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Diallyl diglycol carbonate

HCID 8879
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
142-22-3
Standard SMILES
C=CCOC(=O)OCCOCCOC(=O)OCC=C
InChIKey
JHQVCQDWGSXTFE-UHFFFAOYSA-N
Molecular formula
C12H18O7
Average molar mass
274.27 g/mol
Monoisotopic mass
274.10525291

Names & identifiers

Preferred name
Diallyl diglycol carbonate
IUPAC
2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate
English name
Diallyl 2,2'-oxydiethyl dicarbonate
Molecular formula
C12H18O7
Molecular weight
274.27

Names & synonyms

142-22-3Diallyl 2,2'-oxydiethyl dicarbonateDIALLYL DIGLYCOL CARBONATEAllyl diglycol carbonateDiallyl glycol carbonateNouryset 200Transallyl CR 39Diethylene glycol bis(allylcarbonate)RAV 7N2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propenyl esterCarbonic acid, oxydiethylene diallyl esterDiethylene glycol diallyl dicarbonate
Show more names
cr39Allyl diglycol carbonate monomerDIETHYLENE GLYCOL BIS(ALLYL CARBONATE)01mdagcrav7ts16TastrakCR-39(R)Baryotrak
Diallyl oxydiethylene dicarbonateTS 16AJ5T8CR88IDiethylene glycol, bis(allyl carbonate)Oxydiethylenedicarbonic acid diallyl esterEthanol, 2,2'-oxybis-, bis(2-propenyl carbonate)Carbonic acid, allyl ester, diester with diethylene glycolCarbonic acid, oxydi-2,1-ethanediyl di-2-propenyl ester

Database identifiers

CAS
142-22-3、25656-90-0
PubChem CID
8879
DTXSID
DTXSID7027095
UNII
AJ5T8CR88I
EC Number
205-528-7
Nikkaji
J56.135E

Properties

Computed structural properties

XLogP
2
Topological polar surface area
80.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
7
Rotatable bonds
14
Heavy atoms
19
Formal charge
0
Complexity
260

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Other Monomers
SpringerMaterials PropertiesViscosity
Density · 2 items

1.143 @ 20 °C

1.14 @25 °C

Viscosity9 cS @ 20 °C
Color/FormLiquid
Boiling Point · 2 items

160 °C (4 mm Hg)

162 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting PointFreezing point: -4 °C
Vapor Pressure0.0011 [mmHg]
Refractive IndexIndex of refraction (sodium D-light, 20 °C.): 1.45
Physical DescriptionLiquid; [Hawley] Colorless liquid; [MSDSonline]

Physicochemical properties

Melting point
4 °C · −4 °C(lit.)
Boiling point
161 °C2 · 161 °C2 mm Hg(lit.)
Density
1.15 g/mL · 1.15 g/mL at 25 °C(lit.)
vapor pressure
0.009 Pa · 0.009Pa at 25℃
refractive index
20 · n20/D 1.451(lit.)
Flash point
230 °F · >230 °F
Viscosity
17 mm2/s · 17mm2/s
Water Solubility
2.36 g/L · 2.36g/L at 20℃
Stability
Stability Combustible. Incompatible with strong oxidizing agents.
LogP
1.543 at · 1.543 at 20℃
CAS DataBase Reference
142 · 142-22-3(CAS DataBase Reference)
FDA UNII
5 T8CR88I · AJ5T8CR88I
EPA Substance Registry System
2 · 2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propen-1-yl ester (142-22-3)
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Warning
Hazard statements
373 · H373-H400-H315-H302
Precautionary statements
273 · P273-P391-P501-P264-P270-P301+P312-P330-P501-P260-P314-P501-P264-P280-P302+P352-P321-P332+P313-P362
Hazard Codes
Xn,N
Risk Statements
22 · 22-36/37/38-50-38
Safety Statements
26 · 26-36/37/39-61-37/39-28-7/9
RIDADR
3237 · UN 3237 4.1
WGK Germany
2 · 2
RTECS
2080000 · FG2080000
TSCA
TSCA listed
Hazardous Substances Data
142 · 142-22-3(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 426mg/kg
REACH Registrations
Active

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 63 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Chemical: 2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propenyl ester

2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propen-1-yl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propen-1-yl ester 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)

REACH registered substance: Diallyl 2,2'-oxydiethyl dicarbonate (EC: 205-528-7)

Fire PotentialCombustible when exposed to heat or flame...
Hazards Summary · 1 item

A case of occupational allergic contact dermatitis has been described; [Reference #1] Reproductive effects: no reliable information located; [REPROTOX] An irritant; Readily absorbed through skin; Effects in high-dose animal studies include somnolence and acute tubular necrosis; [MSDSonline]

Hazard Classes and Categories · 2 items

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Hazardous Reactivities and Incompatibilities...Can react with oxidizing material.

Safety & protection

Fire Fighting Procedures... Use water mist or spray, foam, carbon dioxide, dry chem.
Disposal Methods · 1 item

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.

Protective Action Criteria (PAC) · 3 items

1.3 [mg/m3]

14 [mg/m3]

84 [mg/m3]

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
TSCA Test Submissions · 2 items

Teratogenicity of CR-39R (diallyl diglycol carbonate) was evaluated in groups of 5 artificially inseminated New Zealand white rabbits dermally administered occluded doses of 0 (isotonic sa-line), 0.1, 0.5, 1.0, or 3.0 ml/kg/day applied 24 hrs/day gestation days (GD) 6-18. One doe dosed 3.0 ml/kg was killed in extremis GD 18, having exhibited pallor, reduced respiration, and reduced spontaneous activity. All groups showed firm dark areas at dosage sites during treatment which often scabbed afterwards. Treatments sites of all but 0.1 ml/kg showed discrete or diffuse reddening and /or swelling. Food consumption and fecal output decreased in all groups. All groups including control lost weight during treatment; the 3.0 ml/kg group lost significantly (p<0.02) more than the control. Of 3.0 ml/kg does, 3 had yellow areas on liver caudal surfaces on necropsy. Abortions or early deliveries in 0.1, 0.5, 1.0, and 3.0 ml/kg groups were 2, 0, 2, 1l, and 3, respectively. Corpora lutea and number of dead fetuses were unchanged. Intergroup variations in other uterine parameters (numbers of implants, live fetuses, fetal body weights, pre-implantation losses, and sex ratio) were not considered significant. Late resorptions were high in control and most treated groups. Of 0.1, 0.5, and 1 ml/kg groups, 3, 1, and 4 fetuses had hydrocephaly and/or abnormal limb/paw flexure.

Teratogenicity of CR-39R (diallyl diglycol carbonate) was evaluated in groups of 18 inseminated New Zealand white rabbits dermally administered occluded doses of 0 (isotonic saline), 0.1, 0.5, or 1.0, ml/kg per day applied 6 hrs gestation days (GD) 6-18. Seven high-dose does died or were killed in extremis GD 7, 8, 20, 21, and 22, having exhibited poor appetite, labored respiration, weakness, thinness, coldness, prostration, and/or yellow nasal discharge. All treated groups showed red/black areas of dose-related extent, sometimes with red secretions, at dosage sites during treatment which scabbed later. Other clinical effects were reddening of the dorsal cervical region and pinna (high dose) and reddening or swelling in the uro-genital area (mid and high dose). Food consumption and fecal output increased (dose-related) in mid and high dose groups. Mid and high dose groups lost weight GD 6-18, high dose losses continuing GD 18-24. Necropsy showed pale foci in liver (and/or firmness and/or irregular surface), heart, kidneys, and mesentery in mid and high dose groups. Stomach lesions were in all groups, especially high dose; 4 does had dark ingesta. Abortions or early deliveries in 0, 0.1, 0.5, and 1.0 ml/kg groups were 2, 3, 2, and 8, respectively. In low or mid dose groups, number of corpora lutea, implantation sites, live and dead fetuses, resorptions, fetal and litter weights, uterine weights, and pre- and post-implantation losses were similar to controls for does alive on GD 29. Does that died, littered early, or aborted had resorptions in aborta or in utero. Fetuses in mid (p<0.01) and high (p<0.001) dose groups had significantly higher incidence of small lenses, with ocular opacities in high dose groups. Major or minor visceral malformations were similar to controls. Skeletal variants included significant (p<0.05) decrease in single thirteenth ribs, and an increase in incidence of 27 presacral vertebrae (mid dose).

Human Toxicity Excerpts · 1 item

The case was described of a 19 year old woman employed to inject diallylgycol carbonate liquid monomer (used to manufacture high quality prescription lenses) into lens molds who developed contact dermatitis. During work, there were occasional spills of the monomer which could come in contact with the hands and arms of the worker. After 2 weeks of employment, the patient developed blisters and edema of the back of her hands, forearms, knees and thighs that required hospitalization and treatment. Although the irritant nature of the monomer was known, the workers had difficulties working with gloves and protective clothing. Patch tests carried out in ten volunteers with a 1 percent solution of diallylgycol carbonate confirmed the irritant nature of the product, in the form of a minimal or mild edema, with no vesicular reactions. Patch testing carried out in the patient to rule out the possibility of an allergic contact dermatitis revealed that she was highly sensitive to diallylgycol carbonate, a positive reaction being recorded at a concentration as low as 0.001 percent. The authors conclude that the patient developed an allergic contact dermatitis to diallylgycol carbonate, although the product is also a skin irritant.

Non-Human Toxicity ExcerptsPoison by intraperitoneal route. ... The allyl compounds are generally toxic. Experimental reproductive effects.
Antidote and Emergency Treatment · 2 items

/SRP:/ Basic Treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Esters and related compounds/

/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use propaparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

Toxicity DataLC50 (rat) = 1,205 mg/m3

Safety data

wgk
2
tsca
TSCA listed
rtecs
FG2080000
ridadr
UN 3237 4.1
Toxicity
LD50 oral in rat: 426mg/kg
risk_code
22-36/37/38-50-38
Signal word
Warning
Symbol(GHS)
GHS07,GHS08,GHS09
hazard_code
Xn,N
safety_code
26-36/37/39-61-37/39-28-7/9
Hazard statements
H373-H400-H315-H302
REACH Registrations
Active
Precautionary statements
P273-P391-P501-P264-P270-P301+P312-P330-P501-P260-P314-P501-P264-P280-P302+P352-P321-P332+P313-P362
Hazardous Substances Data
142-22-3(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as monomer for allyl resins; [Hawley]

Monomer for allyl resins, particularly in optically clear castings

U.S. Production2023: <50,000 lb
General Manufacturing Information2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propen-1-yl ester: ACTIVE

Applications

UsesTransparent organic glass in the manufacture of optical corrective lenses.

Suppliers4 total

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]

Additional notes

DefinitionA colorless monomer of diethylene glycol bis(allyl carbonate).

Related reactions

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Compound notes

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