Allyl chloride

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Names
Preferred IUPAC name

3-Chloroprop-1-ene

Other names

3-Chloropropene
1-Chloro-2-propene[1]
3-Chloropropylene[1]

Identifiers

CAS Number

* 107-05-1 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:82379

ChEMBL |

* ChEMBL451126 Y

ChemSpider |

* 13836674 Y

EC Number |

* 209-675-8

KEGG |

* C19316

PubChem CID

* 7850

RTECS number |

* UC7350000

UNII |

* V2RFT0R50S N

UN number | 1100

InChI

* InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2 Y

Key: OSDWBNJEKMUWAV-UHFFFAOYSA-N Y

* InChI=1/C3H5Cl/c1-2-3-4/h2H,1,3H2

Key: OSDWBNJEKMUWAV-UHFFFAOYAQ

SMILES

* C=CCCl

Properties

Chemical formula

| C3H5Cl
Molar mass | 76.52 g·mol−1
Appearance  | Colorless, brown, yellow, or purple liquid[1]
Odor | pungent, unpleasant[1]
Density | 0.94 g/mL
Melting point |  −135 °C (−211 °F; 138 K)
Boiling point |  45 °C (113 °F; 318 K)

Solubility in water

| 0.36 g/100 ml (20 °C)
Solubility | soluble in ether, acetone, benzene, chloroform
Vapor pressure | 295 mmHg[1]

Refractive index (nD)

| 1.4055
Viscosity | 0.3130 mPa·s[2]
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H225, H302, H312, H315, H319, H332, H335, H341, H351, H373, H400

GHS precautionary statements

| P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+312, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P308+313, P312, P314
NFPA 704 (fire diamond)  |

Flash point |  −32 °C (−26 °F; 241 K)

Autoignition
temperature

|  390 °C (734 °F; 663 K)
Explosive limits | 2.9-11.2%
Lethal dose or concentration (LD, LC):

LC50 (median concentration)

| 11000 mg/m3 (rat, 2 hr)
11500 mg/m3 (mouse, 2 hr)
5800 mg/m3 (guinea pig, 2 hr)
22500 mg/m3 (rabbit, 2 hr)
10500 mg/m3 (cat, 2 hr)[3]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 1 ppm (3 mg/m3)[1]

REL (Recommended)

| TWA 1 ppm (3 mg/m3)
ST 2 ppm (6 mg/m3)[1]

IDLH (Immediate danger)

| 250 ppm[1]

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):

* PairSizeSet

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.[4]

## Contents

* 1 Production
* 1.1 Laboratory scale
* 1.2 Industrial scale
* 2 Reactions and uses
* 2.1 Illustrative reactions
* 3 Safety
* 4 See also
* 5 External links
* 6 References

## Production

### Laboratory scale

Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride.[5][4] Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.[6]

### Industrial scale

Allyl chloride is produced by the chlorination of propylene. At lower temperatures, the main product is 1,2-dichloropropane, but at 500 °C, allyl chloride predominates, being formed via a free radical reaction:

CH3CH=CH2 \+ Cl2 → ClCH2CH=CH2 \+ HCl

An estimated 800,000 tonnes were produced this way in 1997.[4]

## Reactions and uses

The great majority of allyl chloride is converted to epichlorohydrin.[4] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil),[7] and 1-bromo-3-chloropropane.

As an alkylating agent, it is useful in the manufacture of pharmaceuticals and pesticides, such as mustard oil.

### Illustrative reactions

Illustrative of its reactivity is its cyanation to allyl cyanide (CH2=CHCH2CN).[8] Being a reactive alkyl halide, it undergoes reductive coupling to give diallyl:[9]

2 ClCH2CH=CH2 \+ Mg → (CH2)2(CH=CH2)2 \+ MgCl2

It undergoes oxidative addition to palladium(0) to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2. Dehydrohalogenation gives cyclopropene.

## Safety

Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.[10]

## See also

* Allyl
* Allyl bromide
* Allyl iodide

## External links

* International Chemical Safety Card 0010
* NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0018.html.
* IARC Monograph *Allyl chloride.

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0018.html.
2. ↑ Viswanath, D.S.; Natarajan, G. (1989). Data Book on the Viscosity of Liquids. Hemisphere Publishing Corporation. ISBN 0-89116-778-1.
3. ↑ "Allyl chloride". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/107051.html.
4. ↑ 4.0 4.1 4.2 4.3 Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000.
5. ↑ Hofmann. Augustus William and Cahours. Augustus (1857) "Researches on a new class of alcohols," Philosophical Transactions of the Royal Society of London, 147: 555–574 ; see pp. 558–559.
6. ↑ Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry (5th ed.). London: Longman Science & Technical. pp. 558. ISBN 9780582462366. https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd.
7. ↑ F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim. doi:10.1002/14356007.a26_749
8. ↑ J. V. Supniewski; P. L. Salzberg (1941). "Allyl Cyanide". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=CV1P0046. ;  Collective Volume, 1, pp. 46
9. ↑ Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007.
10. ↑ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. http://siri.org/msds/mf/cards/file/0010.html. Retrieved 13 February 2012.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Allyl_chloride&oldid=814195"
*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H332]: Harmful if inhaled
*[H335]: May cause respiratory irritation
*[H341]: Suspected of causing genetic defects
*[H351]: Suspected of causing cancer
*[H373]: May cause damage to organs through prolonged or repeated exposure
*[H400]: Very toxic to aquatic life
*[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
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[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
*[P273]: Avoid release to the environment
*[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
*[P314]: Get Medical advice/attention if you feel unwell