Allyl isothiocyanate Chemical Properties

Melting point:

-80 °C

Boiling point:

151 °C

Density 

1.013 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.529(lit.)

FEMA 

2034 | ALLYL ISOTHIOCYANATE

Flash point:

115 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Fine Crystalline Powder

color 

White

Odor

at 0.01 % in propylene glycol. strong pungent mustard

Odor Type

sulfurous

Water Solubility 

2 g/L (20 ºC)

Sensitive 

Moisture Sensitive

JECFA Number

1560

Merck 

14,295

BRN 

773748

Dielectric constant

17.199999999999999

Stability:

Stable. Combustible. Incompatible with oxidizing agents, acids, water, alcohols, strong bases, amines. Darkens on aging.

LogP

2.15

CAS DataBase Reference

57-06-7(CAS DataBase Reference)

NIST Chemistry Reference

Allyl isothiocyanate(57-06-7)

IARC

3 (Vol. 73, Sup 7) 1999

EPA Substance Registry System

Allyl isothiocyanate (57-06-7)

Safety Information

Hazard Codes 

T,N

Risk Statements 

10-24/25-36/37/38-42/43-50/53-43-23/24/25-34-25

Safety Statements 

26-36/37-45-60-61-36/37/39-28B-24-16-23-7/8

RIDADR 

UN 1545 6.1/PG 2

WGK Germany 

3

RTECS 

NX8225000

F 

8-9-13-19

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29309070

Hazardous Substances Data

57-06-7(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 339 mg/kg (Jenner)

MSDS

• Language:English Provider:Allyl isothiocyanate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Allyl isothiocyanate Usage And Synthesis

Chemical Properties

Allyl Isothiocyanate is the main component of mustard oil (>95%). It is a highly flammable, colorless to pale yellow, oily liquid with a typical mustard odor. Exposure to air might cause it to darken. It has a pungent, irritating smell and a bitter taste that can cause lacrimatory. It can be synthesized by reacting allyl chloride with alkaline-earth or alkali rhodanides.

Occurrence

In the essential oil from seeds of Brassica nigra Koch, Brassica juncea Hook. and Thoms., and Thlaspi arvense; in the essential oil from roots of Cochlearia armoracia; in the seeds and roots of Alliaria officinalis; in onion juice; and in the seeds of various Cruciferae. Reported found in pineapple (Anans comoscus), raw cabbage, cooked cabbage, sauerkraut, milk, heated beans, horseradish (Armoracia lapathifolia), raw cauliflower, Brussels sprouts, turnip, Chinese cabbage, wasabi (Japanese horseradish) (Wasabi japonica).

Uses

Allyl isothiocyanate, also known as mustard oil, is a synthetic flavoring agent that is used as an artificial oil of mustard and as an imitation horseradish flavor with application in condiments, meats, and pickles at 87 ppm. It has additional applications as an antiseptic, antiamebic, manufacture of flavors and war gas.

Preparation

By distillation of sodium thiocyanate and allyl chloride

Definition

ChEBI: Allyl isothiocyanate is an isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152℃, it is responsible for the pungent taste of mustard, horseradish, and wasabi. It has a role as a lachrymator, a metabolite, an antimicrobial agent, an apoptosis inducer and an antineoplastic agent. It is an isothiocyanate and an alkenyl isothiocyanate.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 3503, 1991 DOI: 10.1016/0040-4039(91)80817-P

General Description

A colorless to pale-yellow oily liquid with an irritating odor. Flash point 135°F. Boiling point 300°F. Poisonous by ingestion and skin absorption. Emits toxic fumes when heated to high temperature. Insoluble in water and slightly denser than water. Hence sinks in water. Used to make other chemicals and as a fumigant. It should be stored in glass containers.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

A routine preparation by interaction of allyl chloride and sodium thiocyanate in an autoclave at 5.5 bar exploded violently at the end of the reaction. Peroxides were not present or involved and no other cause could be found, but extensive decomposition occurred when allyl isothiocyanate was heated to 250°C. in glass ampoules [Ind. Eng. Chem. 1941:19 1408].

Hazard

Toxic via ingestion, inhalation, skin con- tact; fire risk. Questionable carcinogen.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Contact allergens

Allyl isothiocyanate is generated by enzymatic hydrolysis of the glucoside sinigrin, present in Cruciferae- Brassicaceae, mainly the oil from black mustard seed (Brassica nigra Koch). It may induce irritant and sometimes allergic contact dermatitis, mimicking the “tulip finger” dermatitis.

Anticancer Research

This compound was tested on Ehrlich ascites tumor cells transplanted in Swissalbino mice using HEK293 cells as control. There was a significantly reduced ascitessecretion and tumor cell proliferation. Also the vascular endothelial growth factorexpression was inhibited. The apoptosis was induced in tumor cells, and cellcycle was arrested at G1 phase (Ichwan et al. 2014).

Safety Profile

Suspected carcinogen with experimental neoplastigenic and tumorigenic data. Poison by ingestion, skin contact, intravenous, subcutaneous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. An eye irritant. An allergen. May cause contact dermatitis. Mutation data reported. A flammable liquid. Highly reactive. When heated to decomposition (above 250') or on contact with acid or acid fumes it emits highly toxic fumes of CN-, SO,, and NOx. To fight fire, use foam, CO2, dry chemical. See also ALLYL COMPOUNDS and ESTERS.

Potential Exposure

Used in fumigants, veterinary drugs, ointments and counter irritants, mustard plasters, and as a flavoring agent.

Shipping

UN1545 Allyl isothiocyanate, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3 flammable liquids.

Purification Methods

Fractionate the isothiocyanate using an efficient column, preferably in a vacuum. It is a yellow pungent, irritating and TOXIC (suspected CARCINOGEN) liquid. Store it in a sealed tube under N2. The N'-benzylthiourea derivative has m 94.5o (from aqueous EtOH) [Weller et al. J Am Chem Soc 74 1104 1952]. [Beilstein 4 IV 1081.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, alcohols, amines

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