629-12-9

Basic information

• Product Name: PENTYL ISOTHIOCYANATE
• Synonyms: Pentane, 1-isothiocyanato-;1-ISOTHIOCYANATO-PENTANE;1-PENTYL ISOTHIOCYANATE;N-AMYL ISOTHIOCYANATE;N-PENTYL ISOTHIOCYANATE;PENTYL ISOTHIOCYANATE;PENTYL ISOTHIOCYANATE 99%;Pentyl isothiocyanate, 95+%
• CAS NO: 629-12-9
• Molecular Formula: C₆H₁₁NS
• Molecular Weight: 129.22
• EINECS: 211-075-6
• Mol File: 629-12-9.mol

Chemical Properties

• Boiling Point: 95 °C
• Flash Point: 32°C
• Appearance: /
• Density: 0.93
• Vapor Pressure: 0.649mmHg at 25°C
• Refractive Index: 1.4965
• Sensitive: Moisture Sensitive
• BRN: 1746691
• CAS DataBase Reference: PENTYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTYL ISOTHIOCYANATE(629-12-9)
• EPA Substance Registry System: PENTYL ISOTHIOCYANATE(629-12-9)

Safety Data

• Statements: 10-22-23-36/37/38-42
• Safety Statements: 26-36/37/39
• RIDADR: 3080
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 629-12-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to yellow liquid; sharp green irritating aroma

InChI:InChI=1/C6H11NS/c1-2-3-4-5-7-6-8/h2-5H2,1H3

Upstream product

• 463-71-8 thiophosgene 
• 110-58-7 n-Pentylamine 
• 75-15-0 carbon disulfide 
• 646-14-0 1-nitrohexane 
• 17356-08-0 thiourea 
• 87488-23-1 N-hydroxyhexanimidoyl chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 1412426-97-1 C₆H₁₃NS₂*C₆H₁₅N 
• 18971-59-0 1-pentylisonitrile 

Downstream Products

• 6318-96-3 1-carbamoyl-4-pentyl thiosemicarbazide 
• 2834-33-5 1-Phenyl-6-pentyl-hydrazodithiocarbonamid 
• 1516-34-3 n-Pentylthiourea 
• 905831-17-6 1-((2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-3-(tert-butoxycarbonylamino)-2-hydroxy-6-methylheptyl)-3-pentylthiourea 
• 1427279-03-5 1-(3-chlorobenzoyl)-4-pentylthiosemicarbazide 
• 1427279-09-1 C₁₃H₁₆ClN₃S 

Relevant articles and documents

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

Synthesis and biological activity of diisothiocyanate-derived mercapturic acids

This Letter deals with new non-natural diisothiocyanates, their mercapturic acid derivatives - conjugated with N-acetylcysteine as well as their antiproliferative activity towards human colon cancer cell lines and their inhibitory potency towards histone deacetylase activity. The activity of analysed isothiocyanates is not significantly different than their N-acetylcysteine conjugates. In comparison to simple mono-isothiocyanate analogues, aliphatic diisothiocyanates and their conjugates are much more active than the simple presence of two isothiocyanate functionalities could indicate.

Synthesis and structure-activity relationships of aliphatic isothiocyanate analogs as antibiotic agents

Isothiocyanates (ITCs) are one of the many classes of breakdown products of glucosinolates found in plants and exhibit biologic activity against various pathogens. In this work, aliphatic isothiocyanates were prepared and the antimicrobial activities against plant pathogenic fungi and bacteria were tested to understand the structure-activity relationships. The results indicated that longer-chain derivatives exert a steric inhibition on toxicity of ITCs against Rhizoctonia solani because of steric hindrance and the order of the eight aliphatic ITCs was ethyl > n-propyl > methyl > n-hexyl > n-octyl > n-butyl > n-heptyl > n-pentyl. Because the hydrophobicity of ITCs was enhanced by increasing alkyl chain length, the antibacterial activity of ITCs against Erwinia carotovora was moderately intense with an increase in hydrophobicity and the order was n-octyl > n-pentyl > n-heptyl > n-hexyl > n-propyl > n-butyl > methyl > ethyl. The present study revealed that some of the compounds exhibited promising antimicrobial activity and could be used as an acceptable alternative to the traditional synthetic fungicides for controlling R. solani and E. carotovora.

A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate

Alkyl and aryl amines are converted smoothly to the corresponding isothiocyanates via the dithiocarbamates in good to excellent yields using di-tert-butyl dicarbonate (Boc2O) and 1-3 mol % of DMAP or DABCO as catalyst. As most of the byproducts are volatile, the work-up involves simple evaporation of the reaction mixture.

Triazole derivative and pharmaceutical use thereof

An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) STR1 or the following formula (III) STR2 wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all, have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.

A facile one-pot preparation of isothiocyanates from aldoximes

Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.

A convenient synthesis of isothiocyanates from primary nitroalkanes

The reaction of primary nitroalkanes with thiourea in the presence of 4-chlorophenyl isocyanate and a catalytic amount of triethylamine in benzene afforded isothiocyanates in moderate yields.

Mesoionic purinone analogs. 7. In vitro antibacterial activity of mesoionic 1,3,4 thiadiazolo[3,2 a]pyrimidine 5,7 diones

The discovery of in vitro antibacterial activity of mesoionic thiazolo[3,2-αDpyrimidine-5,7-diones and mesoionic 1,3,4-thiadiazolo[3,2-α]pyrimidine-5,7-diones has been recently reported. These compounds are members of a large, virtually unknown, class of mesoionic structures, termed mesoionic purinone analogs, which are isoelectronic and isosteric to the purinones: xanthine, hypoxanthine, or purin-2-one. The formulation, classification, and quantum chemical study of a large number of these heterocyclic structures have been described. A series of alkyl and aryl substituted mesoionic 1,3,4-thiadiazolo[3,2-α]pyrimidine-5,7-diones, mesoionic xanthine analogs, was prepared and examined for antibacterial activity in order to develop structure activity relationships leading to more active derivatives.