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Tosylmethyl isocyanide

CAS No.
36635-61-7
Chemical Name:
Tosylmethyl isocyanide
Synonyms
TOSMIC;isocyanide;P-TOLUENESULFONYLMETHYL ISOCYANIDE;Toluenesulfonyl Methyl isocyanide;Tosylmethy isocyanide ,98%;4-TOLUENESULFONYLMETHYL ISOCYANIDE;P-TOLUENESULPHONYLMETHYL ISOCYANIDE;Tosylmethyl isocyani;LABOTEST-BB LT00159629;TOSYLMETHYL ISOCYANIDE
CBNumber:
CB5311774
Molecular Formula:
C9H9NO2S
Molecular Weight:
195.24
MDL Number:
MFCD00000005
MOL File:
36635-61-7.mol
MSDS File:
SDS
Last updated:2024-02-29 17:01:30

Tosylmethyl isocyanide Properties

Melting point 109-113 °C(lit.)
Density 1.2721 (rough estimate)
refractive index 1.5270 (estimate)
storage temp. 2-8°C
solubility water: slightly soluble
form Liquid
color Clear
Water Solubility insoluble
Sensitive Moisture Sensitive
Merck 14,9556
BRN 3592382
Exposure limits NIOSH: IDLH 25 mg/m3
InChI InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
InChIKey BBNNLJMGPASZPD-UHFFFAOYSA-N
SMILES S(C1C=CC(C)=CC=1)(=O)(=O)C[N+]#[C-]
CAS DataBase Reference 36635-61-7(CAS DataBase Reference)
FDA UNII C35FD6OLH8

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300+H310+H330
Precautionary statements  P262-P280-P301+P310+P330-P302+P352+P310-P304+P340+P310
Hazard Codes  T,Xi
Risk Statements  23/24/25
Safety Statements  36/37-45-38-36/37/39-28A
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
21
Hazard Note  Irritant
HazardClass  6.1(b)
PackingGroup  III
HS Code  29299000
NFPA 704
1
3 1

Tosylmethyl isocyanide price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 188204 p-Toluenesulfonylmethyl isocyanide 98% 36635-61-7 5g $39.9 2024-03-01 Buy
Sigma-Aldrich 188204 p-Toluenesulfonylmethyl isocyanide 98% 36635-61-7 25g $135 2024-03-01 Buy
TCI Chemical T1046 p-Toluenesulfonylmethyl Isocyanide >98.0%(HPLC)(N) 36635-61-7 5g $37 2024-03-01 Buy
TCI Chemical T1046 p-Toluenesulfonylmethyl Isocyanide >98.0%(HPLC)(N) 36635-61-7 25g $116 2024-03-01 Buy
Alfa Aesar A14312 p-Toluenesulfonylmethyl isocyanide, 97% 36635-61-7 5g $36.65 2024-03-01 Buy
Product number Packaging Price Buy
188204 5g $39.9 Buy
188204 25g $135 Buy
T1046 5g $37 Buy
T1046 25g $116 Buy
A14312 5g $36.65 Buy

Tosylmethyl isocyanide Chemical Properties,Uses,Production

Description

Tosylmethyl isocyanide is a versatile synthon in organic chemistry, widely used as a reagent for the preparation of biologically active pyrroles and imidazoles. Tosylmethyl isocyanide undergoes a base-promoted 1,3-dipolar cycloaddition reaction with immobilised imines under microwave irradiation to give 1,5-disubstituted imidazoles.

Chemical Properties

Pale yellow to light brown crystalline powder

Uses

Tosylmethyl Isocyanide is used as a synthetic reagent in the preparation of variety or biologically active heterocycles such as pyrroles and imidazoles. Tosylmethyl Isocyanide is reported to inhibit [ Fe]-hydrogenase with very high affinity.

Definition

Tosylmethyl isocyanide is a chemical compound of cyanide that Versatile synthon in organic chemistry, especially in the synthesis of heterocyclic Compounds.

Preparation

N-(p-Tolylsulfonylmethyl)formamide 1609:
36635-61-7 synthesis
A 3-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, a condenser, and a thermometer, was charged with sodium p-toluenesulfinate 1606 (267 g, 1.5 mol). After the addition of water (750 mL), a 34–37% solution of formaldehyde 1607 (350 mL, 378 g, ca. 4.4 mol), formamide 1608 (600 mL, 680 g, 15 mol), and formic acid (200 mL, 244 g, 5.3 mol), the stirred reaction mixture was heated at 90 C°. The sodium p-toluenesulfinate dissolved during the heating, and the clear solution was kept at 90–95 C° for 2 h. It was then cooled in an ice/salt bath with continued stirring and further cooled overnight in a freezer at 20 C°. The white solid produced was collected by suction filtration. It was washed thoroughly in a beaker by stirring with three 250 mL portions of iced water. The product was dried under reduced pressure over phosphorus pentoxide at 70 C° to provide 134–150 g (42–47%) of crude N-(p-tolylsulfonylmethyl)formamide 1609; mp 106–110 C°. This product was sufficiently pure to be used directly in the following reaction.

Application

Tosylmethyl isocyanide was used:
(1) in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton;
(2) as reagent in the preparation of biologically active pyrroles and imidazoles;
(3) as the isonitrile component in a diastereoselective Passerini reaction employing sugar-derived aldehydes.

Purification Methods

Use an efficient fume cupboard. Purify TOSMIC by dissolving (50g) in CH2Cl2 (150mL) and passing it through a column (40x3cm) containing neutral alumina (100g) in CH2Cl2 and eluting with CH2Cl2. A nearly colourless solution (700mL) is collected, evaporated in vacuo and the residue (42-47g) of TOSMIC (m 113-114o dec) is recrystallised once from MeOH (m 116-117o dec). [Hoogenboom et al. Org Synth 57 102 1977, Lensen Tetrahedron Lett 2367 1972.] It also crystallises from EtOH (charcoal) [Saito & Itano, J Chem Soc, Perkin Trans 1 1 1986].

36635-56-0
36635-61-7
Synthesis of Tosylmethyl isocyanide from N-(p-Tolylsulfonylmethyl)formamide
Global( 555)Suppliers
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ROSEWA HOLDING GROUP CO.,LIMITED
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View Lastest Price from Tosylmethyl isocyanide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tosylmethyl isocyanide pictures 2024-01-06 Tosylmethyl isocyanide
36635-61-7
US $0.00 / kg 1kg 99% 1000000 Hebei Jingbo New Material Technology Co., Ltd
Tosylmethyl isocyanide pictures 2023-08-31 Tosylmethyl isocyanide
36635-61-7
US $100.00 / drum 1drum 99 5000 Hebei Fengqiang Trading Co., LTD
Tosylmethyl isocyanide pictures 2023-04-13 Tosylmethyl isocyanide
36635-61-7
US $0.00-0.00 / kg 1kg 99% 10ton ROSEWA HOLDING GROUP CO.,LIMITED
1-[(isocyanomethyl)sulfonyl]-4-methyl-benzen Tosylmethyl isocyani Isocyanomethyl 4-methylphenyl sulphone 4-[(Isocyanomethyl)sulphonyl]toluene, (Toluene-4-sulphonyl)methyl isocyanide (p-Toluensulfonyl)methylisocyanide (p-Tolylsulfonyl)methyl isocyanide, TosMIC, Tosylmethyl isocyanide (4-Methylphenylsulfonylmethyl) isocyanide 4-Methylphenylsulfonylmethyl isocyanide Tosylmethyl isocyanide,98% p-Toluenesulfonyl Isocyanide P-tolysulfonylmethylisocyanide TosylMethyl isocyanide, 98% 25GR TosylMethyl isocyanide, 98% 5GR 4-TolylsulfonylMethyl Isocyanide IsocyanoMethyl p-Tolyl Sulfone TosMIC Tosylmethyl Isocyanide p-ToluenesulonylMethy isocyanide 4-[(Isocyanomethyl)sulphonyl]toluene, (Toluene-4-sulphonyl)methyl isocyanide, TosMIC TosylMethyl Isocyanide, TOSMIC 4-TOLUENESULFONYLMETHYL ISOCYANIDE FOR S METHYLIDYNE[[(4-METHYLPHENYL)SULFONYL]METHYL]AMMONIUM LABOTEST-BB LT00159629 BENZENE, 1-[(ISOCYANOMETHYL)SULFONYL]-4-METHYL- 1-[(ISOCYANOMETHYL)SULFONYL]-4-METHYLBENZENE 4-TOLUENSULFONYLMETHYL ISOCYANIDE 4-TOLUENESULPHONYLMETHYL ISOCYANIDE (P-TOLYLSULFONYL)METHYL ISOCYANIDE TOSYLMETHYL ISOCYANIDE TOLUENE-4-SULFONYLMETHYL ISOCYANIDE 4-Toluenesulfonylmethyl isocyanate p-Toluenesulfonylmethyl isocyanide, 98+% p-Toluenesulfonylmethylisocyanide,97+% 1-ISOCYANOMETHANESULFONYL-4-METHYL-BENZENE p-toluenesulfonylmethyl isocyande p-Toluenesulfonylmethyl isocyanate P-TOLUENESULFONYLMETHYL ISOCYANIDE 98% p-ToluenesulfonylMethyl isocyanide, 98.5% p-Toluenesulfonylmethyl Isocyanide 4-Toluenesulfonylmethyl isocyanide for synthesis Tosylmethyleisocyanide 1-[(ISOCYANOMETHYL)SULFONYL]- Tosylmethyl isocyanide, 98%, for synthesis Tosylmethyl isocyanide ISO 9001:2015 REACH p-Toluenesulfonyl methylisocyanide (Tosmic, Tosyl methylisocyanide) Tosylmethy isocyanide ,98% Toluenesulfonyl Methyl isocyanide 4-TOLUENESULFONYLMETHYL ISOCYANIDE P-TOLUENESULFONYLMETHYL ISOCYANIDE P-TOLUENESULPHONYLMETHYL ISOCYANIDE TOSMIC isocyanide Toluenesulfonylmethyl isocyanide (TosMIC) P-toluenesulfonylmet hyliscyanide (p-methylphenyl)sulfonylmethyl]isonitrile 36635-61-7 CH3C6H4SO2CH2NC Organic Building Blocks Isocyanides