Cyclohexyl methacrylate

HCID 7561

Basic information

CAS
101-43-9
Standard SMILES
C=C(C)C(=O)OC1CCCCC1
InChIKey
OIWOHHBRDFKZNC-UHFFFAOYSA-N
Molecular formula
C10H16O2
Average molar mass
168.23 g/mol
Monoisotopic mass
168.11502975

Names & identifiers

Preferred name
Cyclohexyl methacrylate
IUPAC
cyclohexyl 2-methylprop-2-enoate
English name
Cyclohexyl methacrylate
Molecular formula
C10H16O2
Molecular weight
168.23

Names & synonyms

CYCLOHEXYL METHACRYLATE101-43-92-Propenoic acid, 2-methyl-, cyclohexyl esterMethacrylic acid, cyclohexyl estercyclohexylmethacrylateUNII-5L9UUV9T6QAgeflex CHMA5L9UUV9T6QACRYESTER CHHSDB 5340EINECS 202-943-5NSC 20968
Show more names
CHMAMETHACRYLIC ACID CYCLOHEXYL ESTERCyclohexylmethacrylatMethcyclohexyl MethacrylateEM71CCHLUMICRYI CHMACyclohexyl 2-methylacrylateCYCLOHEXYL A-METHYLACRYLATE
NSC-20968AI3-33324Cyclohexyl methacrylate, monomerDTXSID7051507CYCLOHEXANOL, METHACRYLATEOIWOHHBRDFKZNC-UHFFFAOYSA-EC 202-943-5CYCLOHEXYL METHACRYLATE [HSDB]

Database identifiers

CAS
101-43-9
PubChem CID
7561
DTXSID
DTXSID7051507
UNII
5L9UUV9T6Q
EC Number
202-943-5
Nikkaji
J68.537B

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
12

Experimental & physicochemical properties

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

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

Cosmetic ingredients (Cyclohexylmethacrylate) -> CIR (Cosmetic Ingredient Review)

LogP2.98
OdorPLEASANT ODOR
Density0.9626 @ 20 °C/20 °C
Viscosity5.0 CENTIPOISES @ 25 °C

Physicochemical properties

Boiling point
68 · 68-70 °C4 mm Hg(lit.)
Density
0.964 g/mL · 0.964 g/mL at 25 °C(lit.)
vapor pressure
18.4 Pa · 18.4Pa at 20℃
refractive index
20 · n20/D 1.458(lit.)
Flash point
181 °F · 181 °F
storage temp.
Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1% (3 of 294) of reports.

Warning

H315 (89.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, 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 294 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Regulatory Information · 4 items

Chemical: 2-Propenoic acid, 2-methyl-, cyclohexyl ester

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

Status: Active Update: 26-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13282

Cyclohexyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialCombustible
Hazards SummaryAn irritant; [MSDSonline] See ACRYLIC RESINS (MONOMERS).
FDA RequirementsCyclohexyl methacrylate is limited to use only in plastic articles intended for repeated use in contact with food.
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.
Hazard Classes and Categories · 2 items

Skin Irrit. 2 (89.1%)

Flammable liquids - Category 4

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: 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.

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.

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 EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
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

FDA RequirementsCyclohexyl methacrylate is limited to use only in plastic articles intended for repeated use in contact with food.
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

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
hs_code
29162090
risk_code
36/37/38-R36/37/38-43-36-22
Signal word
Warning

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: Cyclohexyl methacrylate

CIR ingredient: Cyclohexylmethacrylate

Used in optical lens systems, dental resins, electronics encapsulation, and hydrogel lenses; [HSDB]

Semiconductor Manufacturing [Category: Industry]

OPTICAL LENS SYSTEMS; DENTAL RESINS; ENCAPSULATION OF ELECTRONIC ASSEMBLIES.

MONOMER EG, FOR SURFACE COATINGS.

U.S. Production · 2 items

2023: 2,500,000 - <4,000,000 lb

(1977) AT LEAST 4.54X10+6 G

Industry UsesSurface modifier
Methods of Manufacturing · 2 items

ESTERIFICATION OR TRANSESTERIFICATION OF CYCLOHEXANOL WITH EITHER METHACRYLIC ACID OR METHYL METHACRYLATE

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/

General Manufacturing Information · 2 items

Adhesive Manufacturing

2-Propenoic acid, 2-methyl-, cyclohexyl ester: ACTIVE

Applications · 2 items

DescriptionCyclohexyl Methacrylate (CHMA) is a very useful starting material for chemical synthesis since it easily undergoes addition reactions with a wide range of organic and inorganic compounds. The compound is an ester of Methacrylic acid and is used as a raw material component in synthesizing polymers. It is a monofunctional monomer consisting of a methacrylate group with a characteristic high reactivity and a cyclic hydrophobic group. Copolymers of CHMA can be prepared with (meth)acrylic acid and its salts, amides, and esters and with (meth)acrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, unsaturated polyesters, and drying oils, etc.

UsesCyclohexyl methacrylate (CHMA) is mainly used in coatings, plastics, textiles, leather, and paper industries as a solution polymerization, suspension polymerization monomer, or comonomer.

Upstream & downstream products

Suppliers100 total

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]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Related reactions

12 records

Compound notes

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