Chloromethyl methyl ether

Chloromethyl methyl ether[1]

Names
Preferred IUPAC name

Chloro(methoxy)methane

Other names

MOM-Cl, CMME, MCD, Chlorodimethyl ether, Chloromethoxymethane, Dimethylchloroether, Methylchloromethyl ether

Identifiers

CAS Number

* 107-30-2 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 13852893 N

EC Number |

* 203-480-1

KEGG |

* C19160 N

PubChem CID

* 7864

RTECS number |

* KN6650000

UNII |

* 334G5B96VG N

UN number | 1239

InChI

* InChI=1S/C2H5ClO/c1-4-2-3/h2H2,1H3 N

Key: XJUZRXYOEPSWMB-UHFFFAOYSA-N N

* InChI=1/C2H5ClO/c1-4-2-3/h2H2,1H3

Key: XJUZRXYOEPSWMB-UHFFFAOYAK

SMILES

* COCCl

Properties

Chemical formula

| C2H5ClO
Molar mass | 80.51 g·mol−1
Appearance  | Colorless liquid
Odor | Irritating and acrid
Density | 1.06 g/mL
Melting point |  −103.5 °C (−154.3 °F; 169.7 K)
Boiling point |  55–57 °C (131–135 °F; 328–330 K)

Solubility in water

| reacts
Solubility | Soluble in alcohol and diethylether
Vapor pressure | 192 mmHg (21°C)[2]
Hazards
Main hazards | Carcinogen & Irritant
Safety data sheet | Safety Data Sheet Archived
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H225, H302, H312, H319, H332, H350

GHS precautionary statements

| P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P308+313, P312, P322, P330, P337+313
NFPA 704 (fire diamond)  |

Flash point |  0 °C (32 °F; 273 K) (open cup)[2]
NIOSH (US health exposure limits):

PEL (Permissible)

| OSHA-Regulated Carcinogen, no PEL[2]

REL (Recommended)

| Carcinogenic[2]

IDLH (Immediate danger)

| N.D.[2]

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

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting group,[3] and is thus often called MOM-Cl or MOM chloride. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation.[4]

## Preparation

A convenient synthesis of chloromethyl methyl ether in situ involves the reaction of dimethoxymethane and acetyl chloride in the presence of a Lewis acid catalyst[5] This route affords a methyl acetate solution of chloromethyl methyl ether of high purity. A similar method, using a high-boiling acyl chloride, can be used to prepare pure, dimethoxymethane being the only contaminant.[6] In contrast, the classical procedure reported in Organic Syntheses employing formaldehyde, methanol, and hydrogen chloride yields material significantly contaminated with the dangerous bis(chloromethyl) ether and requires fractional distillation.[7]

## Safety

The amount of time required to destroy residual chloromethyl methyl ether using various standard aqueous quench solutions (ammonium chloride solution, water, and sodium carbonate solution) has been measured. In all cases, a solution of chloromethyl methyl ether in toluene/methyl acetate was destroyed (to within detection limit) after vigorous stirring with the quench solution for 15 minutes.[5]

CMME is a known human carcinogen.[8] Chronic exposure can increase the incidence of respiratory cancers, including small cell carcinoma.[9] It is one of 13 chemicals regulated by the Occupational Safety and Health Administration despite not having an established permissible exposure limit.[10][11]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[12] It listed in Schedule 1 Part 1 of Canada's Prohibition of Certain Toxic Substances Regulations.[13]

## References

1. ↑ Sigma-Aldrich
2. ↑ 2.0 2.1 2.2 2.3 2.4 NIOSH Pocket Guide to Chemical Hazards. "#0129". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0129.html.
3. ↑ Protective Groups in Organic Synthesis, T. W. Greene and P. G. M. Green, 3rd Edition, pages 27-33. ISBN 0-471-16019-9
4. ↑ Wuts, Peter G. M. (2001). "Chloromethyl Methyl Ether". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc118. ISBN 0471936235.
5. ↑ 5.0 5.1 Berliner, Martin A.; Belecki, Katherine (2007). "Synthesis of alpha-Halo Ethers from Symmetric Acetals and in situ Methoxymethylation of an Alcohol". Organic Syntheses 84: 102. doi:10.15227/orgsyn.084.0102.
6. ↑ R.J. Linderman, M. Jaber, B.D. Griedel, J. Org. Chem. 1994, 59, 6499-6500.
7. ↑ C. S. Marvel and P. K. Porter (1929). "Monochloromethyl Ether". Organic Syntheses 9: 58. doi:10.15227/orgsyn.009.0058.
8. ↑ bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
9. ↑ "Chloromethyl methyl ether". U.S. Environmental Protection Agency, Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011.
10. ↑ NIOSH Pocket Guide to Chemical Hazards
11. ↑ Appendix B - Thirteen OSHA-Regulated Carcinogens
12. ↑ 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities (July 1, 2008 ed.). Government Printing Office. http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf. Retrieved October 29, 2011.
13. ↑ "Prohibition of Certain Toxic Substances Regulations, 2012". Government of Canada. p. 11. https://laws-lois.justice.gc.ca/PDF/SOR-2012-285.pdf.

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*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H319]: Causes serious eye irritation
*[H332]: Harmful if inhaled
*[H350]: May cause cancer
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P337+313]: Get medical advice/attention