4-(2-CHLOROACETYL)MORPHOLINE

4-(2-CHLOROACETYL)MORPHOLINE Property

Melting point:

26-30 °C

Boiling point:

152-160 °C(Press: 6 Torr)

Density 

1.257 g/mL at 25 °C

refractive index 

n20/D 1.512

Flash point:

110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-1.26±0.20(Predicted)

form 

Solid

color 

Colourless to Pale Yellow Oil

Stability:

Hygroscopic

CAS DataBase Reference

1440-61-5(CAS DataBase Reference)

EPA Substance Registry System

Morpholine, 4-(chloroacetyl)- (1440-61-5)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

UN3261

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

H319Causes serious eye irritation

Precautionary statements

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P405Store locked up.

4-(2-CHLOROACETYL)MORPHOLINE Chemical Properties,Usage,Production

Chemical Properties

Colorless liquid

Uses

The chloroacetyl derivatives are microbicides for adhesives, cellulose foams, oil emulsions, cooling water, etc.

Synthesis

Step 1: Morpholine (1.00 mL, 11.5 mmol) and toluene (30 mL) were added to a dry three-necked flask equipped with a magnetic stirrer under nitrogen protection. Potassium carbonate (3.17 g, 22.9 mmol) was then added and stirred until completely dissolved. Chloroacetyl chloride (0.91 mL, 11.4 mmol) was slowly added dropwise under the cooling of an ice bath, and after completion of the dropwise addition, the ice bath was removed, the temperature was raised to 60 °C and the reaction was continuously stirred for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered to remove insoluble solids, and the solids were washed with a small amount of toluene. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent to give N-chloroacetylmorpholine as a white solid (1.87 g, quantitative yield). The product was characterized by 1H-NMR (270 MHz, CDCl3): δ 3.51-3.54 (m, 2H), 3.62-3.65 (m, 2H), 3.68-3.74 (m, 4H), 4.07 (s, 2H).

References

[1] Patent: EP1650194, 2006, A1. Location in patent: Page/Page column 34
[2] Patent: WO2012/72019, 2012, A1. Location in patent: Page/Page column 71-72
[3] Molecules, 2015, vol. 20, # 11, p. 19984 - 20013
[4] Patent: WO2016/147144, 2016, A1. Location in patent: Page/Page column 222
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6660 - 6671