[ CAS No. 5415-98-5 ] {[proInfo.proName]}

Name: 5415-98-5|2-((Dimethylamino)methyl)acrylic acid|95%
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Quality Control of [ 5415-98-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 5415-98-5 ]

CAS No. :	5415-98-5	MDL No. :	MFCD19656217
Formula :	C₆H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GANOKKCPYBWVRC-UHFFFAOYSA-N
M.W :	129.16	Pubchem ID :	223581
Synonyms :

Safety of [ 5415-98-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5415-98-5 ]

* 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.

Downstream synthetic route of [ 5415-98-5 ]

[ 5415-98-5 ] Synthesis Path-Downstream 1~11

1
[ 50-00-0 ]
[ 141-82-2 ]
[ 124-40-3 ]
[ 5415-98-5 ]
[ 408307-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Pelletier; Franz [Journal of Organic Chemistry, 1952, vol. 17, p. 855,856]

2
[ 1184-78-7 ]
[ 108-24-7 ]
[ 5415-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	(i) /BRN= 385737/, CHCl₃, (ii) /BRN= 385737/, (heating); Multistep reaction;

Reference： [1]Renaud,R.N.; Leitch,L.C. [Canadian Journal of Chemistry, 1968, vol. 46, p. 385 - 390]

Yield	Reaction Conditions	Operation in experiment
86%		6 2-Dimethylaminomethylacrylic acid. EXAMPLE 6 2-Dimethylaminomethylacrylic acid. Aqueous formaldehyde (162 ml of 37% solution) was slowly added to a solution of malonic acid (104g) and dimethylamine (350 ml 26% of aqueous solution) in water (150 ml) at 15° C with stirring. Carbon dioxide was evolved at a rate dependent upon the rate of addition of formaldehyde. The reaction mixture was stirred for 30 minutes at 15° C and then heated on a steam bath for 1 hour to ensure complete decarboxylation. Evaporation of the solvent under reduced pressure gave a yellow syrup, which was dried further by azeotropic distillation with toluene to obtain a pale brown solid. The crude material was recrystallized from acetone and dried in vacuum over phosphorus pentoxide to give colourless cubes of the product (107g, 86%, melting point 115 to 7° C). Analysis: C6 H10 NO2 requires: C, 55.8%, H, 8.6%, N, 10.8%, Found: C, 54.2%, H, 8.5%, N, 10.7%.
		1 2-Dimethylaminomethylacrylic acid. STR12 EXAMPLE 1 2-Dimethylaminomethylacrylic acid. STR12 Formaldehyde solution (150 ml of 40% solution) was added with stirring to a solution of dimethylamine (218g of 26% solution) and malonic acid (104g) in water (250 ml). The reaction temperature was kept at 20° C during the addition and for a further 2 hours. The solution was then heated on a steam bath for 2 hours and the water was removed under reduced pressure to give a pale yellow syrup which was dried further by azeotropic distillation with benzene. The produce was recrystallized from acetone to give colourless crystals which were dried under vacuum over phosphorous pentoxide for four days. The yield was 92g or 71%. Analysis: C6 H11 NO2 requires: N, 10.85%, Found: N, 10.70%.
	40percent CH2O-Loesung, Malonsaeure in W., Dimethylamin;

	Bis-(dimethylamino)-methan, Malonsaeure;
	Formaldehyd, Malonsaeure, Dimethylamin;

4
[ 5415-98-5 ]
[ 7664-93-9 ]
[ 27315-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In ethanol	5 Ethyl 2-dimethylaminomethylacrylate STR16 EXAMPLE 5 Ethyl 2-dimethylaminomethylacrylate STR16 A solution of the 2-dimethylaminomethylacrylic acid (35 g) compound prepared as in Example 1 in ethanol (350 ml) and concentrated sulphuric acid (60 ml) were boiled under reflux for three hours. The solution was evaporated to half volume and poured into water (1 liter). The aqueous solution was neutralised by the addition of solid sodium carbonate and extracted with ether. Evaporation of the ether solution gave a pale brown oil which was distilled to give a colourless oil (boiling point 84° C/20 mm). The product was identical with that obtained in Example 4.

Reference： [1]Current Patent Assignee: 3M CO - US4074051, 1978, A

5
[ 5415-98-5 ]
[ 27315-97-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium carbonate In ethanol; sulfuric acid; water	10 Ethyl-2-dimethylaminomethylacrylate EXAMPLE 10 Ethyl-2-dimethylaminomethylacrylate A solution of 2-dimethylaminomethylacrylic acid (129g) in concentrated sulphuric acid (105 ml, 98%) and ethanol (500 ml) was boiled under reflux for 3 hours. After evaporating to half volume and pouring the residue into water (1 liter), anhydrous sodium carbonate (212g) was added and the solution was allowed to stand for 3 hours, when it gave a neutral reaction. The aqueous mixture was extracted with ether (3 * 250 ml), after drying over anhydrous sodium sulphate, the ether extract was evaporated at atmospheric pressure. The residual pale yellow oil was distilled under reduced pressure to give ethyl 2-dimethylaminomethylacrylate (86g, 55% boiling point 84° C/20 mm). Analysis: Calculated for C8 H15 NO2: C, 61.1%, H, 9.6%, N, 8.9%, Found: C, 60.7%, H, 10.1%, N, 8.9%.

Reference： [1]Current Patent Assignee: 3M CO - US4074051, 1978, A

6
[ 50-00-0 ]
[ 141-82-2 ]
[ 124-40-3 ]
[ 5415-98-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	In tetrahydrofuran; 1,4-dioxane at 70℃; for 1h;	3.1 1 g of malonic acid and 0.63 g of paraformaldehyde were dissolved in 10 mL of 1,4-dioxane, and 4.8 mL of a 2.0 M dimethylamine solution in tetrahydrofuran was added thereto. Then, the mixture was heated to 70°C and stirred for 1 hour. After the reaction was completed, the mixture was distilled under a reduced pressure. The concentrated liquid-phase residue was crystallized by addition of acetone and then filtered under a reduced pressure to obtain the title compound in a white crystalline (0.4 g, yield: 32%).1H-NMR (300MHz, D20) δ 6.62 (s, 1H), 6.11 (s, 1H), 4.16 (s, 2H), 2.88 (s, 6H); MS (ESI+): m/z = 130.0 [M+H]+.
32%	In tetrahydrofuran; 1,3-dioxane at 70℃; for 1h;	104.1 Example 104: Preparation of l-(3-(4-(3-chloro-2,4-difluorophenylamino)-7- methoxyquinazolin-6-yloxy)azetidin-l-yl)-2-((dimethyIamino)methyl)prop-2- en-l-one; Step 1) 2-((dimethylamino)methyl)acrylic acid; 1 g of malonic acid and 0.63 g of paraformaldehyde were diluted with 10 mi of 1,3-dioxane, and 4.8 m of a 2.0M dimethylamine-containing tetrahydrofuran solution was added thereto. The resulting mixture was heated to 70 "C and stirred for one hour. After the reaction terminated, the resulting solution was distilled under a reduced pressure. The resulting residue was crystallized with acetone and filtered under a reduced pressure to obtain the title compound (0.4 g, 32%) in the form of white crystal.1H-NMR (300MHz, D2O) δ 6.62 (s, IH), 6.11 (s, IH), 4.16 (s, 2H), 2.88 (s, 6H);MS (ESI+): m/z = 130.0 [M+H]+.
	In tetrahydrofuran; 1,4-dioxane at 70℃; for 1h;	Preparation 50: tert-butyl 2-((dimethylamino)methyl)acrylate Paraformaldehyde (1.20 g, 43.2 mmol) was added to a solution of Malonic acid (2.0 g, 19.3 mmol) in 1,4-dioxane (20 mL), followed by a2M solution of dimethylamine in THF (9.60 mL, 19.2 mmol) and the reaction mixture was stirred at 70t for 1 h. The reaction mixture was concentrated in vacuo and the cmde product was recrystallizedusing diethyl ether and acetone to yield the intermediate as a white solid. The intermediate white solid was dissolved in t-BuOH (100 mL) and di-tert-butyl dicarbonate (4.60 mL, 20.7 mmol) was added to the reaction mixture followed by 4- dimethylaminopyridine (511 mg, 4.18 mmol) and the reaction mixture was stirred at rt for 4 h. Methylene chloride (500 mL) was added and the reaction mixture was washed withwater (2 x 500 mL), dried over sodium sulfate and concentrated in vacuo. The crude residue was purified via flash column chromatography using 2% methanol in methylene chloride to yield tert-butyl 2-((dimethylamino)methyl)acrylate (220 mg, 1.19 mmol, 6% yield).

Reference： [1]Current Patent Assignee: HANMI SCIENCE CO LTD - WO2011/99764, 2011, A2 Location in patent: Page/Page column 20-21
[2]Current Patent Assignee: HANMI PHARM CO LTD; HANMI SCIENCE CO LTD - WO2008/150118, 2008, A2 Location in patent: Page/Page column 60-61
[3]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - WO2019/27960, 2019, A1 Location in patent: Page/Page column 110

7
[ 5415-98-5 ]
[ 1092365-56-4 ]
[ 1092365-06-4 ]

Yield	Reaction Conditions	Operation in experiment
3%	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 2h;	104.2 Step 2) l-(3-(4-(3-chloro-2,4-difluorophenylamino)-7-methoxyquinazolin-6- yloxy)azetidin- 1 -yl)-2-((dimethylamino)methyl)prop-2-en- 1 -one; 50 mg of 6-(azetidin-3-yloxy)-N-(3-chloro-2,4-difluorophenyl)-7- methoxyquinazolin-4-amine obtained by repeating the procedure of step 6) of Example 1 except for using N-Boc-3 -hydroxy azetidine instead of (R)-(-)-N-Boc- 3-pyrrolidinol was diluted with 2 m£ of tetrahydrofuran, and 25 mg of the compound obtained in step 1), 37 mg of N-(3 -dimethylaminopropy I)-N- ethylcarbodiimide hydrochloride, and 5 βl of pyridine were added thereto. The resulting mixture was incubated at room temperature for two hours. After the reaction terminated, water was added, and the resulting solution was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (chloroform : methanol = 15 : 1) to obtain the title compound (2 mg, 3%).1H-NMR (300MHz, CDCl3) δ 9.38 (s, IH), 8.54 (s, IH), 8.14 (s, IH), 7.54 (m, IH), 6.99 (m, IH), 6.04 (bm, IH), 5.96 (s, IH), 5.49 (s, IH), 4.91 (m, 2H), 4.03 (s, 3H), 3.96 (m, 2H), 3.84 (s, 2H); MS (ESI+): m/z = 504.3 [M+H]+.

Reference： [1]Current Patent Assignee: HANMI PHARM CO LTD; HANMI SCIENCE CO LTD - WO2008/150118, 2008, A2 Location in patent: Page/Page column 61

8
[ 5415-98-5 ]
[ 1328623-74-0 ]
[ 1328623-76-2 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: 2-(dimethylaminomethyl)acrylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: 5-(4-aminomethyloxazol-2-yl)-N⁽⁴⁾-(3-chloro-4-(pyridin-2-ylmethoxy)phenyl)pyrimidin-4,6-diamine In dichloromethane at 20℃; for 2h;	3.2 4 mg of the compound obtained in step 1) above was dissolved in 2 mL of dichloromethane, and 7 mg of N-(3-dimemylammopropyl)-N'-emylcarbodiirnide hydrochloride and 12 pL of N,N-diisopropylemylamine were added thereto, followed by stirring at room temperature for 5 min. Subsequently, 10 mg of the compound obtained in step 8) of Example 1 was added thereto and stirred at room temperature for 2 hours. After the reaction was completed, a saturated aqueous solution of sodium bicarbonate was added thereto and the reaction mixture was extracted two times with chloroform. The isolated organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The obtained residue was subjected to column chromatography (chloroform : methanol = 15 : 1), to obtain the title compound (6 mg, yield: 47%).1H-NMR (300MHz, CDC13) δ 10.79 (s, 1H), 9.85 (m, 1H), 8.61 m, 1H), 8.21 (s, 1H), 7.77 (m, 2H), 7.68 (s, 2H), 7.47 (m, 1H), 7.26 (m, 1H), 6.99 (d, 1H), 6.28 (d, 1H), 5.44 (s, 1H), 5.30 (s, 2H), 4.52 (d, 2H), 3.13 (s, 2H), 2.19 (s, 6H); MS (ESI+): m/z = 535.4 [M+H]+.

Reference： [1]Current Patent Assignee: HANMI SCIENCE CO LTD - WO2011/99764, 2011, A2 Location in patent: Page/Page column 21

9
[ 5415-98-5 ]
[ 1328624-14-1 ]
[ 1328624-15-2 ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: 2-(dimethylaminomethyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: (5-(4-aminomethyloxazol-2-yl)pyrimidin-4-yl)-(3-chloro-(pyridin-2-ylmethoxy)phenyl)amine In dichloromethane at 20℃; for 3h;	36 2.5 mg of the compound obtained in step 1) of Example 3 was dissolved in 1 mL of dichloromethane, and 4.6 mg of N-(3-dimethylaminopropyl)-N- ethylcarbodiimide hydrochloride, 0.6 mg of N-hydroxybenzotriazole and 8 μ^ of N,N- diisopropylethylamine were gradually added thereto, followed by stirring at room temperature for 5 minutes. 6.5 mg of the compound obtained in step 9) of Example 35 was added thereto, followed by stirring at room temperature for 3 hours. After the reaction was completed, a saturated aqueous solution of sodium bicarbonate was added thereto, and the resulting mixture was extracted twice with chloroform. The separated organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was subjected to column chromatography (chloroform : methanol = 15 : 1) to obtain the title compound (3 mg, yield: 38%).1H-NMR (300MHz, CDC13) δ 10.71 (s, 1H), 9.70 (s, 1H), 8.96 (s, 1H), 8.73 (s, 1H), 8.60 (d, 1H), 7.86 (d, 1H), 7.76 (t, 1H), 7.67 (m, 2H), 7.57 (m, 1H), 7.23 (m, 1H), 7.01 (d, 1H), 6.30 (s, 1H), 5.45 (s, 1H), 5.30 (s, 2H), 4.52 (d, 2H), 3.14 (s, 2H), 2.19 (s, 6H);MS (ESI*): m/z = 520.3 [M+H]+.

Reference： [1]Current Patent Assignee: HANMI SCIENCE CO LTD - WO2011/99764, 2011, A2 Location in patent: Page/Page column 40

10
[ 5415-98-5 ]
[ 1407520-00-6 ]
[ 1407519-27-0 ]

Yield	Reaction Conditions	Operation in experiment
9%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	17 Example 17N-(3-((5-chloro-4-((2-(dimethylphosphoryl)phenyl)amino)pyrimidin-2-yl)amino)-4- methoxyphenyl)-2-((dimethylamino)methyl)acrylamide (40).A synthetic procedure for compound 40 is depicted in Scheme 17.2-(Dimethylaminomethyl)acrylic acid 39 was prepared according to a literature procedure {Synth. Comm. 1995, 25, 641 ). To a solution of 39 (65 mg, 0.5 mmol), coupling reagent TBTU ( 1 .2 eq) and N, N-diisopropylethylamine (3.0 eq) in DMF (5 mL) and DCM (20 mL) was added 5 ( 1 eq). After the mixture was stirred at room temperature overnight, the volatile components were removed on rotavap and the residue was purified by reverse phase prep-HPLC, furnishing the title compound as a tan solid (23 mg, 9%).
9%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	17 2-(Dimethylaminomethyl)acrylic acid 39 was prepared according to a literature procedure {Synth. Comm. 1995, 25, 641). To a solution of 39 (65 mg, 0.5 mmol), coupling reagent TBTU (1.2 eq) and N, N-diisopropylethylamine (3.0 eq) in DMF (5 mL) and DCM (20 mL) was added 5 (1 eq). After the mixture was stirred at room temperature overnight, the volatile components were removed on rotavap and the residue was purified by reverse phase prep-HPLC, furnishing the title compound as a tan solid (23 mg, 9%).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2012/151561, 2012, A1 Location in patent: Page/Page column 52
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2013/169401, 2013, A1 Location in patent: Page/Page column 54

11
[ 5415-98-5 ]
[ 24424-99-5 ]
tert-butyl 2-((dimethylamino)methyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With dmap In <i>tert</i>-butyl alcohol at 20℃; for 4h;	Preparation 50: tert-butyl 2-((dimethylamino)methyl)acrylate Paraformaldehyde (1.20 g, 43.2 mmol) was added to a solution of Malonic acid (2.0 g, 19.3 mmol) in 1,4-dioxane (20 mL), followed by a2M solution of dimethylamine in THF (9.60 mL, 19.2 mmol) and the reaction mixture was stirred at 70t for 1 h. The reaction mixture was concentrated in vacuo and the cmde product was recrystallizedusing diethyl ether and acetone to yield the intermediate as a white solid. The intermediate white solid was dissolved in t-BuOH (100 mL) and di-tert-butyl dicarbonate (4.60 mL, 20.7 mmol) was added to the reaction mixture followed by 4- dimethylaminopyridine (511 mg, 4.18 mmol) and the reaction mixture was stirred at rt for 4 h. Methylene chloride (500 mL) was added and the reaction mixture was washed withwater (2 x 500 mL), dried over sodium sulfate and concentrated in vacuo. The crude residue was purified via flash column chromatography using 2% methanol in methylene chloride to yield tert-butyl 2-((dimethylamino)methyl)acrylate (220 mg, 1.19 mmol, 6% yield).

Reference： [1]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - WO2019/27960, 2019, A1 Location in patent: Page/Page column 110

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[ 5415-98-5 ]

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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. 5415-98-5 ] {[proInfo.proName]}

Quality Control of [ 5415-98-5 ]

Related Doc. of [ 5415-98-5 ]

Product Details of [ 5415-98-5 ]

Safety of [ 5415-98-5 ]

Application In Synthesis of [ 5415-98-5 ]

[ 5415-98-5 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 5415-98-5 ]

Amino Acid Derivatives

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Prevention

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Physical hazards

Health hazards

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[ 5415-98-5 ]