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Tosylmethyl isocyanide

Product Name
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
Formula Weight
195.24
MOL File
36635-61-7.mol
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Tosylmethyl isocyanide Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
188204
Product name
p-Toluenesulfonylmethyl isocyanide
Purity
98%
Packaging
5g
Price
$39.9
Updated
2024/03/01
Sigma-Aldrich
Product number
188204
Product name
p-Toluenesulfonylmethyl isocyanide
Purity
98%
Packaging
25g
Price
$135
Updated
2024/03/01
TCI Chemical
Product number
T1046
Product name
p-Toluenesulfonylmethyl Isocyanide
Purity
>98.0%(HPLC)(N)
Packaging
5g
Price
$37
Updated
2024/03/01
TCI Chemical
Product number
T1046
Product name
p-Toluenesulfonylmethyl Isocyanide
Purity
>98.0%(HPLC)(N)
Packaging
25g
Price
$116
Updated
2024/03/01
Alfa Aesar
Product number
A14312
Product name
p-Toluenesulfonylmethyl isocyanide, 97%
Packaging
5g
Price
$36.65
Updated
2024/03/01
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Tosylmethyl isocyanide Chemical Properties,Usage,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:

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].

Tosylmethyl isocyanide Preparation Products And Raw materials

Raw materials

Preparation Products

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Tosylmethyl isocyanide Suppliers

NINGBO JL NEW MATERIAL CO.,LTD
Tel
0574-88552218 18969899212
Email
sales@jlbio-tech.cn
Country
China
ProdList
715
Advantage
58
Beihua Chemical (Shandong) Co., LTD
Tel
0531-68653689 13127106931
Email
1720760574@qq.com
Country
China
ProdList
53
Advantage
58
Nanjing Puxin Pharmaceutical Technology Co., Ltd
Tel
17366295326
Fax
QQ360829978
Email
puxinpharma_2017@126.com
Country
China
ProdList
2446
Advantage
58
Quzhou HuntBio Co., Ltd.
Tel
0571-64067827 13372408495
Fax
0571-64067827
Email
sales@huntchem.com
Country
China
ProdList
186
Advantage
60
Henan Dongyao Pharmaceutical Technology Co., Ltd
Tel
18519331287
Email
1751713684@qq.com
Country
China
ProdList
172
Advantage
58
Jilin Lianben Technology Development Co., Ltd
Tel
13756693631
Fax
0432-62601618
Email
sunting@lianben.com
Country
China
ProdList
46
Advantage
58
Liyang Kunlu biological technology co.,ltd
Tel
0519-87310015 13813530041
Fax
0519-87310015
Email
200601296@qq.com
Country
China
ProdList
173
Advantage
58
Shanghai Yaoke Biotechnology Co., Ltd
Tel
19943855286
Email
triz-4@trizpharma.cn
Country
China
ProdList
220
Advantage
58
Tangshan Weig Chemical Industry Co. LTD
Tel
15132530078
Email
liuzhen@varsal.cn
Country
China
ProdList
4
Advantage
58
Nanjing Yili Biotechnology Co., Ltd.
Tel
15251862682
Email
2880300874@qq.com
Country
China
ProdList
8134
Advantage
58
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View Lastest Price from Tosylmethyl isocyanide manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Tosylmethyl isocyanide 36635-61-7
Price
US $75.00-20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-06
HebeiShuoshengImportandExportco.,Ltd
Product
Tosylmethyl isocyanide 36635-61-7
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-09
Hebei Longbang Technology Co., Ltd
Product
Tosylmethyl isocyanide 36635-61-7
Price
US $5.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20TONS
Release date
2024-05-13

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