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 α-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), a

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