METHYL ISOCYANOACETATE Chemical Properties

Boiling point:

75-76 °C10 mm Hg(lit.)

Density 

1.09 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.417(lit.)

Flash point:

193 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear yellow to brown

Water Solubility 

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 DataBase Reference

39687-95-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

20/21/22-34

Safety Statements 

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

Storage Class

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

METHYL ISOCYANOACETATE Usage And Synthesis

Chemical Properties

CLEAR YELLOW TO BROWN LIQUID

Uses

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.

Uses

Methyl isocyanoacetate has been used in the copper-catalyzed, diastereoselective synthesis of oxazolines.

General Description

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.

Synthesis

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(39687-95-1)Related Product Information

• ISONICOTINOYL CHLORIDE HYDROCHLORIDE
• 2-Isocyanatoethyl Acrylate
• ISOPROPYLHYDRAZINE HYDROCHLORIDE
• Isopropylsulfonamide
• 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-1R, trans-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylate
• HYDROGEN IONOPHORE IV
• alpha-Cypermethrin
• Isobutaneboronic acid
• Methyl isobutyrate
• Ethyl isobutyrylacetate
• Isopropenylboronic acid pinacol ester
• ETHYL 4-METHYLVALERATE
• URANIUM
• Potassium cyanate
• Ethyl isocyanoacetate
• 2-BROMOPHENYL ISOCYANATE
• Benzyl isocyanate
• 1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione