[ CAS No. 53899-17-5 ] {[proInfo.proName]}

Name: 53899-17-5|8-Methoxy-1,2,3,4-tetrahydroquinoline|98%
Brand: Ambeed
SKU: A482735
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3d Animation Molecule Structure of 53899-17-5

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Quality Control of [ 53899-17-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53899-17-5 ]

Product Details of [ 53899-17-5 ]

CAS No. :	53899-17-5	MDL No. :	MFCD07800307
Formula :	C₁₀H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZPRWUIXDTQZKJO-UHFFFAOYSA-N
M.W :	163.22	Pubchem ID :	5200345
Synonyms :

Safety of [ 53899-17-5 ]

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 [ 53899-17-5 ]

* 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 [ 53899-17-5 ]
Downstream synthetic route of [ 53899-17-5 ]

[ 53899-17-5 ] Synthesis Path-Upstream 1~1

1
[ 53899-17-5 ]
[ 6640-50-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3415 - 3418

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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.
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.
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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.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
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.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Yield	Reaction Conditions	Operation in experiment
91%	With tetrahydroxydiboron; copper diacetate; In acetonitrile; at 40℃; for 12h;	<strong>[938-33-0]8-methoxyquinoline</strong> (0.3 mmol, 48 mg),Tetrahydroxy diboron (0.9mmol, 81mg),Cu (OAc) 2 (0.015 mmol, 2.5 mg) was added to 1 mL of acetonitrile,40 C for 12 hours,Purification by thin layer chromatography gave 44.5 mg of 8-methoxytetrahydroquinoline in a yield of 91% with a purity of 98%
91%	With tetrahydroxydiboron; copper diacetate; In acetonitrile; at 40℃; for 8h;Schlenk technique;	General procedure: A 20 mL Schlenk tube was charged with quinoline (1a; 65 mg,0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4 (135 mg,1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 40 C for 8 h until the reaction was completed (TLC), then cooled to room temperature and concentrated under reduced pressure. Water (10 mL) was added and the mixture was extracted with EtOAc (3 x 10 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography with petroleum ether/ethyl acetate (8:1) as an eluent to give a brown liquid (2a: 65 mg, 98% yield).
84%	With hydrogen;platinum(IV) oxide; In methanol; at 20℃; under 2068.65 Torr; for 4h;	Step B - Synthesis of Compound Int- 19b; A solution of compound Int- 19a (21 g, 0.132 mol) and Pt02 (2 g, 5 mol %) in 80 mL of MeOH was allowed to stir at room temperature for 4 hours under a H2 atmosphere (40 psi). The reaction mixture was filtered and the filtrate was concentrated in vacuo to provide compound Int-19b as yellow oil (18 g, 84%). NMR: (CDC13) delta 6.57-6.64 (m, 3H), 4.25 (br, 1 H), 3.84 (s, 3H), 3.35 (s, 2H), 2.79-2.80 (m, 2H), 1.96-1.99 (m, 2H).

84%	With hydrogen;platinum(IV) oxide; In methanol; at 20℃; under 2068.65 Torr; for 4h;	Step B - Synthesis of Compound Int-19bInt 9a Int 19bA solution of compound Int-19a (21 g, 0.132 mol) and Pt02 (2 g, 5 mol %) in 80 mL of MeOH was allowed to stir at room temperature for 4 hours under a H2 atmosphere (40 psi). The reaction mixture was filtered and the filtrate was concentrated in vacuo to providecompound Int-19b as yellow oil (18 g, 84%). 1H MR: (CDC13) delta 6.57-6.64 (m, 3H), 4.25 (br, 1H), 3.84 (s, 3H), 3.35 (s, 2H), 2.79-2.80 (m, 2H), 1.96-1.99 (m, 2H).
84%	With ethanol; Dimethylphenylsilane; Au-TiO2; In neat (no solvent); at 70℃; for 0.25h;Catalytic behavior;	To a dry vial containing <strong>[938-33-0]8-methoxyquinoline</strong>, 1 (0.048 g, 0.3 mmol), Me2PhSiH (185 muL, 1.2mmol) and ethanol (70 muL, 1.2 mmol), Au/TiO2 (60 mg, 1.0 mol%) was added. The Au contentin catalyst was ~1 wt%. The mixture was heated to 70 oC and the progress of reaction wasmonitored by TLC and GC. After 15 min (100% conversion), ethanol (1 mL) was added and theresulting slurry was filtered under reduced pressure through a short pad of silica gel with the aidof ethanol (2-3 mL) to withhold the supported catalyst. The filtrate was evaporated undervacuum and the residue was chromatographed (n-hexane/ethyl acetate, 10:1) to afford 8-methoxy-1,2,3,4-tetrahydroquinoline (1a) (41 mg, 84% yield).
82%		Add sodium cyanoborohydride (505 g, 8.1 1 mol) in EtOH (1 L) to a solution of 8- methoxy quinoline (425 g, 2.673 mol) in EtOH (9 L), and stir. Cool the reaction mixture to an internal temperature of 0 C and add HC1 (35%, 1.12 L, 10.962 mol) dropwise over 60 min so that the internal temperature did not rise above 20 C. Allow the reaction mixture to warm to ambient temperature and then heat to reflux for 2.5 hours. Cool to ambient temperature and stir overnight. Add ammonium hydroxide (25%, 1 L); dilute with water (15 L); and extract the mixture with dichloromethane (3 x 10 L). Combine the organic layers and dry over sodium sulfate. Remove the solids by filtration. Collect the filtrate and concentrate under reduced pressure to give a residue. Purify the residue by silica gel flash chromatography, eluting with ethyl acetate: hexane (1: 10) to give the title compound (357 g, 82%). ESI (m/z) 164(M+H).

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 33 percent / hydrogen / platinum oxide / trifluoroacetic acid
	Multi-step reaction with 2 steps 2: hydrogen / platinum oxide / methanol / 2250.2 Torr

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide; tetrahydrofuran / 12 h / 20 °C 2: hydrogen / platinum(IV) oxide / methanol / 4 h / 20 °C / 2068.65 Torr
	Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran 2: sodium cyanoborohydride; hydrogenchloride / ethanol; water / 2.5 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: Dimethylphenylsilane; ethanol; Au-TiO₂ / neat (no solvent) / 0.25 h / 70 °C

[ CAS No. 53899-17-5 ] {[proInfo.proName]}

Quality Control of [ 53899-17-5 ]

Related Doc. of [ 53899-17-5 ]

Product Details of [ 53899-17-5 ]

Safety of [ 53899-17-5 ]

Application In Synthesis of [ 53899-17-5 ]

[ 53899-17-5 ] Synthesis Path-Upstream 1~1

[ 53899-17-5 ] Synthesis Path-Downstream 1~50