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Methylene Chloride

Methylene Chloride is a versatile and widely used organic solvent with a variety of applications in scientific research and industrial processes.
Also known as dichloromethane, this chemical compound is a colorless, volatile liquid with a characteristic sweet odor.
Methylene Chloride has a low boiling point and is highly miscible with many organic solvents, making it a valuable tool for extractions, purifications, and other laboratory techniques.
Researchers utilize Methylene Chloride for a broad range of applications, including polymer synthesis, pharmaceutical development, and environmetnal analysis.
However, due to its potential toxicity, it is important to handle Methylene Chloride with care and follow appropriate safety protocols.
PubCompare.ai offers a powerful platform to optimize your Methylene Chloride research, providing access to the best protocols from literature, preprints, and patents, and leveraging AI-driven analysis to identify the most reliable and effective methods for your experiments.

Most cited protocols related to «Methylene Chloride»

In this work, we used as authentic nitro-PAH standards a NIST SRM 2265 (polycyclic aromatic hydrocarbons nitrated in methylene chloride II), which contained 2-nitrofluoranthene (2-NFLT, CAS# 13177-29-2), 3-nitrofluoranthene (3-NFL, CAS# 892-21-7), 1-nitropyrene (1-NPYR, CAS# 5522-43-0), 2-nitropyrene (2-NPYR, CAS# 789-07-1), and 3-nitrobenzanthrone (3-NBA, CAS# 17117-34-9), among others. Their certified concentrations were 5.46 ± 0.15 µg mL−1 (2-NFLT), 6.14 ± 0.13 µg mL−1 (3-NFLT), 6.91 ± 0.27 µg mL−1 (1-NPYR), 6.91 ± 0.27 µg mL−1 (2-NPYR), and 4.39 ± 0.11 µg mL−1 (3-NBA). Since SRM 2265 does not include 2-nitrobenzanthrone (2-NBA, CAS# 111326-48-8), this compound was purchased from Sigma-Aldrich (USA) (>99% purity) and added to that. Authentic standards for fluoranthene (FLT, CAS# 206-44-0), pyrene (PYR, CAS# 129-00-0), benzo[a]pyrene (BaP, CAS# 50-32-8), and benzo[a]anthracene (BaA, CAS# 56-55-3), among others, are included in the EPA 610 PAH mix, at 2000 µg mL−1 each, in methanol: methylene chloride (1:1) (Supelco, USA). In this study, stock and analytical solutions were prepared by successive dilutions in acetonitrile (chromatographic and spectroscopic grade, J.T. Baker, USA).
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Publication 2019
1-nitropyrene 2-nitrobenzanthrone 2-nitrofluoranthene 2-nitropyrene 3-nitrobenzanthrone 3-nitrofluoranthene acetonitrile anthracene Benzo(a)pyrene Chromatography fluoranthene Methanol Methylene Chloride Polycyclic Hydrocarbons, Aromatic pyrene Spectrum Analysis Technique, Dilution
Norbornene-functionalized PEG was prepared by the addition of norbornene acid via the symmetric anhydride N,N’-dicyclohexylcarbodiimid (DCC; Sigma) coupling. The 4-arm PEG, MW 20000 (JenKemUSA, Allen, TX), was dissolved in dichloromethane (DCM) with 5× (with respect to hydroxyls) pyridine and 0.5×4-(dimethylamino)pyridine (DMAP; Sigma). In a separate reaction vessel, DCC 5× with respect to PEG hydroxyls, was reacted at room temperature with 10×5-norbornene-2-carboxylic acid (Sigma). A few seconds after addition of the acid, a white byproduct precipitate formed (dicycolhexylurea), indicating the formation of dinorbornene carboxylic acid anhydride. The anhydride was allowed to stir for 30 min, following which the 4-arm PEG, pyridine, and DMAP solution were added. The reaction was stirred overnight, after which the mixture was filtered. The filtrate was washed with 5% sodium bicarbonate solution and the product was precipitated in ice-cold diethyl ether.
Publication 2009
2-norbornene Acids Anhydrides Bicarbonate, Sodium Blood Vessel Carboxylic Acids Cold Temperature Ethyl Ether Hydroxyl Radical Methylene Chloride Neoplasm Metastasis pyridine

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Publication 2011
Acid Phosphatase ammonium acetate Bath Cells Centrifugation Cytoskeleton Liquid Chromatography Methanol Methylene Chloride Nitrogen Parent Sodium Acetate Sodium Chloride Solid Phase Extraction Tandem Mass Spectrometry

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Publication 2018
Acetate ammonium fluoride Biological Factors Charcoal Estradiol Ethinyl Estradiol etonogestrel Homo sapiens Levonorgestrel Methanol Methylene Chloride Norethindrone Progesterone Serum
All strains, except Trichocoma paradoxa isolates, (Table 1) were grown for 7 and 14 days at 37°C on the solid media YES, CYA, OA, malt extract agar (MEA-B) (Blakeslee formula, Difco malt extract) (Raper and Thom 1949 , p. 67), MEA, Wickerham’s Antibiotic Test Medium (WATM) (Raper and Thom 1949 , pp. 69–70) and Raulin-Thom (Smith 1960 , p. 259) with added oat meal (RTO agar) (using 2.67 g ammonium tartrate and 30 g oatmeal/l) prior to extrolite extraction. Trichocoma paradoxa was grown on the above mentioned agar media for 4 weeks at 25°C. All media contained a trace metal mixture of 5 ppm CuSO4·5H2O and 10 ppm ZnSO4·7H2O (Smith 1949 (link)). Five agar plugs taken along a diameter of the fungal colony were used for extraction. The agar plugs were transferred in ethyl acetate/dichloromethane/methanol (3:2:1, v/v/v) with 1% (v/v) formic acid and ultrasonicated for 50 min. The extracts were transferred to a 1.5 ml autosampler screw-cap vials, evaporated to dryness and re-dissolved in 400 μl methanol by ultrasonication in 10 min. Subsequently, the extracts were filtered through 0.45 μm filter (Minisart RC4, Sartorius, Germany) and kept at −18°C prior to analysis. The extracts were analyzed by ultra high performance liquid chromatography (U-HPLC) using alkylphenone retention indices and diode array UV–VIS detection as described by Frisvad and Thrane (1987 (link)). The U-HPLC used was Dionex Ultimate 3000 with two pumps. The extrolites were separated on a Kinetex C18 (150 × 2.1 mm) column with 2.6 μm particles. The column temperature was held at 60°C. The extract injection volume was 1 μl. A gradient based on water with 50 ppm trifluoroacetic acid (TFA) and acetonitrile (AcCN) with 50 ppm TFA, at a flow rate of 0.8 ml/min, was used: Start conditions 85% H2O with TFA and 15% AcCN with TFA. Gradient: 15–25% AcCN in ½ min, from 25 to 65% AcCN in 5½ min, from 60 to 100% AcCN in 1 min, at 100% AcCH in 1 min, back to 15% AcCN in 1 min and then 1 min constant at 15% AcCN. The run-time was therefore 10 min. UV chromatograms were recorded at 210 and 280 nm, but diode array detection was carried out in a range from 190 to 600 nm. Identification of extrolites was performed by comparison of the UV–Visible spectra and retention times of the extrolites with those present in the collection at Department of Systems Biology, Kgs. Lyngby, Denmark.
Publication 2011
acetonitrile Agar ammonium tartrate Antibiotics ARID1A protein, human ethyl acetate formic acid High-Performance Liquid Chromatographies Metals Methanol Methylene Chloride Retention (Psychology) TRAF3 protein, human Trichocoma paradoxa Trifluoroacetic Acid

Most recents protocols related to «Methylene Chloride»

Example 41

[Figure (not displayed)]
1) Synthesis of Compound 42-1

[Figure (not displayed)]

Potassium carbonate (110 mg) was added to a solution of Compound 39 (200 mg) and ethyl 2-bromoacetate (100 mg) in DMF (5 mL), and the resulting mixture heated to 80° C. and stirred for 1 h under nitrogen protection. The reaction mixture was cooled to room temperature, and filtered. The filter cake was washed with ethyl acetate (2 mL). The filtrate was concentrated to obtain Compound 42-1. LCMS (ESI) m/z: 606 (M+1).

2) Synthesis of Compound 42-2

[Figure (not displayed)]

An aqueous solution of lithium hydroxide monohydrate (1M, 0.7 mL) was added to a solution of Compound 42-1 (200 mg) in tetrahydrofuran (5 mL), and the resulting mixture was stirred at 26° C. for 1 h under nitrogen protection. The reaction mixture was acidified to pH=5-6 with an aqueous solution of dilute hydrochloric acid (1M), and extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain Compound 42-2. LCMS (ESI) m/z: 578 (M+1).

3) Synthesis of Compound 42

[Figure (not displayed)]

Methylamine hydrochloride (18 mg) was added to a solution of Compound 42-2 (100 mg), HATU (80 mg), and triethylamine (50 mg, 494.12 μmol) in dichloromethane (5 mL), and the resulting mixture was stirred at 26° C. for 1 h. The reaction mixture was acidified to pH=5-6 with an aqueous solution of dilute hydrochloric acid (1M), and extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue obtained from the concentration was purified by preparative TLC and preparative HPLC to obtain Compound 42. 1H NMR (400 MHz, CDCl3) δ ppm 8.68 (s, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.88 (d, J=1.5 Hz, 1H), 7.76 (dd, J=8.3, 1.8 Hz, 1H), 7.31-7.36 (m, 1H), 7.29 (dd, J=8.8, 2.0 Hz, 1H), 4.51 (s, 2H), 2.90 (d, J=5.0 Hz, 3H), 2.84 (q, J=7.7 Hz, 2H), 1.62 (s, 6H), 1.29 ppm (t, J=7.5 Hz, 3H); LCMS (ESI) m/z: 591 (M+1).

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Patent 2024
1H NMR Anabolism brine ethyl acetate ethyl bromoacetate High-Performance Liquid Chromatographies Hydrochloric acid Lincomycin lithium hydroxide monohydrate methylamine hydrochloride Methylene Chloride Nitrogen potassium carbonate sodium sulfate tetrahydrofuran triethylamine

Example 11

0.18 of 1-benzoyl-3-(5′-azido-1′-pentyl)pyrrolidine (14) was dissolved in 5 ml of tetrahydrofuran, and then 0.15 g of triphenylphosphine and 2 drops of water were added and refluxed overnight. After concentration under reduced pressure, 10 ml of dichloromethane was added, and washed sequentially with water and a saturated sodium chloride solution. The reaction solution was concentrated under reduced pressure, and separated by column chromatography (dichloromethane/methanol/aqueous ammonia=10:1:0.1 vol/vol/vol), to obtain 0.16 g of an oily product 1-benzoyl-3-(5′-amino-1′-pentyl)pyrrolidine (15). LCMS: 261[M+H].

The following compounds can be prepared according to the above method of preparing the compound 15 starting from the compound 12:

PreparationMS
numberName of CompoundStructure(m/z)
161-(2,6-dimethoxybenzoyl)- 3-(5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
321 (M + 1)
171-(2,6-dimethoxybenzoyl)- 3-(6′-amino-1′- hexyl)pyrrolidine[Figure (not displayed)]
335 (M + 1)
181-benzoyl-3-(6′-amino-1′- hexyl)pyrrolidine[Figure (not displayed)]
275 (M + 1)
191-furoyl-3-(5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
251 (M + 1)
19-11-furoyl-3-(6′-amino-1′- hexyl)pyrrolidine[Figure (not displayed)]
265 (M + 1)
201-(2-thienylformyl)-3-(5′- amino-1′-pentyl)pyrrolidine[Figure (not displayed)]
267 (M + 1)
20-11-(2-thienylformyl)-3-(6′- amino-1′-hexyl)pyrrolidine[Figure (not displayed)]
281 (M + 1)
211-(2-pyrrolylformyl)-3-(5′- amino-1′-pentyl)pyrrolidine[Figure (not displayed)]
250 (M + 1)
221-(2-pyrrolylformyl)-3-(6′- amino-1′-hexyl)pyrrolidine[Figure (not displayed)]
264 (M + 1)
231-(2-pyrrolidinylformyl)-3- (5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
254 (M + 1)
23-11-(2-pyrrolidinylformyl)-3- (6′-amino-1′- hexyl)pyrrolidine[Figure (not displayed)]
268 (M + 1)
241-(2-tetrahydrofurylfuryl)-3- (5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
255 (M + 1)
251-(2- tetrahydrothienylformyl)-3- (5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
271 (M + 1)
25-11-(2- tetrahydrothienylformyl)-3- (6′-amino-1′- hexyl)pyrrolidine[Figure (not displayed)]
285 (M + 1)
25-21-(3-fluoro-2-thienylformyl)- 3-(5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
285 (M + 1)
25-31-(3-fluoro-2- pyrrolylformyl)-3-(5′-amino- 1′-pentyl)pyrrolidine[Figure (not displayed)]
268 (M + 1)
25-41-(3-fluoro-2-furylformyl)-3- (5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
269 (M + 1)
261-(2-indolylformyl)-3-(5′- amino-1′-pentyl)pyrrolidine[Figure (not displayed)]
300 (M + 1)
26-11-(2-indolylformyl)-3-(6′- amino-1′-hexyl)pyrrolidine[Figure (not displayed)]
314 (M + 1)
271-(2-benzofurylformyl)-3- (5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
301 (M + 1)
27-11-(2-benzofurylformyl)-3- (6′-amino-1′- hexyl)pyrrolidine[Figure (not displayed)]
315 (M + 1)
27-21-(2- benzyltetrahydrofurylfuryl)- 3-(5′-amino-1′- pentyl)pyrrolidine[Figure (not displayed)]
303 (M + 1)

[Figure (not displayed)]

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Patent 2024
Ammonia Chromatography Lincomycin Methanol Methylene Chloride Oils Pressure pyrrolidine Saline Solution tetrahydrofuran triphenylphosphine

Example 4

Octadecanoate Functionalized Core (IMS 018 H)

To a round bottom flask was added one or more of the following “core” compounds: tripentaerythritol (“H”) made from the above cores. These were dissolved in tetrahydrofuran. 1.1 molar equivalents (per —OH of the hydroxyl terminated cores or dendrimers) of Octadecanoic Acid were added to the solution of cores. To these reagents were added 1.2 molar equivalents (per —OH of the hydroxyl terminated cores or dendrimers) of dicyclohexylcarbodiimide and 0.1 molar equivalents (per —OH of hydroxyl-terminated core or of dendrimer) of 4-dimethylaminopyridine (DMAP).

The reaction mixture was stirred vigorously for approximately 12 hours at standard temperature and pressure. The reaction was monitored by MALDI-TOF MS to determine completion of the reaction for each of the cores present in the reaction. After complete esterification is observed by MALDI-TOF MS, the flask contents were transferred to a separatory funnel, diluted with dichloromethane, extracted twice with 1M aqueous NaHSO4 (sodium bisulfate) and extracted twice with 1M aqueous NaHCO3 (sodium bicarbonate). The organic layer was reduced in vacuo to concentrate the sample. A MALDI-TOF MS spectra of the purified product confirmed the purity of the mixture of esterified products and is shown in FIG. 11.

FIG. 11 shows MALDI-TOF MS data for IMS 018 H, the product of octadecanoic acid functionalization of core H (IMS018H).

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Patent 2024
4-dimethylaminopyridine Bicarbonate, Sodium Chromatography Dendrimers Dicyclohexylcarbodiimide Esterification Hydroxyl Radical Methylene Chloride Molar Pressure sodium bisulfate Spectrometry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stearates stearic acid tetrahydrofuran

Example 5

In some embodiments, the disclosed ECP has a formula of

[Figure (not displayed)]

The ECP-5 is synthesized by preparing a naphthalene-containing reaction unit and then polymerizing it with an AcDOT unit. The detail method includes the following steps:

Step 5-1: preparing naphthalene-containing reaction unit (compound 10) by two steps.

[Figure (not displayed)]

To a solution of compound 11 in dichloromethane was added dropwise a solution of bromine in dichloromethane over 15 minutes at −78° C. The reaction mixture is stirred for 2 hours at −78° C. and then warmed gradually to room temperature and stay at room temperature for an additional 2 hours. The excess bromine was quenched by saturated aqueous sodium sulfite solution and stirred for 2 hours at room temperature. After extraction with dichloromethane, the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuum.

[Figure (not displayed)]

Compound 12 is dissolved in DMF under N2, K2CO3 is added to the solution, and the reaction mixture is stirred for 15 minutes, after which 2-ethylexyl bromide is added. The reaction mixture is stirred at 100° C. overnight. The reaction is stopped and cooled down to room temperature. The solvent is removed in vacuum, and the residue is dissolved in diethyl ether. The organic phase is washed with water, and the aqueous phases are extracted with ethyl acetate. The combined organic phases are dried by vacuum.

Step 5-2: polymerization: The polymerization method is similar to that in step 1-1, only differs on the reaction units. The reaction units here are the naphthalene-containing reaction unit (compound 10) and AcDOT (compound 8).

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Patent 2024
brine Bromides Bromine ethyl acetate Ethyl Ether Methylene Chloride naphthalene Polymerization potassium carbonate sodium sulfate sodium sulfite Solvents Vacuum

Example 40

[Figure (not displayed)]

To a solution of compound 101 (5.96 g, 35.9 mmol, 1.0 eq.) in anhydrous dichloromethane (200 mL) was added Ac2O (3.2 mL, 33.9 mmol, 2.0 eq.) and HNO3 (65%-68%, 3.5 mL, 50.79 mmol, 3.0 eq.) at room temperature. The mixture was stirred at room temperature for 30 min, and TLC analysis showed that the reaction was completed. The reaction solution was washed with water (3×200 mL), and the aqueous layer was back-extracted with dichloromethane (3×100 mL). The combined dichloromethane solution was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated and purified by SiO2 column chromatography (5:1 hexanes/EtOAc) to give compound 102 as a yellow solid (4.18 g, 72% yield). 1H NMR (500 MHz, CDCl3) δ 10.49 (s, 1H), 7.89 (s, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.09 (d, J=8.6 Hz, 1H), 4.32 (d, J=8.3 Hz, 1H), 4.12 (dd, J=14.0, 7.0 Hz, 2H), 3.80 (s, 1H), 2.76 (dd, J=13.0, 6.8 Hz, 2H), 2.59 (s, 1H), 1.88 (s, 1H), 1.37 (t, J=8.7 Hz, 9H), 1.25 (dd, J=13.5, 6.9 Hz, 4H), 1.16 (t, J=8.0 Hz, 3H). MS ESI m/z calcd for C19H28NaN2O7 [M+Na]+ 419.19, found 419.17.

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Patent 2024
1H NMR Anabolism brine Chromatography Hexanes Methylene Chloride

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Dichloromethane is a clear, colorless, and volatile liquid commonly used as a laboratory solvent. It has a molecular formula of CH2Cl2 and a molar mass of 84.93 g/mol. Dichloromethane is known for its high solvent power and low boiling point, making it suitable for various laboratory applications where a versatile and efficient solvent is required.
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.
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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Dichloromethane is a colorless, volatile organic compound commonly used as a laboratory solvent. It has the chemical formula CH2Cl2 and is a powerful dissolving agent. Dichloromethane is widely employed in various analytical and research applications due to its excellent solvency properties.
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Ethanol is a clear, colorless liquid chemical compound commonly used in laboratory settings. It is a key component in various scientific applications, serving as a solvent, disinfectant, and fuel source. Ethanol has a molecular formula of C2H6O and a range of industrial and research uses.
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Methanol is a colorless, volatile, and flammable liquid chemical compound. It is commonly used as a solvent, fuel, and feedstock in various industrial processes.
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More about "Methylene Chloride"

Methylene Chloride, also known as Dichloromethane or DCM, is a versatile and widely used organic solvent with a variety of applications in scientific research and industrial processes.
This colorless, volatile liquid has a distinctive sweet odor and is highly miscible with many other organic solvents, making it a valuable tool for extractions, purifications, and other laboratory techniques.
Researchers utilize Methylene Chloride for a broad range of applications, including polymer synthesis, pharmaceutical development, and environmental analysis.
It is commonly used as a solvent for reactions involving Polyvinyl Alcohol (PVA), Methanol, Acetonitrile, DMSO, Ethanol, and Chloroform.
Due to its potential toxicity, it is important to handle Methylene Chloride with care and follow appropriate safety protocols.
PubCompare.ai offers a powerful platform to optimize your Methylene Chloride research, providing access to the best protocols from literature, preprints, and patents, and leveraging AI-driven analysis to identify the most reliable and effetive methods for your experiments.
OtherTerms: Dichloromethane, DCM, Organic Solvent, Polymer Synthesis, Pharmaceutical Development, Environmental Analysis, Polyvinyl Alcohol, Methanol, Acetonitrile, DMSO, Ethanol, Chloroform