Phenyl(trichloromethyl)mercury

Identifiers

CAS Number

* 3294-57-3 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 69255

EC Number |

* 221-960-9

PubChem CID

* 76799

UNII |

* JH955G783H Y

InChI

* InChI=1S/C6H5.CCl3.Hg/c1-2-4-6-5-3-1;2-1(3)4;/h1-5H;;

Key: MVIAEGXPYBMVPT-UHFFFAOYSA-N

SMILES

* C1=CC=C(C=C1)[Hg]C(Cl)(Cl)Cl

Properties

Chemical formula

| C7H5Cl3Hg
Molar mass | 396.06 g·mol−1
Appearance  | white solid
Melting point | 117–118 °C (243–244 °F; 390–391 K)
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

| toxicity
GHS labelling:

Pictograms

Signal word

| Danger

Hazard statements

| H300, H310, H330, H373, H410

Precautionary statements

| P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Phenyl(trichloromethyl)mercury is an organomercury compound with the formula C6H5HgCCl3. It is a white solid that is soluble in organic solvents. The compound is used as a source of dichlorocarbene, e.g. in cyclopropanation reactions, because the products are particularly easy to extract from the reaction mixture. Strong nucleophiles may catalyze the reaction by displacing CCl−
3 from mercury, although the free ion is not believed to form in the process. Unusually, the pure organomercury compound reacts with electron-poor alkenes, converting tetrachloroethylene to hexachlorocyclopropane:[1]

C6H5HgCCl3 → C6H5HgCl + CCl2
CCl2 \+ Cl2C=CCl2 → C3Cl6

The compound is prepared by treating phenylmercuric chloride [fi] with sources of dichlorocarbene. These include the base/haloform reaction and thermolysis of sodium trichloroacetate:[2][3]

NaO2CCCl3 \+ C6H5HgCl → C6H5HgCCl3 \+ NaCl + CO2

## Related compounds

[edit]

Closely related compounds include phenyl(bromodichloromethyl)mercury (CAS registry number 3294-58-4) and phenyl(tribromomethyl)mercury (CAS registry number 3294-60-8).[4] According to X-ray crystallography, the former has nearly linear coordination geometry at mercury, with a C-Hg-C angle of 179° and Hg-C distances of 2.047 Å.[5]

Also known is bis(trichloromethyl)mercury, Hg(CCl3)2.

## References

[edit]

1. ^ José Barluenga; Miguel Tomás; José M. González (2001). "Phenyl(trichloromethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp141. ISBN 0-471-93623-5.
2. ^ Ted J. Logan (1966). "Phenyl(trichloromethyl)mercury". Organic Syntheses. 46: 969. doi:10.15227/orgsyn.046.0098.
3. ^ Seyferth, D.; Lambert, R. L. (1969). "Halomethyl-metal compounds XX. An improved synthesis of phenyl(trihalomethyl)mercury compounds". Journal of Organometallic Chemistry. 16: 21–26\. doi:10.1016/S0022-328X(00)81631-9.
4. ^ Shipman, Michael (2001). "Phenyl(tribromomethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp140. ISBN 0-471-93623-5.
5. ^ R. E. Bachman; B. R. Maughon; D. J. McCord; K. H. Whitmire; W. E. Billups (1995). "Bromodichloromethyl)phenylmercury". Acta Crystallogr. C. 51 (10): 2033–2035\. doi:10.1107/S0108270195004501.

* v
* t
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Mercury compounds

Mercury(I)|

* HgH
* Hg2H2
* Hg2Br2
* Hg2Cl2
* Hg2F2
* Hg2I2
* Hg2(NO3)2
* Hg2O
* Hg2CO3
* Hg2SO4
* Hg2S (hypothetical)

Mercury(II)|

* HgH2
* HgNH2Cl
* HgSe
* HgS
* HgTe
* Hg(O2CCH3)2
* HgBr2
* HgCl2
* Hg(CN)2
* HgF2
* Hg(OH)2
* HgI2
* Hg(NO3)2
* HgO
* HgSO4
* Hg(SCN)2
* Hg(CNO)2
* Hg3N2
* Hg(Si(CH3)3)2
* K2HgI4

| Organomercury
compounds|

* Hg(CH3)2
* Hg(C2H5)2
* Hg(C6H5)2
* HgC6H5CH3CO2
* HgC6H5OB(OH)2
* HgC6H5NO3
* HgC6H5CCl3
* HgClC6H4CO2H
* HgOHCH2CHOCH3CH2(NHCO)
* C
36H
70HgO

* HgOHCH2CHOCH3CH2NHCOC6H4OCH2CO2H
* Na2HgOHC6HOBrC6H2OBrOCHC6H4CO2
* HgOC6H2CH3NO2
* NaHgC2H5SC6H4CO2

|

Mercury(IV)|

* HgF4 (hypothetical)

Amalgams|

* Na(Hg)
* Al(Hg)
* K(Hg)
* Au(Hg)
* Tl(Hg)
* Sn(Hg)

Mercury cations|

* Hg2+
* Hg2+2
* Hg2+3
* Hg2+4
* Hg4+3
* HgCH+3
* HgC2H+5
* HgC6H+5

*[CID]: Compound ID
*[H300]: H300: Fatal if swallowed
*[H310]: H310: Fatal in contact with skin
*[H330]: H330: Fatal if inhaled
*[H373]: H373: May cause damage to organs through prolonged or repeated exposure
*[H410]: H410: Very toxic to aquatic life with long lasting effects
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P262]: P262: Do not get in eyes, on skin, or on clothing.
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P273]: P273: Avoid release to the environment.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P284]: P284: Wear respiratory protection.
*[P301+P310]: P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
*[P302+P350]: P302+P350: IF ON SKIN: Gently wash with soap and water.
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P310]: P310: Immediately call a POISON CENTER or doctor/physician.
*[P314]: P314: Get Medical advice/attention if you feel unwell.
*[P320]: P320: Specific treatment is urgent (see ... on this label).
*[P321]: P321: Specific treatment (see ... on this label).
*[P322]: P322: Specific measures (see ... on this label).
*[P330]: P330: Rinse mouth.
*[P361]: P361: Remove/Take off immediately all contaminated clothing.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P391]: P391: Collect spillage.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...
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