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Structure of 2-Isocyanatoethyl acrylate
CAS No.: 13641-96-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 13641-96-8 |
Formula : | C6H7NO3 |
M.W : | 141.12 |
SMILES Code : | C=CC(OCCN=C=O)=O |
MDL No. : | MFCD11112219 |
InChI Key : | DPNXHTDWGGVXID-UHFFFAOYSA-N |
Pubchem ID : | 3014768 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301+H331-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P332+P313+P362+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501 |
Class: | 6.1 |
UN#: | 2810 |
Packing Group: | Ⅲ |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.8% | With dibutyltin dilaurate; 4-methoxy-phenol; In diethyl ether; at 40℃; for 12h;Flow reactor; | Synthesis was performed using the same device as in Synthesis Example 1. That is, in a 50 mL Duran bottle <strong>[3386-18-3]3,6,9,12,15,18,21,24-octaoxahexacosane-1,26-diol</strong>: 41.4 g (0.10 mol), dibutyltin (IV) dilaurate: 29.4 mg and p -Methoxyphenol: 14.7 mg was added and dissolved by stirring with a magnetic stir bar.Then, a solution of 2-isocyanatoethyl acrylate: 14.12 g (0.10 mol) dissolved in 20 mL of ethyl ether was added to the Duran bottle and stirred.The glass beads packed column (column inner diameter 1.0 cm, length 10 cm, glass bead diameter 100 μm, glass bead layer length 9 cm) was circulated at a flow rate of 100 mL / min with a MONO pump (made by Hastelloy Hyjin equipment) pump. .The circulation time was 12 hours, and the Duran bottle was kept warm at 40 C.The initial solution state was opalescent, but became transparent over time.After 12 hours, HPLC and FT-IR measurements were performed.In this case, the sample used was one in which an extremely small amount was collected with a pipette and the solvent was removed with an evaporator.The analytical conditions for HPLC measurement are column ZORBAX-ODS, acetonitrile / distilled water = 7/3, flow rate 0.5 mL / min, multi-scan UV detector, RI detector, MS detector.FT-IR measurement was performed by the ATR method.As a result of HPLC measurement, the raw materials <strong>[3386-18-3]3,6,9,12,15,18,21,24-octaoxahexacosane-1,26-diol</strong> and 2-isocyanatoethyl acrylate disappeared, and a new peak: 31- Hydroxy-4-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-3-azahentriacontyl acrylate (molecular weight 555.62) was confirmed in a yield of 99.8%.Further, as a result of FT-IR measurement, it was confirmed that the absorption of the isocyanate at 2280 to 2250 cm-1 disappeared and the strength of the hydroxy group absorption near 3300 cm-1 was reduced, and the absorption derived from the urethane group was newly confirmed at 1250 cm-1.Next, the ethyl ether solution containing 48.5 g (87.2 mmol) of the precursor compound synthesized by the above operation was transferred to a four-necked flask (300 mL volume) equipped with a stirring blade, a thermometer, a dropping funnel and a cooling tube. Then, (3-isocyanatopropyl) trimethoxysilane: 20.5 g (0.10 mol) was added dropwise with stirring.The reaction temperature was 20 C.After the dropping was completed, the reaction was continued for 12 hours for aging.After aging, HPLC and FT-IR measurements were performed.As a result of HPLC measurement, the raw materials 31-hydroxy-4-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-3-azahentriaconyl acrylate and (3-isocyanatopropyl) The trimethoxysilane peak disappeared and a new peak: 3,3-dimethoxy-8,37-dioxo-2,9,12,15,18,21,24,27,30,33,36-undecaoxa-7,38-diaza-3-silatetracontan-40-yl acrylate (molecular weight: 760.9) was confirmed.In addition, as a result of FT-IR measurement, disappearance of hydroxy group absorption near 3300 cm -1 was confirmed.The chemical structural formulas of the compounds synthesized in this synthesis example are shown below. |
With dibutyltin dilaurate; 4-methoxy-phenol; In tetrahydrofuran; at 75℃; for 5h; | In a four-necked flask (volume of 1 L) equipped with stirring blades, a thermometer, a dropping funnel and a condenser tube, 300 mL of tetrahydrofuran, 41.4 g (0.10 mol) of 3,6,9,12,15,18,21,24-octaoxahexacosan-1,26-diol, 48.5 mg of dibutyltin(IV) dilaurate and 24.2 mg of p-methoxyphenol were charged and dissolved. Subsequently, 7.06 g (0.05 mol) of 2-isocyanatoethyl acrylate was weighed in a beaker and 150 mL of tetrahydrofuran was added, followed by sufficient stirring and further liquid transfer to the dropping funnel. The four-necked flask was immersed in an oil bath heated to 75 C., and 2-isocyanatoethyl acrylate was added dropwise so as not to cause boiling of tetrahydrofuran. After completion of the dropwise addition, the reaction was continued for 5 hours while maintaining the temperature of the oil bath, leading to aging. After completion of the aging, the four-necked flask was removed from the oil bath and the reaction product was returned to room temperature, and then HPLC and FT-IR measurements were performed. In that case, a sample obtained by collecting a very small amount of the reaction product using a pipette and removing a solvent using evaporator was used. Analysis conditions of the HPLC measurement are as follows: a column of ZORBAX-ODS, acetonitrile/distilled water of 7/3, a flow rate of 0.5 mL/min, a multi-scanning UV detector, an RI detector and an MS detector. The FT-IR measurement was performed by an ATR method. As a result of the HPLC measurement, peaks of 3,6,9,12,15,18,21,24-octaoxahexacosan-1,26-diol and 2-isocyanatoethyl acrylate as raw materials disappeared, and new peak of 31-hydroxy-4-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-3-azahentriacontyl acrylate (molecular weight of 555.62) was confirmed. As a result of the FT-IR measurement, the disappearance of the isocyanate absorption at 2,280 to 2,250 cm-1 and a decrease in intensity of the hydroxy group absorption at around 3,300 cm-1 were confirmed, and the absorption attributed to a urethane group was newly confirmed at 1,250 cm-1. Subsequently, to a tetrahydrofuran solution containing 48.5 g (87.2 mmol) of the precursor compound synthesized by the above-mentioned operation, 17.9 g (87.2 mmol) of (3-isocyanatopropyl)trimethoxysilane was added dropwise while stirring so as not to cause boiling of tetrahydrofuran. After completion of the dropwise addition, the reaction was continued for 12 hours, leading to aging. After completion of the aging, HPLC and FT-IR measurements were performed. As a result of the HPLC measurement, peaks of 31-hydroxy-4-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-3-azahentriacontyl acrylate and (3-isocyanatopropyl)trimethoxysilane as raw materials disappeared, and new peak of 3,3-dimethoxy-8,37-dioxo-2,9,12,15,18,21,24,27,30,33,36-undecaoxa-7,38-diaza-3-silatetracontan-40-yl acrylate (molecular weight of 760.9) was confirmed. As a result of the FT-IR measurement, the disappearance of the hydroxy group absorption at around 3,300 cm-1 was confirmed. The chemical structure of the compound synthesized in the present Synthesis Example is mentioned below. |
Tags: 13641-96-8 synthesis path| 13641-96-8 SDS| 13641-96-8 COA| 13641-96-8 purity| 13641-96-8 application| 13641-96-8 NMR| 13641-96-8 COA| 13641-96-8 structure
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