Basic information
- CAS
39687-95-1- Standard SMILES
C=NCC(=O)OC- InChIKey
ZRGVTTCCASYOFN-UHFFFAOYSA-N- Molecular formula
- C4H7NO2
- Average molar mass
- 101.1 g/mol
- Monoisotopic mass
- 101.04767847
Names & identifiers
- Preferred name
- Methyl 2-(methylideneamino)acetate
- IUPAC
- methyl 2-(methylideneamino)acetate
- English name
- Methyl isocyanoacetate
- Molecular formula
- C4H5NO2
- Molecular weight
- 99.09
Names & synonyms
methyl 2-(methylideneamino)acetateMethyl N-methylideneglycinateSCHEMBL255150DTXSID40960295Methyl 2-isocyanoacetateISOCYANOACETIC ACID METHYL ESTERMethyl isocyanoformateROXA-015Methyl isocyanoacetateMethyl Isocyanoacetate >Methyl Isocyanoacetate,>97%Methyl isocyanoacetate , tech.2-Oxo-2-methoxyethyl isocyanide
Show more names
(2-Oxo-2-methoxyethyl) isocyanide
Database identifiers
- CAS
39687-95-1- PubChem CID
- 3084751
- DTXSID
DTXSID40960295- Nikkaji
- J3.296.496F
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 38.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 79.8
Physicochemical properties
- Boiling point
- 75 · 75-76 °C10 mm Hg(lit.)
- Density
- 1.09 g/mL · 1.09 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.417(lit.)
- Flash point
- 193 °F · 193 °F
- storage temp.
- 2 · 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 · 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 · 39687-95-1(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8-9-32-13-19
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 2922 8/PG 2
- hs_code
- 29291090
- risk_code
- 20/21/22-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H302+H312+H332-H314
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- Precautionary statements
- P261-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Applications
UsesMethyl 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.
UsesMethyl isocyanoacetate has been used in the copper-catalyzed, diastereoselective synthesis of oxazolines.
General DescriptionMethyl 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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