2-Bromo-N,N-dimethylacetamide

2-Bromo-N,N-dimethylacetamide Property

Melting point:

72-73 °C(Solv: toluene (108-88-3))

Boiling point:

63-65 °C(Press: 1 Torr)

Density 

1.5412

refractive index 

1.5097

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-1.04±0.70(Predicted)

form 

liquid

color 

Colourless to light yellow

InChI

InChI=1S/C4H8BrNO/c1-6(2)4(7)3-5/h3H2,1-2H3

InChIKey

QPIOVNJLOVNTMW-UHFFFAOYSA-N

SMILES

C(N(C)C)(=O)CBr

Safety

RIDADR 

UN2735

HazardClass 

IRRITANT

HS Code 

2924190090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

2-Bromo-N,N-dimethylacetamide Chemical Properties,Usage,Production

Synthesis

To a stirred solution of N,N-dimethylamine hydrochloride (2 g, 24.52 mmol) in dichloromethane (20 mL) was added sequentially N,N-diisopropylethylamine (DIPEA, 12.6 mL, 73.55 mmol) and bromoacetobromide (9.89 g, 19.04 mmol) under an inert atmosphere, maintaining the reaction temperature at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. The reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel fast column chromatography with 30% ethyl acetate/hexane as eluent to give N,N-dimethyl-bromoacetamide (1.7 g, 42% yield) as a brown liquid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.86 (s, 2H), 3.10 (s, 3H), 2.99 (s, 3H); LC-MS purity: 71.2%; (M + 2) measured value = 168 (column: XBridge C-18, 50 x 3.0 mm, 3.5 μm; mobile phase: 5 mM NH4OAc ACN; flow rate: 0.8 mL/min).

References

[1] Tetrahedron, 2000, vol. 56, # 42, p. 8253 - 8262
[2] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5415 - 5427
[3] Patent: WO2015/48301, 2015, A1. Location in patent: Paragraph 00435
[4] Tetrahedron, 2012, vol. 68, # 24, p. 4710 - 4718
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 19, p. 5079 - 5084