57-06-7

Basic information

• Product Name: Allyl isothiocyanate
• Synonyms: 1-Propene, 3-isothiocyanato-;1-Propene,3-isothiocyanato-;3-isothiocyanato-1-propen;3-iso-Thiocyanatoprop-1-ene;3-isothiocyanato-prop-1-ene;3-isothiocyanato-propen;3-isothiocyanato-propene;Allyl isosulfocyanate
• CAS NO: 57-06-7
• Molecular Formula: C₄H₅NS
• Molecular Weight: 99.15
• EINECS: 200-309-2
• Product Categories: thioester Flavor;VIOFORM
• Mol File: 57-06-7.mol
• Article Data: 33

Chemical Properties

• Melting Point: -80 °C
• Boiling Point: 151 °C
• Flash Point: 115 °F
• Appearance: White/Fine Crystalline Powder
• Density: 1.013 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.57mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: 2 g/L (20 ºC)
• Sensitive: Moisture Sensitive
• Stability: Stable. Combustible. Incompatible with oxidizing agents, acids, water, alcohols, strong bases, amines. Darkens on aging.
• Merck: 14,295
• BRN: 773748
• CAS DataBase Reference: Allyl isothiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl isothiocyanate(57-06-7)
• EPA Substance Registry System: Allyl isothiocyanate(57-06-7)

Safety Data

• Hazard Codes: T,N
• 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
• Hazardous Substances Data: 57-06-7(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 57-06-7 differently. You can refer to the following data:
1. colourless or light amber oily liquid
2. Allyl isothiocyanate is a highly flammable, colorless to pale yellow, oily liquid. Air contact may cause darkening. Pungent, irritating odor and acrid taste
3. Allyl Isothiocyanate is the main component of mustard oil (>95%). It is a colorless oil with a typical mustard odor and can be prepared by reacting allyl chloride with alkaline-earth or alkali rhodanides.
4. A colorless liquid with very pungent, irritating odor and acrid taste; lacrimatory

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

Different sources of media describe the Uses of 57-06-7 differently. You can refer to the following data:
1. Allyl Isothiocyanate is a synthetic flavoring agent that is a moder- ately stable, colorless to pale yellow liquid of pungent and irritating odor. it should be stored in glass containers. it is used as an artificial oil of mustard and as an imitation horseradish flavor with applica- tion in condiments, meats, and pickles at 87 ppm. it is also termed mustard oil.
2. antiseptic, antiamebic
3. manufacture of flavors; war gas.

Preparation

By distillation of sodium thiocyanate and allyl chloride

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.

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

InChI:InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2

Upstream product

• 506-68-3 bromocyane 
• 6937-97-9 allyl(benzyl)sulfide 
• 860574-47-6 N-acetyl-N'-allyl-N-(4-chloro-phenyl)-thiourea 
• 860750-34-1 N-acetyl-N'-allyl-N-(4-bromo-phenyl)-thiourea 
• 143-33-9 sodium cyanide 
• 109-57-9 Allylthiourea 
• 103-71-9 phenyl isocyanate 
• 7341-63-1 1-allyl-3-phenyl-thiourea 
• 860750-31-8 N'-allyl-N-benzoyl-N-phenyl-thiourea 
• 71-43-2 benzene 
• 2835-21-4 allyl isocyanide 
• 333-20-0 potassium thioacyanate 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 64574-86-3 N-allyl-pyrrolidine-1-carbothioamide 
• 880-14-8 1-allyl-3-(pyridin-2-yl)thiourea 
• 15886-24-5 4-allyl-1-(2-furoyl)-3-thiosemicarbazide 
• 17073-29-9 N-α-naphthyl-N'-allylthiourea 
• 1207-94-9 N-Allyl-N'-<2-methoxy-phenyl>-thioharnstoff 
• 331-37-3 N-allyl-N'-(3-trifluoromethyl-phenyl)-thiourea 
• 1205-89-6 1-allyl-3-(4-methylphenyl)-thiourea 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 
• 463-56-9 thiocyanic acid 
• 1138-72-3 N-allyl-N'-(4-methoxy-phenyl)-thiourea 
• 21263-59-2 3-prop-2-en-1-yl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one 
• 105-81-7 1-allyl-3-(2-hydroxyethyl)-2-thiourea 
• 463-58-1 carbon oxide sulfide 
• 692-33-1 N-allylacetamide 

Relevant articles and documents

Effects of intact glucosinolates and products produced from glucosinolates in myrosinase-catalyzed hydrolysis on the potato cyst nematode (Globodera rostochiensis cv. Woll)

The potato cyst nematode (Globodera rostochiensis cv. Woll) is responsible for large yield losses in the potato crop, and opportunities for reducing the attack of these plant nematode species are, therefore, important. This study has been devoted to the testing of the in vitro effects on the potato cyst nematode of eight glucosinolates [prop-2-enyl-, but-3-enyl-, (R)-4-methylsulfinylbut-3-enyl-, benzyl-, phenethyl-, 4-hydroxybenzyl-, (2S)-2-hydroxybut-3-enyl-, and (2R)-2-hydroxy-2-phenylethylglucosinolate] as well as the effects of the products of this myrosinase-catalyzed hydrolysis. The glucosinolates were used at three concentrations, 0.05, 0.3, and 1.0 mg/mL, in the presence or absence of the enzyme myrosinase. The effects of the compounds on the mortality were monitored every 8 h for a 72 h period. No effects were found for any of the intact glucosinolates. However, when active myrosinase was included with 1 mg/mL phenethylglucosinolate at pH 6.5, 100% mortality was observed within just 16 h. A similar effect was achieved at the same concentration of benzyl-and prop-2-enylglucosinolates in the myrosinase-containing solutions, although longer exposures were required (24 and 40 h, respectively). The main aglucone products released from the glucosinolates with pronounced effects on the nematodes were shown to be the corresponding isothiocyanates. The results suggest that mixtures of these specific glucosinolates and active myrosinase or autolysis of plant materials containing these enzymes and glucosinolates might be used to control the potato cyst nematode in the soil.

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Synthesis method for high purity allyl isothiocyanate and cosmetic composition comprising high purity allyl isothiocyanate

The present invention relates to a synthesis method for a high-purity allyl isothiocyanate compound, and a functional cosmetic composition containing the allyl isothiocyanate compound according to the synthesis method as an active ingredient. More particularly, as it has been confirmed that the purity of allyl isothiocyanate synthesized through a three-step synthesis method using allylamine as a starting material is 99%, high-purity allyl isothiocyanate synthesized by the synthesis method may be provided as a functional cosmetic composition for preventing or ameliorating atopic dermatitis or acne.COPYRIGHT KIPO 2020

Preparation method of isothiocyano compound

The invention discloses a preparation method of an isothiocyano compound. An ammonium thiocyanate, sodium thiocyanate or potassium thiocyanate water solution and a halide are used as raw materials, and an isothiocyano compound is synthesized under the action of a phase transfer catalyst. The requirements that the thiocyanate radical in each batch of reaction is excessive by 10% and the yield is high are met, the purpose that the concentration of thiocyanic acid in wastewater is very low is realized, complex wastewater treatment equipment and treatment operation are avoided, and environmental protection pressure is reduced. The preparation method is a green preparation method, and solves the problems of extremely difficult degradation and high biotoxicity of thiocyanate-containing wastewater in conventional isothiocyano compound production. The method is simple to operate and is suitable for industrial production.