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71868-10-5

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  • Photoinitiator 907 2-Methyl-4'-(methylthio)-2-morpholinopropiophenone Manufacturer Factory CAS 71868-10-5

    Cas No: 71868-10-5

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71868-10-5 Usage

Application fields

2-Methyl-4'-(Methylthio)-2-Morpholinopropiophenone is an efficient UV photoinitiator for initiating UV polymerization of unsaturated prepolymer systems, Such as acrylic resins and monofunctional and multifunctional vinyl monomers. The initiator molecule has a certain light absorption capacity in the ultraviolet region (250-400 nm) or the visible region (400-800 nm). After direct or indirect absorption of light energy, the initiator molecules transition from the ground state to the excited singlet state, through intersystem conversion to excited triple state. After undergoing a single molecular or bimolecular chemistry, initiator molecules produce reactive debris that initiates polymerization of the monomers, which may be free radicals, cations, anions, etc. According to the different initiation mechanism, the photoinitiator can be divided into free radical polymerization photoinitiator and cationic photoinitiator, among which the most widely used is free radical polymerization photoinitiator. The characteristic of high absorbency of 2-Methyl-4'-(Methylthio)-2-Morpholinopropiophenone makes it particularly suitable for UV curable inks and colored coatings. UV inks contain a greater amount of photoinitiator, and it is these photoinitiators that promote the rapid drying of the ink during the printing process. These photoinitiators themselves are not stable, even in the dark, and it is also prone to dark reaction, resulting in one by one ink glue nucleus, followed by a large area of retrogradation. Especially in the preservation of metal ink, similar situation occur more often. Therefore, it is recommended that the ink pigment and the binder separately stored. If used, stir and mix the two with a large machine. Highly efficient photoinitiator can be used in UV curing systems to extend storage with non-yellowing for a long time. It is an initiator specifically for pigmented UV-curable coatings, inks and adhesives colored solidification system, and it could be used with184, ITX and other initiators. It can be used for colored ink systems, paper/metal and plastic varnish and electronic inks. It is also as a UV absorber for cosmetics and other industries with suggested supplementation of 2-6%.

Application

Used as an initiator in a photo-curable material UV-curable coatings and inks Highly efficient photoinitiator can be used in UV curing systems to extend storage with non-yellowing for a long time.

Chemical Properties

White powder

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 71868-10-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,8,6 and 8 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 71868-10:
(7*7)+(6*1)+(5*8)+(4*6)+(3*8)+(2*1)+(1*0)=145
145 % 10 = 5
So 71868-10-5 is a valid CAS Registry Number.

71868-10-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methyl-4-(Methylthio)-2-Morpholinopropiophenone

1.2 Other means of identification

Product number -
Other names 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71868-10-5 SDS

71868-10-5Synthetic route

morpholine
110-91-8

morpholine

2-methoxy-3,3-dimethyl-2-(4-methylthiophenyl)oxirane

2-methoxy-3,3-dimethyl-2-(4-methylthiophenyl)oxirane

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
With calcium hydroxide at 20 - 138℃; for 20h;90.2%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide for 8h; Reflux;43%
at 105 - 110℃; for 20h; Temperature;119.3 g
at 105 - 115℃; for 20h;112.57 g
With water at 105℃; for 12h; Reagent/catalyst; Large scale;
1-methoxy-4-methylsulfanyl-benzene
1879-16-9

1-methoxy-4-methylsulfanyl-benzene

4-(2-methyl-2-morpholinopropanoyl)benzonitrile

4-(2-methyl-2-morpholinopropanoyl)benzonitrile

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In o-xylene at 140℃; for 24h; Glovebox; Inert atmosphere;74%
morpholine
110-91-8

morpholine

2-methyl-1-(4-(methylthio)phenyl)-propan-1-one
53207-58-2

2-methyl-1-(4-(methylthio)phenyl)-propan-1-one

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Stage #1: 2-methyl-1-(4-(methylthio)phenyl)-propan-1-one With hexachloroethane; sodium methylate In methanol at 40℃; for 24h;
Stage #2: morpholine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide for 10h; Reagent/catalyst; Temperature; Reflux;
61%
morpholine
110-91-8

morpholine

2-bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one
88324-55-4

2-bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Stage #1: morpholine With aluminum (III) chloride In 1,2-dichloro-ethane at 40℃; for 0.5h;
Stage #2: 2-bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one In 1,2-dichloro-ethane at 40℃; for 6h;
60.57%
2-methyl-1-(4-(methylthio)phenyl)-propan-1-one
53207-58-2

2-methyl-1-(4-(methylthio)phenyl)-propan-1-one

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine / 2 h / 20 - 30 °C
2.1: aluminum (III) chloride / 1,2-dichloro-ethane / 0.5 h / 40 °C
2.2: 6 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: bromine / 2 h / 20 - 30 °C
2: 1 h / 20 °C
3: 20 h / 105 - 115 °C
View Scheme
Multi-step reaction with 2 steps
1: hexachloroethane / 20 °C
2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / 8 h / Reflux
View Scheme
methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 7.5 h / 15 - 35 °C
2.1: bromine / 2 h / 20 - 30 °C
3.1: aluminum (III) chloride / 1,2-dichloro-ethane / 0.5 h / 40 °C
3.2: 6 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: aluminum (III) chloride / dichloromethane / 7.5 h / 15 - 35 °C
2: bromine / 2 h / 20 - 30 °C
3: 1 h / 20 °C
4: 20 h / 105 - 115 °C
View Scheme
2-chloro-2-methyl-1-(4-methylthiophenyl)-1-propanone

2-chloro-2-methyl-1-(4-methylthiophenyl)-1-propanone

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 1 h / 20 °C
2: 20 h / 105 - 115 °C
View Scheme
2-bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one
88324-55-4

2-bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: morpholine; sodium methylate / 28 - 85 °C / 760.05 Torr / Large scale
2: water / 12 h / 105 °C / Large scale
View Scheme
terephthalonitrile
623-26-7

terephthalonitrile

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

4-(2-methyl-2-morpholinopropanoyl)benzonitrile

4-(2-methyl-2-morpholinopropanoyl)benzonitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In o-xylene at 140℃; for 24h; Glovebox; Inert atmosphere;94%
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

1-(4-(cyclohexylthio)phenyl)-2-methyl-2-morpholinopropan-1-one

1-(4-(cyclohexylthio)phenyl)-2-methyl-2-morpholinopropan-1-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); lithium hexamethyldisilazane; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 12h; Glovebox; Inert atmosphere;91%
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

methyl 2-((4-(2-methyl-2-morpholinopropanoyl)phenyl)thio)acetate
1353758-87-8

methyl 2-((4-(2-methyl-2-morpholinopropanoyl)phenyl)thio)acetate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 100℃; for 24h;89%
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

aniline
62-53-3

aniline

C20H24N2O2

C20H24N2O2

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); lithium hexamethyldisilazane; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 12h; Buchwald-Hartwig Coupling;68%
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

A

2-morpholino propan-2-yl radical
141888-27-9

2-morpholino propan-2-yl radical

B

C8H7OS
141913-26-0

C8H7OS

Conditions
ConditionsYield
In various solvent(s) at -40.1℃; Irradiation; Title compound not separated from byproducts;
In acetonitrile UV-irradiation;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

dicyclohexyl itaconate
15700-62-6

dicyclohexyl itaconate

poly(dicyclohexyl itaconate) dimethyl(morpholino)methyl-terminated; monomer(s): dicyclohexyl itaconate; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

poly(dicyclohexyl itaconate) dimethyl(morpholino)methyl-terminated; monomer(s): dicyclohexyl itaconate; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
at 20℃; pulsed lazer irradiation;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

poly(methyl acrylate), p-methylthiobenzoyl- and dimethyl(morpholino)methyl-terminated; monomer(s): methyl acrylate; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

poly(methyl acrylate), p-methylthiobenzoyl- and dimethyl(morpholino)methyl-terminated; monomer(s): methyl acrylate; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
at -34℃; pulsed lazer irradiation;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

poly(ethylene glycol) diacrylate

poly(ethylene glycol) diacrylate

poly(ethylene glycol) diacrylate with C(O)-C6H4-SCH3-p end group, product of photopolymerization

poly(ethylene glycol) diacrylate with C(O)-C6H4-SCH3-p end group, product of photopolymerization

Conditions
ConditionsYield
at 70℃; UV-irradiation;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

dimethyl sulfate
77-78-1

dimethyl sulfate

dimethyl-[4-(2-methyl-2-morpholin-4-ium-4-yl-propanoyl)phenyl]sulfonium methyl sulfate

dimethyl-[4-(2-methyl-2-morpholin-4-ium-4-yl-propanoyl)phenyl]sulfonium methyl sulfate

Conditions
ConditionsYield
In water; acetonitrile at 25 - 60℃;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

2-methyl-1-[4-(methylsulfinyl)-phenyl]-2-morpholinopropan-1-one

2-methyl-1-[4-(methylsulfinyl)-phenyl]-2-morpholinopropan-1-one

Conditions
ConditionsYield
Stage #1: 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2.5h; Cooling with ice;
Stage #2: With sodium hydroxide In dichloromethane; water
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ium-4-yl-propan-1-one tetrafluoroborate

2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ium-4-yl-propan-1-one tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid In diethyl ether for 2h; Cooling with ice;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

dimethyl-[4-(2-methyl-2-morpholino-propanoyl)phenyl]sulfonium methyl sulfate
1353758-57-2

dimethyl-[4-(2-methyl-2-morpholino-propanoyl)phenyl]sulfonium methyl sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile; water / 25 - 60 °C
2: sodium hydroxide; sodium carbonate / water / 0.5 h / 25 °C / pH 9
View Scheme
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

dimethyl-[4-(2-methyl-2-morpholino-propanoyl)phenyl]sulfonium hexafluorophosphate

dimethyl-[4-(2-methyl-2-morpholino-propanoyl)phenyl]sulfonium hexafluorophosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile; water / 25 - 60 °C
2: sodium hexaflorophosphate; sodium carbonate / water / pH 9.2
View Scheme
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ium-4-yl-propan-1-one chloride
1353758-31-2

2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ium-4-yl-propan-1-one chloride

Conditions
ConditionsYield
With hydrogenchloride In propan-1-ol; water for 1h;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

triethyloxonium fluoroborate
368-39-8

triethyloxonium fluoroborate

ethyl-methyl-[4-(2-methyl-2-morpholino-propanoyl)phenyl]sulfonium tetrafluoroborate

ethyl-methyl-[4-(2-methyl-2-morpholino-propanoyl)phenyl]sulfonium tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane at 25℃; for 5h;90 %Spectr.
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

A

2-methyl-2-(4-morpholinyl)-1-[4-(dichloromethylthio)phenyl]-1-propanone hydrochloride

2-methyl-2-(4-morpholinyl)-1-[4-(dichloromethylthio)phenyl]-1-propanone hydrochloride

B

2-methyl-2-(4-morpholinyl)-1-[4-(trichloromethylthio)phenyl]-1-propanone hydrochloride

2-methyl-2-(4-morpholinyl)-1-[4-(trichloromethylthio)phenyl]-1-propanone hydrochloride

Conditions
ConditionsYield
With sulfuryl dichloride In 1,2-dichloro-ethane at 20 - 30℃; for 4h; Reagent/catalyst; Temperature; Overall yield = 16.5 g;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

2-methyl-2-(4-morpholinyl)-1-(4-mercaptophenyl)-1-propanone

2-methyl-2-(4-morpholinyl)-1-(4-mercaptophenyl)-1-propanone

Conditions
ConditionsYield
Stage #1: 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one With sulfuryl dichloride In 1,2-dichloro-ethane for 1h;
Stage #2: With carbonic acid dimethyl ester; sodium hydroxide In methanol for 6.25h; Inert atmosphere; Reflux;
8.5 g
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

1-chloroacetophenone
532-27-4

1-chloroacetophenone

C23H28NO3S(1+)*Cl(1-)

C23H28NO3S(1+)*Cl(1-)

Conditions
ConditionsYield
In acetone for 2h; Inert atmosphere;
2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
71868-10-5

2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one

1-chloroacetophenone
532-27-4

1-chloroacetophenone

C23H28NO3S(1+)*F6P(1-)

C23H28NO3S(1+)*F6P(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 2 h / Inert atmosphere
2: potassium hexafluorophosphate / acetone / 2 h / Heating
View Scheme

71868-10-5Relevant articles and documents

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

Delcaillau, Tristan,Boehm, Philip,Morandi, Bill

supporting information, p. 3723 - 3728 (2021/04/07)

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

PROCESS FOR THE PREPARATION OF ALPHA-FUNCTIONALIZED KETONES

-

Page/Page column 49; 50; 51; 52, (2018/11/22)

The present invention refers to a process for the preparation of an α-functionalized ketone, an α-functionalized ketone obtained by said process, a photopolymerizable composition comprising the α-functionalized ketone and at least one photopolymerizable unsaturated compound, a method of preparing an article, an article obtained by said method, as well as the use of the α-functionalized ketone or the photopolymerizable composition as photoinitiator.

Synthetic method of free-radical photoinitiator

-

Paragraph 0053; 0054; 0063; 0064; 0075; 0102, (2018/07/30)

The invention discloses a synthetic method of a free-radical photoinitiator. The synthetic method is characterized by comprising the following steps: (1) under the action of aluminium trichloride, methyl phenyl sulfide is adopted as a raw material and generates Friedel-Crafts acylation reaction with 2-chloroisobutyryl chloride to prepare an intermediate A with a structure shown in a formula (I); (2) under the action of alkaline, the intermediate A carries out ring-closure reaction to prepare an intermediate B with a structure shown in a formula (II); (3) the intermediate B and morpholine carryout ring-opening reaction to obtain a target product with a structure shown in a formula (III), namely the free-radical photoinitiator. The synthetic method disclosed by the invention has the beneficial effects that the photoinitiator is synthesized by the steps of adopting the 2-chloroisobutyryl chloride and methyl phenyl sulfide to carry out Friedel-Crafts acylation reaction, then carrying outcyclization and ring opening and the like, the obtained product contains fewer impurities, the yield is high, the process route is convenient in operation, and generates less three wastes (waste water, waste solid and waste air) so as to be more environment-friendly.

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