基本情報
- 標準SMILES
O=C(Cl)OC(Cl)(Cl)Cl- InChIKey
HCUYBXPSSCRKRF-UHFFFAOYSA-N- 分子式
- C2Cl4O2
- 平均分子量
- 197.8 g/mol
- 単同位体質量
- 195.86523996
概要
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.
名称と識別子
- 優先名称
- Diphosgene
- IUPAC
- trichloromethyl carbonochloridate
- 現地名
- (トリクロロメトキシ)ぎ酸クロリド
- 英語名
- Diphosgene
- 分子式
- C2Cl4O2
- 分子量
- 197.83
名称と別名
名称をさらに表示
データベース識別子
- CAS
503-38-8- PubChem CID
- 10426
- DTXSID
DTXSID60862065- UNII
- PO4Q4R80LV
- EC Number
- 207-965-9
- Nikkaji
- J12.981J
物性
構造計算による物性
- XLogP
- 3.1
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 1
- 重原子数
- 8
- 形式電荷
- 0
- 複雑度
- 94.7
実験および物理化学的性質
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
物理化学的性質
- 融点
- -57 °C · -57 °C
- 沸点
- 20 °C10 · 20 °C10 mm Hg(lit.)
- 比重(密度)
- 1.64 · 1.64
- 蒸気圧
- 13 hPa · 13 hPa ( 20 °C)
- 屈折率
- 20 · n20/D 1.458
- 闪点
- 110 °C · >110°C
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- Chloroform (Soluble), Ethyl Acetate (Sparingly)
- 外見
- 液体
- 色
- 無色透明
- 水溶解度
- 分解する可能性があります
- Merck
- 14 · 14,3334
- BRN
- 970225 · 970225
- 安定性
- 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 データベース
- 503 · 503-38-8(CAS DataBase Reference)
- NISTの化学物質情報
- Trichloromethyl chloroformate(503-38-8)
- EPAの化学物質情報
- Carbonochloridic acid, trichloromethyl ester (503-38-8)
化学的性質
化学的特性clear colorless liquid
安全と法規制
GHS分類
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.
危険有害性情報
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.
安全と保護具
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.
毒性情報
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.
安全データ
- F
- 8-10-19
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LQ7350000
- ridadr
- UN 3277 6.1/PG 2
- 毒性
- LC100 in rabbits (10-20 minutes exposure to vapor): 0.9 mg/l air (Klika, Mysliveckova)
- hs_code
- 29159000
- risk_code
- 26/28-34-26/27/28-36/37/38
- hazard_code
- T+,Xi
- safety_code
- 26-28-36/37/39-45-28A-36
- hazard_class
- 6.1
- packing_group
- II
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 4 OralSkin Corr. 1B
- ストレージクラス
- 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- 有毒物質データの
- 503-38-8(Hazardous Substances Data)
化学と産業
用途と製造
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
応用分野
解説ジホスゲン(diphosgene) ホスゲンに似た窒息性臭をもつ無色の液体。化学式 ClCOOCCl3 毒作用はホスゲンと似ているが中毒の持続性は高い。毒ガスとして利用。うすい濃度で吸うと、数時間後に突然死ぬことがある。
用途ジホスゲン(Diphosgene)は炭素と酸素と塩素の化合物である。ホスゲンダイマーとも呼ばれる。常温で無色の液体であり、有機合成の有用な試薬として用いられている。また、ホスゲン同様に毒性が強いため化学兵器として使用されたこともある。 ジホスゲンは、紫外線の下でクロロギ酸メチルを急速に塩素化させることによって生成する。また、ジホスゲンを熱分解するとホスゲンが生成する。 ホスゲンを使用する反応に代替物質として利用される。たとえば、イソシアン酸塩からのアミン生成、塩化カルボニル化合物から第二級アミン生成、カルボン酸から酸塩化物の合成、ホルムアミドからイソシアン化物の合成などが挙げられる。
説明Diphosgene (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.
使用In organic synthesis; as war gas.
一般的な説明Colorless liquid, odorless to fruity.
上流・下流製品情報
下流製品
サプライヤー50 社
補足説明
定義diphosgene: 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.
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