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75-09-2

Basic Information
CAS No.: 75-09-2
Name: Dichloromethane
Article Data: 291
Cas Database
Molecular Structure:
Molecular Structure of 75-09-2 (Dichloromethane)
Formula: CH2Cl2
Molecular Weight: 84.9329
Synonyms: Dichloromethane [UN1593] [Poison];methane, dichloro-;Methylene chloride (NF);Aerothene MM;Methylene Chloride;
EINECS: 200-838-9
Density: 1.252 g/cm3
Melting Point: -97 °C
Boiling Point: 39.6 °C at 760 mmHg
Flash Point: 39-40 °C
Solubility: Water solubility: 20 g/L (20 °C)
Appearance: colorless liquid
Hazard Symbols: HarmfulXn,ToxicT,FlammableF
Risk Codes: 40-39/23/24/25-23/24/25-11
Safety: 23-24/25-36/37-45-16-7
Transport Information: UN 1593 6.1/PG 3
PSA: 0.00000
LogP: 1.42150
Synthetic route
84101-40-6

tris(cyclopentadienyl)hafnium hydride

A

75-09-2

dichloromethane

B

((C5H5)2HfCl)2O*C4H8O

Conditions
ConditionsYield
With chloroform In toluene under Ar; stirred at 20°C for 5 h; stored overnight at 0-5°C; evaporated, extracted (THF); elem. anal.;A 57%
B 88%
540-59-0

1,2-Dichloroethylene

A

75-09-2

dichloromethane

B

2504-64-5

1,2-bis(trichlorosilyl)ethane

C

692-52-4

1,2-bis(trichlorosilyl)ethene

D

4142-85-2

1,1,1,3,3,3-hexachloro-1,3-disilapropane

Conditions
ConditionsYield
With hexachlorodisilane at 550℃; for 0.00833333h;A n/a
B n/a
C 83%
D n/a
2943-70-6

1,3-bis-dichloromethyl-1,1,3,3-tetramethyl-disiloxane

75-09-2

dichloromethane

Conditions
ConditionsYield
With KOH In water; butan-1-ol heating of (CH3)2(CHCl2)SiOSi(CH3)2(CHCl2) and 10% KOH in n-butanol/H2O at 45°C under reduced pressure;;78%
With KOH In potassium hydroxide aq. KOH; (CH3)2(CHCl2)SiOSi(CH3)2(CHCl2) and 40% aq. KOH;;
With potassium hydroxide In potassium hydroxide (CH3)2(CHCl2)SiOSi(CH3)2(CHCl2) and 40% aq. KOH;;

tris(cyclopentadienyl)zirconiumhydride

A

75-09-2

dichloromethane

B

((C5H5)2ZrCl)2O*2C4H8O

Conditions
ConditionsYield
With chloroform In toluene under Ar; excess of CHCl3 added to suspension of Cp3ZrH in PhMe; stirred at about 20°C for 5 h; stored overnight at 0-5°C; evaporated, extracted (THF), filtered; filtrate evapd.; elem. anal.;A 70%
B 42%
34557-54-5

methane

A

75-09-2

dichloromethane

B

124-63-0

methanesulfonyl chloride

Conditions
ConditionsYield
With sulfur dioxide; chlorine at 25℃; under 2250.23 Torr; for 1h; Concentration; Wavelength; Irradiation;A n/a
B 69%

Schwartz's reagent

A

1291-32-3

zirconocene dichloride

B

75-09-2

dichloromethane

Conditions
ConditionsYield
With chloroform In toluene under Ar; elem. anal.;A 67%
B 43%
34557-54-5

methane

A

56-23-5

tetrachloromethane

B

74-87-3

methylene chloride

C

75-09-2

dichloromethane

D

67-66-3

chloroform

E

124-63-0

methanesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; sulfur dioxide; chlorine at 63 - 67℃; under 6750.68 Torr; Photolysis;A n/a
B n/a
C n/a
D n/a
E 55%
34557-54-5

methane

A

75-09-2

dichloromethane

B

67-66-3

chloroform

C

124-63-0

methanesulfonyl chloride

Conditions
ConditionsYield
With sulfur dioxide; chlorine at 65℃; under 2250.23 Torr; for 1h; Temperature; Irradiation;A n/a
B n/a
C 54.9%
56-23-5

tetrachloromethane

A

75-09-2

dichloromethane

B

67-66-3

chloroform

Conditions
ConditionsYield
With tetra-n-butylphosphonium formate In water at -20 - 22℃; for 1.33333h; Reagent/catalyst;A 26%
B 52%
With [RuCl(1-butyl-3-methyl-imidazole)(1,3,5-triaza-7-phosphatricyclo[3.3.1.1]3,7decane)(η6-p-cymene)]Cl; hydrogen; sodium formate In water at 80℃; under 7500.75 Torr; for 2h; Schlenk technique; Sealed tube;A 12.9%
B 29%
With isopropyl alcohol; dimanganese decacarbonyl at 120℃; Product distribution; catalyst and temperature effects;
75-11-6

diiodomethane

A

75-09-2

dichloromethane

B

593-71-5

Chloroiodomethane

Conditions
ConditionsYield
With iodine trichloride Product distribution; further iodoalkanes;A 34%
B 50%
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Specification

Basic Information of Dichloromethane:
Dichloromethane (CAS NO.75-09-2) is a colorless liquid with a sweet, penetrating-like ether. If exposed to high temperatures , it may emit toxic chloride fumes. Vapors are narcotic in high concentrations. Used as a solvent and paint remover. It is somewhat soluble in water, subjected to slow hydrolysis which is accelerated by light. It has some kinds of uses. Solvent is the most important use of methylene chloride. Dichloromethane with the dissolving ability, low boiling point and relatively low toxicity, so it has be made as the highest frequency use in organic synthesis. It can be used as extraction solvent, mainly as the extraction of caffeine in coffee beans, besides it can be used as hops, spices oil-resin extraction solvents, pigment thinner, organic synthesis. As a solvent for resins and plastics industry is widely used in pharmaceutical, plastics and film industries.

Physical properties about Dichloromethane are:
 (1)ACD/LogP: 1.405; (2)ACD/LogD (pH 5.5): 1.41; (3)ACD/LogD (pH 7.4): 1.41; (4)ACD/BCF (pH 5.5): 6.88; (5)ACD/BCF (pH 7.4): 6.88; (6)ACD/KOC (pH 5.5): 138.38; (7)ACD/KOC (pH 7.4): 138.38; (8)Index of Refraction: 1.398; (9)Molar Refractivity: 16.38 cm3; (10)Molar Volume: 67.812 cm3; (11)Polarizability: 6.494 10-24cm3; (12)Surface Tension: 23.1989994049072 dyne/cm; (13)Density: 1.252 g/cm3; (14)Flash Point: -14.127 °C; (15)Enthalpy of Vaporization: 28.06 kJ/mol; (16)Boiling Point: 39.639 °C at 760 mmHg; (17)Vapour Pressure: 448.006011962891 mmHg at 25°C

Preparation of Dichloromethane:
Dichloromethane is produced by treating either methyl chloride or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and methyl chloride undergo a series of reactions producing progressively more chlorinated products.
CH4 + Cl2 → CH3Cl + HCl
CH3Cl + Cl2 → CH2Cl2 + HCl
CH2Cl2 + Cl2 → CHCl3 + HCl
CHCl3 + Cl2 → CCl4 + HCl
The output of these processes is a mixture of methyl chloride, dichloromethane, chloroform, and carbon tetrachloride. These compounds are separated by distillation.

Uses of Dichloromethane: 
DCM's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes. Concerns about its health effects have led to a search for alternatives in many of these applications. It is widely used as a paint stripper and a degreaser. In the food industry, it has been used to decaffeinate coffee and tea as well as to prepare extracts of hops and other flavorings.[2] Its volatility has led to its use as an aerosol spray propellant and as a blowing agent for polyurethane foams.

You can still convert the following datas into molecular structure:
(1)InChI=1S/CH2Cl2/c2-1-3/h1H2;
(2)InChIKey=YMWUJEATGCHHMB-UHFFFAOYSA-N;
(3)Smiles=C(Cl)Cl;

The toxicity data of Dichloromethane is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 1329ug/kg/31D (1.329mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED American Journal of Gastroenterology. Vol. 83, Pg. 576, 1988.
 
man TDLo oral 21mg/kg/26W-I (21mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Postgraduate Medical Journal. Vol. 63, Pg. 311, 1987.
mouse LD50 intraperitoneal 13300mg/kg (13300mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 811, 1980.
mouse LD50 intravenous > 18mg/kg (18mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 811, 1980.
mouse LD50 oral 2gm/kg (2000mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 35, Pg. 77, 1983.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 235, 1982.
rat LD50 intraperitoneal 14200mg/kg (14200mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 811, 1980.
rat LD50 oral > 15gm/kg (15000mg/kg)   Drugs in Japan Vol. 6, Pg. 235, 1982.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 235, 1982.