3,3-Bis(chloromethyl)oxetane supplier

Name
3,3-Dichloromethyloxolane
EINECS 201-136-5
CAS No. 78-71-7
Article Data12
CAS DataBase
Density 1.236 g/cm³
Solubility
Melting Point
Formula C₅H₈Cl₂O
Boiling Point 208.9 °C at 760 mmHg
Molecular Weight 155.024
Flash Point 115.8 °C
Transport Information
Appearance
Safety 23-26-36/37/39-45
Risk Codes 22-26-36/37/38
Molecular Structure
Hazard Symbols T+
Synonyms 3,3-Bis(chloromethyl)-1-oxacyclobutane;3,3-Bis(chloromethyl)oxacyclobutane;NSC 650608;
PSA 9.23000
LogP 1.48060

Synthetic route

: 813-99-0
3-chloro-(2,2-chloromethyl)propan-1-ol

: 78-71-7
3,3-bis(chloromethyl)oxetane

Conditions

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide; benzene
With alkaline solution

: 115-77-5
Pentaerythritol

copper: copper

: 78-71-7
3,3-bis(chloromethyl)oxetane

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In water	99.5%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In methanol at 80℃; for 240h;	82%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 6325-93-5
p-nitrobenzenesulfonamide

: C11H12N2O5S

Conditions

Conditions	Yield
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

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

...Expand

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 2402-82-6
3,3-Bis(iodomethyl)oxacyclobutane

Conditions

Conditions	Yield
With sodium iodide In acetone for 52h; Heating;	75%
With sodium iodide In acetone for 56h; Heating;	75%
With butanone; sodium iodide

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 141-52-6
sodium ethanolate

: 10404-85-0
3,3-di(ethoxymethyl)oxetane

Conditions

Conditions	Yield
In ethanol at 90℃; for 330h;	75%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 57-14-7
1,1-dimethylhydrazine

: 3-(1,1-dimethylhydraziniomethyl)-3-(chloromethyl)oxetane chloride

Conditions

Conditions	Yield
Alkylation;	75%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 107149-26-8
2,2-bis(chloromethyl)propane-1,3-diol dinitrate

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 15℃; for 5h;	73%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 5455-59-4
2-Nitrobenzenesulfonamide

: C11H12N2O5S

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 18h;	73%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 50-00-0
formaldehyd

: 61729-08-6
5,5-bis(chloromethyl)-1,3-dioxane

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane at 90 - 100℃; for 5h;	70%
With sulfuric acid In 1,4-dioxane for 5h; Heating;

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 2372-45-4
sodium butanolate

: 1522-91-4
3,3-bis-butoxymethyl-oxetane

Conditions

Conditions	Yield
In butan-1-ol at 105℃; for 270h;	68%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 100-52-7
benzaldehyde

: 6103-09-9
2-phenyl-5,5-bis(chloromethyl)-1,3-dioxane

Conditions

Conditions	Yield
With sulfuric acid In toluene at 110℃; for 4.5h;	68%
With sulfuric acid In 1,4-dioxane for 5h; Heating;

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 125906-12-9
2-oxa-6,7-ditelluraspiro<3.4>octane

Conditions

Conditions	Yield
With potassium tellurocyanate In dimethyl sulfoxide	65%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 13195-64-7
diisopropyl malonate

: 1023817-50-6
diisopropyl 2-oxaspiro[3.3]heptane-6,6-dicarboxylate

Conditions

Conditions	Yield
Stage #1: diisopropyl malonate With sodium hydride In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: 3,3-bis(chloromethyl)oxetane With potassium iodide at 140℃; for 10h; Reflux; Inert atmosphere;	64%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: N-(but-2-yn-1-yl)-2-ethynyl-N-methylaniline

: 5-{2-[but-2-yn-1-yl(methyl)amino]phenyl}-2,2-bis(chloromethyl)pent-4-yn-1-ol

Conditions

Conditions	Yield
Stage #1: N-(but-2-yn-1-yl)-2-ethynyl-N-methylaniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #3: 3,3-bis(chloromethyl)oxetane In tetrahydrofuran; hexane at -78℃; Inert atmosphere;	63%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 123-63-7
paracetaldehyde

: 13727-37-2
2-methyl-5,5-bis(chloromethyl)-1,3-dioxane

Conditions

Conditions	Yield
With sulfuric acid In toluene at 60℃; for 4.5h;	62%

: 5464-28-8
1,3-dioxolane-4-methanol

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 127719-58-8
4-(3-Chloromethyl-oxetan-3-ylmethoxymethyl)-[1,3]dioxolane

Conditions

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether for 4h; Ambient temperature;	60%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 100-46-9
benzylamine

: 46246-91-7
2-benzyl-6-oxa-2-azaspiro[3.3]-heptane

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; for 18h;	57%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 120-72-9
indole

: 1314235-53-4
3,3-bis(indol-1-ylmethyl)oxetane

Conditions

Conditions	Yield
Stage #1: 3,3-bis(chloromethyl)oxetane; indole In butanone Reflux; Stage #2: With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide In butanone for 48h; Reflux;	53%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 35842-61-6
3-(Iodomethyl)-3-(chloromethyl)oxetane

Conditions

Conditions	Yield
With sodium iodide In acetone for 6h; Heating;	52%
With sodium iodide In acetone for 6h; Heating;	52%
With sodium iodide In acetone for 6.5h; Product distribution; Heating; oth. time;	1.23 g

: 78-71-7
3,3-bis(chloromethyl)oxetane

A: 3296-86-4
2,2-bis(chloromethyl)-1,3-diacetoxypropane

B: 69213-72-5
5,5-bis-chloromethyl-[1,3,2]dioxaphosphinane 2-oxide

Conditions

Conditions	Yield
With phosphonic Acid; acetic anhydride In 1,4-dioxane for 2h; Heating; Title compound not separated from byproducts;	A n/a B 47.9%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 108-91-8
cyclohexylamine

: 97401-34-8
6-Cyclohexyl-2-oxa-6-azaspiro<3.3>heptane

Conditions

Conditions	Yield
With sodium hydroxide at 120℃; for 0.666667h;	45%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 2393-23-9
4-methoxy-benzylamine

: 6-(4-methoxybenzyl)-2-oxa-6-azaspiro[3.3]heptane

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 18h;	45%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 64-19-7
acetic acid

: 13431-60-2
2,2-Bis(chloromethyl)propyl acetate

Conditions

Conditions	Yield
With potassium iodide; zinc at 120℃; for 10h;	36%

: 78-71-7
3,3-bis(chloromethyl)oxetane

A: 338-61-4
3,3-bis-fluoromethyl-oxetane

B: 74465-76-2
3-Chloromethyl-3-fluoromethyl-oxetane

Conditions

Conditions	Yield
With potassium fluoride; 18-crown-6 ether at 100℃; for 23h;	A 18% B 35%

: 5464-28-8
1,3-dioxolane-4-methanol

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 127719-61-3
C13H22O7

Conditions

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether for 4h; Ambient temperature;	30%

: 78-71-7
3,3-bis(chloromethyl)oxetane

: 2209-86-1
2,2-bis(chloromethyl)-1,3-propanediol

Conditions

Conditions	Yield
With sulfuric acid In water	28%

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.

Product Name

3,3-Dichloromethyloxolane

Synthetic route

3,3-Bis(chloromethyl)oxetane Consensus Reports

3,3-Bis(chloromethyl)oxetane Specification

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