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1461-96-7

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1461-96-7 Usage

Description

CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID, also known as (1R,2S)-rel-1,2-Cyclopentanedicarboxylic Acid, is an organic compound with a unique cyclopentane structure and two carboxylic acid functional groups. It is characterized by its potential to inhibit specific enzymes and has been identified for its possible applications in various industries.

Uses

Used in Pharmaceutical Industry:
CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID is used as a possible inhibitor of prolidase for its potential therapeutic effects. Prolidase is an enzyme involved in the breakdown of imidodipeptides, and its inhibition may be beneficial in treating certain conditions related to abnormal peptide accumulation.
Used in Research and Development:
In the field of research and development, CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID serves as a valuable compound for studying the structure-activity relationships of prolidase inhibitors. This knowledge can be applied to the design and synthesis of more potent and selective inhibitors, which may lead to the development of new drugs for various medical conditions.
Used in Chemical Synthesis:
CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID can be utilized as a building block or intermediate in the synthesis of more complex organic molecules. Its unique cyclopentane framework and functional groups make it a versatile starting material for the creation of novel compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 1461-96-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,6 and 1 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1461-96:
(6*1)+(5*4)+(4*6)+(3*1)+(2*9)+(1*6)=77
77 % 10 = 7
So 1461-96-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O4/c8-6(9)4-2-1-3-5(4)7(10)11/h4-5H,1-3H2,(H,8,9)(H,10,11)/t4-,5+

1461-96-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (±)-cis-Cyclopentane-1,2-dicarboxylic acid

1.2 Other means of identification

Product number -
Other names (1R,2S)-cyclopentane-1,2-dicarboxylic acid

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:1461-96-7 SDS

1461-96-7Synthetic route

ethyl 2-oxocyclohexane carboxylate
1655-07-8

ethyl 2-oxocyclohexane carboxylate

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
Stage #1: ethyl 2-oxocyclohexane carboxylate In chloroform at 0 - 20℃;
Stage #2: With potassium hydroxide In water at 0 - 20℃; Favorskii rearrangement;
74%
Stage #1: ethyl 2-oxocyclohexane carboxylate With bromine In chloroform at 0 - 20℃;
Stage #2: With potassium hydroxide In water at 0℃; for 6h;
Stage #3: With hydrogenchloride In water pH=5;
63%
Multi-step reaction with 2 steps
1: Br2 / CH2Cl2
2: aq. KOH; aq. HCl
View Scheme
ethyl 3-bromo-2-oxocyclohexanecarboxylate
30132-23-1

ethyl 3-bromo-2-oxocyclohexanecarboxylate

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide Favorskii rearrangement;73%
With hydrogenchloride; potassium hydroxide
Multi-step reaction with 2 steps
1: aq. NaOH / ethanol
2: (i) AcCl, (ii) OH-
View Scheme
2,4-dimethoxybicyclo<3.2.1>octane
79692-84-5

2,4-dimethoxybicyclo<3.2.1>octane

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
54%
cyclopent-1-ene-1,2-dicarboxylic acid
3128-15-2

cyclopent-1-ene-1,2-dicarboxylic acid

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With platinum Hydrogenation;
trans-1,2-cyclopentanedicarboxylic acid
80656-14-0

trans-1,2-cyclopentanedicarboxylic acid

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With acetic anhydride Loesen in Wasser oder in Kalilauge und Ansaeuern;
(i) AcCl, (ii) OH-; Multistep reaction;
Multi-step reaction with 2 steps
1: 1.5 h / 200 °C
2: H2O / Heating
View Scheme
cis-1,2-divinylcyclopentane
62732-15-4

cis-1,2-divinylcyclopentane

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
(i) O3, AcOH, (ii) aq. H2O2; Multistep reaction;
exo-cis-6,7-Dihydroxy-cis-bicyclo<3,2,0>heptan
19042-30-9

exo-cis-6,7-Dihydroxy-cis-bicyclo<3,2,0>heptan

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid at 15 - 20℃; for 1h;
cyclopentane-cis-1,2-dicarboxylic acid anhydride
35878-28-5, 743438-34-8

cyclopentane-cis-1,2-dicarboxylic acid anhydride

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With water Heating;
carbon dioxide
124-38-9

carbon dioxide

carbon monoxide
201230-82-2

carbon monoxide

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); (c-C6H11)2PCH2CH2-2-pyridyl; sulfuric acid 1) THF, 20 deg C, 48 h, 2) THF, room temperature, 10 h; Yield given. Multistep reaction;
ethyl 5-bromo-2-oxocyclohexanecarboxylate
118577-36-9

ethyl 5-bromo-2-oxocyclohexanecarboxylate

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide at 0℃; for 2h; Yield given;
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

KOH-solution

KOH-solution

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
durch Ansaeuern; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
(+-)-cis-bicyclo<3.2.0>heptan-6-one

(+-)-cis-bicyclo<3.2.0>heptan-6-one

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With nitric acid
1-cyano-cyclopentane-dicarboxylic acid-(1.2)-diethyl ester

1-cyano-cyclopentane-dicarboxylic acid-(1.2)-diethyl ester

A

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

trans-1,2-cyclopentanedicarboxylic acid
80656-14-0

trans-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride Isolierung ueber das Anhydrid;
rac-bicyclo[3.2.0]hept-2-en-6-one
13756-54-2

rac-bicyclo[3.2.0]hept-2-en-6-one

nitric acid
7697-37-2

nitric acid

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

hydrogenchloride
7647-01-0

hydrogenchloride

Ethyl 1-cyanocyclopentane-1,2-dicarboxylate
143102-48-1

Ethyl 1-cyanocyclopentane-1,2-dicarboxylate

A

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

trans-1,2-cyclopentanedicarboxylic acid
80656-14-0

trans-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
optically inactive substance of bp 3.5: 135-136deg;
1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester
50708-47-9

1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: glacial acetic acid; concentrated sulfuric acid; water
2: acetic acid anhydride / Loesen in Wasser oder in Kalilauge und Ansaeuern
View Scheme
cis-1,2-Cyclopentan-diessigsaeure-bis-dimethylamid
91972-94-0

cis-1,2-Cyclopentan-diessigsaeure-bis-dimethylamid

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4
2: (i) aq. H2O2, (ii) (thermolysis)
3: (i) O3, AcOH, (ii) aq. H2O2
View Scheme
(cis-cyclopentane-1,2-diyl)-di-acetic acid
95259-54-4

(cis-cyclopentane-1,2-diyl)-di-acetic acid

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: (i) SOCl2, (ii) /BRN= 605257/
2: LiAlH4
3: (i) aq. H2O2, (ii) (thermolysis)
4: (i) O3, AcOH, (ii) aq. H2O2
View Scheme
cis-1.2-Bis-<2-dimethylamino-ethyl>-cyclopentan
104282-33-9

cis-1.2-Bis-<2-dimethylamino-ethyl>-cyclopentan

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) aq. H2O2, (ii) (thermolysis)
2: (i) O3, AcOH, (ii) aq. H2O2
View Scheme
(3aR,3bS,6aR,6bS)-Hexahydro-1,3-dioxa-cyclobutadicyclopenten-2-one

(3aR,3bS,6aR,6bS)-Hexahydro-1,3-dioxa-cyclobutadicyclopenten-2-one

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / 2 h / 60 °C
2: K2Cr2O7, H2SO4 / 1 h / 15 - 20 °C
View Scheme
cis-1,2-cyclopentanecarboxylic acid

cis-1,2-cyclopentanecarboxylic acid

cyclopent-1-ene-1,2-dicarboxylic acid
3128-15-2

cyclopent-1-ene-1,2-dicarboxylic acid

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With hydrogen; aluminum nickel In phosphorus pentaoxide; ethanol
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

cyclopentane-cis-1,2-dicarboxylic acid anhydride
35878-28-5, 743438-34-8

cyclopentane-cis-1,2-dicarboxylic acid anhydride

Conditions
ConditionsYield
With acetic anhydride for 20h; Reflux;89%
With acetic anhydride for 10h; Heating;85%
With acetic anhydride for 20h; Heating;81%
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

cis-1,2-bis(hydroxymethyl)cyclopentane
75658-83-2

cis-1,2-bis(hydroxymethyl)cyclopentane

Conditions
ConditionsYield
With lithium aluminium tetrahydride65%
With lithium aluminium tetrahydride In diethyl ether
With Trimethyl borate; dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;
Multi-step reaction with 2 steps
1: 220 °C
2: LiAlH4
View Scheme
Multi-step reaction with 2 steps
1: diethyl ether
2: LiAlH4
View Scheme
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

dimethyl cis-1,2-cyclopentanedicarboxylate
4841-91-2

dimethyl cis-1,2-cyclopentanedicarboxylate

Conditions
ConditionsYield
With diethyl ether
In methanol
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

cis-hexahydro-cyclopentimidazol-2-one
63243-23-2, 933775-94-1

cis-hexahydro-cyclopentimidazol-2-one

Conditions
ConditionsYield
With chloroform; tris-(2-chloro-ethyl)-amine; sulfuric acid anschliessendes Erhitzen mit wss. HCl und Behandeln des Reaktionsprodukts in wss. KOH mit COCl2 in Toluol;
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

trans-1,2-cyclopentanedicarboxylic acid
80656-14-0

trans-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride at 180℃;
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

Conditions
ConditionsYield
at 150 - 160℃; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
Multi-step reaction with 2 steps
1: concentrated hydrochloric acid / 180 °C
2: acetyl chloride / 140 °C / im Einschlussrohr
View Scheme
With acetic anhydride for 20h; Heating / reflux;
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

cis-cyclopentane-1,2-dicarboxylic acid-anhydride
5763-49-5, 35878-28-5, 147148-10-5

cis-cyclopentane-1,2-dicarboxylic acid-anhydride

Conditions
ConditionsYield
With acetic anhydride
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

cis-Cyclopentan-1,2-dicarbamid
13195-85-2

cis-Cyclopentan-1,2-dicarbamid

Conditions
ConditionsYield
(i) SOCl2, (ii) aq. NH3; Multistep reaction;
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

[5-(thiophen-2-yl)thiophen-2-yl]methanamine
4380-96-5

[5-(thiophen-2-yl)thiophen-2-yl]methanamine

(1R,2S)-2-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-cyclopentanecarboxylic acid

(1R,2S)-2-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-cyclopentanecarboxylic acid

Conditions
ConditionsYield
Stage #1: cis-1,2-cyclopentanedicarboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran
Stage #2: [5-(thiophen-2-yl)thiophen-2-yl]methanamine In tetrahydrofuran
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate

methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2.1: phosphorus tribromide / -10 - 85 °C
3.1: ethanol / 100 °C
4.1: DOWEX 550A (OH), activated / H2O
5.1: 130 - 200 °C / 200 Torr
6.1: 99 percent / benzene / 48 h / 20 °C
7.1: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
8.1: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C
9.1: oxalyl chloride / toluene / 20 °C
10.1: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr
11.1: triethylamine-zinc chloride complex / benzene / 20 - 40 °C
12.1: O3 / methanol; CH2Cl2 / -7 °C
13.1: PhSeCl; pyridine / CH2Cl2 / 0.5 h / 0 °C
13.2: 48 percent / aq. H2O2 / CH2Cl2 / 0.5 h / 0 °C
View Scheme
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

6-formyl-octahydro-indene-5-carboxylic acid methyl ester
932698-05-0

6-formyl-octahydro-indene-5-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2: phosphorus tribromide / -10 - 85 °C
3: ethanol / 100 °C
4: DOWEX 550A (OH), activated / H2O
5: 130 - 200 °C / 200 Torr
6: 99 percent / benzene / 48 h / 20 °C
7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
8: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C
9: oxalyl chloride / toluene / 20 °C
10: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr
View Scheme
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

6-oxo-octahydro-indene-5-carboxylic acid methyl ester
926644-62-4

6-oxo-octahydro-indene-5-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2: phosphorus tribromide / -10 - 85 °C
3: ethanol / 100 °C
4: DOWEX 550A (OH), activated / H2O
5: 130 - 200 °C / 200 Torr
6: 99 percent / benzene / 48 h / 20 °C
7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
8: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C
9: oxalyl chloride / toluene / 20 °C
10: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr
11: triethylamine-zinc chloride complex / benzene / 20 - 40 °C
12: O3 / methanol; CH2Cl2 / -7 °C
View Scheme
cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

octahydro-2-oxa-s-indacene-1,3-dione
932698-11-8

octahydro-2-oxa-s-indacene-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2: phosphorus tribromide / -10 - 85 °C
3: ethanol / 100 °C
4: DOWEX 550A (OH), activated / H2O
5: 130 - 200 °C / 200 Torr
6: 99 percent / benzene / 48 h / 20 °C
7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
View Scheme

1461-96-7Downstream Products

1461-96-7Relevant articles and documents

Bickel et al.

, p. 230,235 (1960)

-

Peters

, p. 1761,1765 (1959)

-

NOVEL HEPATITIS C VIRUS INHIBITORS

-

Page/Page column 35, (2013/07/05)

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

Validation of diacyl glycerolacyltransferase I as a novel target for the treatment of obesity and dyslipidemia using a potent and selective small molecule inhibitor

Zhao, Gang,Souers, Andrew J.,Voorbach, Martin,Falls, H. Doug,Droz, Brian,Brodjian, Sevan,Yau, Yi Lau,Iyengar, Rajesh R.,Gao, Ju,Judd, Andrew S.,Wagaw, Seble H.,Ravn, Matthew M.,Engstrom, Kenneth M.,Lynch, John K.,Mulhern, Mathew M.,Freeman, Jennifer,Dayton, Brian D.,Wang, Xiaojun,Grihalde, Nelson,Fry, Dennis,Beno, David W. A.,Marsh, Kennan C.,Su,Diaz, Gilbert J.,Collins, Christine A.,Sham, Hing,Reilly, Regina M.,Brune, Michael E.,Kym, Philip R.

, p. 380 - 383 (2008/09/17)

A highly potent and selective DGAT-1 inhibitor was identified and used in rodent models of obesity and postprandial chylomicron excursion to validate DGAT-1 inhibition as a novel approach for the treatment of metabolic diseases. Specifically, compound 4a conferred weight loss and a reduction in liver triglycerides when dosed chronically in DIO mice and depleted serum triglycerides following a lipid challenge in a dose-dependent manner, thus, reproducing major phenotypical characteristics of DGAT-1-/- mice.

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