Product Name

  • Name

    Diphosgene

  • EINECS 207-965-9
  • CAS No. 503-38-8
  • Article Data25
  • CAS DataBase
  • Density 1.64
  • Solubility may decompose
  • Melting Point -57 ºC
  • Formula C2Cl4 O2
  • Boiling Point 128 ºC
  • Molecular Weight 197.833
  • Flash Point >110°C
  • Transport Information UN 1076/3277
  • Appearance clear, colorless liquid
  • Safety Low toxicity by inhalation. A corrosive liquid. When heated to decomposition it emits toxic vapors of Cl.
  • Risk Codes R26/27/28;R34   
  • Molecular Structure Molecular Structure of 503-38-8 (Diphosgene)
  • Hazard Symbols
  • Synonyms Formicacid, chloro-, trichloromethyl ester (6CI,7CI,8CI); Methanol, trichloro-,chloroformate (8CI); Diphosgen; Diphosgene; Trichloromethyl chlorocarbonate;Trichloromethyl chloroformate
  • PSA 26.30000
  • LogP 2.68950

Synthetic route

methyl chloroformate
79-22-1

methyl chloroformate

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Conditions
ConditionsYield
With chlorine at 75 - 85℃; for 35h;84%
bei Chlorierung im Sonnenlicht;
bei der Chlorierung schliesslich;
bei der Chlorierung im UV-Licht; die Bildungsgeschwindigkeit waechst mit steigender Temperatur bis 110-112grad;
beim Chlorieren im Sonnenlicht;
carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

A

dichloromethoxycarbonyl chloride
22128-63-8

dichloromethoxycarbonyl chloride

B

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Conditions
ConditionsYield
With chlorine for 61h;A 76%
B n/a
With chlorine for 61h; Yields of byproduct given;
Methyl formate
107-31-3

Methyl formate

A

dichloromethoxycarbonyl chloride
22128-63-8

dichloromethoxycarbonyl chloride

B

carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

C

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Conditions
ConditionsYield
Bei der Chlorierung im Licht;
With oxygen; chlorine at 22.85℃; Kinetics; Further Variations:; Reagents;
Methyl formate
107-31-3

Methyl formate

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Conditions
ConditionsYield
bei der Chlorierung im UV-Licht; die Bildungsgeschwindigkeit waechst mit steigender Temperatur bis 110-112grad;
beim Chlorieren im Sonnenlicht;
With diacetyl peroxide; chlorine at 60℃; unter Ausschluss von Licht;
durch photochemische Chlorierung;
With chlorine im Licht einer Metallfadenlampe;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

A

phosgene
75-44-5

phosgene

B

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Conditions
ConditionsYield
beim Destillieren;
beim Destillieren;
With chloride In hexane at 20℃; Kinetics;
distn. or warming at reflux cooling;
Methyl formate
107-31-3

Methyl formate

chlorine
7782-50-5

chlorine

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Conditions
ConditionsYield
mit ueberschuessigem Chlor;
im Sonnenlicht entsteht zunaechst Chlorameisensaeuremethylester;
mit ueberschuessigem Chlor;
4,5-methylenedioxyanthranilic acid
20332-16-5

4,5-methylenedioxyanthranilic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione
57385-14-5

1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione

Conditions
ConditionsYield
In 1,4-dioxane for 6h; Heating;100%
2-(2-nitrophenyl)propanol
64987-77-5

2-(2-nitrophenyl)propanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

2-(2-nitrophenyl)propyl chloroformate
179691-31-7

2-(2-nitrophenyl)propyl chloroformate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
With triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) room temperature, 2 h;96%
Yield given;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3.75h;
With 4-methyl-morpholine In tetrahydrofuran
(E)-hexa-3,5-dien-1-ol
73670-87-8

(E)-hexa-3,5-dien-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C7H9ClO2

C7H9ClO2

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 3h;100%
2-(5-bromo-2-nitrophenyl)propan-1-ol
335201-57-5

2-(5-bromo-2-nitrophenyl)propan-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

2-(5-bromo-2-nitrophenyl)propyl carbonochloridate
335201-61-1

2-(5-bromo-2-nitrophenyl)propyl carbonochloridate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
In tetrahydrofuran; triethylamine at 0℃; for 1h;99%
trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

(d)-5-phenyl-1,3-dioxolan-2,4-dione
42783-36-8

(d)-5-phenyl-1,3-dioxolan-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(4-chloro-phenyl)-[1,3]dioxolane-2,4-dione

5-(4-chloro-phenyl)-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
4-bromo-DL-mandelic acid
6940-50-7

4-bromo-DL-mandelic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(4-bromo-phenyl)-[1,3]dioxolane-2,4-dione

5-(4-bromo-phenyl)-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 8h;100%
1-naphthylglycolic acid
6341-54-4

1-naphthylglycolic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-naphthalen-1-yl-[1,3]dioxolane-2,4-dione

5-naphthalen-1-yl-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
phenyllactic acid
828-01-3

phenyllactic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-benzyl-1,3-dioxolane-2,4-dione
421545-77-9

5-benzyl-1,3-dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione

5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(2-chloro-phenyl)-[1,3]dioxolane-2,4-dione

5-(2-chloro-phenyl)-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
2-hydroxy-4-phenylbutanoic acid
4263-93-8

2-hydroxy-4-phenylbutanoic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-phenethyl-[1,3]dioxolane-2,4-dione

5-phenethyl-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
4-isopropylmandelic acid
4607-63-0

4-isopropylmandelic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(4-isopropyl-phenyl)-[1,3]dioxolane-2,4-dione
421545-72-4

5-(4-isopropyl-phenyl)-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
4-(trifluoromethyl)mandelic acid
395-35-7

4-(trifluoromethyl)mandelic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(4-trifluoromethyl-phenyl)-[1,3]dioxolane-2,4-dione

5-(4-trifluoromethyl-phenyl)-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
2-(3,4-difluorophenyl)-2-hydroxyacetic acid

2-(3,4-difluorophenyl)-2-hydroxyacetic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

5-(3,4-difluoro-phenyl)-[1,3]dioxolane-2,4-dione

5-(3,4-difluoro-phenyl)-[1,3]dioxolane-2,4-dione

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 20℃; for 8h;100%
ethyl anti-(+/-)-3-(4-methoxyphenylamino)-2-hydroxy-3-phenylpropanoate

ethyl anti-(+/-)-3-(4-methoxyphenylamino)-2-hydroxy-3-phenylpropanoate

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

(4R,5R)-3-(4-Methoxy-phenyl)-2-oxo-4-phenyl-oxazolidine-5-carboxylic acid ethyl ester

(4R,5R)-3-(4-Methoxy-phenyl)-2-oxo-4-phenyl-oxazolidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃;100%
(2R*,3S*)-ethyl 3-(4-methoxyphenylamino)-2-hydroxy-3-phenylpropanoate

(2R*,3S*)-ethyl 3-(4-methoxyphenylamino)-2-hydroxy-3-phenylpropanoate

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

(4R,5S)-3-(4-Methoxy-phenyl)-2-oxo-4-phenyl-oxazolidine-5-carboxylic acid ethyl ester

(4R,5S)-3-(4-Methoxy-phenyl)-2-oxo-4-phenyl-oxazolidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃;100%
[2-(3-chlorophenoxy)-1-ethyl]ethanol
157943-97-0

[2-(3-chlorophenoxy)-1-ethyl]ethanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

[2-(3-chlorophenoxy)-1-ethyl]ethyl chloroformate
551937-23-6

[2-(3-chlorophenoxy)-1-ethyl]ethyl chloroformate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 25℃; for 3h;100%
1-(3-nitro-2-thienyl)ethanol
56920-93-5

1-(3-nitro-2-thienyl)ethanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C7H6ClNO4S

C7H6ClNO4S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
(3-nitro-2-thienyl)methanol
20898-87-7

(3-nitro-2-thienyl)methanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C6H4ClNO4S

C6H4ClNO4S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
α-phenyl-2-nitrophenethyl alcohol
16764-13-9

α-phenyl-2-nitrophenethyl alcohol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C15H12ClNO4

C15H12ClNO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
8-nitro-1-hydrohymethylnaphthoic acid
19190-46-6

8-nitro-1-hydrohymethylnaphthoic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C12H8ClNO4

C12H8ClNO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
4-(hydroxymethyl)-5-nitro-1,2,3,4-tetrahydronaphtalene
102781-43-1

4-(hydroxymethyl)-5-nitro-1,2,3,4-tetrahydronaphtalene

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C12H12ClNO4

C12H12ClNO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
(3-nitronaphthalen-2-yl)methanol
73428-04-3

(3-nitronaphthalen-2-yl)methanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C12H8ClNO4

C12H8ClNO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
2-(4-bromo-2-nitrophenyl)propan-1-ol
244140-70-3

2-(4-bromo-2-nitrophenyl)propan-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C10H9BrClNO4
244140-73-6

C10H9BrClNO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
2-(4-chloro-2-nitrophenyl)propan-1-ol
244140-69-0

2-(4-chloro-2-nitrophenyl)propan-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C10H9Cl2NO4
244140-72-5

C10H9Cl2NO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
2-(4-iodo-2-nitrophenyl)propan-1-ol
244140-71-4

2-(4-iodo-2-nitrophenyl)propan-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C10H9ClINO4
244140-74-7

C10H9ClINO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
2-(3-nitro-2-thienyl)ethanol
702643-69-4

2-(3-nitro-2-thienyl)ethanol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C7H6ClNO4S

C7H6ClNO4S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
2-(3-nitro-2-thienyl)propan-1-ol

2-(3-nitro-2-thienyl)propan-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C8H8ClNO4S

C8H8ClNO4S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
3-(2-nitrophenyl)butan-2-ol
702643-35-4

3-(2-nitrophenyl)butan-2-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

C11H12ClNO4

C11H12ClNO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%

Diphosgene Chemical Properties

IUPAC Name:Trichloromethyl carbonochloridate (503-38-8)
Synonyms: Carbonochloridic acid, trichloromethyl ester ; Carbonochloridicacid,trichloromethylester ; Carbonochloridicacidtrichloromethylester ; Chloro-formicacitrichloromethylester ; Difosgen ; Diphosgen ; DP ; Formic acid, chloro-, trichloromethyl ester
CAS: 503-38-8
MF: C2Cl4O2

MS:
MW: 197.83
EINECS: 207-965-9
Product Categories: Pharmaceutical Intermediates
Mol File: 503-38-8.mol
Surface Tension: 44.2 dyne/cm 
Density: 1.788 g/cm
Flash Point: 32.2 °C
Melting Point:-57 °C 
Enthalpy of Vaporization: 36.57 kJ/mol 
Boiling Point: 128 °C at 760 mmHg 
Vapour Pressure: 10.8 mmHg at 25°C 
Refractive index  n20/D 1.458
Storage temp:  2-8°C
Water Solubility:  may decompose
Sensitive:  Moisture Sensitive
Merck : 14,3334
BRN : 970225

Diphosgene Uses

 Trichloromethyl chloroformate (503-38-8) has effects on  tearing.

Diphosgene Production

1.Cl-CO-OCH3 + 3 Cl2 (hv) Cl-CO-OCCl3 + 3 HCl

2.H-CO-OCH3 + 4 Cl2 (hv) Cl-CO-OCCl3 + 4 HCl

 

Diphosgene Safety Profile

Hazard Codes:  T+,Xi
Risk Statements:  34-26/27/28-36/37/38
34: Trichloromethyl chloroformate (503-38-8) can causes burns.
26/27/28:  Very Toxic by inhalation, in contact with skin and if swallowed
36/37/38:  Irritating to eyes, respiratory system and skin
Safety Statements:  26-28-36/37/39-45
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR:  UN 3277 6.1/PG 2
WGK Germany: 3 
RTECS:  LQ7350000
F : 8-10-19
HazardClass:  6.1
PackingGroup:  II

Diphosgene Specification

1.General Description: Trichloromethyl chloroformate (503-38-8) is colorless liquid, odorless to fruity.
2.Air & Water Reactions: Decomposes slowly in water or moist air (or when inhaled) to form very corrosive hydrogen chloride gas (hydrochloric acid) and carbon monoxide.
3.Fire Hazard :Some may burn but none ignite readily. Vapors from liquefied gas are initially heavier than air and spread along ground. Some of these materials may react violently with water. Cylinders exposed to fire may vent and release toxic and/or corrosive gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

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