75-68-3

Basic information

• Product Name: 1-Chloro-1,1-difluoroethane
• Synonyms: 1,1,1-chlorodifluoroethane;1-Chlor-1,1-difluorethan;1-chloro-1,1-difluoro;1-chloro-1,1-difluoro-ethan;alpha-Chloroethylidene fluoride;alpha-chloroethylidenefluoride;CFC 142b;cfc142b
• CAS NO: 75-68-3
• Molecular Formula: C₂H₃ClF₂
• Molecular Weight: 100.5
• EINECS: 200-891-8
• Product Categories: Industrial/Fine Chemicals;HCFC;refrigerants;Organics;Chemical Synthesis;Specialty Gases;Synthetic Reagents
• Mol File: 75-68-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: −131 °C(lit.)
• Boiling Point: −10 °C(lit.)
• Appearance: colourless gas
• Density: 1.108
• Vapor Density: 3.49 (vs air)
• Vapor Pressure: 2196 mm Hg ( 21 °C)
• Refractive Index: 1.3672 (estimate)
• Explosive Limit: 18%
• Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents, metals - use brass regulators, steel cylinders for storage.
• CAS DataBase Reference: 1-Chloro-1,1-difluoroethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-1,1-difluoroethane(75-68-3)
• EPA Substance Registry System: 1-Chloro-1,1-difluoroethane(75-68-3)

Safety Data

• Hazard Codes: F+,N,Xi
• Statements: 12-59
• Safety Statements: 38-59
• RIDADR: UN 2517 2.1
• WGK Germany: 1
• RTECS: KH7650000
• HazardClass: 2.1
• Hazardous Substances Data: 75-68-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 75-68-3 differently. You can refer to the following data:
1. colourless gas
2. Chlorodifluoroethane is a flammable, colorless gas. Nearly odorless.
3. Chlorodifluoroethane is a liquefied gas and exists as a liquid at room temperature when contained under its own vapor pressure, or as a gas when exposed to room temperature and atmospheric pressure. The liquid is practically odorless and colorless. Chlorodifluoroethane is noncorrosive and nonirritating.

Uses

Please view www.aldrich.com/epaods regarding the EPA′s request for application information of Ozone Depleting Substances

Production Methods

Chlorodifluoroethane is prepared by the chlorination of difluoroethane in the presence of a suitable catalyst; hydrochloric acid is also formed. The chlorodifluoroethane is purified to remove all traces of water and hydrochloric acid, as well as traces of the starting and intermediate materials.

General Description

A colorless, odorless gas shipped as a liquid under own vapor pressure. Contact with the unconfined liquid may cause frostbite by evaporative cooling. Easily ignited. Vapors heavier than air. A leak may be either liquid or vapor. May asphyxiate by the displacement of air. Prolonged exposure to fire or intense heat may cause the containers to violently rupture and rocket.

Air & Water Reactions

Highly flammable.

Reactivity Profile

1-Chloro-1,1-difluoroethane is chemically inert in many situations, but can react violently with strong reducing agents such as the very active metals and the active metals. Can react with strong oxidizing agents or weaker oxidizing agents under extremes of temperature.

Hazard

Flammable gas. Explosive limits in air 9.0– 14.8%.

Pharmaceutical Applications

Chlorodifluoroethane is a hydrochlorofluorocarbon (HCFC) aerosol propellant previously used in topical pharmaceutical formula- tions. However, it is no longer permitted for use in pharmaceutical formulations because of its harmful effects on the environment. It was also generally used in conjunction with difluoroethane to form a propellant blend with a specific gravity of 1. Chlorodifluoroethane was also used in combination with chlorodifluoromethane and hydrocarbon propellants. Chlorodifluoroethane may be used as a vehicle for dispersions and emulsions.

Safety Profile

Very ddly toxic by inhalation. Mutation data reported. A very dangerous fire hazard when exposed to heat, flame, or oxidzing materials. To fight fire, stop flow of gas. Can react vigorously with oxidizing materials. When heated to decomposition it emits toxic fumes of Fand Cl-.

Safety

Chlorodifluoroethane is no longer permitted for use as an aerosol propellant in topical pharmaceutical formulations. It is generally regarded as an essentially nontoxic and nonirritant material. Deliberate inhalation of excessive quantities of chlorofluorocarbon propellant may result in death, and the following ‘warning’ statements must appear on the label of all aerosols: WARNING: Avoid inhalation. Keep away from eyes or other mucous membranes. (Aerosols designed specifically for oral and nasal inhalation need not contain this statement.) WARNING: Do not inhale directly; deliberate inhalation of contents can cause death. or WARNING: Use only as directed; intentional misuse by deliberately concentrating and inhaling the contents can be harmful or fatal. Additionally, the label should contain the following information: WARNING: Contents under pressure. Do not puncture or incinerate container. Do not expose to heat or store at room temperature above 120°F (498℃). Keep out of the reach of children. In the USA, the Environmental Protection Agency (EPA) additionally requires the following information on all aerosols containing chlorofluorocarbons as the propellant: WARNING: Contains a chlorofluorocarbon that may harm the public health and environment by reducing ozone in the upper atmosphere.

Potential Exposure

Chlorodifluoroethane is used in refrigerants; solvents; as a propellant in aerosol sprays; and as an intermediate in the production of highly specialized fluoropolymers.

storage

Chlorodifluoroethane is a nonreactive and stable material. The liquefied gas is stable when used as a propellant and should be stored in a metal cylinder in a cool, dry place.

Shipping

UN25171-Chloro-1,1-difluoroethane or Refrigerant gas R-142b, Hazard Class: 2.1; Labels: 2.1- Flammable gas. Cylinders must be transported in a secure upright position, in a well-ventilated truck. Protect cylinder and labels from physical damage. The owner of the compressed gas cylinder is the only entity allowed by federal law (49CFR) to transport and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express written permission of the owner.

Incompatibilities

Different sources of media describe the Incompatibilities of 75-68-3 differently. You can refer to the following data:
1. Compatible with the usual ingredients used in the formulation of pharmaceutical aerosols. Chlorodifluoroethane can react vigorously with oxidizing materials.
2. The liquefied gas poured into water may be violently explosive. This is due to the phase transition from superheated liquid to vapor. Chlorodifluoroethane is generally chemically inert; however, it can react violently with strong reducing agents such as hydrides and highly active metals. It will react with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides strong oxidizing agents. It can also react with weak oxidizers under extreme temperatures. Decomposes in heat to form phosgene; HF and hydrogen chloride

InChI:InChI=1/C2H3ClF2/c1-2(3,4)5/h1H3

Synthetic route

1,1-Dichloroethylene (75-35-4) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6)

Conditions	Yield
With hydrogen fluoride; SbCl5 on Carbon at 100℃; under 760.051 Torr; for 0.00277778h;	A 80% B n/a C n/a

1,1-difluoroethane (75-37-6) → 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
With chlorine In gas at 21.9℃; under 760 Torr; for 0.000666667h; Irradiation; time history of ignition;
bei der Photochlorierung;
beim Chlorieren im Sonnenlicht;

1,1-difluoroethane (75-37-6) → 1-Chloro-1,1-difluoroethane (75-68-3) + 1,2-dichloro-1,1-difluoroethane (1649-08-7)

Conditions	Yield
beim Chlorieren im Sonennlicht;

1,1,1-trichloroethane (71-55-6) → 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
With hydrogen fluoride at 200℃; under 175051 Torr;
With antimony dichloride trifluoride; antimony(III) fluoride

1,1-Dichloroethylene (75-35-4) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
With hydrogen fluoride; diphenylamine at 180 - 195℃; unter Druck;

1,1-Dichloroethylene (75-35-4) → 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
With hydrogen fluoride; diphenylamine at 140℃; im Autoklaven;

HCFC-141b (1717-00-6) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + 1-chloro-1-fluoroethane (2317-91-1) + 1,1-Dichloroethylene (75-35-4) + acetic acid (64-19-7)

Conditions	Yield
fluorinated γ-alumina at 300℃; Product distribution; other temperatures; also with HCl or HF as reagents;

1-chloro-1-fluoroethane (2317-91-1) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + Vinylidene fluoride (75-38-7) + acetic acid (64-19-7)

Conditions	Yield
fluorinated γ-alumina at 300℃; Product distribution; other temperatures;

1-chloro-1-fluoroethane (2317-91-1) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + Vinylidene fluoride (75-38-7) + 1,1-Dichloroethylene (75-35-4) + acetic acid (64-19-7)

Conditions	Yield
With hydrogenchloride; fluorinated γ-alumina at 300℃; Product distribution; other temperatures;

HCFC-141b (1717-00-6) → 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
With hydrogen fluoride Heating;

1,1,1-trichloroethane (71-55-6) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6) + chlorotrifluoromethane (75-72-9) + 1,1-Dichloroethylene (75-35-4)

Conditions	Yield
With fluorinated indium(III) oxide Product distribution; Ambient temperature; further reagent: fluorinated gallium(III) oxide;

1,1-Dichloroethylene (75-35-4) → 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6) + chlorotrifluoromethane (75-72-9)

Conditions	Yield
With fluorinated gallium(III) oxide Product distribution; Ambient temperature;

1,1-dichloro-1-nitroethane (594-72-9) + hydrogen fluoride (7664-39-3) + antimony dichloride trifluoroide → 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
at 115℃;

1,1-Dichloroethylene (75-35-4) + diphenylamine (122-39-4) + HF (6 mol) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3)

Conditions	Yield
at 140 - 210℃; unter Druck;entstehen je nach der Reaktionsdauer wechselnde Mengen;

1,1,1-trichloroethane (71-55-6) + hydrogen fluoride (7664-39-3) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6)

1,1,1-trichloroethane (71-55-6) + hydrogen fluoride (7664-39-3) + antimonypentachloride (7647-18-9) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6)

1,1,1-trichloroethane (71-55-6) + antimony(III) fluoride (7783-56-4) → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6)

1,1,1-trichloroethane (71-55-6) + chlorinated SbF3 → 2,2,2-trifluoroethanol (420-46-2) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6)

1,1-Dichloroethylene (75-35-4) + HF (4 mol) → 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6) + 1,1,1-trichloroethane (71-55-6)

Conditions	Yield
at 65℃; unter Druck;

dichloromethane (75-09-2) → pentaerythrityl tetrachloride (3228-99-7) + Isobutane (75-28-5) + 1-Chloro-1,1-difluoroethane (75-68-3) + HCFC-141b (1717-00-6) + 1,2-dichloro-1,1-difluoroethane (1649-08-7) + pentachloroethane (76-01-7) + (ClCH2)3CCl

Conditions	Yield
With fluorinated gallium(III) oxide Product distribution; Mechanism; Ambient temperature;

1-Chloro-1,1-difluoroethane (75-68-3) → 2,2,2-trifluoroethanol (420-46-2)

Conditions	Yield
at 200℃; for 2h; Conversion of starting material;	100%
With hydrogen fluoride; chlorine; antimonypentachloride at 15 - 20℃; under 6750.68 Torr;	97%
With hydrogen fluoride; chromium(III) water-soluble salt; graphite; magnesium oxide; water; mixture of, dried at 150 C, hydrofluorinated at 200-350 C at 200℃; under 7500.75 Torr; Continious process;
With neodymium(III) oxide; hydrogen fluoride; antimony pentafluoride at 10℃; under 2250.23 Torr; Reagent/catalyst; Large scale;

1-Chloro-1,1-difluoroethane (75-68-3) + 5-Bromo-1-indanone (34598-49-7) → 5-(1,1-difluoroethyl)-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	83%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-bromoohenyl methyl sulfone (3466-32-8) → 1-(1,1-difluoroethyl)-4-(methylsulfonyl)benzene

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	80%

1-Chloro-1,1-difluoroethane (75-68-3) + para-bromoacetophenone (99-90-1) → 1-(4-(1,1-difluoroethyl)phenyl)ethan-1-one

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	78%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-iodo-biphenyl (1591-31-7) → 4-(1,1-difluoroethyl)-1,1’-biphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	74%

1-Chloro-1,1-difluoroethane (75-68-3) + (4-bromophenyl)(phenyl)methanone (90-90-4) → (4-(1,1-difluoroethyl)phenyl)(phenyl)methanone

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	73%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-(1,1-difluoroethyl)-1,1’-biphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	72%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-biphenylboronic acid (5122-94-1) → 4-(1,1-difluoroethyl)-1,1’-biphenyl

Conditions	Yield
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	70%
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling;	70%

4-(carbazol-9-yl)phenylboronic acid (419536-33-7) + 1-Chloro-1,1-difluoroethane (75-68-3) → 9-(4-(1,1-difluoroethyl)phenyl)-9H-carbazole

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	62%
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	59%

1-Chloro-1,1-difluoroethane (75-68-3) + fenofibrate (49562-28-9) → 2-(4-(4-(1,1-difluoroethyl)benzoyl)phenoxy)-2-methylpropionoic acid isopropyl ester

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	62%

1-Chloro-1,1-difluoroethane (75-68-3) + (4'-ethyl[1,1'-biphenyl]-4-yl)boronic acid (153035-62-2) → 4-(1,1-difluoroethyl)-4'-ethyl-1,1'-biphenyl

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	61%
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	58%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-(4-bromophenyl)-4-oxobutanoic acid ethyl ester (30913-87-2) → 4-(4-(1,1-difluoroethyl)phenyl)-4-oxobutanoic acid ethyl ester

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	61%

1-Chloro-1,1-difluoroethane (75-68-3) + 1-bromo-4-(4'-ethylphenyl)benzene (58743-79-6) → 4-(1,1-difluoroethyl)-4'-ethyl-1,1'-biphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	58%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-bromo-4'-pentyloxybiphenyl (63619-51-2) → 4-(1,1-difluoroethyl)-4'-(pentyloxy)-1,1'-biphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	56%

4-(naphthalene-2-yl)phenylboronic acid pinacol ester (918655-03-5) + 1-Chloro-1,1-difluoroethane (75-68-3) → 2-(4-(1,1-difluoroethyl)phenyl)naphthalene

Conditions	Yield
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	55%
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	55%

1-Chloro-1,1-difluoroethane (75-68-3) + 3-Biphenylboronic acid (5122-95-2) → 3-(1,1-difluoroethyl)-1,1'-biphenyl

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	54%
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	49%

1-Chloro-1,1-difluoroethane (75-68-3) + N-(4-bromophenyl)carbazole (57102-42-8) → 9-(4-(1,1-difluoroethyl)phenyl)-9H-carbazole

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	54%

4-(4-n-pentyloxyphenyl)phenylboronic acid (158937-25-8) + 1-Chloro-1,1-difluoroethane (75-68-3) → 4-(1,1-difluoroethyl)-4'-(pentyloxy)-1,1'-biphenyl

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	51%
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	48%

1-Chloro-1,1-difluoroethane (75-68-3) + 4'-biphenyl chloride (2051-62-9) → 4-(1,1-difluoroethyl)-1,1’-biphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	49%

6-bromo-isoquinoline (34784-05-9) + 1-Chloro-1,1-difluoroethane (75-68-3) → 6-(1,1-difluoroethyl)isoquinoline

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	46%

6-bromoquinoline (5332-25-2) + 1-Chloro-1,1-difluoroethane (75-68-3) → 6-(1,1-difluoroethyl)quinoline

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	44%

2-bromodibenzothiophene (22439-61-8) + 1-Chloro-1,1-difluoroethane (75-68-3) → 2-(1,1-difluoroethyl)dibenzo[b,d]thiophene

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	43%

1-Chloro-1,1-difluoroethane (75-68-3) + 3-bromobiphenyl (2113-57-7) → 3-(1,1-difluoroethyl)-1,1'-biphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	40%

1-Chloro-1,1-difluoroethane (75-68-3) + 3,5-diphenylphenylboronic acid (128388-54-5) → 5'-(1,1-difluoroethyl)-1,1':3',1"-terphenyl

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	39%
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	34%

1-Chloro-1,1-difluoroethane (75-68-3) + 1-bromo-3,5-diphenylbenzene (103068-20-8) → 5'-(1,1-difluoroethyl)-1,1':3',1"-terphenyl

Conditions	Yield
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc In dimethyl sulfoxide at 110℃; for 10h; Schlenk technique;	39%

1-Chloro-1,1-difluoroethane (75-68-3) + 4-(4-morpholinyl)phenylboronic acid (186498-02-2) → 4-(4-(1,1-difluoroethyl)phenyl)morpholine

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	28%
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	22%

1-Chloro-1,1-difluoroethane (75-68-3) + (3-(naphthalen-1-yl)phenyl)boronic acid (881913-20-8) → 1-(3-(1,1-difluoroethyl)phenyl)naphthalene

Conditions	Yield
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	26%

(4-(naphthalen-1-yl)phenyl)boronic acid (870774-25-7) + 1-Chloro-1,1-difluoroethane (75-68-3) → C18H14F2

Conditions	Yield
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	26%

1-Chloro-1,1-difluoroethane (75-68-3) + (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) → 2-(4-(1,1-difluoroethyl)phenyl)-1-phenyl-1H-benzo[d]imidazole

Conditions	Yield
With dmap; bis(triphenylphosphine)nickel(II) chloride; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Schlenk technique; Inert atmosphere;	16%
With dmap; trans-[Ni(Cl)2(PPh3)2]; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h; Suzuki-Miyaura Coupling;	16%

Upstream product

• 75-37-6 1,1-difluoroethane 
• 594-72-9 1,1-dichloro-1-nitroethane 
• 71-55-6 1,1,1-trichloroethane 
• 75-35-4 1,1-Dichloroethylene 
• 1717-00-6 HCFC-141b 
• 7664-39-3 hydrogen fluoride 
• 122-39-4 diphenylamine 
• 7647-18-9 antimonypentachloride 
• 7783-56-4 antimony(III) fluoride 
• 75-09-2 dichloromethane 
• 3518-66-9 1-chloro-ethanesulfonyl chloride 
• 75-38-7 Vinylidene fluoride 
• 2317-91-1 1-chloro-1-fluoroethane 
• 2834-23-3 chlorodifluoroacetic anhydride 

Downstream Products

• 25352-91-4 (1,1-difluoro-ethyl)-(2,2,2-trifluoro-ethyl)-ether 
• 76-11-9 1,1-difluorotetrachloroethane 
• 1649-08-7 1,2-dichloro-1,1-difluoroethane 
• 75-38-7 Vinylidene fluoride 
• 354-21-2 1,1,2-trichloro-2,2-difluoroethane 
• 420-46-2 2,2,2-trifluoroethanol 
• 2317-91-1 1-chloro-1-fluoroethane 
• 75-71-8 Dichlorodifluoromethane 
• 67-72-1 hexachloroethane 
• 79-35-6 1,1'-dichloro-2,2'-difluoroethene 
• 55453-81-1 1,1-Dichlorethanphosphonsaeuredichlorid 
• 21510-59-8 trichloromethylphosphonyl dichloride 
• 75-35-4 1,1-Dichloroethylene 
• 64-19-7 acetic acid 

Relevant articles and documents

Estimation of atmospheric lifetimes of hydrofluorocarbons, hydrofluoroethers, and olefins by chlorine photolysis using gas-phase NMR spectroscopy

An empirical correlation has been derived between accepted atmospheric lifetimes of a set of hydrofluorocarbons and hydrofluoroethers and relative rates of reaction with photolyzed chlorine in excess at ambient temperature. These kinetic systems were studied by nuclear magnetic resonance (NMR) spectroscopy in the gas phase, marking the first application of NMR spectroscopy to this field. The square of the Pearson coefficient R for the linear correlation between observed reaction rates and accepted atmospheric lifetimes was 0.87 for compounds of lifetime less than 20 years. The method was extended to the study of ethene and propene; the rate of reaction of propene was found to be 1.25 times that of ethene at 23°C. The chief advantage of this method is its simplicity and reliance only on common tools and techniques of an industrial chemical laboratory.

γ-Alumina-supported boron trifluoride: Catalysis, radiotracer studies and computations

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Catalyst and method for producing 1,1-difluoroethane

The present invention relates to a catalyst for producing 1,1-difluoroethane (HCFC-152a) and producing method thereof. More particularly, it is to provide the catalyst prepared by impregnating palladium on the active carbon pretreated with an aqueous hydrogen fluoride solution and an aqueous hydrogen chloride solution in series and its use in the production of 1,1-difluoroethane (HCFC-142b) by dehydrochlorinating 1,1-difluoro-1-chloroethane at 240-300° C. in the supplying molar ratio of 2-6 (H2/HCFC-142b) with maximizing a selectivity toward the product of HCFC-152a.