2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE
- Product Name
- 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE
- CAS No.
- 33143-29-2
- Chemical Name
- 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE
- Synonyms
- AKOS 91886;6-CYANO-2,2-DIMETHYLCHROMENE;2,2-DiMethyl-6-cyanochroMene;6-Cyano-2,2-dimethyl-2H-chromene;2,2-Dimethylchromene-6-carbonitrile;2,2-DiMethyl-6-cyano-2H-1-benzopyran;2,2-Dimethyl-2H-chromeme-6-carbonitrile;6-CYANO-2,2-DIMETHYL-2H-BENZO-[B]-PYRAN;2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE;2,2-DIMETHYL-2H-1-BENZOPYRAN-6-CARBONITRILE
- CBNumber
- CB8254153
- Molecular Formula
- C12H11NO
- Formula Weight
- 185.22
- MOL File
- 33143-29-2.mol
2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Property
- Melting point:
- 45-49 °C(lit.)
- Flash point:
- >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Acetone, Chloroform, Dichloromethane, DMSO, Ethyl Acetate
- form
- Solid
- color
- Pale Yellow Crystalline
- CAS DataBase Reference
- 33143-29-2(CAS DataBase Reference)
Safety
- WGK Germany
- 3
- HS Code
- 2932990090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 477982
- Product name
- 2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile
- Purity
- 97%
- Packaging
- 1g
- Price
- $74.8
- Updated
- 2025/07/31
- Product number
- C979325
- Product name
- 6-Cyano-2,2-dimethyl-2H-benzo-[b]-pyran
- Packaging
- 100mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- FC20608
- Product name
- 6-Cyano-2,2-dimethyl-2H-benzo-[b]-pyran
- Packaging
- 50mg
- Price
- $120.5
- Updated
- 2021/12/16
- Product number
- CS-M3436
- Product name
- 6-Cyano-2,2-dimethyl-2H-chromene
- Purity
- 96.26%
- Packaging
- 250mg
- Price
- $139
- Updated
- 2021/12/16
- Product number
- 085925
- Product name
- 2,2-Dimethyl-2H-chromene-6-carbonitrile
- Purity
- 97%
- Packaging
- 1g
- Price
- $195
- Updated
- 2021/12/16
2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Chemical Properties,Usage,Production
Chemical Properties
Pale Yellow Crystalline Solid
Uses
6-Cyano-2,2-dimethyl-2H-benzo-[b]-pyran (cas# 33143-29-2) is a compound useful in organic synthesis.
Uses
2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile (6-Cyano-2,2-dimethylchromene) may be used in the synthesis of 3,4-epoxy-6-cyano-2,2-dimethylchromene via epoxidation.
Synthesis Reference(s)
The Journal of Organic Chemistry, 37, p. 841, 1972 DOI: 10.1021/jo00971a006
General Description
2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile (6-Cyano-2,2-dimethyl-2H-1-benzopyran) is a substituted 2,2-dimethyl-2H-1-benzopyran. It can be synthesized by the condensation reaction between 1,1-diethoxy-3-methyl-2-butene and 4-cyanophenol in the presence of pyridine.
Synthesis
33143-92-9
33143-29-2
General procedure for the synthesis of 2,2-dimethyl-6-cyano-2H coumarin from 4-((2-methylbut-3-yn-2-yl)oxy)benzonitrile: 4-((2-methylbut-3-yn-2-yl)oxy)benzonitrile (1.0 g, 5.40 mmol) was dissolved in ethylene glycol (5 mL/g of substrate), and the reaction mixture was heated to 210-215 °C,. maintained for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with water. The mixture was extracted with ether (2 x 25 mL), the organic layers were combined, dried over anhydrous magnesium sulfate and filtered. The solvent was removed by concentration under reduced pressure to give a bright yellow solid. Recrystallization by petroleum ether gave 2,2-dimethyl-6-cyano-2H coumarin as a yellow powder (1.0 g, quantitative yield) with a melting point of 47-48 °C (literature value: 47 °C). IR spectrum (thin film method, cm^-1): 3054, 2985, 2226, 1605, 1487, 1421, 1369, 1265, 1212, 1148, 1128, 1107, 961, 896, 828, 739, 705. ^1H NMR (400MHz, CDCl3): δ 1.45 (s, 6H). 5.70 (d, 1H, J=11.6Hz), 6.28 (d, 1H, J=11.6Hz), 6.78 (d, 1H, J=8.4Hz), 7.24 (d, 1H, J=4.0Hz), 7.37 (dd, 1H, J=8.4Hz, 4.0Hz). ^13C NMR (100 MHz, CDCl3): δ 28.4, 77.9, 103.8, 117.2, 119.3, 120.6, 121.7, 130.1, 132.2, 133.3, 156.8.
References
[1] Tetrahedron, 2016, vol. 72, # 51, p. 8406 - 8416
[2] Organic Process Research and Development, 2001, vol. 5, # 6, p. 636 - 645
[3] Synthesis, 1995, # 6, p. 707 - 712
[4] Journal of Medicinal Chemistry, 1983, vol. 26, # 11, p. 1582 - 1589
[5] Chemical Communications, 2011, vol. 47, # 9, p. 2586 - 2588
2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Preparation Products And Raw materials
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