| Identification | More | [Name]
(1R)-3-Chloro-1-phenyl-propan-1-ol | [CAS]
100306-33-0 | [Synonyms]
(1r)-3-chloro-1-phenyl-propan-1-ol
3-CHLORO-1-PHENYLPROPAN-1-OL
ALPHA-(2-CHLOROETHYL)-BENZYL ALCOHOL
(R)-(+)-3-CHLORO-1-PHENYL-1-PROPANOL
(R)-3-CHLORO-1-PHENYL-1-PROPANOL
(R)-3-CHLORO-1-PHENYL-PROPAN-1-OL
R(+)-3-CHLORO-1-PHENYLPROPANOL
R(+)-ALPHA-(2-CHLOROETHYL)BENZYL ALCOHOL
(R)-(+)-3-CHLORO-1-PHENYL-1-PROPANOL, 98 % (99% EE/GLC)
(r)-(+)-α-(2-chloroethyl)benzyl alcohol
α-(2-chloroethyl)benzyl alcohol
α-(2-Chloroethyl)benzyl alcohol, (R)-(+)-α-(2-Chloroethyl)benzyl alcohol, (R)-(+)-3-Chloro-1-phenylpropanol | [EINECS(EC#)]
627-168-3 | [Molecular Formula]
C9H11ClO | [MDL Number]
MFCD00075128 | [Molecular Weight]
170.64 | [MOL File]
100306-33-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
58-60 °C (lit.) | [alpha ]
26 º (c=1, chloroform) | [Boiling point ]
296.4±20.0 °C(Predicted) | [density ]
1.149±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
13.92±0.20(Predicted) | [color ]
White to yellow | [Optical Rotation]
[α]24/D +26°, c = 1 in chloroform | [BRN ]
5250766 | [InChI]
InChI=1/C9H11ClO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6-7H2/t9-/s3 | [InChIKey]
JZFUHAGLMZWKTF-SECBINFHSA-N | [SMILES]
[C@@H](C1C=CC=CC=1)(O)CCCl |&1:0,r| | [CAS DataBase Reference]
100306-33-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29062990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
Intermediate in the preparation of (S)-Norfluoxetine | [Synthesis]
Step 1: To a dry flask was added (S)-(-)-α,α-diphenylprolinol (0.30 g, 1.19 mmol) and anhydrous toluene (7 mL). The reaction system was placed under a nitrogen atmosphere by evacuating and displacing three times with nitrogen. A solution of borane tetrahydrofuran complex [BH3?THF; 1 M solution of THF] stabilized with 5 mM NaBH4 (0.35 mL, 3.56 mmol) was added slowly and dropwise at 30 °C, followed by stirring the clarified solution for 30 min.
Step 2: To the above stirred solution was added a solution of anhydrous toluene (1 mL) of 3-chloro-1-phenylpropan-1-one (1 g, 5.93 mmol). The reaction mixture was stirred at room temperature for 15 min before BH3?THF (6 mL, 61.44 mmol) was added within 3 min. After continued stirring for 9 min, the reaction flask was cooled in an ice bath, the reaction was quenched sequentially with methanol (10 mL), isopropanol (10 mL), and hydrochloric acid (3 mL), and filtered through a pad of diatomaceous earth. The filtrate was concentrated to dryness and the product was crystallized from hexane to give (R)-(+)-3-chloro-1-phenyl-1-propanol as a white fluffy solid (4.91 g).
Yield: 97%; Melting point: 57-59°C; [α]D25 = +25.7° (c 1, CHCl3); 1H NMR (400 MHz, CDCl3): δ 2.07-2.16 (m, 2H), 2.20-2.32 (m, 1H), 3.51-3.62 (m, 1H), 3.71-3.80 (m, 1H), 4.91 -4.98 (m, 1H), 7.37-7.43 (m, 5H); 13C NMR (400 MHz, CDCl3): δ 41.45, 41.73, 71.34, 125.80, 127.94, 128.69, 143.71; MS (EI+) m/z: 170 [M+], 172 [M+2], relative intensity ratio ca. is 3:1. | [References]
[1] Tetrahedron Letters, 1989, vol. 30, # 39, p. 5207 - 5210
[2] Synthetic Communications, 2009, vol. 39, # 15, p. 2737 - 2746
[3] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 431 - 435
[4] Chemical Communications, 2015, vol. 51, # 26, p. 5725 - 5727
[5] European Journal of Medicinal Chemistry, 2016, vol. 109, p. 157 - 172 |
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