CAS 39687-95-1 Methyl isocyanoacetate (HCID 547815)

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Basic information

CAS: 39687-95-1
Standard SMILES: [C-]#[N+]CC(=O)OC
InChIKey: CRXFROMHHBMNAB-UHFFFAOYSA-N
Molecular formula: C4H5NO2
Average molar mass: 99.09 g/mol
Monoisotopic mass: 99.0320284

Names & identifiers

Preferred name: Methyl isocyanoacetate
IUPAC: methyl 2-isocyanoacetate
English name: Methyl isocyanoacetate
Molecular formula: C4H5NO2
Molecular weight: 99.09

Names & synonyms

Methyl isocyanoacetate39687-95-1Acetic acid, isocyano-, methyl esterRefChem:157906254-593-8CRXFROMHHBMNAB-UHFFFAOYSA-NEINECS 254-593-8InChI=1/C4H5NO2/c1-5-3-4(6)7-2/h3H2,2HMethyl 2-isocyanoacetateIsocyanoacetic acid methyl esterMFCD00000006methylisocyanoacetate

Show more names

Methyl isocyanoformateROXA-015Methyl Isocyanoacetate >Methyl Isocyanoacetate,>97%Methyl isocyanoacetate , tech.2-Oxo-2-methoxyethyl isocyanide(2-Oxo-2-methoxyethyl) isocyanide

Isocyano-acetic acid methyl estermethyl-isocyanoacetatemethyl isocyano-acetatemethyl alpha-isocyanoacetateSCHEMBL160120SCHEMBL11419732GEO-03019AKOS015950609

Database identifiers

CAS: 39687-95-1
PubChem CID: 547815
EC Number: 254-593-8
Nikkaji: J236.418B

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 30.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 7
Formal charge: 0
Complexity: 110

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

GHS classification

GHS Classification · 5 items

Danger

H302 (95.7%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (95.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H331 (13%): Toxic if inhaled [Danger Acute toxicity, inhalation]；H332 (87%): Harmful if inhaled [Warning Acute toxicity, inhalation]

P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (95.7%)；Acute Tox. 4 (95.7%)；Skin Corr. 1B (100%)；Acute Tox. 3 (13%)；Acute Tox. 4 (87%)

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

Chemistry & industry

Applications · 3 items

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.