Oxetane, 3,3-bis(chloromethyl)-

HCID 6550

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

3,3-Bis(chloromethyl)oxetane78-71-7OXETANE, 3,3-BIS(CHLOROMETHYL)-Penton3,3-DichloromethyloxycyclobutaneHSDB 6322EINECS 201-136-5N12TP81ATKBRN 01033543,3-bis(chloromethyl)oxacyclobutaneNSC-650608DTXSID9058816
Show more names
CXURGFRDGROIKG-UHFFFAOYSA-3,3-BIS(CHLOROMETHYL)-1-OXACYCLOBUTANERefChem:8571153,3Bis(chloromethyl)oxetane3,3DichloromethyloxycyclobutaneDTXCID8048103OXETANE, 3,3-BIS(CHLOROMETHYL)OXETANE, 3,3-BIS(CHLOROMETHYL)-[HSDB]

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesFusion temperature
Density · 2 items

1.4

1.4 @25 °C

Color/Form · 2 items

Finely divided powder for coatings

Natural, black, or olive green molding powder.

Boiling Point · 2 items

217 °F at 30 mmHg (EPA, 1998)

200 °C @760 [mm Hg]

Melting Point · 2 items

66 °F (EPA, 1998)

18.7 °C

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Fire PotentialSelf extinguishing
Hazards Summary · 1 item

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]

Reactive GroupEthers
Reactivity Profile3,3-BIS(CHLOROMETHYL)OXETANE is a chlorinated ether.
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
CERCLA Reportable Quantities · 1 item

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 · 1 item

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 · 2 items

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) · 3 items

0.18 [mg/m3]

2.0 [mg/m3]

7.0 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

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

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Non-Human Toxicity Excerpts · 1 item

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.

Toxicity DataLC50 (mice) = 200 mg/m3/2h

Regulatory information

CERCLA Reportable Quantities · 1 item

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 · 6 items

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 · 1 item

... 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 · 3 items

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

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
上海策嵘生物科技有限公司[email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
上海腾准生物科技有限公司19821570922 · [email protected]

Related reactions

13 records

Compound notes

Loading…