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Methyl N,N-dimethylaminoacrylate, with the molecular formula C7H13NO2, is a colorless liquid characterized by a fruity odor. It is a chemical compound belonging to the acrylate family and is primarily utilized as a monomer in the synthesis of polymers and resins.

999-59-7

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999-59-7 Usage

Uses

Used in Polymer and Resin Production:
Methyl N,N-dimethylaminoacrylate is used as a monomer for the production of polymers and resins, contributing to the formation of various materials with specific properties.
Used in Adhesives Industry:
In the adhesives industry, Methyl N,N-dimethylaminoacrylate is used as a component in the formulation of adhesives, enhancing their bonding capabilities and durability.
Used in Coatings Industry:
Methyl N,N-dimethylaminoacrylate is employed as a component in the production of coatings, improving their protective qualities and resistance to environmental factors.
Used in Sealants Industry:
Methyl N,N-dimethylaminoacrylate is used as an ingredient in sealants, providing them with enhanced sealing properties and resistance to various conditions.
Used as a Crosslinking Agent in Copolymer Production:
Methyl N,N-dimethylaminoacrylate serves as a crosslinking agent in the synthesis of copolymers, which is crucial for achieving desired material characteristics such as strength and flexibility.
Used in the Formation of Polymethyl Methacrylate:
It can be polymerized to form polymethyl methacrylate, a transparent and shatter-resistant plastic with a wide range of applications, including in the production of automotive components, signs, and protective barriers.
Safety Considerations:
It is essential to handle Methyl N,N-dimethylaminoacrylate with care due to its classification as a hazardous substance. It can cause irritation to the skin, eyes, and respiratory system, necessitating proper safety measures during its use and storage.

Check Digit Verification of cas no

The CAS Registry Mumber 999-59-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,9 and 9 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 999-59:
(5*9)+(4*9)+(3*9)+(2*5)+(1*9)=127
127 % 10 = 7
So 999-59-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO2/c1-7(2)5-4-6(8)9-3/h4-5H,1-3H3/b5-4+

999-59-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl N,N-dimethylaminoacrylate

1.2 Other means of identification

Product number -
Other names (E)-methyl 3-(dimethylamino)acrylate

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:999-59-7 SDS

999-59-7Synthetic route

dimethyl amine
124-40-3

dimethyl amine

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

Conditions
ConditionsYield
In diethyl ether at 20℃; for 1h;100%
With benzene
diethylamine
109-89-7

diethylamine

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

Conditions
ConditionsYield
In diethyl ether at 20℃; for 1h;100%
acetic acid methyl ester
79-20-9

acetic acid methyl ester

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

Conditions
ConditionsYield
In toluene at 110℃; Inert atmosphere;
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

N-benzyloxyamine
622-33-3

N-benzyloxyamine

methyl 3-(benzyloxyimino)propanoate
561068-87-9

methyl 3-(benzyloxyimino)propanoate

Conditions
ConditionsYield
With camphor-10-sulfonic acid In xylene for 24h; Heating;93%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

C13H10O3
1241667-97-9

C13H10O3

methyl 3-acetyl-5-(2-hydroxybenzoyl)benzoate

methyl 3-acetyl-5-(2-hydroxybenzoyl)benzoate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 3h; regioselective reaction;92%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

C13H9ClO4
55593-92-5

C13H9ClO4

dimethyl 5-(5-chloro-2-hydroxybenzoyl)isophthalate

dimethyl 5-(5-chloro-2-hydroxybenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 3h; regioselective reaction;86%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

3-Formylchromone
17422-74-1

3-Formylchromone

dimethyl 5-(2-hydroxybenzoyl)isophthalate

dimethyl 5-(2-hydroxybenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; regioselective reaction;85%
With indium(III) triflate In acetonitrile at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent;85%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

6-nitro-4-oxo-4H-chromene-3-carbaldehyde
42059-80-3

6-nitro-4-oxo-4H-chromene-3-carbaldehyde

dimethyl 5-(2-hydroxy-5-nitrobenzoyl)isophthalate

dimethyl 5-(2-hydroxy-5-nitrobenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 7h; regioselective reaction;84%
With indium(III) triflate In acetonitrile at 20℃; for 7h;84%
6-fluorochromone-3-carboxaldehyde
69155-76-6

6-fluorochromone-3-carboxaldehyde

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

dimethyl 5-(5-fluoro-2-hydroxybenzoyl)isophthalate

dimethyl 5-(5-fluoro-2-hydroxybenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 8h; regioselective reaction;83%
dichloroacethyl chloride
79-36-7

dichloroacethyl chloride

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

methyl 2-dichloroacetyl-3-dimethylaminoacrylate

methyl 2-dichloroacetyl-3-dimethylaminoacrylate

Conditions
ConditionsYield
Stage #1: dichloroacethyl chloride; methyl 3-(N,N-dimethylamino)-2-propenoate In toluene at 0 - 20℃; for 0.5h;
Stage #2: With sodium hydroxide In water; toluene at 0 - 20℃; for 3 - 3.33333h;
82.3%
3-formyl-6-methylchromone
42059-81-4

3-formyl-6-methylchromone

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

dimethyl 5-(2-hydroxy-5-methylbenzoyl)isophthalate

dimethyl 5-(2-hydroxy-5-methylbenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 8h; regioselective reaction;82%
6-bromo-4-oxo-4H-chromene-3-carbaldehyde
52817-12-6

6-bromo-4-oxo-4H-chromene-3-carbaldehyde

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

dimethyl 5-(5-bromo-2-hydroxybenzoyl)isophthalate

dimethyl 5-(5-bromo-2-hydroxybenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 8h; regioselective reaction;82%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

6-chloro-7-methyl-4-oxo-4H-chromene-3-carbaldehyde
64481-12-5

6-chloro-7-methyl-4-oxo-4H-chromene-3-carbaldehyde

dimethyl 5-(5-chloro-2-hydroxy-4-methylbenzoyl)isophthalate

dimethyl 5-(5-chloro-2-hydroxy-4-methylbenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 9h; regioselective reaction;81%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

C14H12O5

C14H12O5

dimethyl 5-(2-hydroxy-5-methoxybenzoyl)isophthalate

dimethyl 5-(2-hydroxy-5-methoxybenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 5h; regioselective reaction;81%
3-formyl-6-isopropylchromone
49619-58-1

3-formyl-6-isopropylchromone

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

dimethyl 5-(2-hydroxy-5-isopropylbenzoyl)isophthalate

dimethyl 5-(2-hydroxy-5-isopropylbenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 9h; regioselective reaction;78%
With indium(III) triflate In acetonitrile at 20℃; for 9h;78%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

C13H8Br2O4

C13H8Br2O4

dimethyl 5-(3,5-dibromo-2-hydroxybenzoyl)isophthalate

dimethyl 5-(3,5-dibromo-2-hydroxybenzoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 5h; regioselective reaction;78%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

C15H25N5O

C15H25N5O

N2-[4-[4-(dimethylamino)-1-piperidyl]-2-methoxyphenyl]amino-4(1H)-pyrimidone

N2-[4-[4-(dimethylamino)-1-piperidyl]-2-methoxyphenyl]amino-4(1H)-pyrimidone

Conditions
ConditionsYield
In toluene Reflux;77.3%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

6,7-methylenedioxychromone-3-carboxaldehyde

6,7-methylenedioxychromone-3-carboxaldehyde

dimethyl 5-(6-hydroxybenzo[d][1,3]dioxole-5-carbonyl)isophthalate

dimethyl 5-(6-hydroxybenzo[d][1,3]dioxole-5-carbonyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 60℃; for 12h; regioselective reaction;76%
With indium(III) triflate In acetonitrile at 60℃; for 12h;76%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

4-oxo-4H-1-naphtho<2,3-c>pyran-3-carboxaldehyde
57051-28-2

4-oxo-4H-1-naphtho<2,3-c>pyran-3-carboxaldehyde

dimethyl 5-(1-hydroxy-2-naphthoyl)isophthalate

dimethyl 5-(1-hydroxy-2-naphthoyl)isophthalate

Conditions
ConditionsYield
With indium(III) triflate In acetonitrile at 20℃; for 10h; regioselective reaction;75%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

1-(4-cyanophenyl)guanidine
5637-42-3

1-(4-cyanophenyl)guanidine

4-((4-hydroxypyrimidin-2-yl)amino)benzonitrile
189956-45-4

4-((4-hydroxypyrimidin-2-yl)amino)benzonitrile

Conditions
ConditionsYield
In toluene at 117℃; for 26h;75%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

2,2-difluoroacetaldehyde oxime

2,2-difluoroacetaldehyde oxime

methyl 3-(difluoromethyl)isoxazole-4-carboxylate

methyl 3-(difluoromethyl)isoxazole-4-carboxylate

Conditions
ConditionsYield
Stage #1: 2,2-difluoroacetaldehyde oxime With N-chloro-succinimide In chloroform at 20℃;
Stage #2: methyl 3-(N,N-dimethylamino)-2-propenoate In chloroform at 20℃; regioselective reaction;
73%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

(1-phenylcycloprop-2-en-1-yl)methyl acetate
682760-57-2

(1-phenylcycloprop-2-en-1-yl)methyl acetate

methyl (E)-3-formyl-5-phenylhexa-3,5-dienoate

methyl (E)-3-formyl-5-phenylhexa-3,5-dienoate

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 20℃; Inert atmosphere;52%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

urea
57-13-6

urea

uracil
66-22-8

uracil

Conditions
ConditionsYield
Stage #1: urea In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 4h;
Stage #2: methyl 3-(N,N-dimethylamino)-2-propenoate With polyoxyethylene lauryl ether phosphate sodium salt In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 110℃; for 6h; Temperature; Time; Solvent; Reagent/catalyst;
30%
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

benzene
71-43-2

benzene

1,3,5-tris-(methoxycarbonyl)benzene
2672-58-4

1,3,5-tris-(methoxycarbonyl)benzene

Conditions
ConditionsYield
With hydrogen bromide
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

methyl 2-nitroacetate
2483-57-0

methyl 2-nitroacetate

4-methoxycarbonylmethyl-2-oxy-4,5-dihydro-isoxazole-3,5-dicarboxylic acid dimethyl ester
53183-90-7

4-methoxycarbonylmethyl-2-oxy-4,5-dihydro-isoxazole-3,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In methanol
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

2-Methoxycarbonyl-3-<4-dimethylamino-phenyl>-prop-2-enyl-dimethylimmonium

2-Methoxycarbonyl-3-<4-dimethylamino-phenyl>-prop-2-enyl-dimethylimmonium

Conditions
ConditionsYield
With pyridinium perchlorate
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

3-dimethylaminoacrolein
927-63-9

3-dimethylaminoacrolein

4-Methoxycarbonyl-5-dimethylamino-penta-2,4-dienyl-dimethylimonium

4-Methoxycarbonyl-5-dimethylamino-penta-2,4-dienyl-dimethylimonium

Conditions
ConditionsYield
With pyridinium perchlorate
9H-fluorene
86-73-7

9H-fluorene

methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

C17H14O2

C17H14O2

Conditions
ConditionsYield
Stage #1: 9H-fluorene In tetrahydrofuran at -78 - 0℃;
Stage #2: methyl 3-(N,N-dimethylamino)-2-propenoate In tetrahydrofuran at -78 - 0℃;
methyl 3-(N,N-dimethylamino)-2-propenoate
999-59-7

methyl 3-(N,N-dimethylamino)-2-propenoate

2,3,4,5-tetrafluorobenzoyl chloride
94695-48-4

2,3,4,5-tetrafluorobenzoyl chloride

methyl 2-(2,3,4,5-tetrafluorophenyl)formyl-3-(N,N-dimethylamino)acrylate

methyl 2-(2,3,4,5-tetrafluorophenyl)formyl-3-(N,N-dimethylamino)acrylate

Conditions
ConditionsYield
With triethylamine In toluene at 53℃; Temperature; Solvent; Reagent/catalyst;

999-59-7Relevant academic research and scientific papers

Silylamination of electrophilic alkynes

Baines, Kim M.,McOnie, Sarah L.

supporting information, (2021/12/23)

The addition of simple silylamines to dialkyl acetylenecarboxylates was investigated yielding both E and Z-silylenamines in contrast to an earlier report. Silylamination was also achieved with propiolates, expanding the scope of the silylamination reactio

An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units

Jiang, Chengzhou,Wu, Jiamin,Han, Jiabin,Chen, Kai,Qian, Yang,Zhang, Zhengyu,Jiang, Yaojia

supporting information, p. 5710 - 5713 (2021/06/16)

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.

Formation of Enamines via Catalytic Dehydrogenation by Pincer-Iridium Complexes

Lu, Yansong J.,Zhang, Xiawei,Malakar, Santanu,Krogh-Jespersen, Karsten,Hasanayn, Faraj,Goldman, Alan S.

supporting information, p. 3020 - 3028 (2020/03/23)

Di-isopropylphosphino-substituted pincer-ligated iridium catalysts are found to be significantly more effective for the dehydrogenation of simple tertiary amines to give enamines than the previously reported di-t-butylphosphino-substituted species. It is

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

Chen, Jie,Guo, Pan,Zhang, Jianguo,Rong, Jiaxin,Sun, Wangbin,Jiang, Yaojia,Loh, Teck-Peng

supporting information, p. 12674 - 12679 (2019/08/07)

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

ENZYMATIC SYNTHESIS OF CARBA-NAD

-

Page/Page column 3-4, (2012/06/01)

The disclosure concerns the enzymatic synthesis of stable analogues of nicotinamide adenine dinucleotide NAD/NADH and nicotinamide adenine dinucleotide phosphate NADP/NADPH, the so-called “carba-NADs”, i.e. analogues of NAD/NADH or NADP/NADPH, respectively, comprising a carbacyclic sugar instead of ribose.

Synthesis of 2-aminofurans and 2-unsubstituted furans via carbenoid-mediated [3 + 2] cycloaddition

Jiang, Yaojia,Khong, Vanessa Zhong Yue,Lourdusamy, Emmanuvel,Park, Cheol-Min

experimental part, p. 3133 - 3135 (2012/05/04)

An efficient dual synthetic manifold for 2-aminofurans and 2-unsubstituted furans has been developed. The carbenoid-mediated [3 + 2] cycloaddition of copper carbenoids with enamines provides 2-amino-2,3-dihydrofurans which serve as common intermediates for both 2-aminofurans and 2-unsubstituted furans. The Royal Society of Chemistry 2012.

METHOD AND SUBSTANCES FOR PREPARATION OF N-SUBSTITUTED PYRIDINIUM COMPOUNDS

-

Page/Page column 8-9, (2011/02/24)

The present invention relates to a method for the synthesis of N-substituted carboxylated pyridinium compounds by reacting a pentamethine precursor with a primary amine. In this reaction an N-substituted alkoxycarbonyl pyridinium heterocycle is formed.

A new synthesis of alkyl (E)-(3-dimethylamino)acrylates

Robertson, Jeffrey M.,Jones, Ian W.,Kayne, Kevin M.,Contreras, Cristina G.,Witter, Daniel J.,Bates, Robert B.,Hall Jr.

experimental part, p. 6080 - 6081 (2011/11/29)

A highly stereoselective one-step method for the synthesis of alkyl (E)-(3-dimethylamino)acrylates from N,N-dimethylformamide and ketene acetals is reported.

Stereoselective synthesis of α-Diazo oxime ethers and their application in the synthesis of highly substituted pyrroles through a [3+2] cycloaddition

Lourdusamy, Emmanuvel,Yao, Lin,Park, Cheol-Min

supporting information; experimental part, p. 7963 - 7967 (2011/01/08)

The stereoselective diazo transfer reaction with oxime ethers offers an efficient route to the corresponding α-diazo oxime ethers. The utility of these compounds has been demonstrated by the synthesis of highly substituted pyrroles through a [3+2] cycloaddition of α-oximino carbenoids with enamines (see scheme).

Efficient synthesis of β-enaminoesters via highly stereoselective Reformatsky reaction with disubstituted formamides as novel electrophiles

Ke, Yi-Yin,Li, Yu-Jin,Jia, Jian-Hong,Sheng, Wei-Jian,Han, Liang,Gao, Jian-Rong

experimental part, p. 1389 - 1391 (2009/06/08)

An efficient synthesis of various β-enaminoesters has been achieved via Reformatsky reaction with disubstituted formamides as novel electrophiles. The exclusive β-enaminoester E-isomers were obtained in 60-72% yield.

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