109-75-1 | 3-Butenenitrile

Packsize	Purity	Availability	Price	Discounted Price
5g	98%(GC)	in stock	$25.00	$18.00
25g	97%	in stock	$42.00	$30.00
100g	97%	in stock	$106.00	$75.00
500g	97%	in stock	$387.00	$271.00

Description

• Catalog Number: AB64594
• Chemical Name: 3-Butenenitrile
• CAS Number: 109-75-1
• Molecular Formula: C5H6
• Molecular Weight: 66.1011
• MDL Number: MFCD00001962
• SMILES: C=CCC#C
• NSC Number: 2583

Computed Properties

• Complexity: 65
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 5
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 0.4

Upstream Synthesis Route

3-Butenenitrile, also known as allyl cyanide, is a versatile compound widely used in chemical synthesis. Its primary application lies in the production of various valuable chemicals through different chemical reactions. 3-Butenenitrile serves as a crucial building block in organic synthesis due to its ability to undergo several important reactions, making it a key player in the creation of complex molecules. One of the primary uses of 3-Butenenitrile is as a precursor in the preparation of various pharmaceuticals, agrochemicals, and specialty chemicals. It can be utilized in the synthesis of pharmaceutical intermediates such as anti-cancer drugs and antibiotics. Additionally, 3-Butenenitrile is a vital component in the production of fragrances, dyes, and polymers, contributing to the creation of a wide range of consumer products. Its versatility and reactivity make it a valuable tool in the hands of chemists for designing and constructing diverse molecular structures and functional materials.

Literature

• Vestibulotoxic properties of potential metabolites of allylnitrile.

  Toxicological sciences : an official journal of the Society of Toxicology 20130901

• New tetraphosphorus ligands for highly linear selective hydroformylation of allyl and vinyl derivatives.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20120806

• Role of CYP2E1-mediated metabolism in the acute and vestibular toxicities of nineteen nitriles in the mouse.

  Toxicology letters 20120125

• Branching fractions of the CN + C3H6 reaction using synchrotron photoionization mass spectrometry: evidence for the 3-cyanopropene product.

  The journal of physical chemistry. A 20111124

• Asymmetric synthesis of isothiazoles through Cu catalysis: direct catalytic asymmetric conjugate addition of allyl cyanide to α,β-unsaturated thioamides.

  Angewandte Chemie (International ed. in English) 20110816

• A new unifying hypothesis for lathyrism, konzo and tropical ataxic neuropathy: nitriles are the causative agents.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110301

• Butenenitriles have low axonopathic potential in the rat.

  Toxicology letters 20110205

• Direct catalytic asymmetric addition of allyl cyanide to ketones via soft Lewis acid/hard Brønsted base/hard Lewis base catalysis.

  Journal of the American Chemical Society 20100421

• Preconditioning with subneurotoxic allyl nitrile: protection against allyl nitrile neurotoxicity.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100201

• Synthesis and application of modular phosphine-phosphoramidite ligands in asymmetric hydroformylation: structure-selectivity relationship.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20100118

• Elementary reactions and their role in gas-phase prebiotic chemistry.

  International journal of molecular sciences 20090501

• Direct catalytic asymmetric addition of allyl cyanide to ketones.

  Journal of the American Chemical Society 20090311

• Allylnitrile metabolism by CYP2E1 and other CYPs leads to distinct lethal and vestibulotoxic effects in the mouse.

  Toxicological sciences : an official journal of the Society of Toxicology 20090201

• Direct catalytic asymmetric addition of allylic cyanides to ketoimines.

  Journal of the American Chemical Society 20081105

• Reaction dynamics on the formation of 1- and 3-cyanopropylene in the crossed beams reaction of ground-state cyano radicals (CN) with propylene (C3H6) and its deuterated isotopologues.

  The journal of physical chemistry. A 20081002

• Modular chiral bidentate phosphonites: design, synthesis, and application in catalytic asymmetric hydroformylation reactions.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

• Adsorption of 125I-labeled immunoglobulin G, its F(ab')2 and Fc fragments onto plasma-polymerized films.

  Biosensors & bioelectronics 20070515

• Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations.

  Journal of agricultural and food chemistry 20061004

• Induction of detoxication enzymes in mice by naturally occurring allyl nitrile.

  Journal of agricultural and food chemistry 20051116

• Surface reactions of 3-butenenitrile on the Si(001)-2 x 1 surface at room temperature.

  The journal of physical chemistry. B 20050707

• Binolam-AlCl: a two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20050620

• Synthesis of unsaturated amino alcohols through unexpectedly selective Ru-catalyzed cross-metathesis reactions.

  Organic letters 20050526

• Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.

  Journal of the American Chemical Society 20050413

• Parallel ligand screening on olefin mixtures in asymmetric hydroformylation reactions.

  Organic letters 20040916

• Synthesis and application of a new bisphosphite ligand collection for asymmetric hydroformylation of allyl cyanide.

  The Journal of organic chemistry 20040611

• Kinetics, thermodynamics, and effect of BPh3 on competitive C-C and C-H bond activation reactions in the interconversion of allyl cyanide by [Ni(dippe)].

  Journal of the American Chemical Society 20040324

• In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040301

• Allylnitrile: generation from cruciferous vegetables and behavioral effects on mice of repeated exposure.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040301

• Pi-halogen dimer interactions and the inclusion chemistry of a new tetrahalo aryl host.

  Organic & biomolecular chemistry 20040121

• Removal of nitriles from synthetic wastewater by acrylonitrile utilizing bacteria.

  Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering 20040101

• Competition and selectivity in the reaction of nitriles on ge(100)-2x1.

  Journal of the American Chemical Society 20030423

• Plant-derived biomolecules in fermented cabbage.

  Journal of agricultural and food chemistry 20021106

• [Determination of isothiocyanates and related compounds in mustard extract and horseradish extract used as natural food additives].

  Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20020201

• Glucosinolate breakdown products as insect fumigants and their effect on carbon dioxide emission of insects.

  BMC ecology 20020101

• The effect of chlorination on organocyanide compounds.

  Water environment research : a research publication of the Water Environment Federation 20020101

• Biodegradation of glucosinolates in brown mustard seed meal (Brassica juncea) by Aspergillus sp. NR-4201 in liquid and solid-state cultures.

  Biodegradation 20020101

• Behavioural disturbances and sensory pathology following allylnitrile exposure in rats.

  Brain research 20010622

• The ototoxic effects induced in rats by treatment for 12 weeks with 2-butenenitrile, 3-butenenitrile and cis-2-pentenenitrile.

  Pharmacology & toxicology 20010301

• Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster.

  Planta 20010301