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Butanediol dimethacrylate

HCID 16387
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Basic information

CAS
2082-81-7
Standard SMILES
C=C(C)C(=O)OCCCCOC(=O)C(=C)C
InChIKey
XOJWAAUYNWGQAU-UHFFFAOYSA-N
Molecular formula
C12H18O4
Average molar mass
226.27 g/mol
Monoisotopic mass
226.12050905

Names & identifiers

Preferred name
Butanediol dimethacrylate
IUPAC
4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate
English name
Polybutyleneglycol dimethacrylate
Molecular formula
(C4H8O)nC8H10O3
Molecular weight
0

Names & synonyms

1,4-BUTANEDIOL DIMETHACRYLATE2082-81-72-Propenoic acid, 2-methyl-, 1,4-butanediyl ester1,4-Butylene glycol dimethacrylateButylene dimethacrylate1,4-Butylene dimethacrylateTetramethylene glycol dimethacrylateButanediol dimethacrylateTetramethylene methacrylateKX6732HE0UMethacrylic acid, tetramethylene esterOligotetramethylene glycol dimethacrylate
Show more names
Polybutyleneglycol dimethacrylatePOLYBUTANEDIOL 600 DIMETHACRYLATEPOLYBUTANEDIOL 2000 DIMETHACRYLATEPolytetramethyleneglycoldimethacrylatePOLYTETRAMETHYLENE GLYCOL 600 DIMETHACRYLATEPOLYTETRAMETHYLENE GLYCOL 2000 DIMETHACRYLATEalpha-(2-methyl-1-oxo-2-propenyl)-omega-[(2-methyl-poly(oxy-4-butanediyl)Poly(oxy-1,4-butanediyl), α-(2-methyl-1-oxo-2-propen-1-yl)-ω-[(2-methyl-1-oxo-2-propen-1-yl)oxy]-4-butanediyl),.alpha.-(2-methyl-1-oxo-2-propenyl)-.omega.-[(2-methyl-1-oxo-2-propenyl)oxy]-Poly(oxy-1
X 970butanediyl dimethacrylateRefChem:731581,4-BDMA218-218-1Tetramethylene dimethacrylateButane-1,4-diyl bis(2-methylacrylate)4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate

Database identifiers

CAS
2082-81-7、28883-57-0
PubChem CID
16387
DTXSID
DTXSID4044870
ChEMBL
CHEMBL3184875
UNII
KX6732HE0U
EC Number
218-218-1
Nikkaji
J112.782I

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
9
Heavy atoms
16
Formal charge
0
Complexity
261

Experimental & physicochemical properties

PolymersPlastics & Rubber -> (Meth)acrylates
Density1.011 @ 25 °C/15.6 °C
Color/FormLiquid
Boiling Point110 °C @ 3 MM HG
Polymerization · 1 item

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

Food Contact Substances · 3 items

FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

Refractive Index · 2 items

INDEX OF REFRACTION: 1.4502 @ 25 °C

Index of refraction: 1.4872 at 20 °C/D

Physical Description · 2 items

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

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 7% (24 of 341) of reports.

Warning

H315 (59.5%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Regulatory Information · 6 items

Chemical: Poly(oxy-1,4-butanediyl), .alpha.-(2-methyl-1-oxo-2-propen-1-yl)-.omega.-[(2-methyl-1-oxo-2-propen-1-yl)oxy]-

Chemical: 2-Propenoic acid, 2-methyl-, 1,4-butanediyl ester

2-Propenoic acid, 2-methyl-, 1,1'-(1,4-butanediyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 1,1'-(1,4-butanediyl) 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)

FRI - indicates a polymeric substance containing no free-radical initiator in its Inventory name but is considered to cover the designated polymer made with any free-radical initiator regardless of the amount used.

REACH registered substance: Tetramethylene dimethacrylate (EC: 218-218-1)

2-Propenoic acid, 2-methyl-, 1,4-butanediyl ester: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAllergic contact dermatitis reported in dental technicians; [Kanerva, p. 1739] Stabilized with 100 ppm of p-methoxyphenol; [ChemIDplus] An irritant and lachrymator; May cause skin sensitization; [Aldrich MSDS]
TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

Chemistry & industry

Pharmacology

Metabolism/MetabolitesSMALL QUANTITIES OF METHACRYLATES MAY READILY BE METABOLIZED BY SAPONIFICATION INTO THE ALCOHOL AND METHACRYLIC ACID. THE LATTER MAY FORM AN ACETYL-COENZYME A DERIVATIVE, WHICH THEN ENTERS THE NORMAL LIPID METABOLISM. /METHACRYLATES/

Uses & manufacturing

Uses · 5 items

Used as a monomer for resins and crosslinking agent for UV curable coatings and polymer used in contact lenses; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

MONOMER FOR RESINS.

CROSSLINKING AGENT FOR POLYMER USED IN CONTACT LENSES.

CROSSLINKING AGENT FOR UV CURABLE COATINGS.

U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesMonomers
Industry UsesAdhesion/cohesion promoter
Methods of Manufacturing · 2 items

The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/

TRANSESTERIFICATION OR ESTERIFICATION OF 1,4-BUTANEDIOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID.

General Manufacturing Information · 4 items

Miscellaneous Manufacturing

2-Propenoic acid, 2-methyl-, 1,1'-(1,4-butanediyl) ester: ACTIVE

Poly(oxy-1,4-butanediyl), .alpha.-(2-methyl-1-oxo-2-propen-1-yl)-.omega.-[(2-methyl-1-oxo-2-propen-1-yl)oxy]-: ACTIVE

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

Suppliers

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Related reactions

1 records
New reaction record
HRID 1665896 reaction equation
HRID 1665896As productuspto-grants-2011_10

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Liquid; CBI; Wet Solid

Liquid; [HSDB] Colorless liquid; [Aldrich MSDS]

Physicochemical properties

Specific Gravity
0.998 · 0.998
InChI
InChI=1S/C12H18O4/c1-9(2)11(13)15-7-5-6-8-16-12(14)10(3)4/h1,3,5-8H2,2,4H3
InChIKey
XOJWAAUYNWGQAU-UHFFFAOYSA-N
SMILES
C(=O)(C(=C)C)O{-}CCCC{+n}OC(=O)C(=C)C
EPA Substance Registry System
Poly(oxy-1,4-butanediyl), .alpha.-(2-methyl-1-oxo-2-propenyl)-.omega.-[(2-methyl-1-oxo-2-propenyl)oxy]- (28883-57-0)
TSCA
TSCA listed
Hazard Classes and Categories · 3 items

Skin Irrit. 2 (59.5%)

Skin sensitization - Category 1B

Skin Sens. 1B

Skin, Eye, and Respiratory IrritationsMethacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/

Safety & protection

Storage Conditions · 1 item

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

Preventive Measures · 3 items

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Personal Protective Equipment (PPE)SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/

Toxicology

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
Human Toxicity Excerpts · 1 item

BIOLOGICALLY, METHACRYLATES RESEMBLE ACRYLATES, EXCEPT FOR LOWER REACTIVITY & THUS DECR TOXICITY. THIS IS PROBABLY DUE TO STERIC HINDRANCE BY ITS METHYL GROUP & IN TURN DECR RATES OF MEMBRANE TRANSPORT & SYSTEMIC TRANSLOCATION. /METHACRYLIC ESTERS/

Regulatory information

TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

Safety data

tsca
TSCA listed

Applications

UsesPOLYBUTYLENE GLYCOL DIMETHACRYLATE is a material intermediate used in the manufacture of resins, coatings and contact lens materials, amongst other applications.