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メタクリル酸 テトラヒドロフルフリル

Tetrahydrofurfuryl Methacrylate

HCID 17151
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
2455-24-5
標準SMILES
C=C(C)C(=O)OCC1CCCO1
InChIKey
LCXXNKZQVOXMEH-UHFFFAOYSA-N
分子式
C9H14O3
平均分子量
170.21 g/mol
単同位体質量
170.0942943

概要

Tetrahydrofurfuryl methacrylate is a member of oxolanes.

名称と識別子

優先名称
Tetrahydrofurfuryl Methacrylate
IUPAC
oxolan-2-ylmethyl 2-methylprop-2-enoate
現地名
メタクリル酸 テトラヒドロフルフリル
英語名
Tetrahydrofurfuryl methacrylate
分子式
C9H14O3
分子量
170.21

名称と別名

TETRAHYDROFURFURYL METHACRYLATE2455-24-5Sartomer SR 203Methacrylic acid tetrahydrofurfuryl ester2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl esterTetrahydrofurfurylmethacrylateMethacrylic acid, tetrahydrofurfuryl esterSR 203ACRYESTER THFDTXSID0022191NSC-32634120GN9C472
名称をさらに表示
メタクリル酸 テトラヒドロフルフリルメタクリル酸テトラヒドロフラン-2-イルメチルテトラヒドロフルフリルメタクリレートサルトマーSR203メタクリル酸(テトラヒドロフラン)-2-イルメチルメタクリル酸2-オキソラニルメチルメタクリル酸[(テトラヒドロフラン)-2-イル]メチルメタクリル酸(テトラヒドロフラン-2-イル)メチル2-メチルプロペン酸(テトラヒドロフラン-2-イル)メチルメタクリル酸テトラヒドロフルフリルアクリエステルTHFメタクリル酸(テトラヒドロ-2-フラニル)メチルsr203sartomersr203Photomer 2142UNII:120GN9C472CHLUMICRYL THFMA MonomerTetrahydrofurfuryl methacrylaTetrahydrofurfurylmethacrylat
DTXCID502191THFM-ARefChem:188670219-529-5(tetrahydrofuran-2-yl)methyl methacrylateoxolan-2-ylmethyl 2-methylprop-2-enoateMFCD00014515HSDB 5461

データベース識別子

CAS
2455-24-5
PubChem CID
17151
DTXSID
DTXSID0022191
ChEMBL
CHEMBL3561338
ChEBI
CHEBI:189338
UNII
120GN9C472
EC Number
219-529-5
Nikkaji
J208.715D

物性

構造計算による物性

XLogP
1.5
極性表面積
35.5 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
4
重原子数
12
形式電荷
0
複雑度
186

実験および物理化学的性質

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

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 件

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 件

Liquid

Colorless or yellow liquid; [MSDSonline]

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

物理化学的性質

沸点
52 °C0.4 · 52 °C0.4 mm Hg(lit.)
比重(密度)
1.044 g/mL · 1.044 g/mL at 25 °C(lit.)
蒸気圧
27 Pa · 27Pa at 20℃
屈折率
20 · n20/D 1.458(lit.)
闪点
195 °F · 195 °F
貯蔵温度
Keep in dark place,Sealed in dry,Room Temperature
外見
clear liquid
色
Colorless to Almost colorless
比重
1.044 · 1.044
水溶解度
18.99 g/L · 18.99g/L at 20℃
BRN
117423 · 117423
化粧品成分の機能
フィルム形成
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 データベース
2455 · 2455-24-5(CAS DataBase Reference)
NISTの化学物質情報
2 · 2-Propenoic acid, 2-methyl-, (tetrahydro-2-furanyl)methyl ester(2455-24-5)
EPAの化学物質情報
Tetrahydrofurfuryl methacrylate (2455-24-5)

化学的性質

化学的特性Colorless liquid

化学性质非プロトン性極性溶剤

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Regulatory Information · 5 件

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 件

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/

安全と保護具

Storage Conditions · 1 件

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 件

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 件

... 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/

毒性情報

Ecotoxicity Values · 1 件

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 件

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 件

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 件

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 件

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/

安全データ

wgk
1
tsca
TSCA listed
ridadr
3272
hs_code
29321900
risk_code
10-36/37/38
化審法
(5)-57
消防法
危-4-3-III
safety_code
36
hazard_class
3
packing_group
III
ストレージクラス
10 - Combustible liquids
有毒物質データの
2455-24-5(Hazardous Substances Data)

化学と産業

薬理情報

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/

用途と製造

Uses · 6 件

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 件

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

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Consumer UsesMonomers
Industry UsesMonomers
Methods of Manufacturing · 2 件

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 件

Rubber Product Manufacturing

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/

応用分野 · 3 件

用途有機合成原料。

説明Tetrahydrofurfuryl 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].

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

調製方法

合成方法1,4-ブタンジオールを,リン酸,硫酸あるいは酸性イオン交換樹脂による酸触媒環化で製造される。また,フルフラールの脱カルボニル化および水素添加による製造方法も知られている

上流・下流製品情報

上流原料

テトラヒドロフルフリルアルコールメタクリル酸 エチルメタクリル酸メチルメタクリル酸

サプライヤー100 社

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補足説明

定義本品は、次の化学式で表される複素環式化合物である。

関連反応

1 件
反応記録を作成
HRID 1881660 の反応式
HRID 1881660溶媒としてuspto-grants-2012_11

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート