Product Name

  • Name

    Triphosgene

  • EINECS 250-986-3
  • CAS No. 32315-10-9
  • Article Data15
  • CAS DataBase
  • Density 1.898 g/cm3
  • Solubility practically insoluble in water
  • Melting Point 78-82 °C
  • Formula C3Cl6O3
  • Boiling Point 204.5 °C at 760 mmHg
  • Molecular Weight 296.749
  • Flash Point 53.3 °C
  • Transport Information UN 2928 6.1/PG 2
  • Appearance White solid
  • Safety 36/37/39-45-9-26-36-7/9
  • Risk Codes 26-34-29-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 32315-10-9 (Triphosgene)
  • Hazard Symbols VeryT+, HarmfulXn
  • Synonyms Carbonicacid, bis(trichloromethyl) ester (6CI,8CI);Methanol, trichloro-, carbonate(2:1) (9CI);Bis(trichloromethyl) carbonate;Bis(trichloromethyl)carbonate;
  • PSA 35.53000
  • LogP 3.79500

Synthetic route

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
With chlorine In tetrachloromethane for 18h; Irradiation;100%
With chlorine In tetrachloromethane for 28h; Irradiation;97%
With chlorine for 33h; chlorination;88%
carbonic acid chloromethyl ester-dichloromethyl ester
207804-71-5

carbonic acid chloromethyl ester-dichloromethyl ester

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
bei der Chlorierung;
methyl 1,1,1-trichloromethyl carbonate
101970-86-9

methyl 1,1,1-trichloromethyl carbonate

A

carbonic acid chloromethyl ester-trichloromethyl ester

carbonic acid chloromethyl ester-trichloromethyl ester

B

carbonic acid dichloromethyl ester-trichloromethyl ester

carbonic acid dichloromethyl ester-trichloromethyl ester

C

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
Chlorierung;
...Expand
methyl 1,1,1-trichloromethyl carbonate
101970-86-9

methyl 1,1,1-trichloromethyl carbonate

A

carbonic acid dichloromethyl ester-trichloromethyl ester

carbonic acid dichloromethyl ester-trichloromethyl ester

B

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
Chlorierung;
methyl 1,1,1-trichloromethyl carbonate
101970-86-9

methyl 1,1,1-trichloromethyl carbonate

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
bei Chlorierung;
durch Chlorierung;
methyl chloroformate
79-22-1

methyl chloroformate

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
vollstaendiges Chlorierung;
chlorothio-trichloro-methane
594-42-3

chlorothio-trichloro-methane

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Conditions
ConditionsYield
With sulfur dioxide In dichloromethane; water at 10℃; for 4h;
cis-1,2-cyclohexane
1792-81-0

cis-1,2-cyclohexane

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(3aR,7aS)-hexahydrobenzo[d][1,3]dioxol-2-one
4389-22-4, 19456-20-3, 20192-66-9

(3aR,7aS)-hexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;100%
With pyridine In dichloromethane at -70℃;90%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(-)-menthol
2216-51-5

(-)-menthol

(1R,2S,5R)-menthyl chloroformate
14602-86-9

(1R,2S,5R)-menthyl chloroformate

Conditions
ConditionsYield
With pyridine In tetrachloromethane at 55 - 60℃; for 6h;100%
Stage #1: bis(trichloromethyl) carbonate With pyridine In toluene at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (-)-menthol In toluene at 20℃; for 15h; Inert atmosphere;		100%
Stage #1: bis(trichloromethyl) carbonate With pyridine In toluene at 0℃; Inert atmosphere;
Stage #2: (-)-menthol In toluene at 0 - 20℃; Inert atmosphere;		100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-adamantanol
700-57-2

1-adamantanol

2-adamantyl chloroformate
53120-53-9

2-adamantyl chloroformate

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h; Ambient temperature;100%
With pyridine In dichloromethane for 1h; Ambient temperature;
With pyridine In dichloromethane; ethyl acetate
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

benzylamine
100-46-9

benzylamine

benzyl isothiocyanate
3173-56-6

benzyl isothiocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In ethyl acetate for 4h; Heating;56%
With triethylamine In dichloromethane for 1h; Heating;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

β-cyanoethyl chlorocarbonate
30436-27-2

β-cyanoethyl chlorocarbonate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 3-Hydroxypropionitrile In tetrahydrofuran at 0 - 20℃;
Stage #2: With pyridine In tetrahydrofuran at 0 - 20℃;		100%
In pyridine; toluene at 0℃;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(-)-(2R,3S,6S)-2-hydroxymethyl-3-methyl-6-phenyl-4-piperidone
181783-40-4

(-)-(2R,3S,6S)-2-hydroxymethyl-3-methyl-6-phenyl-4-piperidone

(2R,3S,6S)-1-aza-3-methyl-6-phenyl-8-oxa-4,7-dioxobicyclo[4.3.0]nonane
181783-52-8

(2R,3S,6S)-1-aza-3-methyl-6-phenyl-8-oxa-4,7-dioxobicyclo[4.3.0]nonane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 0.25h;100%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

n-dodecyl chloroformate
24460-74-0

n-dodecyl chloroformate

Conditions
ConditionsYield
With pyridine In tetrachloromethane at -15 - 20℃;100%
With pyridine In tetrahydrofuran for 2h;
With pyridine In chloroform for 2h; ice cooling;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

5,17-diamino-25,26,27,28-tetrakis(propyloxy)calix[4]arene
156874-49-6, 169436-70-8, 950744-70-4, 1078151-72-0

5,17-diamino-25,26,27,28-tetrakis(propyloxy)calix[4]arene

5,17-bis(isocyanato)-25,26,27,28-tetrapropoxy[4]arene
199923-86-9

5,17-bis(isocyanato)-25,26,27,28-tetrapropoxy[4]arene

Conditions
ConditionsYield
In toluene Heating;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

cis-2-hydroxycyclohexanecarbonitrile
70367-35-0

cis-2-hydroxycyclohexanecarbonitrile

C8H10ClNO2

C8H10ClNO2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(1S,4aR,5S,6S,9R,10R,11S,12S,12aS)-1,12-(Isopropylidenedioxy)-9,12a,13,13-tetramethyl-4-methylenetetradecahydro-6,10-methanobenzocyclodecene-5,6,9,10,11-pentaol
202340-92-9

(1S,4aR,5S,6S,9R,10R,11S,12S,12aS)-1,12-(Isopropylidenedioxy)-9,12a,13,13-tetramethyl-4-methylenetetradecahydro-6,10-methanobenzocyclodecene-5,6,9,10,11-pentaol

(4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-11,12-(Carbonyldioxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-5,7,8-triol
222727-00-6

(4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-11,12-(Carbonyldioxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-5,7,8-triol

Conditions
ConditionsYield
With pyridine In dichloromethane at -45℃;100%
With pyridine In dichloromethane at -45℃; for 1.16667h; Acylation; Cyclization;100%
N-methylcyclohexylamine
100-60-7

N-methylcyclohexylamine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

N-methyl-N-cyclohexylaminocarbonyl chloride
35028-38-7

N-methyl-N-cyclohexylaminocarbonyl chloride

Conditions
ConditionsYield
With pyridine In toluene100%
With pyridine In toluene
With pyridine In dichloromethane at 20℃; for 2h;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

D-serine methyl ester
2104-89-4, 2788-84-3, 24184-43-8

D-serine methyl ester

(R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester
144542-43-8

(R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane 0-5 deg C, 2 h; room temperature, 48 h;100%
In tetrahydrofuran at 65℃; for 4h;
In tetrahydrofuran at 65℃; for 4h; Condensation;
With potassium carbonate In toluene at 20℃;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

labda-12,14-dien-7α,8α-diol

labda-12,14-dien-7α,8α-diol

labda-12,14-dien-7α,8α-cyclocarbonate
220595-40-4

labda-12,14-dien-7α,8α-cyclocarbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at -78 - 0℃; for 4h;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(1S,3S)-1-{(1S,2S)-1,3-Bis-(3,4-dimethoxy-phenyl)-2-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-propyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
234117-19-2

(1S,3S)-1-{(1S,2S)-1,3-Bis-(3,4-dimethoxy-phenyl)-2-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-propyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

(1S,2S,6S,12bS)-2-(3,4-Dimethoxy-benzyl)-1-(3,4-dimethoxy-phenyl)-3-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethyl]-4-oxo-1,2,3,4,6,7,12,12b-octahydro-pyrimido[1',6':1,2]pyrido[3,4-b]indole-6-carboxylic acid methyl ester

(1S,2S,6S,12bS)-2-(3,4-Dimethoxy-benzyl)-1-(3,4-dimethoxy-phenyl)-3-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethyl]-4-oxo-1,2,3,4,6,7,12,12b-octahydro-pyrimido[1',6':1,2]pyrido[3,4-b]indole-6-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane at 20℃; Cyclization;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

aniline
62-53-3

aniline

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In ethyl acetate at 0 - 5℃; for 3h; Solvent; Cooling with ice; Reflux;89%
In chloroform at 20℃; for 1h; Cooling with ice;85%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

1-iodo-4-isocyanatobenzene
15845-62-2

1-iodo-4-isocyanatobenzene

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In ethyl acetate for 4h; Heating;74%
With triethylamine In dichloromethane at -35 - 20℃; for 2h;60%
meta-fluoroaniline
372-19-0

meta-fluoroaniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-fluoro-3-isocyanatobenzene
404-71-7

1-fluoro-3-isocyanatobenzene

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In benzene for 3h; Heating;75%
With triethylamine In benzene acylation; Heating;41%
2-Fluoroaniline
348-54-9

2-Fluoroaniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-Fluoro-2-isocyanato-benzene
16744-98-2

1-Fluoro-2-isocyanato-benzene

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In benzene for 3h; acylation; Heating;36%
With triethylamine In benzene for 3h; Condensation; Heating;32%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

4-fluoroaniline
371-40-4

4-fluoroaniline

para-fluorophenyl isocyanate
1195-45-5

para-fluorophenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In toluene for 7h; Reflux; Cooling with ice;76.6%
In 1,4-dioxane at 80℃; for 24h;73.1%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

tert-butyl 4-aminobenzoate
18144-47-3

tert-butyl 4-aminobenzoate

4-nitro-aniline
100-01-6

4-nitro-aniline

1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea
301317-92-0

1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 4-nitro-aniline With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 0.833333h; Substitution;
Stage #2: tert-butyl 4-aminobenzoate In tetrahydrofuran at 20℃; for 42h; Substitution;		100%
...Expand
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate
59878-28-3

tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 25℃; for 1h;89%
Stage #1: 1-t-Butoxycarbonylpiperazine With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: bis(trichloromethyl) carbonate In dichloromethane at 0℃; for 1h; Inert atmosphere;		86%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

anthranilic acid
118-92-3

anthranilic acid

isatoic anhydride
118-48-9

isatoic anhydride

Conditions
ConditionsYield
In tetrahydrofuran at 45℃; for 12h;100%
In 1,2-dichloro-ethane for 3.25h; Reflux;96%
In tetrahydrofuran for 4h; Reflux;95%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(+/-)-trans-2-methylcyclohexanol
7443-52-9

(+/-)-trans-2-methylcyclohexanol

allyl α-syn-oximino-α-(2-pyridyl)acetate
355023-73-3

allyl α-syn-oximino-α-(2-pyridyl)acetate

allyl α-syn-[(trans-2-methylcyclohexyloxy)carbonyl]oximino-α-(2-pyridyl)acetate

allyl α-syn-[(trans-2-methylcyclohexyloxy)carbonyl]oximino-α-(2-pyridyl)acetate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; (+/-)-trans-2-methylcyclohexanol With pyridine In dichloromethane at 50℃; for 1.5h;
Stage #2: allyl α-syn-oximino-α-(2-pyridyl)acetate With triethylamine In dichloromethane at 25℃; for 1.5h; Further stages.;		100%
...Expand
2,6-diethylaniline
579-66-8

2,6-diethylaniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2,6-diethylphenylisocyanate
20458-99-5

2,6-diethylphenylisocyanate

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane Heating;100%
With triethylamine In 1,2-dichloro-ethane
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

5-monoamino-25,26,27,28-tetrakis(propyloxy)-calix[4]arene
199923-84-7

5-monoamino-25,26,27,28-tetrakis(propyloxy)-calix[4]arene

C41H47NO5
496067-40-4

C41H47NO5

Conditions
ConditionsYield
In toluene Heating;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-[(1S,5S,7R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-6-aza-spiro[4.5]dec-7-yl]-ethanol
498542-65-7

2-[(1S,5S,7R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-6-aza-spiro[4.5]dec-7-yl]-ethanol

C29H39NO3Si
498542-66-8

C29H39NO3Si

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

m-Anisidine
536-90-3

m-Anisidine

3-methoxyphenyl isocyanate
18908-07-1

3-methoxyphenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In dichloromethane at 20℃; for 1.5h;
In toluene at 100℃; Cooling with ice;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

1-Isocyanato-2-methoxy-benzene
700-87-8

1-Isocyanato-2-methoxy-benzene

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In dichloromethane at 20℃; for 1.5h;
In dichloromethane at 0℃; for 0.5h;
With triethylamine In 1,2-dichloro-ethane at 0 - 85℃; for 8.5h; Inert atmosphere;
With triethylamine In 1,2-dichloro-ethane at 0 - 85℃; for 8.5h; Inert atmosphere;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-Methoxyphenyl isocyanate
5416-93-3

4-Methoxyphenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
Stage #1: bis(trichloromethyl) carbonate; 4-methoxy-aniline In dichloromethane at 20℃; for 0.5h;
Stage #2: With triethylamine In dichloromethane at -35 - 20℃; for 2h;		92%
In chloroform at 20℃; for 1h; Cooling with ice;85%

Triphosgene Chemical Properties

Molecular Structure of Triphosgene (CAS NO.32315-10-9):

IUPAC Name: bis(trichloromethyl) carbonate
Molecular formula:: C3Cl6O3
Molecular Weight: 296.75 g/mol
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 35.53Å2
Index of Refraction: 1.532
Molar Refractivity: 48.49 cm3
Molar Volume: 156.3 cm3
Surface Tension: 50.5 dyne/cm
Density: 1.898 g/cm3
Flash Point: 53.3 °C
Enthalpy of Vaporization: 44.07 kJ/mol
Boiling Point: 204.5 °C at 760 mmHg
Vapour Pressure: 0.263 mmHg at 25°C
Melting point: 78-82 °C
Storage temp: 2-8°C
Water Solubility: practically insoluble
Sensitive: Moisture Sensitive
BRN: 1787583
Product Categories: Other Reagents

Triphosgene Production

  Triphosgene (CAS NO.32315-10-9) is prepared by exhaustive chlorination of dimethyl carbonate. The preparing process is the chlorination of methyl carbonate in the presence of fluorescence, ultraviolet ray and mixed medium and low temperature initiator in the amount of not more than 2 % of the material. The whole chlorination is completed in three stages at 15-50 deg.c, 50-70 deg.c and 70-90 deg.c separately. The said technological process obtains product of high purity and smelting point of 80-83 deg.c at a yield over 90 %.

Triphosgene Safety Profile

Hazard Codes: VeryT+,HarmfulXn
Risk Statements: 26-34-29-36/37/38-20/21/22
R26:Very toxic by inhalation. 
R34:Causes burns. 
R29:Contact with water liberates toxic gas. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-45-9-26-36-7/9
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S9:Keep container in a well-ventilated place. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S7:Keep container tightly closed.
RIDADR: UN 2928 6.1/PG 2
WGK Germany: 2
F: 10-19-21
HazardClass: 6.1
PackingGroup: II
HS Code: 29209010

Triphosgene Specification

  Triphosgene , with CAS number of 32315-10-9, can be called Bis(trichloromethyl)carbonate ; Bis(trichloromethyl) carbonate ; Methanol, trichloro-, carbonate(2:1) (9CI) ; Carbonicacid, bis(trichloromethyl) ester (6CI,8CI) . It is a white solid. Triphosgene (CAS NO.32315-10-9) is a chemical compound that is used as a safer substitute for phosgene, because at room temperature it is a solid crystal, as opposed to phosgene which is a gas, the crystals decompose at around 130 °C, although, the decomposition temperature of impure samples can be much lower. It is used in organic synthesis to bond one carbonyl group to two alcohols, as in the synthesis of octalactin B.

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