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270997 Sigma-Aldrich

Dichloromethane

anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

Synonym: DCM, Methylene chloride

  • CAS Number 75-09-2

  • Empirical Formula (Hill Notation) CH2Cl2

  • Molecular Weight 84.93

  •  Beilstein/REAXYS Number 1730800

  •  EC Number 200-838-9

  •  MDL number MFCD00000881

  •  PubChem Substance ID 57648216

  •  NACRES NA.21

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Properties

Related Categories Anhydrous, Anhydrous Solvents, Dichloromethane (Methylene chloride), Returnable Containers, Solvent by Type,
Quality Level   200
grade   anhydrous
vapor density   2.9 (vs air)
vapor pressure   24.45 psi ( 55 °C)
  6.83 psi ( 20 °C)
  6.86 psi ( 20 °C)
assay   ≥99.8%
form   liquid
autoignition temp.   1223 °F
contains   40-150 ppm amylene as stabilizer
expl. lim.   22 %
application(s)   gas chromatography (GC): suitable
impurities   ≤0.001% water
  ≤0.005% water (100 mL pkg)
evapn. residue   <0.0005%
refractive index   n20/D 1.424 (lit.)
bp   39.8-40 °C (lit.)
mp   −97 °C (lit.)
density   1.325 g/mL at 25 °C (lit.)
SMILES string   ClCCl
InChI   1S/CH2Cl2/c2-1-3/h1H2
InChI key   YMWUJEATGCHHMB-UHFFFAOYSA-N

Description

General description

Dichloromethane has been tested as a solvent medium for the dipyridine-chromium(VI) oxide. Solubility was reported to be 12.5g/100ml. Role of quantity of TiO2 loading on activated carbon support employed in the photodecomposition of dichloromethane has been investigated.

Dichloromethane is a chlorinated organic solvent that is susceptible to degradation with time. This can be suppressed by adding amylene as a stabilizer.

Application

Dichloromethane has been used for the quantification of herbivore (gypsy moth) induced blueberry volatiles by gas chromatography (GC).

Dichloromethane may be used as a solvent for the oxidation of primary and secondary alcohols using dipyridine-chromium(VI) oxide. Lithium perchlorate suspended in DCM is an effective medium for Mukaiyama aldol reactions of aldehydes with silyl ketene acetal. DCM may also be used as solvent for the synthesis of 2-bromo-6-lithiopyridine from 2,6-dibromopyridine via lithium-bromine exchange reaction.

Packaging

1, 6×1, 2, 4×2 L in Sure/Seal™

18 L in Pure-Pac™ 1

20 L in Pure-Pac™ 2

View returnable container options.

100, 12×100 mL in Sure/Seal™

200 L in Pure-Pac™ 1

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Target organs 
Central nervous system
RIDADR 
UN 1593 6.1 / PGIII
WGK Germany 
WGK 2
RTECS 
PA8050000
Flash Point(F) 
does not flash
Flash Point(C) 
does not flash

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Chlorides with K4[Fe(CN)6]

The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity (>97%) at the ?-carbon of the allylboron reagent in the pre...
Keywords: Chromatography, Coupling reactions, Cross couplings, Flash chromatography

A new palladium catalyst system for the cyanation of aryl chlorides with K4[Fe(CN)6]

Potassium 1-(alkoxy/acyloxy)alkyltrifluoroborates have been synthesized through a copper-catalyzed?diboration of aldehydes and subsequent conversion of the?resulting potassium 1-(hydroxy)alkyltrifluo...
Keywords: Catalysis, Chromatography, Column chromatography, Cross couplings, Eliminations

Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of N-Arylbenzimidazoles

A wide-ranging study�of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme). This method is highly versatile (a single procedure was used for all substrates, includi...
Keywords: Chromatography, Column chromatography, Suzuki reactions

Copper-Free Sonogashira Coupling of Cyclopropyl Iodides with Terminal Alkynes

An efficient palladium-catalyzed cyanation of aryl chlorides is established. In the presence of a highly effective Pd/CM-phos catalyst, cyanation of aryl chlorides proceeds at 71 �C in general, which...
Keywords: Catalysis, Chromatography, Column chromatography, Gas chromatography, Ligands, Nuclear magnetic resonance spectroscopy

Cross-Coupling of Mesylated Phenol Derivatives with Potassium Cyclopropyltrifluoroborate

A robust and efficient protocol for the introduction of the dioxolanylethyl moiety onto various aryl and heteroaryl halides has been developed, providing cross-coupling yields up to 93%. Copper-catal...
Keywords: Catalysis, Chromatography, Cross couplings, Flash chromatography, Purification

KitAlysis High-Throughput Metal Scavenger Reaction Screening Kit

The screening sets come pre-loaded with 12 scavengers / resins (10mg or 50mg) in each vial according to the following design.
Keywords: Metal scavengers

Palladium-Catalyzed Amination of Unprotected Five-Membered Heterocyclic Bromides

An efficient method for the palladium-catalyzed amination of unprotected bromoimidazoles and bromopyrazoles is presented. The transformation is facilitated by the use of our newly developed Pd precat...
Keywords: Aminations, Catalysis, Chromatography, Column chromatography, Ligands, transformation

Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases

We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C-N cross-coupling reactions to date. Often low ca...
Keywords: Arylations, Catalysis, Coupling reactions, Cross couplings, Ligands, Pharmaceutical

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

Rational and Predictable Chemoselective Synthesis of Oligoamines via Buchwald-Hartwig Amination of (Hetero)Aryl Chlorides Employing Mor-DalPhos

We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C-N cross-coupling reactions to date. Often low ca...
Keywords: Catalysis, Coupling reactions, Cross couplings, Ligands, Pharmaceutical

Reversed-Polarity Synthesis of Diaryl Ketones through Palladium- Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes

The title reaction leads to satisfactory yields of dihydrodibenzoazepines�1?a�from norbornene. The dibenzoazepines�2�can also be accessed from compounds of type�1?b�when norbornadiene is used as a re...
Keywords: Chromatography, Column chromatography

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Peer-Reviewed Papers
15

References

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