Basic information
- CAS
25323-58-4- Standard SMILES
ClCC1(CCl)COC1- InChIKey
CXURGFRDGROIKG-UHFFFAOYSA-N- Molecular formula
- C5H8Cl2O
- Average molar mass
- 155.02 g/mol
- Monoisotopic mass
- 153.99522024
Overview
The monomer unit of a thermoplastic resin trademarked Penton.
Names & identifiers
- Preferred name
- Oxetane, 3,3-bis(chloromethyl)-
- IUPAC
- 3,3-bis(chloromethyl)oxetane
- English name
- 3,3-Dichloromethyloxolane
- Molecular formula
- C5H8Cl2O
- Molecular weight
- 155.02
Names & synonyms
Show more names
Database identifiers
- CAS
25323-58-4、78-71-7- PubChem CID
- 6550
- DTXSID
DTXSID9058816- ChEMBL
CHEMBL1988189- UNII
- N12TP81ATK
- EC Number
- 201-136-5
- Nikkaji
- J65.715H
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 9.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 74.5
Experimental & physicochemical properties
Density
1.4
1.4 @25 °C
Color/Form
Finely divided powder for coatings
Natural, black, or olive green molding powder.
Boiling Point
217 °F at 30 mmHg (EPA, 1998)
200 °C @760 [mm Hg]
Melting Point
66 °F (EPA, 1998)
18.7 °C
Physical Description
The monomer unit of a thermoplastic resin trademarked Penton.
Natural, black, or olive green solid; [HSDB] "The monomer unit of a thermoplastic resin trademarked Penton. " mp = 18.9 deg C; [CAMEO] Liquid; [MSDSonline]
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazards Summary
Causes somnolence in lethal-dose feeding studies of rats; Causes lacrimation, somnolence, and kidney damage in high-dose inhalation studies; [RTECS] An irritant and lachrymator; Highly toxic by inhalation; Targets blood, kidneys, and CNS; [Aldrich MSDS]
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Oxetane, 3,3-bis(chloromethyl)- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Safety & protection
First Aid
Signs and Symptoms of Oxetane, 3,3-Bis(chloromethyl)- Exposure: Signs and symptoms of acute exposure to oxetane, 3,3-bis(chloromethyl)- may include headache, dizziness, weakness and nausea. Also, irritation of the eyes, skin, respiratory tract may be observed. Esophagus or gastrointestinal tract irritation is possible if ingested. Longer term exposure may lead to allergic hypersensitivity dermatitis or asthma with bronchospasm and wheezing.
Cleanup Methods
Purification of waste water from the synthesis of 3,3-di-(chloromethyl) oxycyclobutane.
Biological clarification of sewage from production of 3,3-bis(chloromethyl) oxycyclobutane.
Protective Action Criteria (PAC)
0.18 [mg/m3]
2.0 [mg/m3]
7.0 [mg/m3]
Personal Protective Equipment (PPE)
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
Toxicology
Non-Human Toxicity Excerpts
A series of oxetanes containing iodomethyl, alkoxymethyl, and alkylaminomethyl groups were synthesized. The toxicity and broncholytic activity of these compounds were determined in mice and cats. Iodo- and alkyloxy-containing oxetanes possessed lower toxicity, and N-containing oxetanes had higher toxicity than 3,3-bis(chloromethyl)oxetane, the initial product of the synthesis. All compounds containing oxetane ring manifested a pronounced broncholytic effect. 3-(Chloromethyl)-3-(butoxymethyl)oxetane, 3,3-bis(propoxymethyl)oxetane, and 3-(chloromethyl)-3-(iodomethyl)oxetane possessed the same broncholytic effect, as that of euphyllin.
Regulatory information
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Oxetane, 3,3-bis(chloromethyl)- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Chemistry & industry
Uses & manufacturing
Uses
Used for solid and lined valves, pumps, pipes, and fittings; Also used as a monofilament for filter supports and column packing, as a thermoplastic polymer, and for biological purification of waste waters from the manufacture of pentaplast; [HSDB] Penton is the resin derived from 3,3-Bis(chloromethyl)oxetane. [Hawley]
Sewer and Wastewater Treatment [Category: Industry]
Solid and lined valves, pumps, pipe and fittings; Monofilament for filter supports and column packing.
A thermoplastic polymer ... /with/ a high melting temperature of 180 °C. /Poly(3,3-bis-(chloromethyl)oxetane)/
Biological purification of waste waters from the manufacture of pentaplast.
Suggested uses of poly (3,3-bischloromethyl) oxetane includes valves, bearings, precision gears, corrosion free coatings, wedges and slot liners for stators in electric motors, films, and rope. /Poly(3,3-bischloromethyl) oxetane/
Methods of Manufacturing
... Full scale commercial introduction has never been realized. Since the monomer /of poly(3,3-bis-(chloromethyl)oxetane)/ requires a careful purification procedure and the synthesis requires several steps from pentaerythritol ... . /Poly(3,3-bis-(chloromethyl)oxetane)/
General Manufacturing Information
Oxetane, 3,3-bis(chloromethyl)-: ACTIVE
Penton: Trademark for a thermoplastic resin derived from 3,3-bis(chloromethyl)oxetane ...
Poly(3,3-bis-(chloromethyl)oxetane) (PBCMO) was available commercially as Penton but it is no longer marketed. /Poly(3,3-bis-(chloromethyl)oxetane)/
Suppliers95 total
Related reactions
Compound notes
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