tert-butyl 2-bromoacetate

• ChemBase ID: 12195
• Molecular Formular: C6H11BrO2
• Molecular Mass: 195.05434
• Monoisotopic Mass: 193.99424159
• SMILES: C(C(=O)OC(C)(C)C)Br
• Canonical SMILES: BrCC(=O)OC(C)(C)C
• InChI: InChI=1S/C6H11BrO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3
• InChIKey: BNWCETAHAJSBFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-bromoacetate
• IUPAC Traditional name: tert-butyl 2-bromoacetate
• Synonyms: 2-Bromo-1-(tert-butoxy)ethan-1-one; tert-Butyl bromoacetate 98%; tert-Butyl bromoacetate; tert-Butyl bromoacetate; tert-butyl 2-bromoacetate; Bromoacetic acid tert-butyl ester; 溴乙酸叔丁酯

Database IDs

• CAS Number: 5292-43-3
• EC Number: 226-133-6
• MDL Number: MFCD00000188
• Beilstein Number: 1753010
• PubChem SID: 24847606; 160975502; 24850297
• PubChem CID: 79177

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.699347
• LogD (pH = 7.4): 1.699347
• Log P: 1.699347
• Molar Refractivity: 38.9551 cm^3
• Polarizability: 15.423692 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 175°C; 50 °C/10 mmHg(lit.); 50-51°C/10mm
• Flash Point: 120.2 °F; 49 °C; 49°C; 49°C(120°F)
• Density: 1.321 g/mL at 25 °C(lit.); 1.33; 1.330
• Refractive Index: 1.445; 1.4450; n20/D 1.445; n20/D 1.445(lit.)
• Hydrophobicity(logP): 1.892

Safety Information

• Storage Warning: Flammable/Harmful/Lachrymatory/Light Sensitive; IRRITANT-HARMFUL, LACHRYMATOR, FLAMMABLE
• European Hazard Symbols: Corrosive (C); X; Irritant (Xi)
• UN Number: 1993; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-22-34; 10-36/37/38
• Safety Statements: 26; 26-36/37/39-45
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335; H314-H318-H226-H302
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P303+P361+P353-P305+P351+P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥97.0% (GC); 95%; 95+%; 97%; 98%
• Grade: purum
• Linear Formula: BrCH2COOC(CH3)3

DETAILS

Sigma Aldrich - 124230

Packaging
10, 50, 250 g in glass bottle
Application
Common alkylating agent. Used in the synthesis of the collagenase inhibitor (S,S,R)-(-)-actinonin.1Building block for substituted t-butyl acetates.2Employed in the synthesis of a dihydropyranyl prelinker which was used, in turn, in an efficient polymer-assisted deprotection of oligosacchararides.3

Sigma Aldrich - 17035

Other Notes
Reagent used in Reformatzky reactions1; Alkylation of Reformatzky reagents2

REFERENCES

• In the Reformatsky synthesis of ?-hydroxy acids, competing ?-elimination and retro-aldol type cleavage are minimized by the use of the t-butyl ester, and heating the reaction mixture in dry benzene leads directly to the hydroxy acid, avoiding the need for a separate hydrolysis step: Chem. Commun., 679 (1969); J. Chem. Soc. (C), 2799 (1969). For a review of advances in the Reformatsky reaction, see: Synthesis, 571 (1989). Addition of the same organozinc reagent to nitriles gives amino acrylates, which can be hydrolyzed to ?-keto-esters (Blaise reaction). For extension of this reaction to hindered nitriles, see: J. Org. Chem., 48, 3833 (1983).