Methylisocyanacetat

Bezeichnung:Methylisocyanacetat

CAS-Nr39687-95-1

Englisch Name:METHYL ISOCYANOACETATE

CBNumberCB0700977

SummenformelC4H5NO2

Molgewicht99.09

MOL-Datei39687-95-1.mol

Synonyma

Methylisocyanacetat

Methylisocyanacetat physikalisch-chemischer Eigenschaften

Siedepunkt	75-76 °C10 mm Hg(lit.)
Dichte	1.09 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.417(lit.)
Flammpunkt	193 °F
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Aggregatzustand	Liquid
Farbe	Clear yellow to brown
Wasserlöslichkeit	Miscible with organic solvents. Slightly miscible with water.
BRN	3537963
InChI	1S/C4H5NO2/c1-5-3-4(6)7-2/h3H2,2H3
InChIKey	CRXFROMHHBMNAB-UHFFFAOYSA-N
SMILES	COC(=O)C[N+]#[C-]
CAS Datenbank	39687-95-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	20/21/22-34
S-Sätze:	26-36/37/39-45
RIDADR	UN 2922 8/PG 2
WGK Germany	3
F	8-9-32-13-19
HazardClass	8
PackingGroup	II
HS Code	29291090
Speicherklasse	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Dam. 1 Skin Corr. 1B

Gefahreninformationscode (GHS)

METHYL ISOCYANOACETATE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Chemische Eigenschaften
CLEAR YELLOW TO BROWN LIQUID
Verwenden
Methyl isocyanoacetate has been used in the copper-catalyzed, diastereoselective synthesis of oxazolines.
Verwenden
Methyl isocyanoacetate is used in the copper-catalyzed, diastereoselective synthesis of oxazolines. It is involved in the direct aldol reaction with carbonyl compounds to prepare corresponding oxazoline by using catechol-copper network catalyst. Further, it is also involved in four-component Ugi condensation reaction. It undergoes asymmetric aldol reaction with fluorinated benzaldehyde using gold(I) as a catalyst.
Allgemeine Beschreibung
Methyl isocyanoacetate undergoes direct aldol reaction with carbonyl compounds in the presence of solid-phase catechol-copper network catalyst to yield corresponding oxazolines. It also participates in four-component Ugi condensation reaction.
Synthese
Methyl -isocyanoacetate was synthesized in the following steps: 2.75 g (23.5 mmol) of methyl N-formylglycinate was was dissolved in 100 mL of redistilled anhydrous dichloromethylcoon (DCM), followed by the addition of triethylamine 8.1 mL (58.7 mmol), and the reaction mixture was placed in an ice bath and stirred and cooled for 15 min. after the cooling was complete, phosphorus triclosan was added slowly and dropwise 2.2 mL (23.5 mmol) to the antiligand system, while the reaction continued to be stirred in an ice bath for 1 h. Subsequently, the solution was brought to room temperature and saturated Na2CO3 solution was added slowly until the pH showed alkaline, stirring was continued until the aqueous and organic phases were sufficiently partitioned, and the partition funnel was used to separate out the organic layer, while the aqueous layer was extracted with DCM (30 mLx3). The organic layer was combined, washed with saturated brine for 3 times, the organic phase was dried with anhydrous MgSO4, filtered and washed, the filtrate was combined and spun dry to obtain the crude -isocyanoacetic acid methyl ester, which was separated and purified by RP-HPLC, and after vacuum drying, the dark brown liquid with a very strong pungent odor was obtained as 1.51g, yield 65.0%.

METHYL ISOCYANOACETATE Upstream-Materialien And Downstream Produkte

Methylisocyanacetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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