HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Tetrahydrofurfuryl Methacrylate

HCID 17151
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
2455-24-5
Standard SMILES
C=C(C)C(=O)OCC1CCCO1
InChIKey
LCXXNKZQVOXMEH-UHFFFAOYSA-N
Molecular formula
C9H14O3
Average molar mass
170.21 g/mol
Monoisotopic mass
170.0942943

Overview

Tetrahydrofurfuryl methacrylate is a member of oxolanes.

Names & identifiers

Preferred name
Tetrahydrofurfuryl Methacrylate
IUPAC
oxolan-2-ylmethyl 2-methylprop-2-enoate
English name
Tetrahydrofurfuryl methacrylate
Molecular formula
C9H14O3
Molecular weight
170.21

Names & synonyms

TETRAHYDROFURFURYL METHACRYLATE2455-24-5Sartomer SR 203Methacrylic acid tetrahydrofurfuryl ester2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl esterTetrahydrofurfurylmethacrylateMethacrylic acid, tetrahydrofurfuryl esterSR 203ACRYESTER THFDTXSID0022191NSC-32634120GN9C472
Show more names
sr203sartomersr203Photomer 2142UNII:120GN9C472CHLUMICRYL THFMA MonomerTetrahydrofurfuryl methacrylaTetrahydrofurfurylmethacrylat
DTXCID502191THFM-ARefChem:188670219-529-5(tetrahydrofuran-2-yl)methyl methacrylateoxolan-2-ylmethyl 2-methylprop-2-enoateMFCD00014515HSDB 5461

Database identifiers

CAS
2455-24-5
PubChem CID
17151
DTXSID
DTXSID0022191

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
35.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
12
Formal charge
0
Complexity
186

Experimental & physicochemical properties

PolymersPlastics & Rubber -> (Meth)acrylates
Cosmetics · 2 items

Cosmetic ingredients (Tetrahydrofurfuryl Methacrylate) -> CIR (Cosmetic Ingredient Review)

Cosmetic ingredients (Tetrahydrofurfuryl methacrylate) -> CIR (Cosmetic Ingredient Review)

Boiling Point59-62 °C at 0.080 kPa (0.6 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/

Vapor Pressure0.16 [mmHg]
Refractive IndexIndex of refraction: 1.4552 at 20 °C/D
Physical Description · 2 items

Liquid

Colorless or yellow liquid; [MSDSonline]

Stability/Shelf Life... Readily polymerized and easily cross-linked by exposure to heat, peroxide catalysts or UV radiation.

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

Danger

H315 (56%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 323 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Hazard information

Regulatory Information · 5 items

Chemical: 2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl ester

Hazard Traits - Reproductive Toxicity

2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl 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: Tetrahydrofurfuryl methacrylate (EC: 219-529-5)

2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationEvaluation - Tetrahydrofurfuryl acrylate and tetrahydrofurfuryl methacrylate
Hazards SummaryDanger of skin sensitization; [MAK] A mild eye irritant; Possible sensitizer; [MSDSonline] See ACRYLIC RESINS (MONOMERS).
Hazard Classes and Categories · 2 items

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 · 6 items

CIR ingredient: Tetrahydrofurfuryl Methacrylate

CIR ingredient: Tetrahydrofurfuryl methacrylate

Used in artificial nails, dental resins, electrical cable coatings, contact lenses, and in curing nitrile rubber; [HSDB]

MINOR INGREDIENT IN ARTIFICIAL FINGERNAILS; IN PROVISIONAL DENTAL RESINS.

MONOMER FOR POLYMERS USED IN ELECTRICAL CABLE COATINGS.

MONOMER FOR POLYMERS USED IN CONTACT LENSES.

U.S. Production · 2 items

2023: 1,000,000 - <2,500,000 lb

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Consumer UsesMonomers
Industry UsesMonomers
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 TETRAHYDROFURFURYL ALCOHOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID

Household ProductsInformation on 2 consumer products that contain Tetrahydrofurfuryl methacrylate in the following categories is provided:
General Manufacturing Information · 3 items

Rubber Product Manufacturing

Related reactions

1 records
New reaction record
HRID 1881660 reaction equation
HRID 1881660As solventuspto-grants-2012_11

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL3561338
ChEBI
CHEBI:189338
UNII
120GN9C472
EC Number
219-529-5
Nikkaji
J208.715D

Physicochemical properties

Boiling point
52 °C0.4 · 52 °C0.4 mm Hg(lit.)
Density
1.044 g/mL · 1.044 g/mL at 25 °C(lit.)
vapor pressure
27 Pa · 27Pa at 20℃
refractive index
20 · n20/D 1.458(lit.)
Flash point
195 °F · 195 °F
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
form
clear liquid
Specific Gravity
1.044 · 1.044
color
Colorless to Almost colorless
Viscosity
2.74 mm2/s · 2.74mm2/s
Water Solubility
18.99 g/L · 18.99g/L at 20℃
Sensitive
Light Sensitive
BRN
117423 · 117423
Cosmetics Ingredients Functions
FILM FORMING
InChI
1S/C9H14O3/c1-7(2)9(10)12-6-8-4-3-5-11-8/h8H,1,3-6H2,2H3
InChIKey
LCXXNKZQVOXMEH-UHFFFAOYSA-N
SMILES
CC(=C)C(=O)OCC1CCCO1
LogP
1.76 at · 1.76 at 22.6℃
CAS DataBase Reference
2455 · 2455-24-5(CAS DataBase Reference)
EWG's Food Scores
2 · 2-5
FDA UNII
120 GN9C472 · 120GN9C472
NIST Chemistry Reference
2 · 2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl ester(2455-24-5)
EPA Substance Registry System
Tetrahydrofurfuryl methacrylate (2455-24-5)
UNSPSC Code
12162002 · 12162002
NACRES
23 · NA.23
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
227 · H227-H315-H319-H335
Precautionary statements
302 · P302+P352-P305+P351+P338
PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Risk Statements
10 · 10-36/37/38
Safety Statements
36 · 36
RIDADR
3272 · 3272
WGK Germany
1 · 1
TSCA
TSCA listed
HazardClass
3 · 3
PackingGroup
III
HS Code
29321900 · 29321900
Storage Class
10 · 10 - Combustible liquids
Hazardous Substances Data
2455 · 2455-24-5(Hazardous Substances Data)
REACH Registrations
Active

Skin Irrit. 2 (56%)

Flammable liquids - Category 4

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/

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.

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

Ecotoxicity Values · 1 item

LC50 Pimephales promelas (fathead minnows) 34.7 g/l/96 hr (95% confidence limit 31.1-38.8 g/l); age 29 days old, water hardness 45.8 mg/l calcium carbonate, temp 24.1 °C, pH 7.57, dissolved oxygen 7.3 mg/l, alkalinity 43.1 mg/l (CaCO3), Tank vol: 2.0 l, additions: 18 vol/day (flow-through bioassay), sample purity: > 97%

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Toxicity Summary · 2 items

Based on available data, the CIR Expert Panel concluded that ... Tetrahydrofurfuryl Methacrylate is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.

Safe for use in cosmetics, with qualifications

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/

Non-Human Toxicity Excerpts · 1 item

TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING TETRAHYDROFURFURYL METHACRYLATE, WERE SCANNED FOR THEIR ABILITY TO INDUCE CONTACT SENSITIVITY, USING 5 DIFFERENT SENSITIZATION PROTOCOLS. CONTACT REACTIONS OF VARYING INTENSITIES WERE PRODUCED TO ALL THE MONO-, DI-, AND TRIACRYLATES TESTED. METHACRYLATES DID NOT SENSITIZE GUINEA PIGS.

Antidote and Emergency Treatment · 2 items

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/

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 TKO /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 proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
1
tsca
TSCA listed
ridadr
3272
hs_code
29321900
risk_code
10-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
36
hazard_class
3
Storage Class
10 - Combustible liquids
packing_group
III
Hazard statements
H227-H315-H319-H335
REACH Registrations
Active
Precautionary statements
P302+P352-P305+P351+P338
Hazardous Substances Data
2455-24-5(Hazardous Substances Data)

2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl ester: 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/

Applications · 2 items

DescriptionTetrahydrofurfuryl methacrylate (THFMA) is derived from renewable resources and is obtained by chemical modification of furfural produced from hemicellulose. THFMA was used as a biobased reactive diluent that reduces the viscosity of AESO in DLP 3D printing. According to stress relaxation tests, THFMA was found to be a suitable monomer in the UV-curing of HPPA and AESO because the formed dynamic networks could rapidly undergo thermoactivated network topology rearrangements. The addition of THFMA to the resins contributed to weldability, repairability, shape memory, and reprocessability properties[2].

UsesTetrahydrofurfuryl methacrylate is used as methacrylic component in dental materials, such as crown and bridge products; in artificial nails.

Upstream & downstream products

Upstream raw materials

Tetrahydrofurfuryl alcoholEthyl methacrylateMethyl methacrylateMethacrylic acid

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]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
上海仲因实业有限公司2537653158 16621191650 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
陕西林奈生物化工有限公司15327269642 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
山东穗泰生物科技有限公司15689727968 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
Esstech Inc.+1 (610) 521-3800 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
吉良化学21-62165282 · [email protected]
苏州启航生物科技有限公司18662190603;18151111370 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
Syntor Fine Chemicals Ltd.+44 (0) 1928 579865 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
广州吉昕泰新材料科技有限公司13710082414 13924128221 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
杭州宇昊化工科技有限公司0571-82693216 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
青岛瑞那斯高分子材料有限公司0532-0532-86867058 18562606086 · [email protected]
武汉弘德悦欣医药科技有限公司027-83855396 15271852016 · [email protected]
上海兴鲁化工科技有限公司02120970332 · [email protected]
溧阳市瑞普新材料有限公司+86-0519-82038123,18951201333
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
上海珈得尔化学技术有限公司13564435016 13564435016 · [email protected]
成都润泽本土化工有限公司028-88469284 18000562381 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]

Additional notes

DefinitionChEBI: Tetrahydrofurfuryl methacrylate is a member of oxolanes.