Basic information
- CAS
503-38-8- Standard SMILES
O=C(Cl)OC(Cl)(Cl)Cl- InChIKey
HCUYBXPSSCRKRF-UHFFFAOYSA-N- Molecular formula
- C2Cl4O2
- Average molar mass
- 197.8 g/mol
- Monoisotopic mass
- 195.86523996
Overview
Diphosgene is a moderately persistent synthetic organic compound, formed by chlorination of methyl chloroformate, that is a respiratory irritant and lachrymator. Trichloromethyl Chloroformate has been used as a chemical warfare agent and is characterized as a colorless liquid with an odor that is like newly mown hay. Exposure occurs by inhalation, ingestion, or contact.
Names & identifiers
- Preferred name
- Diphosgene
- IUPAC
- trichloromethyl carbonochloridate
- English name
- Diphosgene
- Molecular formula
- C2Cl4O2
- Molecular weight
- 197.83
Names & synonyms
Show more names
Database identifiers
- CAS
503-38-8- PubChem CID
- 10426
- DTXSID
DTXSID60862065- UNII
- PO4Q4R80LV
- EC Number
- 207-965-9
- Nikkaji
- J12.981J
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 94.7
Experimental & physicochemical properties
Density
1.6525 @ 14 °C
1.6 g/cm³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.08
Solubility
INSOL IN WATER; SOL IN ETHANOL, VERY SOL IN ETHER
SOL IN BENZENE, ALCOHOL, AND ETHER
Solubility in water: reaction
Boiling Point
128 °C @ 760 MM HG
Suffocating liquid; Boiling point = 49 °C at 50 mm Hg; Stable at room temp, decomposes to phosgene at approximately 300 °C
at 101.3 kPa: 128 °C
Melting Point
-57 °C
-57 °C
Vapor Pressure
10 MM HG @ 20 °C
Vapor pressure, kPa at 20 °C: 1.3
Physicochemical properties
- Melting point
- -57 °C · -57 °C
- Boiling point
- 20 °C10 · 20 °C10 mm Hg(lit.)
- Density
- 1.64 · 1.64
- vapor pressure
- 13 hPa · 13 hPa ( 20 °C)
- refractive index
- 20 · n20/D 1.458
- Flash point
- 110 °C · >110°C
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Soluble), Ethyl Acetate (Sparingly)
- form
- Liquid
- color
- Clear colorless
- Water Solubility
- may decompose
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,3334
- BRN
- 970225 · 970225
- Stability
- Hygroscopic, Moisture Sensitive
- InChI
- 1S/C2Cl4O2/c3-1(7)8-2(4,5)6
- InChIKey
- HCUYBXPSSCRKRF-UHFFFAOYSA-N
- SMILES
- ClC(=O)OC(Cl)(Cl)Cl
- CAS DataBase Reference
- 503 · 503-38-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 Q4R80LV · PO4Q4R80LV
- NIST Chemistry Reference
- Trichloromethyl chloroformate(503-38-8)
- EPA Substance Registry System
- Carbonochloridic acid, trichloromethyl ester (503-38-8)
- UNSPSC Code
- 12352108 · 12352108
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300-H314-H330
- Precautionary statements
- 264 · P264-P270-P260-P280-P271-P284-P301+P310-P330-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P305+P351+P338-P405-P403+P233-P501
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- T+,Xi
- Risk Statements
- 26 · 26/28-34-26/27/28-36/37/38
- Safety Statements
- 26 · 26-28-36/37/39-45-28A-36
- RIDADR
- 3277 · UN 3277 6.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 7350000 · LQ7350000
- F
- 8 · 8-10-19
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29159000 · 29159000
- Storage Class
- 6.1 B · 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 InhalationAcute · Acute Tox. 2 InhalationAcute Tox. 4 OralSkin Corr. 1B
- Hazardous Substances Data
- 503 · 503-38-8(Hazardous Substances Data)
- Toxicity
- 100 in · LC100 in rabbits (10-20 minutes exposure to vapor): 0.9 mg/l air (Klika, Mysliveckova)
- Limited Quantities
- 100 ml · 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (87%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P320, P321, P330, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Carbonochloridic acid, trichloromethyl ester
Trichloromethyl chloroformate: Does not have an individual approval but may be used under an appropriate group standard
DOT Emergency Guidelines
If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.
If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.
If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.
If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.
For more DOT Emergency Guidelines (Complete) data for DIPHOSGENE (12 total), please visit the HSDB record page.
Safety & protection
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth.
Exposure Control and Personal Protection
TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].
Spillage Disposal
Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Toxicology
Signs and Symptoms
Burning sensation. Chest tightness. Sore throat. Cough. Laboured breathing. Shortness of breath. Symptoms may be delayed.
Redness.
Watering of the eyes. Redness.
Sore throat.
Human Toxicity Excerpts
EYE IRRITATION, IRRITATION OF UPPER RESPIRATORY TRACT, & SURFACE BURNS HAVE BEEN PRINCIPAL FINDINGS IN EXPOSED HUMANS. PULMONARY EDEMA WOULD UNDOUBTEDLY OCCUR WITH HIGHER LEVELS OF EXPOSURE. EYE IRRITATION MAY PERSIST SOME TIME AFTER EXPOSURE CEASES. SKIN SENSITIZATION MAY OCCUR. /CHLOROFORMATES/
INSIDIOUS POISON AS IT IS NOT IRRITATING IMMEDIATELY, EVEN WHEN FATAL CONCN ARE INHALED. MAY CAUSE SEVERE PULMONARY EDEMA (MAY BE QUICKLY FATAL) OR PNEUMONIA. INHALATION OF HIGH CONCN CAUSES CHOKING, CONSTRICTED FEELING IN CHEST, COUGHING, PAINFUL BREATHING, BLOODY SPUTUM. VAPORS STRONGLY IRRITATING TO THE EYES. /PHOSGENE/
HIGHLY TOXIC BY INHALATION & INGESTION. STRONG IRRITANT TO TISSUE.
Non-Human Toxicity Excerpts
NO EVIDENCE EXISTS FOR A SYSTEMIC ACTION OF INHALED PHOSGENE, BUT VASOCONSTRICTION OF PULMONARY VASCULATURE HAS BEEN DESCRIBED IN RABBITS. SEQUELAE INCLUDE PULMONARY SCARRING, LOBULAR EMPHYSEMA, SMALL IRREGULAR AREAS OF ATELECTASIS & BRONCHITIS. /PHOSGENE/
SOME POSSIBLE MECHANISMS OF REDUCED ACTIVITY OF LUNG SURFACTANT IN ACUTE PULMONARY EDEMA WERE STUDIED IN ALBINO RATS & RABBITS. MOST OF THE EDEMOGENIC SUBSTANCES DID NOT CHANGE SURFACTANT ACTIVITY WHILE DIPHOSGENE REDUCED IT.
The purpose of this study was to examine the changes of pulmonary hemodynamics, cardiac impedance parameters and the number of pulmonary microembolus, and leukocyte after diphosgene inhalation in rabbits. Fifty-three rabbits were randomized into two sets, one set was used to monitor the pulmonary hemodynamics, the other set was used to determine the cardiac impedance parameters, microemboli and leukocytes were obtained directly from the pulmonary microcirculation by use of the retrograde perfusion method. As compared with control group, lt was found that pulmonary artery pressure rose and pulmonary vascular resistance increased (p < 0.05), but did not correlate with lung water parameters (p > 0.05). At 1, 6 hr after diphosgene inhalation cardiac Impedance parameters did not change (p > 0.05~, as compared with before inhalation. Microemboli (21.8 increased (p< 0.05), as compared with the control group (106/L, 430e pulmonary hemodynamics, but could not effectively reduce the degree of pulmonary edema.
Safety data
- F
- 8-10-19
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LQ7350000
- ridadr
- UN 3277 6.1/PG 2
- hs_code
- 29159000
- Toxicity
- LC100 in rabbits (10-20 minutes exposure to vapor): 0.9 mg/l air (Klika, Mysliveckova)
- risk_code
- 26/28-34-26/27/28-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- T+,Xi
- safety_code
- 26-28-36/37/39-45-28A-36
- hazard_class
- 6.1
- Storage Class
- 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H300-H314-H330
- Limited Quantities
- 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 4 OralSkin Corr. 1B
- Precautionary statements
- P264-P270-P260-P280-P271-P284-P301+P310-P330-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P305+P351+P338-P405-P403+P233-P501
- Hazardous Substances Data
- 503-38-8(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as a chemical intermediate and miltary weapon; [CAMEO]
ORGANIC SYNTHESIS; MILITARY POISON GAS
Used in synthesis of isocyanides
Methods of Manufacturing
Prepared by photochlorination of methyl formate: W Hentschel, J Prakt Chem 36: 209 (1887); F Grignard et al, CR Acad Sci 169: 1074 (1919); eidem, ibid 1143; by photochlorination of methyl chloroformate: A Kling et al, ibid 1046; K Kurita, Y Iwakura, Org Syn 59: 195 (1980).
Formulations/Preparations
GRADE: TECHNICAL.
99% purity
Typical specifications of commercial chloroformates: purity, 98%; phosgene, <0.1%, iron, <10 ppm; acidity as HCl, <0.1%; alcohol or phenol, <2% /Chloroformic esters/
Commercial products have concentrations of 97-99 wt% /Chloroformic esters/
General Manufacturing Information
Carbonochloridic acid, trichloromethyl ester: ACTIVE
Most chloroformate production is used captively and production figures are not available /Chloroformic esters/
On a laboratory scale, trichloromethyl chloroformate (diphosgene) ... can be used as substitute for phosgene to synthesize isocyanates from amines
Applications
DescriptionDiphosgene (DP), trichloromethyl chloroformate, is a clear, colorless liquid with an odor similar to phosgene. It is noncombustible, a strong irritant to the eyes and tissues, and is toxic by inhalation and ingestion. DP has a boiling point of 127°C–128°C (263°F) and a vapor pressure of 4.2 at 68°F (20°C). The liquid density is 1.65, which is heavier than water, and a melting/freezing point of 314°F (157°C). Inhalation LC50 is 3600 mg/m3 for 10 min. Effects of exposure are quite similar to phosgene gas. Its molecular formula is ClCOOCCl3, and the structure and molecular formula are shown in Figure 8.38. The DOT lists diphosgene as a 6.1 poison liquid. The NFPA 704 designation for CG is estimated to be health 4, flammability 0, reactivity 1, and special 0. It has a four-digit UN identification number of 2972.
UsesTrichloromethyl chloroformate is used as a reagent in the synthesis of organic compounds. It serves as a source of phosgene used in some laboratory preparations. Also, it is used as a reactant for the synthesis of cyclic carbamimidates, N-alkenyl and cycloalkyl carbamates and prostate-specific membrane antigen-targeted anticancer prodrugs. In addition, it is involved in the preparation of an erythromycin A derivatives and antibody-drug conjugates. It is utilized in the conversion of amines, carboxylic acids, formamides in to isocyanates, acid chlorides and isocyanides respectively.
UsesReactant for preparation of:Cyclic carbamimidates using a monophosphine gold(i) catalystN-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligandsProstate-specific membrane antigen-targeted anticancer prodrugsPotential west nile virus protease inhibitorsAntibody-drug conjugates (ADCs)Erythromycin A derivatives
UsesIn organic synthesis; as war gas.
General DescriptionColorless liquid, odorless to fruity.
Upstream & downstream products
Downstream products
Suppliers83 total
Additional notes
Definitiondiphosgene: A colourless liquid,ClCO.O.CCl3, originally used in 1916by Germany in World War I as achemical warfare agent. It is nowused as a reagent in organic synthesis.See also carbonyl chloride.
Related reactions
Compound notes
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