3-((5,7-Difluorochroman-4-yl)oxy)-N,N-dimethyl-4-nitrobenzamide (6) Compound 4 (210mg, 1mmol), compound 5 (186mg, 1mmol), triphenylphosphine (314 mg, 1.2mmol) were dissolved in anhydrous THF (5mL), protected by argon, cooled in an ice water bath, and then DIAD ( A mixed solution consisting of 236 μL, 1.2 mmol) and anhydrous THF (0.3 mL) was dripped and stirred for 5 hours. Concentrate and purify by silica gel column chromatography (0-2% ethyl acetate in dichloromethane solution). Compound 6 was obtained, with a total of 339 mg of off-white solid, with a yield of 89.7%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A Location in patent: Paragraph 0163-0170

6
[ 2820178-15-0 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
92.4%	With methanol; sodium tetrahydridoborate; lithium hydroxide monohydrate at 20℃; for 1h;	1.S4 ((R)-5,7-difluorochroman-4-yl)4-nitrobenzoate (A-5) (2.26 g, 6.7 mmol) was added to 20 mL of methanol, and sodium hydroxide ( 0.6g, 15mmol), water 10mL, stirred at room temperature for 1h, and monitored the reaction progress by thin-layer chromatography until the reaction was complete; concentrated and evaporated most of the methanol, adjusted the pH to 7 with 1N hydrochloric acid, precipitated a solid, suction filtered, washed with water, 50 Drying at gave (R)-5,7-difluorochroman-4-ol (III) 1.16 g of a near-white solid with a yield of 92.4%.

Reference： [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A Location in patent: Paragraph 0042; 0054

7
[ 917248-51-2 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C
	Multi-step reaction with 3 steps 1: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C

Reference： [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A
[2]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A

8
[ 2820178-14-9 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With methanol; sodium tetrahydridoborate; lithium hydroxide monohydrate at 20℃; for 1h;	1.S3 S3: add (R)-5,7-difluorochroman-4-ol acetate (A-3) (1.8 g, 7.9 mmol) prepared in step S2 into 20 mL of methanol, add sodium hydroxide (0.7 g, 17.5 mmol), 10 mL of water, stirred at room temperature for 1 h, and monitored the reaction progress by thin-layer chromatography until the reaction was complete; concentrated and evaporated most of the methanol, adjusted the pH to 7 with 1N hydrochloric acid, and precipitated a solid, suction filtered, washed with water, 50 Drying at gave (R)-5,7-difluorochroman-4-ol (III) 1.37 g of a near-white solid with a yield of 93.4%.

Reference： [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A Location in patent: Paragraph 0042; 0049-0052

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Code	Phrase
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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.
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P321
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P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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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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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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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.
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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.
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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
H204	Fire or projection hazard
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H226	Flammable liquid and vapour
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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
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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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. 1270294-05-7 ]

Quality Control of [ 1270294-05-7 ]

Related Doc. of [ 1270294-05-7 ]

Product Details of [ 1270294-05-7 ]

Calculated chemistry of [ 1270294-05-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1270294-05-7 ]

Application In Synthesis of [ 1270294-05-7 ]

[ 1270294-05-7 ] Synthesis Path-Downstream 1~8

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry