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3,3-Bis(chloromethyl)oxetane

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Name

3,3-Bis(chloromethyl)oxetane

EINECS 201-136-5
CAS No. 78-71-7 Density 1.236 g/cm3
PSA 9.23000 LogP 1.48060
Solubility N/A Melting Point N/A
Formula C5H8Cl2O Boiling Point 208.9 °C at 760 mmHg
Molecular Weight 155.024 Flash Point 115.8 °C
Transport Information N/A Appearance N/A
Safety 23-26-36/37/39-45 Risk Codes 22-26-36/37/38
Molecular Structure Molecular Structure of 78-71-7 (3,3-Dichloromethyloxolane) Hazard Symbols VeryT+
Synonyms

3,3-Bis(chloromethyl)-1-oxacyclobutane;3,3-Bis(chloromethyl)oxacyclobutane;NSC 650608;

Article Data 12

3,3-Bis(chloromethyl)oxetane Synthetic route

813-99-0

3-chloro-(2,2-chloromethyl)propan-1-ol

78-71-7

3,3-bis(chloromethyl)oxetane

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 72h; Heating / reflux;80%
With potassium hydroxide In ethanol for 0.5h; Reflux;74%
With potassium hydroxide
13103-49-6

acetic acid-(3-chloro-2,2-bis-chloromethyl-propyl ester)

78-71-7

3,3-bis(chloromethyl)oxetane

Conditions
ConditionsYield
With potassium hydroxide; benzene
With alkaline solution
115-77-5

Pentaerythritol

copper

copper

78-71-7

3,3-bis(chloromethyl)oxetane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2, pyridine / 14 h / Heating
2: KOH / ethanol / 5 h / Heating
View Scheme
115-77-5

Pentaerythritol

78-71-7

3,3-bis(chloromethyl)oxetane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated aqueous hydrochloric acid / 185 °C
2: ethanolic KOH-solution
View Scheme
Multi-step reaction with 2 steps
1: water; hydrochloric acid / 185 °C
2: ethanolic KOH-solution
View Scheme
Multi-step reaction with 2 steps
1: pyridine; thionyl chloride
2: ethanolic NaOH-solution
View Scheme
Multi-step reaction with 2 steps
1: pyridine; thionyl chloride / 22 h / 65 - 130 °C
2: potassium hydroxide / ethanol / 0.5 h / Reflux
View Scheme
78-71-7

3,3-bis(chloromethyl)oxetane

17607-20-4

3,3-bis(azidomethyl)-oxetane

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In water99.5%
With sodium azide In N,N-dimethyl-formamide at 90 - 100℃; for 2h;76%
With sodium azide In N,N-dimethyl-formamide at 90 - 100℃; for 2h;76%
With sodium azide In dimethyl sulfoxide at 65℃;
78-71-7

3,3-bis(chloromethyl)oxetane

2857-97-8

trimethylsilyl bromide

79271-75-3

2,2-Bis-3-bromo-1-trimethylsiloxypropane

Conditions
ConditionsYield
at 100℃; for 2h;93%
78-71-7

3,3-bis(chloromethyl)oxetane

paraformaldehyde

paraformaldehyde

61729-08-6

5,5-bis(chloromethyl)-1,3-dioxane

Conditions
ConditionsYield
With sulfuric acid In toluene at 100℃; for 4.5h;84%
78-71-7

3,3-bis(chloromethyl)oxetane

124-41-4

sodium methylate

10404-84-9

3,3-di(methoxymethyl)oxetane

Conditions
ConditionsYield
In methanol at 80℃; for 240h;82%
78-71-7

3,3-bis(chloromethyl)oxetane

6325-93-5

p-nitrobenzenesulfonamide

C11H12N2O5S

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 18h;82%
78-71-7

3,3-bis(chloromethyl)oxetane

647-42-7

1H,1H,2H,2H-tridecafluoro-n-octanol

A

3-chloromethyl-3-(1,1,2,2-tetrahydro-perfluoro-octyloxy)methyl oxetane

B

3,3-Bis-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxymethyl)-oxetane

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 70℃; for 10h;A 80%
B 16%

3,3-Bis(chloromethyl)oxetane Consensus Reports

EPA Extremely Hazardous Substances List.

3,3-Bis(chloromethyl)oxetane Specification

The 3,3-Bis(chloromethyl)oxetane, with the CAS registry number 78-71-7, is also known as Oxetane, 3,3-bis-(chloromethyl). Its EINECS registry number is 201-136-5. This chemical's molecular formula is C5H8Cl2O and molecular weight is 155.02. Its systematic name is called 3,3-bis(chloromethyl)oxetane.

Physical properties of 3,3-Bis(chloromethyl)oxetane: (1)ACD/LogP: 0.85; (2)ACD/LogD (pH 5.5): 0.85; (3)ACD/LogD (pH 7.4): 0.85; (4)ACD/BCF (pH 5.5): 2.61; (5)ACD/BCF (pH 7.4): 2.61; (6)ACD/KOC (pH 5.5): 69.2; (7)ACD/KOC (pH 7.4): 69.2; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.461; (11)Molar Refractivity: 34.43 cm3; (12)Molar Volume: 125.3 cm3; (13)Surface Tension: 39.7 dyne/cm; (14)Density: 1.236 g/cm3; (15)Flash Point: 115.8 °C; (16)Enthalpy of Vaporization: 42.7 kJ/mol; (17)Boiling Point: 208.9 °C at 760 mmHg; (18)Vapour Pressure: 0.301 mmHg at 25°C.

Uses of 3,3-Bis(chloromethyl)oxetane: it can be used to produce 3,3-bis-iodomethyl-oxetane. This reaction will need solvent butanone and sodium iodide.

When you are using this chemical, please be cautious about it as the following:
This chemical that at very low levels can cause damage to health. It is harmful if swallowed. It is very toxic by inhalation. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: ClCC1(CCl)COC1
(2)InChI: InChI=1/C5H8Cl2O/c6-1-5(2-7)3-8-4-5/h1-4H2
(3)InChIKey: CXURGFRDGROIKG-UHFFFAOYAZ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LC inhalation > 250mg/m3/1H (250mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(7), Pg. 31, 1964.
mouse LC50 inhalation 200mg/m3/2H (200mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(7), Pg. 31, 1964.
mouse LD50 oral 300mg/kg (300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Farmakologiya i Toksikologiya Vol. 5, Pg. 157, 1970.
mouse LD50 unreported 545mg/kg (545mg/kg)   Russian Pharmacology and Toxicology Vol. 48, Pg. 67, 1985.
rat LD50 oral 600mg/kg (600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Farmakologiya i Toksikologiya Vol. 5, Pg. 157, 1970.

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