1,3,5-Trioxane

HCID 8081

Basic information

CAS
110-88-3
Standard SMILES
C1OCOCO1
InChIKey
BGJSXRVXTHVRSN-UHFFFAOYSA-N
Molecular formula
C3H6O3
Average molar mass
90.08 g/mol
Monoisotopic mass
90.03169405

Overview

Transparent crystals or white crystalline solid with a pleasant odor resembling the odor of chloroform. Melts at 62 °C; boils at 115 °C without polymerization. The cyclic trimer of formaldehyde.

Names & identifiers

Preferred name
1,3,5-Trioxane
IUPAC
1,3,5-trioxane
English name
1,3,5-trioxane
Molecular formula
C3H6O3
Molecular weight
90.08

Names & synonyms

1,3,5-TRIOXANEs-Trioxane110-88-3TrioxymethyleneTrioxaneMetaformaldehydeTriformolFormaldehyde, trimerTrioxansym-Trioxane1,3,5-TrioxacyclohexaneAldeform
Show more names
Paraformal
Marvosans-TrixaneTriossimetileneTrioxymethyleenTrioxymethylenTrioxin1,3,5-TrioxanDTXSID4021925

Database identifiers

CAS
110-88-3
PubChem CID
8081
DTXSID
DTXSID4021925
ChEMBL
CHEMBL1495792
ChEBI
CHEBI:38043
UNII
46BNU65YNY
EC Number
203-812-5
Nikkaji
J2.452J

Properties

Computed structural properties

XLogP
-0.4
Topological polar surface area
27.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aldehydes
SpringerMaterials PropertiesDunham energy parameter
Pesticides · 2 items

Fungicides

Active substance -> EU Pesticides database: Not approved

OdorCHARACTERISTIC CHLOROFORM-LIKE ODOR
Density · 2 items

1.17 at 149 °F (NTP, 1992) - Denser than water; will sink

1.17 @ 65 °C

Color/Form · 3 items

CRYSTALLINE SOLID

RHOMBIC NEEDLES FROM ETHER

WHITE

Physicochemical properties

Melting point
59 · 59-62 °C(lit.)
Boiling point
112 · 112-115 °C
Density
1.17 · 1.17
vapor pressure
7.5 hPa · 7.5 hPa (20 °C)
refractive index
1.4168 · 1.4168 (estimate)
Flash point
113 °F · 113 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H228: Flammable solid [Danger Flammable solids]

P203, P210, P240, P241, P261, P271, P280, P304+P340, P318, P319, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H228 (100%): Flammable solid [Danger Flammable solids]

P203, P210, P240, P241, P261, P271, P280, P304+P340, P318, P319, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: 1,3,5-Trioxane

Regulation (EC) No 1935/2004 (amended)

1,3,5-Trioxane is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3,5-Trioxane are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2002/2076

Status: Active Update: 13-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15244

1,3,5-Trioxane: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1,3,5-Trioxane: Human health tier II assessment
DOT LabelFlammable Solid
Fire HazardsThis chemical is combustible. (NTP, 1992)
Fire Potential · 2 items

MODERATE FIRE RISK.

VOLATILE SOLID THAT GIVES OFF FLAMMABLE VAPOR OF FORMALDEHYDE WHEN HEATED. /PARAFORMALDEHYDE/

Health HazardsACUTE/CHRONIC HAZARDS: This compound is toxic and flammable. It can emit toxic fumes on contact with acid or acid fumes. (NTP, 1992)

Safety & protection

Fire FightingFires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting Procedures · 3 items

USE WATER SPRAY, CARBON DIOXIDE, DRY CHEM OR "ALCOHOL" FOAM. WATER SPRAY MAY BE USED TO FLUSH SPILLS AWAY FROM EXPOSURES. /PARAFORMALDEHYDE/

WATER SPRAY MAY BE USED TO EXTINGUISH THE FIRE BECAUSE MATERIAL CAN BE COOLED BELOW ITS FLASH POINT.

ALCOHOL FOAM.

Storage ConditionsSTORE IN COOL, DRY, WELL-VENTILATED PLACE AWAY FROM SOURCES OF HEAT & IGNITION. SEPARATE FROM COMBUSTIBLES, & ACIDIC, ALKALINE, & OXIDIZING MATERIALS. /PARAFORMALDEHYDE/
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 2 items

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.

Incineration & landfill: Mix with a combustible solvent and incinerate using an afterburner or bury in an approved landfill.

Toxicology

Human Toxicity Excerpts · 5 items

MALE & FEMALE 4TH YR DENTAL STUDENTS SHOWED HIGH INCIDENCE OF LATENT ALLERGIES, 65% COMPARED TO 13.6% FOR SAME STUDENTS @ END OF 2ND YR. ATTRIBUTED TO EXPOSURE TO ALLERGY-PRODUCING SUBSTANCES SUCH AS TRIOXYMETHYLENE.

SAME INTERNAL TOXICITY AS FORMALDEHYDE, WHICH IT SLOWLY RELEASES AT BODY TEMP.

SEE FORMALDEHYDE. SYMPTOMATOLOGY: A. INHALATION. 1. IRRITATION OF MUCOUS MEMBRANES, ESP OF EYES, NOSE & UPPER RESP TRACT. 2. WITH HIGHER CONCN, COUGH, DYSPHAGIA, BRONCHITIS, PNEUMONIA, EDEMA OR SPASM OF LARYNX. /FORMALDEHYDE/

SEE FORMALDEHYDE. SYMPTOMATOLOGY: B. INGESTION. 1. ...PAIN IN MOUTH, PHARYNX & STOMACH. 2. NAUSEA, VOMITING, HEMATEMESIS, ABDOMINAL PAIN, &...DIARRHEA (WHICH MAY BE BLOODY). 3. ...SHOCK. 4. DIFFICULT MICTURITION, HEMATURIA, ANURIA. 5. VERTIGO, CONVULSIONS...COMA. 6. DEATH DUE TO RESP FAILURE. /FORMALDEHYDE/

SEE FORMALDEHYDE. SYMPTOMATOLOGY: SKIN CONTACT. 1. IRRITATION & HARDENING OF SKIN. STRONG SOLN PRODUCE COAGULATION NECROSIS. 2. DERMATITIS & HYPERSENSITIVITY FROM PROLONGED EXPOSURE. /FORMALDEHYDE/

Probable Routes of Human ExposurePARAFORM INTRODUCES BOTH A DUST & A FORMALDEHYDE GAS EXPOSURE... /PARAFORM/
Antidote and Emergency Treatment · 3 items

SEE FORMALDEHYDE. 1. ADMIN BY MOUTH 1 OR MORE OF FOLLOWING: WATER, MILK, 0.2% AMMONIA WATER...AMMONIUM ACETATE (3 TEASPOONSFUL IN WATER), EGG WHITES, ACTIVATED CHARCOAL. AMMONIUM SALTS ARE PROBABLY BEST BECAUSE THEY TRANSFORM FORMALDEHYDE INTO METHENAMINE... /FORMALDEHYDE/

SEE FORMALDEHYDE. 2. DEMULCENTS: MILK, EGGS, ALUMINUM HYDROXIDE GELS. 3. MORPHINE FOR CONTROL OF PAIN... 4. COMBAT SHOCK BY IV ADMIN OF ISOTONIC SALINE, PLASMA, OR WHOLE BLOOD... 5. TO CORRECT ACIDOSIS, GIVE SODIUM BICARBONATE OR M/6 SODIUM LACTATE SOLN IV... 6. ARTIFICIAL RESP, IF INDICATED... /FORMALDEHYDE/

SEE FORMALDEHYDE. 7. PENICILLIN OR OTHER ANTIBIOTIC IF INFECTION APPEARS... 8. WASH AFFECTED SKIN WITH LARGE QUANTITIES OF SOAP & WATER. LAB. URINALYSIS MAY REVEAL RED BLOOD CELLS (SOMETIMES GROSS HEMATURIA) & CASTS. /FORMALDEHYDE/

Toxicity DataLC50 (rat) > 10,463 ppm

Safety data

wgk
1
tsca
TSCA listed
rtecs
YK0350000
ridadr
UN 1325 4.1/PG 2
hs_code
2912 50 00
Toxicity
LD50 orally in Rabbit: 8190 mg/kg LD50 dermal Rabbit > 3980 mg/kg

Chemistry & industry

Pharmacology

Metabolism/MetabolitesSAME INTERNAL TOXICITY AS FORMALDEHYDE, WHICH IT SLOWLY RELEASES AT BODY TEMP.

Uses & manufacturing

Uses · 3 items

Used for organic synthesis, as a disinfectant, and in fuel; [Hawley]

Using Disinfectants or Biocides [Category: Clean]

ORG SYNTHESIS; DISINFECTANT; NONLUMINOUS, ODORLESS FUEL

U.S. Production2023: 150,000,000 - <500,000,000 lb
Consumer UsesIntermediate
Industry UsesMonomers
Methods of Manufacturing... BY DISTILLATION OF FORMALDEHYDE WITH AN ACID CATALYST, & EXTRACTION WITH SOLVENT.
General Manufacturing Information · 6 items

Plastics Material and Resin Manufacturing

1,3,5-Trioxane: ACTIVE

SYM-TRIOXANE...A TRIMER OF FORMALDEHYDE; NOT TO BE CONFUSED WITH PARAFORMALDEHYDE...WHICH CONSISTS OF 8 OR MORE FORMALDEHYDE UNITS.

IN NON-AQ SYSTEMS, READILY CONVERTED TO MONOMERIC FORMALDEHYDE BY SMALL CONCN STRONG ACIDS @ RATE DETERMINED BY ACID CONCN.

SUBLIMABLE PERFUME COMPOUNDS CONTAIN TRIOXYMETHYLENE.

CYCLIC ETHERS SUCH AS SYM-TRIOXANE ARE USED TO PREVENT DECOMP OF HALOAMIDE ANTIMICROBIAL AGENTS, SUCH AS DBNPA.

Applications · 3 items

Uses1,3,5-Trioxane is used in organic chemical processes such as aldol condensation of amides and syntheses of chloromethyl esters or other plastics.

Uses1,3,5-Trioxane is widely used as a source of anhydrous formaldehyde.It can be used to synthesize:Polyoxymethylene and hyperbranched polyesters.Calixarenes such as calix[4]resorcinarene, calix[6]resorcinarene and para-tert-butylcalix[8] and [9]arene.Various natural products including ()-motuporin, (+)-sundiversifolide, (+)-lyconadin A and ()-lyconadin B.

General DescriptionTransparent crystals or white crystalline solid with a pleasant odor resembling the odor of chloroform. Melts at 62°C; boils at 115°C without polymerization. The cyclic trimer of formaldehyde.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
上海比阳实业有限公司+86-21-52699951; +8613917686115 · [email protected]
湖北鑫杰成化工科技有限公司13554075426 · [email protected]

Additional notes

DefinitionChEBI: A saturated organic heteromonocyclic parent that is cyclohexane in which the carbon atoms at positions 1, 3 and 5 are replaced by oxygen atoms.

Related reactions

73 records

Compound notes

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