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[ CAS No. 94-05-3 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 94-05-3

Chemical Structure| 94-05-3

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Quality Control of [ 94-05-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 94-05-3 ]

SDS Specification

Alternatived Products of [ 94-05-3 ]

Product Citations

Product Details of [ 94-05-3 ]

CAS No. :	94-05-3	MDL No. :	MFCD00009136
Formula :	C₈H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	(NC)(COOC₂H₅)CCHOC₂H₅	InChI Key :	KTMGNAIGXYODKQ-VOTSOKGWSA-N
M.W :	169.18	Pubchem ID :	1715183
Synonyms :

Safety of [ 94-05-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P264-P261-P270-P271-P272-P280-P285-P305+P351+P338-P310-P302+P352-P304+P340-P330-P342+P311-P362+P364-P403+P233-P501	UN#:	3335
Hazard Statements:	H302-H315-H317-H318-H334-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 94-05-3 ]

* 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 [ 94-05-3 ]
Downstream synthetic route of [ 94-05-3 ]

[ 94-05-3 ] Synthesis Path-Upstream 1~4

1
[ 2986-19-8 ]
[ 94-05-3 ]
[ 89487-99-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In ethanol for 48 h; Heating / reflux	2-Methyl-2-thiopseudourea (5 mmol) and ethyl ethoxymethylenecyanoacetate (5 mmol) were dissolved in 20 ml EtOH. To this was added K₂CO₃(10 mmol). After the mixture was refluxed for 48 h, it was cooled to room temperature and filtered. The solvent was concentrated in vacuo and purified by column chromatography to give 4-hydroxy-2-(methylthio) pyrimidine-5-carbonitrile in a yield of 65percent.

Reference： [1] Patent: US2008/255172, 2008, A1, . Location in patent: Page/Page column 70

2
[ 94-05-3 ]
[ 89487-99-0 ]

Reference： [1] Patent: US2009/270389, 2009, A1, . Location in patent: Page/Page column 43

3
[ 14527-26-5 ]
[ 94-05-3 ]
[ 89487-99-0 ]

Reference： [1] Patent: US2003/158218, 2003, A1,

4
[ 6829-40-9 ]
[ 94-05-3 ]
[ 853058-40-9 ]

Reference： [1] Patent: US6693193, 2004, B1, . Location in patent: Page column 14
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 218 - 222

[ 94-05-3 ] Synthesis Path-Downstream 1~4

1
[ 371-14-2 ]
[ 94-05-3 ]
[ 138907-68-3 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1562 - 1575
[2]Patent: EP1176140,2002,A1 .Location in patent: Page 45 - 46

2
[ 823-85-8 ]
[ 94-05-3 ]
[ 138907-68-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine; In ethanol; for 2.5h;Heating / reflux;	Ethyl(ethoxymethylene)cyanoacetate (20.80 g, 123 mmol) and triethylamine (17.1 ml_, 123 mmol) were added to a solution of 4-fluorophenylhydrazine hydrochloride (20.00 g, 123 mmol). The reaction mixture was refluxed for 2.5 hours and allowed to cool to room temperature. A solid was collected by filtration, washed with small amounts of ethanol and EPO <DP n="37"/>heptane and allowed to dry under reduced pressure to afford the title compound as a beige solid (22.18 g, 72 % yield). m/z 250 [M+H]+. 1H NMR (300 MHz, CDCI3) 7.80 (1 H, s), 7.58-7.51 (2H, m), 7.27 (2H, m), 5.27 (2H, br s), 4.33 (2H1 q, J=7.2 Hz), 1.39 (2H, t, J=7.2 Hz).
65%	With triethylamine; In ethanol; at 20 - 80℃; for 8h;	General procedure: To ethyl 2-cyano-3-ethoxyacrylate (2.00 g, 11.8 mmol) and 4-methoxyphenyl hydrazine hydrochloride (2.06 g, 11.8 mmol) in ethanol (75 mL) at room temperature was added triethylamine (1.65 mL, 11.8 mmol). The mixture was stirred at 80 C for 8 h. After cooling the reaction mixture to room temperature, ethanol was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1) to give the desired product 2b (2.42 g, 78 %). 1H NMR (300 MHz, CDCl3): delta=7.76 (s, 1H), 7.42 (d, J=6.9Hz, 2H), 7.01 (d, J=6.9Hz, 2H), 5.19 (br s, 2H), 4.30 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.36 (t, J=7.1Hz, 3H) ppm; MS (ESI): m/z: 262 [M+H+].
	With triethylamine; In ethanol; for 3.5h;Heating / reflux;	Intermediate 8: Ethyl 5-amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxvlate. To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76g, 60mmol) in ethanol (250ml) was added triethylamine (9.2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15g, 60mmol). The solution was heated at reflux temperature for 3.5hr. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid. 1 H NMR (400 MHz, DMSOd6) deltappm 7.70 (s, 1 H) 7.55 (s, J=5.0 Hz, 2 H) 7.34 - 7.41 (m, 2 H) 6.34 (br. s., 2 H) 4.21 (q, J=7.0, 7.0 Hz, 2 H) 1.26 (t, J=7.0 Hz, 3 H).

	With triethylamine; In ethanol; for 3.5h;Heating / reflux;	Intermediate 8; Ethyl 5-amiotano-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxylateTo a stirred suspension of 4-fluorophenylhydraziotane hydrochloride (9 76g, 60mmol) in ethanol (250ml) was added triethylamine (9 2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10 15g, 60mmol) The solution was heated at reflux temperature for 3 5 hours The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12 1g) as an off white solid1H NMR (400 MHz, DMSO-d6) delta ppm 7 70 (s, 1 H) 7 55 (s, J=5 0 Hz, 2H) 7 34 - 7 41 (m, 2 H) 6 34 (br s , 2H) 4 21 (q, J=I 0, 7 0 Hz, 2H) 1 26 (t, J=I 0 Hz, 3H)
	With triethylamine; In ethanol; for 3.5h;Heating / reflux;	To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76g, 60mmol) in ethanol (250ml) was added triethylamine (9.2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15g, 60mmol). The solution was heated at reflux temperature for 3.5 hours. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid.1H NMR (400 MHz, DMSO-cfe) delta ppm 7.70 (s, 1 H) 7.55 (s, J=5.0 Hz, 2 H) 7.34 - 7.41 (m, 2 H) 6.34 (br. s., 2 H) 4.21 (q, J=7.0, 7.0 Hz, 2 H) 1.26 (t, J=7.0 Hz, 3 H).
	With sodium acetate; In ethanol; at 95℃; for 3.5h;	(i) Ethyl-2-cyano-3-(ethyloxy)-2-propenoate (5.0 g, 29.56 mmol), (4- fluorophenyl)hydrazine hydrochloride (4.81 g, 29.56 mmol) and sodium acetate (2.43 g, 29.56 mmol) were dissolved in ethanol (100 ml) and heated for 3.5 hrs at 95C. The mixture was then cooled to room temperature and diluted with dichloromethane (-150 ml) and water (50 ml). The organic layer was separated using a hydrophobic <n="105"/>frit, dried over anhydrous sodium sulphate, filtered and to give ethyl 5-amino-1-(4- fluorophenyl)-1 H-pyrazole-4-carboxylate (6.83 g) as an orange solid. This was used in the next step without further purification.

Reference： [1]Patent: WO2008/53136,2008,A1 .Location in patent: Page/Page column 35-36
[2]Tetrahedron,2017,vol. 73,p. 5959 - 5973
[3]Patent: WO2008/74814,2008,A1 .Location in patent: Page/Page column 55
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4724 - 4728
[5]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1680 - 1684
[6]Patent: WO2008/777,2008,A2 .Location in patent: Page/Page column 58
[7]Patent: WO2007/144327,2007,A2 .Location in patent: Page/Page column 70
[8]Patent: WO2008/138876,2008,A1 .Location in patent: Page/Page column 103-104

3
[ 168268-00-6 ]
[ 94-05-3 ]
6-benzyloxy-7-fluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[168268-00-6]4-benzyloxy-3-fluoroaniline</strong> (6.06 g, 27.9 mmol) (US 5,622, 967) and ethyl (ethoxymethylene) cyanoacetate (5.08 g, 30.0 mmol) was heated at 120C for 45 minutes then cooled to room temperature. This solid was added in portions to a 3: 1 mixture of diphenyl ether: biphenyl at 245 C. This mixture was heated at 245C for 3 hours then cooled and the solids were collected by filtration, washing with hexane and diethyl ether to provide 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4- dihydro-3-quinolinecarbonitrile, mp >250C. MS 293.1 (M-H) -
	at 120℃; for 0.75h;	A mixture of <strong>[168268-00-6]4-benzyloxy-3-fluoroaniline</strong> (6.06 g, 27.9 mmol) (U.S. Pat. No. 5,622,967) and ethyl (ethoxymethylene)cyanoacetate (5.08 g, 30.0 mmol) is heated at 120 C. for 45 minutes then cooled to room temperature. This solid is added in portions to a 3:1 mixture of diphenyl ether:biphenyl at 245 C. This mixture is heated at 245 C. for 3 hours then cooled and the solids are collected by filtration, washing with hexane and diethyl ether to provides 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4-dihydro-3-quinolinecarbonitrile, mp>250 C. [0198] MS 293.1 (M-H)-

Reference： [1]Patent: WO2005/47259,2005,A1 .Location in patent: Page/Page column 11; 22-23
[2]Patent: US2003/212276,2003,A1 .Location in patent: Page/Page column 12

4
[ 637-60-5 ]
[ 94-05-3 ]
[ 15001-11-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In ethanol; at 20 - 80℃; for 8.0h;	General procedure: To ethyl 2-cyano-3-ethoxyacrylate (2.00 g, 11.8 mmol) and 4-methoxyphenyl hydrazine hydrochloride (2.06 g, 11.8 mmol) in ethanol (75 mL) at room temperature was added triethylamine (1.65 mL, 11.8 mmol). The mixture was stirred at 80 C for 8 h. After cooling the reaction mixture to room temperature, ethanol was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1) to give the desired product 2b (2.42 g, 78 %). 1H NMR (300 MHz, CDCl3): delta=7.76 (s, 1H), 7.42 (d, J=6.9Hz, 2H), 7.01 (d, J=6.9Hz, 2H), 5.19 (br s, 2H), 4.30 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.36 (t, J=7.1Hz, 3H) ppm; MS (ESI): m/z: 262 [M+H+].

Reference： [1]Tetrahedron,2017,vol. 73,p. 5959 - 5973

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Technical Information

? Acyl Group Substitution ? Blaise Reaction ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Heat of Combustion ? Hydride Reductions ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Reactions with Organometallic Reagents ? Ritter Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Thorpe-Ziegler Reaction

Historical Records

Pharmaceutical Intermediates of
[ 94-05-3 ]

Bosutinib Intermediates

[ 380844-49-5 ]

7-(3-Chloropropoxy)-4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxyquinoline-3-carbonitrile

[ 846023-24-3 ]

2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

[ 5317-33-9 ]

3-(4-Methylpiperazin-1-yl)propan-1-ol

[ 98446-49-2 ]

2,4-Dichloro-5-methoxyaniline

[ 87-13-8 ]

Diethyl 2-(ethoxymethylene)malonate

Neratinib Related Intermediates

[ 848133-75-5 ]

N-(3-Cyano-7-ethoxy-4-hydroxyquinolin-6-yl)acetamide

[ 179687-79-7 ]

2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

[ 619-08-9 ]

2-Chloro-4-nitrophenol

[ 848133-76-6 ]

N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide

[ 524955-09-7 ]

3-Chloro-4-(pyridin-2-ylmethoxy)aniline

Related Functional Groups of
[ 94-05-3 ]

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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.
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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.
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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.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P320
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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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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:
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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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.
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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
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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
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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.
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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Ghs Hazard Statements

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

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