1-(2-nitrophenyl)ethanol Chemical Properties

Melting point:

40-41℃

Boiling point:

106-107°C 1mmHg.

Density 

1.2300 g/cm³ (20 ºC)

refractive index 

1.5572 (589.3 nm 20℃)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ether, Ethyl Acetate, Methanol

form 

Solid

pka

13.84±0.20(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C8H9NO3/c1-6(10)7-4-2-3-5-8(7)9(11)12/h2-6,10H,1H3

InChIKey

DSDBYQDNNWCLHL-UHFFFAOYSA-N

SMILES

C(C1C=CC=CC=1N(=O)=O)(O)C

CAS DataBase Reference

3205-25-2

Safety Information

HS Code 

2906290090

1-(2-nitrophenyl)ethanol Usage And Synthesis

Chemical Properties

Yellow Oil

Uses

(R,S)-1-(2-Nitrophenyl)ethanol (cas# 3205-25-2) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of (S)-1-(2-nitrophenyl)ethan-1-ol from o-nitroacetophenone: Synthesis of (RS)-1-(2-nitrophenyl)ethan-1-ol: Sodium borohydride (0.69 g, 18.16 mmol) was added in small portions to a mixed solution of 2-nitroacetophenone (1.0 g, 6.06 mmol) dissolved in methanol (9 mL) and 1,4-dioxane (6 mL) (cf. Dong et al., 2005). The reaction mixture was stirred at room temperature for 30 min and then concentrated under vacuum. The residue was diluted with ethyl acetate (50 mL) and washed sequentially with water (10 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuum to give racemic (RS)-1-(2-nitrophenyl)ethanol (1.02 g, 100% yield). 1H NMR (400 MHz, CDCl3) data: δ 7.90 (m, 1H, Ph-H), 7.84 (m, 1H, Ph-H), 7.66 (m, 1H, Ph-H), 7.44 (m, 1H, Ph-H), 5.42 (m, 1H, Ph-CH), 2.33 (d, 1H, J = 3.5 Hz, OH), 1.58 (d, 3H, J = 5.1 Hz, CH3).

References

[1] Patent: US9200319, 2015, B2. Location in patent: Page/Page column 57
[2] Journal of Organometallic Chemistry, 2016, vol. 808, p. 68 - 77
[3] Chemistry - A European Journal, 2012, vol. 18, # 31, p. 9628 - 9637
[4] Applied Organometallic Chemistry, 2018, vol. 32, # 3,
[5] Organic Letters, 2018, vol. 20, # 11, p. 3403 - 3407

1-(2-nitrophenyl)ethanol(3205-25-2)Related Product Information

• 1-(2-Nitrophenyl)-1,2-ethanediol
• CAGED ATP, DISODIUM SALT
• 'CAGED GTP
• ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE, P1-(2-NITROPHENYL)ETHYL ESTER
• NITR 5/AM
• NITR 5 TETRASODIUM SALT
• [3-(2-NITROPHENYL)OXIRAN-2-YL](PHENYL)METHANONE
• CAGED CGMP
• CAGED GLUTAMIC ACID
• 1-(ALPHA-GLYCEROPHOSPHORYL)-D-MYO-INOSITOL 4,5-BISPHOSPHATE, P4(5)-1-(2-NITROPHENYL)ETHYL ESTER, 3NA
• CAGED ASPARTIC ACID, SODIUM SALT
• nitr 5
• HYDROXY(2-NITROPHENYL)ACETONITRILE
• 1-(2-NITROPHENYL)ETHYL PHOSPHATE, DIAMMONIUM SALT
• nitr 2
• CAGED INS(1,4,5)P3, TRISODIUM SALT
• 4-BROMO A-23187, 1-(4,5-DIMETHOXY-2-NITROPHENYL)ETHYL ESTER
• nitr 7