32315-10-9

Basic information

• Product Name: Triphosgene
• Synonyms: TRIPHOSGEN;Bis(trichloroMethyl) carbonate puruM, >=99.0% (AT);Triphosgene reagent grade, 98%;Three chloroMethyl carbonate;Triphosgene, 98.0%(T);TRIPHOSGENE;BIS(TRICHLOROMETHYL) CARBONATE;CARBONIC ACID BISTRICHLOR METHYL ESTER
• CAS NO: 32315-10-9
• Molecular Formula: C₃Cl₆O₃
• Molecular Weight: 296.75
• EINECS: 250-986-3
• Product Categories: Other Reagents;Aliphatics
• Mol File: 32315-10-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 79-83 °C(lit.)
• Boiling Point: 203-206 °C(lit.)
• Flash Point: 203-206°C
• Appearance: White to off-white/Crystalline Powder, Crystals and/or Chunks
• Density: 1.78
• Vapor Pressure: 0.263mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: 2-8°C
• Water Solubility: practically insoluble
• Sensitive: Moisture Sensitive
• BRN: 1787583
• CAS DataBase Reference: Triphosgene(CAS DataBase Reference)
• NIST Chemistry Reference: Triphosgene(32315-10-9)
• EPA Substance Registry System: Triphosgene(32315-10-9)

Safety Data

• Hazard Codes: T+,Xn,T
• Statements: 26-34-29-36/37/38-20/21/22-23/24/25
• Safety Statements: 36/37/39-45-9-26-36-7/9
• RIDADR: UN 2928 6.1/PG 2
• WGK Germany: 2
• F: 10-19-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 32315-10-9(Hazardous Substances Data)

Usage

Chemical Description

Triphosgene is a chemical compound with the formula C3Cl6O3, which is used as a reagent in organic synthesis.

Chemical Description

Triphosgene is a highly electrophilic reagent that is used to activate the carboxylate group in the alkali metal salt, leading to lactamization.

Chemical Description

Triphosgene is a reagent used to convert amines to isocyanates.

InChI:InChI=1/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9

Synthetic route

carbonic acid dimethyl ester (616-38-6) → bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
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) → bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
bei der Chlorierung;

methyl 1,1,1-trichloromethyl carbonate (101970-86-9) → carbonic acid chloromethyl ester-trichloromethyl ester + carbonic acid dichloromethyl ester-trichloromethyl ester + bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
Chlorierung;

methyl 1,1,1-trichloromethyl carbonate (101970-86-9) → carbonic acid dichloromethyl ester-trichloromethyl ester + bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
Chlorierung;

methyl 1,1,1-trichloromethyl carbonate (101970-86-9) → bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
bei Chlorierung;
durch Chlorierung;

methyl chloroformate (79-22-1) + carbonic acid dimethyl ester (616-38-6) → bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
vollstaendiges Chlorierung;

chlorothio-trichloro-methane (594-42-3) → bis(trichloromethyl) carbonate (32315-10-9)

Conditions	Yield
With sulfur dioxide In dichloromethane; water at 10℃; for 4h;

cis-1,2-cyclohexane (1792-81-0) + bis(trichloromethyl) carbonate (32315-10-9) → (3aR,7aS)-hexahydrobenzo[d][1,3]dioxol-2-one (4389-22-4, 19456-20-3, 20192-66-9)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With pyridine In dichloromethane at -70℃;	90%

bis(trichloromethyl) carbonate (32315-10-9) + (-)-menthol (2216-51-5) → (1R,2S,5R)-menthyl chloroformate (14602-86-9)

Conditions	Yield
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) + 1-adamantanol (700-57-2) → 2-adamantyl chloroformate (53120-53-9)

Conditions	Yield
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) + benzylamine (100-46-9) → benzyl isothiocyanate (3173-56-6)

Conditions	Yield
With triethylamine In dichloromethane	100%
In ethyl acetate for 4h; Heating;	56%
With triethylamine In dichloromethane for 1h; Heating;

bis(trichloromethyl) carbonate (32315-10-9) + 3-Hydroxypropionitrile (109-78-4) → β-cyanoethyl chlorocarbonate (30436-27-2)

Conditions	Yield
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) + (-)-(2R,3S,6S)-2-hydroxymethyl-3-methyl-6-phenyl-4-piperidone (181783-40-4) → (2R,3S,6S)-1-aza-3-methyl-6-phenyl-8-oxa-4,7-dioxobicyclo[4.3.0]nonane (181783-52-8)

Conditions	Yield
With triethylamine In tetrahydrofuran for 0.25h;	100%

1-dodecyl alcohol (112-53-8) + bis(trichloromethyl) carbonate (32315-10-9) → n-dodecyl chloroformate (24460-74-0)

Conditions	Yield
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) + 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-bis(isocyanato)-25,26,27,28-tetrapropoxy[4]arene (199923-86-9)

Conditions	Yield
In toluene Heating;	100%

bis(trichloromethyl) carbonate (32315-10-9) + cis-2-hydroxycyclohexanecarbonitrile (70367-35-0) → C8H10ClNO2

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%

bis(trichloromethyl) carbonate (32315-10-9) + (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 (202340-92-9) → (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)

Conditions	Yield
With pyridine In dichloromethane at -45℃;	100%
With pyridine In dichloromethane at -45℃; for 1.16667h; Acylation; Cyclization;	100%

N-methylcyclohexylamine (100-60-7) + bis(trichloromethyl) carbonate (32315-10-9) → N-methyl-N-cyclohexylaminocarbonyl chloride (35028-38-7)

Conditions	Yield
With pyridine In toluene	100%
With pyridine In toluene
With pyridine In dichloromethane at 20℃; for 2h;

bis(trichloromethyl) carbonate (32315-10-9) + D-serine methyl ester (2104-89-4, 2788-84-3, 24184-43-8) → (R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester (144542-43-8)

Conditions	Yield
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) + labda-12,14-dien-7α,8α-diol → labda-12,14-dien-7α,8α-cyclocarbonate (220595-40-4)

Conditions	Yield
With pyridine In dichloromethane at -78 - 0℃; for 4h;	100%

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

bis(trichloromethyl) carbonate (32315-10-9) + aniline (62-53-3) → phenyl isocyanate (103-71-9)

Conditions	Yield
With triethylamine In dichloromethane	100%
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) + p-aminoiodobenzene (540-37-4) → 1-iodo-4-isocyanatobenzene (15845-62-2)

Conditions	Yield
With triethylamine In dichloromethane	100%
In ethyl acetate for 4h; Heating;	74%
With triethylamine In dichloromethane at -35 - 20℃; for 2h;	60%

meta-fluoroaniline (372-19-0) + bis(trichloromethyl) carbonate (32315-10-9) → 1-fluoro-3-isocyanatobenzene (404-71-7)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In benzene for 3h; Heating;	75%
With triethylamine In benzene acylation; Heating;	41%

2-Fluoroaniline (348-54-9) + bis(trichloromethyl) carbonate (32315-10-9) → 1-Fluoro-2-isocyanato-benzene (16744-98-2)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In benzene for 3h; acylation; Heating;	36%
With triethylamine In benzene for 3h; Condensation; Heating;	32%

bis(trichloromethyl) carbonate (32315-10-9) + 4-fluoroaniline (371-40-4) → para-fluorophenyl isocyanate (1195-45-5)

Conditions	Yield
With triethylamine In dichloromethane	100%
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) + tert-butyl 4-aminobenzoate (18144-47-3) + 4-nitro-aniline (100-01-6) → 1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea (301317-92-0)

Conditions	Yield
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%

bis(trichloromethyl) carbonate (32315-10-9) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate (59878-28-3)

Conditions	Yield
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) + anthranilic acid (118-92-3) → isatoic anhydride (118-48-9)

Conditions	Yield
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) + (+/-)-trans-2-methylcyclohexanol (7443-52-9) + allyl α-syn-oximino-α-(2-pyridyl)acetate (355023-73-3) → allyl α-syn-[(trans-2-methylcyclohexyloxy)carbonyl]oximino-α-(2-pyridyl)acetate

Conditions	Yield
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%

2,6-diethylaniline (579-66-8) + bis(trichloromethyl) carbonate (32315-10-9) → 2,6-diethylphenylisocyanate (20458-99-5)

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane Heating;	100%
With triethylamine In 1,2-dichloro-ethane

bis(trichloromethyl) carbonate (32315-10-9) + 5-monoamino-25,26,27,28-tetrakis(propyloxy)-calix[4]arene (199923-84-7) → C41H47NO5 (496067-40-4)

Conditions	Yield
In toluene Heating;	100%

bis(trichloromethyl) carbonate (32315-10-9) + 2-[(1S,5S,7R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-6-aza-spiro[4.5]dec-7-yl]-ethanol (498542-65-7) → C29H39NO3Si (498542-66-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%

bis(trichloromethyl) carbonate (32315-10-9) + m-Anisidine (536-90-3) → 3-methoxyphenyl isocyanate (18908-07-1)

Conditions	Yield
With triethylamine In dichloromethane	100%
In dichloromethane at 20℃; for 1.5h;
In toluene at 100℃; Cooling with ice;

bis(trichloromethyl) carbonate (32315-10-9) + 2-methoxy-phenylamine (90-04-0) → 1-Isocyanato-2-methoxy-benzene (700-87-8)

Conditions	Yield
With triethylamine In dichloromethane	100%
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) + 4-methoxy-aniline (104-94-9) → 4-Methoxyphenyl isocyanate (5416-93-3)

Conditions	Yield
With triethylamine In dichloromethane	100%
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%

Upstream product

• 207804-71-5 carbonic acid chloromethyl ester-dichloromethyl ester 
• 101970-86-9 methyl 1,1,1-trichloromethyl carbonate 
• 616-38-6 carbonic acid dimethyl ester 
• 594-42-3 chlorothio-trichloro-methane 
• 79-22-1 methyl chloroformate 

Downstream Products

• 75-44-5 phosgene 
• 628-50-2 carbonochloridic acid 3-methyl-butyl ester 
• 7144-08-3 Cholesteryl chloroformate 
• 108-24-7 acetic anhydride 
• 102-09-0 bis(phenyl) carbonate 
• 861340-55-8 carbonic acid phenyl ester-trichloromethyl ester 
• 503-38-8 trichloromethyl chloroformate 
• 1885-14-9 phenyl chloroformate 
• 96751-61-0 (S)-4-methoxycarbonyl-oxazolidin-2-one 
• 616-38-6 carbonic acid dimethyl ester 
• 128595-03-9 p-phenylbenzyloxycarbonyloxysuccinimide 
• 74124-79-1 di(succinimido) carbonate 
• 17952-82-8 1,2,3,4-tetrahydronorharman-1-one 
• 105-58-8 Diethyl carbonate 

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