CAS 1816-92-8 Methyl 2-azidoacetate (HCID 4020482)

Names & identifiers

Preferred name: Methyl 2-azidoacetate
IUPAC: methyl 2-azidoacetate
English name: Azidoacetic acid methyl ester
Molecular formula: C3H5N3O2
Molecular weight: 115.0907

Names & synonyms

Methyl 2-azidoacetate1816-92-8DTXSID70398587RefChem:1089321DTXCID00349446Methyl azidoacetateMETHYLAZIDOACETATEMFCD01311034Acetic acid, 2-azido-, methyl estermethyl 3-diazo-3-azaprop-3-enoateAzidoacetic acid methyl esterAcetic acid, azido-, methyl ester

Show more names

Methyl 2-azidoacetate 97%Methyl Azido Acetate-BulkMethyl 2-azidoacetate - M34612-Azido-acetic acid Methyl ester

azido-acetic acid methyl esterAzidoacetic acid, methyl estermethyl azido acetatemethyl azido-acetatemethyl-2-azidoacetateMethyl 2-azidoacetate, 97%SCHEMBL13482799SBB001917

Database identifiers

CAS: 1816-92-8
PubChem CID: 4020482
DTXSID: DTXSID70398587
EC Number: 687-878-4
Nikkaji: J1.247.582I

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 40.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 8
Formal charge: 0
Complexity: 126

Physicochemical properties

Boiling point: 35 °C · 35 °C
Density: 1.182 g/mL · 1.182 g/mL at 25 °C
refractive index: 20 · n20/D1.440
Flash point: 48 ℃ · 48℃
form: liquid
InChI: InChI=1S/C3H5N3O2/c1-8-3(7)2-5-6-4/h2H2,1H3
InChIKey: RXYCUKSOYJWGPE-UHFFFAOYSA-N
SMILES: C(=O)(OC)CN=[N+]=[N-]
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Warning
Hazard statements: 226 · H226-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 5 · 5-10-36/37/38
Safety Statements: 26 · 26
RIDADR: 1993 C · UN 1993C 3 / PGIII
WGK Germany: 3 · 3
HazardClass: 3 · 3
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Flam · Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

wgk: 3
ridadr: UN 1993C 3 / PGIII
risk_code: 5-10-36/37/38
Signal word: Warning
Symbol(GHS): GHS02,GHS07
hazard_code: Xi
safety_code: 26
hazard_class: 3
Storage Class: 3 - Flammable liquids
target organs: Respiratory system
Hazard statements: H226-H315-H319-H335
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 1 item

UsesMethyl 2-azidoacetate is widely used as a precursor to build triazole derivatives via alkyne-azide click chemistry. Some of the examples include the synthesis of coumarin-triazole derivatives as potential antiplasmodial agents and macrocyclic triazole containing largazole analogs as histone deacetylases-1 (HDAC1) inhibitors.It can be used to synthesize various pyrrole derivatives by Knoevenagel condensation as in the synthesis of near-infrared boron dipyrromethene (BODIPY) donors for organic tandem solar cells.It can also be used in Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles.Synthesis of highly fluorescent pyreno[2,1-b]pyrroles using methyl 2-azidoacetate as one of the reagents.

Preparation methods · 1 item

PreparationAzidoacetic acid methyl ester is widely used in the azidoclick chemistry synthesis of triazole derivatives. Some examples include the synthesis of coumarin-triazole derivatives as potential antimalarial drugs and histone deacetylase-1 (HDAC1) inhibitors containing macrocyclic triazole compounds. It can be used to synthesize various pyrrole derivatives via Knoevenagel condensation, similar to its use in the synthesis of near-infrared bispyrrole (BODIPY) donors for organic tandem solar cells. It can also be used in the hemetsberg-knittel synthesis of substituted 5-, 6-, and 7-azaindole. Highly fluorescent pyrene [2,1-b]pyrrole can be synthesized using Azidoacetic acid methyl ester as a reagent.