3D Mol Similar

TRIMETHYLENE OXIDE

: Iupac Name：oxetane; CAS No.: 503-30-0; Molecular Weight：58.07914; Modify Date.: 2022-10-27 04:01; Introduction:
TRIMETHYLENE OXIDE, with the chemical formula C3H6O and CAS registry number 503-30-0, is a compound known for its applications in various chemical processes. This colorless liquid, also referred to as oxetane, is characterized by its three-membered ring containing one oxygen atom. It is commonly used as a monomer in the production of polymers, such as polytrimethylene oxide, which find applications in the textile, automotive, and medical industries. TRIMETHYLENE OXIDE is also utilized as a solvent for various organic compounds and as a starting material for the synthesis of pharmaceuticals and agrochemicals. It exhibits low toxicity and volatility, making it suitable for use in environmentally friendly processes. Overall, TRIMETHYLENE OXIDE is a versatile compound with diverse applications in different fields.
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1. Names and Identifiers

: 1.1 Name; TRIMETHYLENE OXIDE; 1.2 Synonyms; 1,3-EPOXYPROPAN 1,3-EPOXYPROPANE 1,3-PROPYLENE OXIDE 1,3-TRIMETHYLENE OXIDE alpha,gamma-Propane oxide alpha,gamma-propaneoxide Cyclooxabutane EINECS 207-964-3 MFCD00005167 Oxacyclobutane OXETANE Trimethylene oxide (8CI) Trimethylene oxide/Oxetane; View all

1.3 CAS No.: 503-30-0

1.4 CID: 10423

1.5 EINECS(EC#): 207-964-3

1.6 Molecular Formula: C3H6O (isomer)

1.7 Inchi: InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2

1.8 InChIkey: AHHWIHXENZJRFG-UHFFFAOYSA-N

1.9 Canonical Smiles: C1COC1

1.10 Isomers Smiles: C1COC1

2. Properties

2.1 Density: 0.89

2.1 Melting point: -97°C

2.1 Boiling point: 50-50℃

2.1 Refractive index: 1.392

2.1 Flash Point: °C

2.1 Precise Quality: 58.04190

2.1 PSA: 9.23000

2.1 logP: 0.40670

2.1 Solubility: 1000g/l

2.2 Appearance: Clear, colorless liquid

2.3 Atmospheric OH Rate Constant: 1.03e-11 cm3/molecule*sec

2.4 Storage: Keep Cold.

2.5 Chemical Properties: CLEAR COLOURLESS LIQUID

2.6 Color/Form: Oil

2.7 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.8 Odor: Agreeable aromatic odor

2.9 Water Solubility: soluble in water

2.10 Spectral Properties: MAX ABSORPTION (GAS): 167 NM (LOG E= 3.04); 170.5 NM (LOG E= 3.29); 174.2 NM (LOG E= 3.44); 184 NM (LOG E= 3.1); 187.5 NM (LOG E= 3.30)
Index of refraction: 1.3895 @ 25 deg C/D
UV: OES 4-9 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: SAD 16829 (Sadtler Research Laboratories Spectral Collection)
MS: 135 NIST (NIST/EPA/MSDC Mass Spectral Database, 1990 version)

2.11 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.

3.2 General Description: Clear, colorless liquid with an agreeable aromatic odor.

3.3 Purification Methods: Distil oxetane twice from sodium metal and then fractionate it through a small column at atmospheric pressure, b 47.0-47.2o. It can also be purified by preparative gas chromatography using a 2m silica gel column. Alternatively, add KOH pellets (50g for 100g of oxetane) and distil it through an efficient column or a column packed with 1/4in Berl Saddles with the main portion boiling at 45-50o being collected and redistilled over fused KOH. [Noller Org Synth Coll Vol III 835 1955, Dittmer et al. J Am Chem Soc 79 4431 1957, Beilstein 17 H 6, 17 I 3, 17 II 12, 17 III/IV 13, 17/1 V 11.] TRIMETHYLENE OXIDE Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Symbol: GHS02, GHS07

4.1 Hazard Codes: F; Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R11;R20/21/22

4.1 Safety Statements: S16;S26;S29;S9

4.1 Packing Group: II

4.1 Octanol/Water Partition Coefficient: log Kow= -0.14

4.2 Fire Hazard: TRIMETHYLENE OXIDE is flammable.

4.3 Hazard Class: 3

4.3 Hazard Declaration: H225-H302-H312-H332

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: UN 1993

4.4 Safety Profile: Moderately toxic by subcutaneous route. May be narcotic in high concentrations. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes

4.5 Caution Statement: P210-P280

4.5 WGK Germany: 1

4.5 RTECS: RQ6825000

4.5 Reactivities and Incompatibilities: Strained ring oxygen heterocycles such as epoxides and exetanes react with the oxide in dichloromethane at sub-ambient temperatures to form high yields of the powerfully explosive glycol dinitrate esters.

4.6 Report: Reported in EPA TSCA Inventory.

4.7 Specification

The IUPAC name of Oxetane is oxetane. With the CAS registry number 503-30-0, it is also named as 1,3-Epoxypropane. The product's categories are Heterocyclic Compounds; Oxetanes; Simple 4-Membered Ring Compounds. Besides, it is clear, colorless liquid with an agreeable aromatic odor which should be stored in sealed, cool and ventilated place at 2-8 °C. In addition, it is soluble in water.

The other characteristics of this product can be summarized as: (1)EINECS: 207-964-3; (2)ACD/LogP: -0.24; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -0.24; (5)ACD/LogD (pH 7.4): -0.24; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 17.69; (9)ACD/KOC (pH 7.4): 17.69; (10)H bond acceptors: 1; (11)H bond donors: 0; (12)Freely Rotating Bonds: 0; (13)Index of Refraction: 1.412; (14)Molar Refractivity: 15.44 cm³; (15)Molar Volume: 62 cm³; (16)Surface Tension: 29.6 dyne/cm; (17)Density: 0.936 g/cm³; (18)Flash Point: -20 °C; (19)Melting Point: -97 °C; (20)Enthalpy of Vaporization: 28.67 kJ/mol; (21)Boiling Point: 49 °C at 760 mmHg; (22)Vapour Pressure: 317 mmHg at 25 °C.

Preparation of Oxetane: this chemical can be prepared by the reaction of Potassium hydroxide with 3-Chloropropyl acetate at 150 °C. And the yield is 40 %.

Uses of Oxetane: it can react with Piperidine to get 3-Piperidin-1-yl-propan-1-ol.

This reaction needs LiBF₄ and Acetonitrile at ambient temperature for 23 hours. The yield is 93 %.

When you are using this chemical, please be cautious about it as the following: it is highly flammable. Please keep away from sources of ignition. It is also harmful by inhalation, in contact with skin and if swallowed. Please keep container in a well-ventilated place. And you should not empty into drains. Moreover, in case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES:O1CCC1
(2)InChI:InChI=1/C3H6O/c1-2-4-3-1/h1-3H2
(3)InChIKey:AHHWIHXENZJRFG-UHFFFAOYAE
(4)Std. InChI:InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2
(5)Std. InChIKey:AHHWIHXENZJRFG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	subcutaneous	500mg/kg (500mg/kg)		Zeitschrift fuer Krebsforschung. Vol. 74, Pg. 241, 1970.

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4.8 Toxicity: mmo-sat 3333 mg/plate EMMUEG 11(Suppl 12),1,88

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H225 Highly flammable liquid and vapour H302 Harmful if swallowed H312 Harmful in contact with skin H332 Harmful if inhaled
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.
Storage	P403+P235 Store in a well-ventilated place. Keep cool.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

503-30-0Total: 20 Synthesis Route

74-98-6 101 Suppliers

503-30-0 41 Suppliers

116-09-6 82 Suppliers

Literatures:
Journal of Physical Chemistry A, , vol. 116, # 50 p. 12214 - 12228
Yield: null

627-18-9 153 Suppliers

503-30-0 41 Suppliers

Literatures:
Fujiwara, Masahiro; Hitomi, Kazuhisa; Baba, Akio; Matsuda, Haruo Synthesis, 1990 , # 2 p. 106 - 109
Yield: ~59%

111-66-0 32 Suppliers

503-30-0 41 Suppliers

Literatures:
Brehon, Annick; Couture, Axel; Combier, Lablache Journal de Chimie Physique et de Physico-Chimie Biologique, 1985 , vol. 82, # 9 p. 851 - 860
Yield: ~5%

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7. Other Information

7.0 Usage: Trimethylene oxide useful for the synthesis of 3-substituted propanols by reaction with Grignards or organolithiums in the presence of CuBr.

7.1 Merck: 14,9715

7.2 BRN: 102382

7.3 Chemical Properties: CLEAR COLOURLESS LIQUID

7.4 Definition: ChEBI: A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.

7.5 General Description: Clear, colorless liquid with an agreeable aromatic odor.

7.6 Air & Water Reactions: Highly flammable. Water soluble.

7.7 Reactivity Profile: TRIMETHYLENE OXIDE reacts with Grignard reagents and organolithium compounds. TRIMETHYLENE OXIDE is also incompatible with oxidizing agents and strong acids. . An explosion occurred when propylene oxide was added to epoxy resin. Polymerization was catalyzed by amine accelerator in the resin [Bretherick 1995]. Propylene oxide and sodium hydroxide base-catalyzed the polymerization of the former, causing ignition and explosion of a drum of the crude product. [Combust Sci. Technol., 1983].

7.8 Fire Hazard: TRIMETHYLENE OXIDE is flammable.

7.9 Safety Profile: Moderately toxic by subcutaneous route. May be narcotic in high concentrations. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes

7.10 Purification Methods: Distil oxetane twice from sodium metal and then fractionate it through a small column at atmospheric pressure, b 47.0-47.2o. It can also be purified by preparative gas chromatography using a 2m silica gel column. Alternatively, add KOH pellets (50g for 100g of oxetane) and distil it through an efficient column or a column packed with 1/4in Berl Saddles with the main portion boiling at 45-50o being collected and redistilled over fused KOH. [Noller Org Synth Coll Vol III 835 1955, Dittmer et al. J Am Chem Soc 79 4431 1957, Beilstein 17 H 6, 17 I 3, 17 II 12, 17 III/IV 13, 17/1 V 11.]

8. Computational chemical data

Molecular Weight: 58.07914g/mol
Molecular Formula: C₃H₆O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 58.041864811
Monoisotopic Mass: 58.041864811
Complexity: 17.2
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 9.2
Heavy Atom Count: 4
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBAIAAAAAAAAAAAAAAAAABIAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACACggAIAAAAABAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9. Question & Answer

What are the background, preparation, and applications of TRIMETHYLENE OXIDE? Jun 23 2021
Background and Overview[1] TRIMETHYLENE OXIDE, also known as 1,3-epoxypropane, can be obtained by cyclization of 3-bromo-1-propanol. It has been reported in the literature that it can be used for the ..
Grignard reagents react with epoxides but dissolve in THF, what happens in oxetane (four membered ether ring)? Jun 10 2021
Ring strain causes the epoxides to react and THF does not react because the ring strain is not large enough. Does the four membered ring react or not? Does it favor reaction with the harder or softer..

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