methyl 2-bromoacetate

• ChemBase ID: 104200
• Molecular Formular: C3H5BrO2
• Molecular Mass: 152.9746
• Monoisotopic Mass: 151.9472914
• SMILES: COC(=O)CBr
• Canonical SMILES: COC(=O)CBr
• InChI: InChI=1S/C3H5BrO2/c1-6-3(5)2-4/h2H2,1H3
• InChIKey: YDCHPLOFQATIDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-bromoacetate
• IUPAC Traditional name: methyl 2-bromoacetate
• Synonyms: Methyl bromoacetate; Bromoacetic acid methyl ester; methyl 2-bromoacetate; 2-Amino-4-hydroxypyrimidine; ISOCYTOSINE; METHYL BROMOACETATE; 溴乙酸甲酯

Database IDs

• CAS Number: 108-53-2; 96-32-2
• EC Number: 202-499-2; 203-592-0
• MDL Number: MFCD00000189
• Beilstein Number: 506256
• PubChem SID: 162091634; 24850306; 24849708
• PubChem CID: 60984

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6453874
• LogD (pH = 7.4): 0.6453874
• Log P: 0.6453874
• Molar Refractivity: 25.1495 cm^3
• Polarizability: 10.105674 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -50°C
• Boiling Point: 144-145°C; 51-52 °C/15 mmHg(lit.)
• Flash Point: 147.2 °F; 62°C(143°F); 64 °C
• Density: 1.616 g/mL at 25 °C(lit.); 1.655
• Refractive Index: 1.4585; n20/D 1.458; n20/D 1.458(lit.)
• Hydrophobicity(logP): 0.435

Safety Information

• Storage Condition: 0°C
• RTECS: AF6300000
• European Hazard Symbols: Corrosive (C); Toxic (T)
• UN Number: 2643; UN2643
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 25-34; 25-34-37; R:34
• Safety Statements: 20-23-26-36/37/39-45-60; 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H314-H318-H227; H301-H314-H335
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P280-P301 + P310-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2643 6.1/PG 2

Product Information

• Purity: ≥97.0% (GC); 95%; 95+%; 97%; 98+%
• Grade: purum
• Linear Formula: BrCH2COOCH3

DETAILS

MP Biomedicals - 02155090

(2-Amino-4-hydroxypyrimidine) Crystalline

Sigma Aldrich - 157910

Packaging
25, 100 g in glass bottle

REFERENCES

• For further reactions of ɑ-bromo esters, see Ethyl bromoacetate, A10448.
• The reaction with aldehydes in the presence of zinc and tri-n-butylphosphine gives ɑ?-unsaturated esters directly: Tetrahedron Lett., 29, 6119 (1988).
• Addition of the organozinc derivative to nitriles (Blaise reaction), gives ?-amino acrylates, which can be hydrolyzed to ?-keto esters. For conditions allowing the use of hindered nitriles, see: J. Org. Chem., 48, 3833 (1983):