598-77-6

Basic information

• Product Name: 1,1,2-TRICHLOROPROPANE
• Synonyms: (R,S)-1,1,2-trichloropropane;(R,S)-1,1,2-trichloro-propane;(R,S)-propane,1,1,2-trichloro-;1,1,2-trichloro-propan;Propane, 1,1,2-trichloro-;Propane,1,1,2-trichloro-;2-CHLOROPROPYLIDENE CHLORIDE;1,1,2-TRICHLOROPROPANE
• CAS NO: 598-77-6
• Molecular Formula: C₃H₅Cl₃
• Molecular Weight: 147.43
• EINECS: 209-951-8
• Mol File: 598-77-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: -36.84°C (estimate)
• Boiling Point: 133 °C
• Flash Point: 44.3°C
• Appearance: /
• Density: 1.35
• Vapor Pressure: 14.8mmHg at 25°C
• Refractive Index: 1.4670-1.4700
• CAS DataBase Reference: 1,1,2-TRICHLOROPROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2-TRICHLOROPROPANE(598-77-6)
• EPA Substance Registry System: 1,1,2-TRICHLOROPROPANE(598-77-6)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1993
• RTECS: TZ8925000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 598-77-6(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic by ingestion.Mildly toxic by inhalation and skin contact. A skin andsevere eye irritant. When heated to decomposition it emitstoxic fumes of Clí.

InChI:InChI=1/C3H5Cl3/c1-2(4)3(5)6/h2-3H,1H3

Synthetic route

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
With aluminum (III) chloride; sulfuryl dichloride at 60℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere;	33%
With chlorine im Sonnenlichte;
With antimonypentachloride

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,2,2-trichloropropane (3175-23-3) + 1,1,2,2-tetrachloropropane (13116-60-4) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4) + 1,2,2,3-tetrachloropropane (13116-53-5) + 1,1,2,3-tetrachloropropane (18495-30-2)

Conditions	Yield
With sulfuryl dichloride at 55 - 60℃;	A 18% B 13.2% C 8.9% D 20.3% E 10.1% F 15.6%
With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) at 55 - 60℃;	A 19.7% B 17.8% C 6.5% D 14.8% E 11.8% F 15.6%
With sulfuryl dichloride at 55 - 60℃; Product distribution / selectivity;
With chlorine; dimethyl 2,2'-azobis(isobutyrate) In tetrachloromethane at 70℃; under 8517.48 Torr; for 32h; Product distribution / selectivity; Inert atmosphere;

propene (187737-37-7) → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
With chlorine at 52 - 65℃; im Dunkeln;

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
With Iodine monochloride at 160℃;
With iron(III) chloride; chlorine at 100℃; under 7224.57 Torr; for 5h; Product distribution / selectivity; Inert atmosphere;
With aluminum (III) chloride; sulfuryl dichloride; iodine at 55 - 60℃; Reagent/catalyst;
With aluminum (III) chloride; sulfuryl dichloride at 55 - 60℃; for 0.5h;
With aluminum (III) chloride; chlorine In tetrachloromethane at 60℃; for 1h; Inert atmosphere; Overall yield = 22 %;

1-Chloropropane (540-54-5) → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
With chlorine
With antimonypentachloride

1,1-dichloropropane (78-99-9) → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
With chlorine im Sonnenlichte;
With chlorine
With antimonypentachloride

1,2-Dichloropropane (26198-63-0, 78-87-5) + antimonypentachloride (7647-18-9) → 1,1,2-trichloropropane (598-77-6)

chloroform (67-66-3) + 1,1-dichloropropane (78-99-9) + antimonypentachloride (7647-18-9) → 1,1,2-trichloropropane (598-77-6)

1,2-Dichloropropane (26198-63-0, 78-87-5) + chlorine (7782-50-5) + iron → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
bei Siedetemperatur; 1.2-dichloro-propane;

aluminium trichloride (7446-70-0) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + chlorine (7782-50-5) → 1,2,2-trichloropropane (3175-23-3) + 1,1,2-trichloropropane (598-77-6)

propene (187737-37-7) + chlorine (7782-50-5) + iron → 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,1,2-trichloropropane (598-77-6)

1,2-Dichloropropane (26198-63-0, 78-87-5) + chlorine (7782-50-5) + iron → 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
at 50 - 55℃; im UV-Licht.Irradiation; 1.2-dichloro-propane;

sulfuryl dichloride (7791-25-5) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + dilauryl peroxide (105-74-8) → 1,2,2-trichloropropane (3175-23-3) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
Product distribution; 1.2-dichloro-propane;

sulfuryl dichloride (7791-25-5) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + dibenzoyl peroxide (94-36-0) → 1,2,2-trichloropropane (3175-23-3) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
Product distribution; 1.2-dichloro-propane;

propene (187737-37-7) + chlorine (7782-50-5) → 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
at 52 - 66℃; in Gegenwart von fluessigen Anteilen des Reaktionsprodukts; aus 3 Mol Propylen und l Mol Chlor im Dunkeln;

propene (187737-37-7) + chlorine (7782-50-5) + aqueous KOH → 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
at 52 - 66℃; aus 3 Mol Propylen und l Mol Chlor im Dunkeln;

propene (187737-37-7) + chlorine (7782-50-5) + iodo-KI → 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4)

Conditions	Yield
at 52 - 66℃; aus 3 Mol Propylen und l Mol Chlor im Dunkeln;

1,3-Dichloropropane (142-28-9) + 1-chloro-3-hydroxypropane (627-30-5) → glycidyl methyl ether (930-37-0) + 1,2-Epoxyhexane (1436-34-6) + 2,3-Dichloroprop-1-ene (78-88-6) + 2-chloroallyl alcohol (5976-47-6) + 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + (Z)-1,3-dichloropropene (10061-01-5) + 1,2,3-trichloro-1-propene (13116-58-0) + (1Z)-1,2,3-trichloroprop-1-ene (96-19-5, 13116-58-0, 13116-57-9) + 1,3,3-trichloro-propene (2953-50-6) + 1t,3,3-trichloro-propene (2598-01-8) + chlorodibromomethane (124-48-1) + 1,1,2-trichloropropane (598-77-6) + 2,3-Dichloro-1-propanol (616-23-9) + 1,3-Dichloro-2-propanol (96-23-1) + 1,2,3-trichloropropane (96-18-4) + 3,3-dichloropropene (563-57-5) + 3,3-dichloroallyl chloride (2567-14-8) + acetaldehyde (75-07-0) + allyl alcohol (107-18-6) + hydroxy-2-propanone (116-09-6) + chloroacetone (78-95-5) + cyclopentanone (120-92-3) + chlorobenzene (108-90-7) + isopropyl alcohol (67-63-0) + 3-monochloro-1,2-propanediol (96-24-2) + acrolein (107-02-8) + epichlorohydrin (106-89-8) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With sodium hydroxide; water at 45 - 62.4℃; under 112.511 - 750.075 Torr; Product distribution / selectivity;

...Expand

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,2,2-trichloropropane (3175-23-3) + 1,1,2,2-tetrachloropropane (13116-60-4) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4) + 1,2,2,3-tetrachloropropane (13116-53-5) + 1,1,2,3-tetrachloropropane (18495-30-2) + 1,1,2,3,3-pentachloropropane (15104-61-7)

Conditions	Yield
With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) at 55 - 60℃;

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,2,2-trichloropropane (3175-23-3) + 1,1,2,2-tetrachloropropane (13116-60-4) + 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4) + 1,1,2,3-tetrachloropropane (18495-30-2)

Conditions	Yield
With chlorine; 2,2'-azobis-(2,4-dimethylvaleronitrile) In tetrachloromethane at 70℃; under 6723.1 Torr; for 3.26667h; Product distribution / selectivity; Inert atmosphere;

isopropyl chloride (75-29-6) → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
With aluminum (III) chloride; sulfuryl dichloride at 55 - 60℃;

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4) + 1,1,2,2,3-pentachloropropane (16714-68-4)

Conditions	Yield
With aluminum (III) chloride; sulfuryl dichloride; sodium iodate at 60℃; for 4h;	A 1.4 g B 0.8 g C 2.3 g

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4) + 1,2,2,3-tetrachloropropane (13116-53-5) + 1,1,2,2,3-pentachloropropane (16714-68-4)

Conditions	Yield
With aluminum (III) chloride; sulfuryl dichloride; iodine at 55 - 70℃; for 7h; Inert atmosphere;

1,2-Dichloropropane (26198-63-0, 78-87-5) → 1,1,2-trichloropropane (598-77-6) + 1,2,3-trichloropropane (96-18-4) + 1,1,2,2,3-pentachloropropane (16714-68-4) + 1,1,2,2,3,3-hexachloropropane (15600-01-8)

Conditions	Yield
With aluminum (III) chloride; iodine; chlorine In dichloromethane at 70℃; under 7224.57 - 7741.73 Torr; for 2h; Sealed tube;

1,1,2-trichloropropane (598-77-6) → 2-chloro-1,1-difluoro-propane (430-93-3)

Conditions	Yield
With hydrogen fluoride; mercury(II) oxide at 100℃;

1,1,2-trichloropropane (598-77-6) → 1,2-dichloro-1-fluoro-propane (7799-55-5)

Conditions	Yield
With hydrogen fluoride; mercury(II) oxide at 100℃;

1,1,2-trichloropropane (598-77-6) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With sodium hydroxide
With benzyltrimethylammonium chloride; sodium hydroxide In water at 70℃; for 4h;
With sodium hydroxide

1,1,2-trichloropropane (598-77-6) → 1,1,2,3-tetrachloropropane (18495-30-2)

Conditions	Yield
With aluminium trichloride; chlorine

1,1,2-trichloropropane (598-77-6) + carbon monoxide (201230-82-2) + benzene (71-43-2) → 1,1-diphenyl-1-propene (778-66-5) + (±)-2-methyl-2-phenyl-2,3-dihydro-1H-inden-1-one (1005420-27-8, 10474-32-5, 887255-49-4)

Conditions	Yield
With aluminium trichloride at 24 - 27℃; for 3h;

→ 1,1,2-trichloropropane

1,1,2-trichloropropane (598-77-6) + 20 percent NaOH → 1,1-dichloropropene (563-58-6)

1,1,2-trichloropropane (598-77-6) + antimonypentachloride (7647-18-9) → 1,1,1,2,2-pentachloropropane (64240-29-5)

Conditions	Yield
at 155℃;

1,1,2-trichloropropane (598-77-6) + hydrogen fluoride (7664-39-3) + mercury oxide → 2-chloro-1,1-difluoro-propane (430-93-3) + 1,2-dichloro-1-fluoro-propane (7799-55-5) + 1,1,2-trifluoropropane (66794-35-2)

Conditions	Yield
at 100℃;

Upstream product

• 540-54-5 1-Chloropropane 
• 78-99-9 1,1-dichloropropane 
• 26198-63-0 1,2-Dichloropropane 
• 7647-18-9 antimonypentachloride 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 7446-70-0 aluminium trichloride 
• 187737-37-7 propene 
• 7791-25-5 sulfuryl dichloride 
• 105-74-8 dilauryl peroxide 
• 94-36-0 dibenzoyl peroxide 
• 142-28-9 1,3-Dichloropropane 
• 627-30-5 1-chloro-3-hydroxypropane 
• 75-29-6 isopropyl chloride 

Downstream Products

• 430-93-3 2-chloro-1,1-difluoro-propane 
• 563-58-6 1,1-dichloropropene 
• 18495-30-2 1,1,2,3-tetrachloropropane 
• 778-66-5 1,1-diphenyl-1-propene 
• 1005420-27-8 (±)-2-methyl-2-phenyl-2,3-dihydro-1H-inden-1-one 
• 16714-68-4 1,1,2,2,3-pentachloropropane 
• 15600-01-8 1,1,2,2,3,3-hexachloropropane 
• 96-18-4 1,2,3-trichloropropane 
• 7799-55-5 1,2-dichloro-1-fluoro-propane 
• 66794-35-2 1,1,2-trifluoropropane 

Relevant articles and documents

-

-

PROCESS FOR THE PRODUCTION OF CHLORINATED ALKANES

Processes for the production of chlorinated alkanes are provided. The present processes comprise reacting one or more mono- and/or dichloroalkanes to form tri-, tetra- and/or pentachloroalkanes, with high regioselectivity. In those embodiments wherein a dichloroalkane is desirably utilized, it may advantageously be a vicinal dichloroalkane. Further, only one catalyst is utilized. The present processes make use of sulfuryl chloride as a chlorinating agent, rather than a gaseous chlorinating agent such as chlorine gas. Finally, the process uses lower intensity process conditions than at least some conventional processes, and thus, operating costs are saved.

SULFURYL CHLORIDE AS CHLORINATING AGENT

The use of sulfuryl chloride, either alone or in combination with chlorine, as a chlorinating agent is disclosed.