4-ACETAMIDOBENZYL ALCOHOL

4-ACETAMIDOBENZYL ALCOHOL Property

Melting point:

120-122°C

Boiling point:

120-122

Density 

1.211±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

14.37±0.10(Predicted)

color 

Off-White

λmax

246nm(MeOH)(lit.)

InChI

InChI=1S/C9H11NO2/c1-7(12)10-9-4-2-8(6-11)3-5-9/h2-5,11H,6H2,1H3,(H,10,12)

InChIKey

XEYORFKUJZEQCH-UHFFFAOYSA-N

SMILES

C(NC1=CC=C(CO)C=C1)(=O)C

CAS DataBase Reference

16375-88-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2906290090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

4-ACETAMIDOBENZYL ALCOHOL Chemical Properties,Usage,Production

Chemical Properties

White to off-white powder

Uses

4-Acetamidobenzyl Alcohol is a useful research chemical, a metabolites of a blocked chloramphenicol producer. It can be used to regulate plant growth.

Synthesis

4-Acetamidobenzaldehyde (10 g, 61.3 mmol) was dissolved in methanol (100 mL) at room temperature, followed by batchwise addition of sodium borohydride (800 mg). The reaction mixture was stirred overnight at room temperature and the reaction progress was monitored by thin layer chromatography (TLC) using 4:1 hexane:ethyl acetate as eluent. Completion of the reduction reaction was indicated when TLC showed complete disappearance of the feedstock. Subsequently, the reaction mixture was concentrated using a rotary evaporator. The concentrated residue was partitioned between water (25 mL) and ethyl acetate (4 x 50 mL), and the organic layer was separated and washed with brine (25 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to give the light yellow solid product N-[4-(hydroxymethyl)phenyl]acetamide. The product was dried under high vacuum to give a final 8.6 g (85% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H).

References

[1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 4, p. 676 - 681
[2] Chemical Communications, 2015, vol. 51, # 46, p. 9567 - 9570
[3] Organic Letters, 2017, vol. 19, # 13, p. 3656 - 3659
[4] Catalysis Science and Technology, 2013, vol. 3, # 1, p. 81 - 84
[5] Patent: US2007/149462, 2007, A1. Location in patent: Page/Page column 22