3,3-BIS(CHLOROMETHYL)OXETANE Chemical Properties

Melting point:

18.7°C

Boiling point:

198 °C(lit.)

Density 

1.29 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.486(lit.)

Flash point:

114 °C

storage temp. 

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

form 

Liquid

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C5H8Cl2O/c6-1-5(2-7)3-8-4-5/h1-4H2

InChIKey

CXURGFRDGROIKG-UHFFFAOYSA-N

SMILES

O1CC(CCl)(CCl)C1

CAS DataBase Reference

78-71-7(CAS DataBase Reference)

EPA Substance Registry System

3,3-Bis(chloromethyl)oxetane (78-71-7)

Safety Information

Hazard Codes 

T+,Xn

Risk Statements 

22-26-36/37/38

Safety Statements 

23-26-36/37/39-45

RIDADR 

2810

WGK Germany 

3

RTECS 

RQ6826000

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

78-71-7(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 600 mg/kg FATOBP 5,157,70

3,3-BIS(CHLOROMETHYL)OXETANE Usage And Synthesis

Uses

3,3-Bis(chloromethyl)oxetane is used in preparation of light curing ink and its application.

General Description

The monomer unit of a thermoplastic resin trademarked Penton.

Reactivity Profile

3,3-BIS(CHLOROMETHYL)OXETANE is a chlorinated ether.

Safety Profile

Poison by ingestion andinhalation. When heated to decomposition it emits toxicfumes of Cl-.

Synthesis

The general procedure for the synthesis of 3,3-bis(chloromethyl)oxetane from 3-chloro-2,2-dichloromethylpropan-1-ol is as follows: Step a) Preparation of compound 2: A mixture of 3-chloro-2,2-dichloromethylpropan-1-ol (1.0 g, 5.22 mmol) and potassium hydroxide (0.345 g, 85% purity, 5.22 mmol) in ethanol (2 mL) was heated and refluxed for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered to remove the solid generated in the reaction. The filtrate was concentrated to give compound 2 (0.65 g, 80% yield) as a colorless liquid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.47 (s, 4H), 3.95 (s, 4H).

Purification Methods

Shake it with aqueous NaHCO3 or FeSO4 to remove peroxides, separate, dry with anhydrous Na2SO4, then distil it under reduced pressure from a little CaH2 [Dainton et al. Trans Faraday Soc 56 1784 1960, Farthing J Chem Soc 3648 1955]. The 3,3-bis(phenoxymethyl) derivative is described below. [Beilstein 17 III/IV 68.] Lachrymatory.

References

[1] Patent: US2005/282826, 2005, A1. Location in patent: Page/Page column 28-29
[2] Patent: KR101592370, 2016, B1. Location in patent: Paragraph 0204; 0205; 0209-0211
[3] Journal of the Chemical Society, 1955, p. 3648,3651
[4] Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen, 1940, vol. 2, # 5, p. 3,16
[5] Kogyo Kagaku Zasshi, 1956, vol. 59, p. 77

3,3-BIS(CHLOROMETHYL)OXETANE(78-71-7)Related Product Information

• 1,3-Dichloropropane
• 2-(CHLOROMETHYL)-2-METHYL-1,3-EPOXYPROPANE
• TRIMETHYLENE OXIDE
• 3-Chloro-1-propanol
• 2,2-Dimethyl-1,3-dichloropropane
• 3,3-BIS(CHLOROMETHYL)OXETANE
• 3-Chloro-2,2-dimethyl-1-propanol
• OXETANE, 3-(CHLOROMETHYL)-
• 1-CHLORO-2,2-DIMETHYLPROPANE
• 3,3-DIMETHYLOXETANE