Benzoic acid, 4-cyano-, hydrazide (9CI)

Benzoic acid, 4-cyano-, hydrazide (9CI) Property

Melting point:

202-203 °C

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

11?+-.0.10(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

Benzoic acid, 4-cyano-, hydrazide (9CI) Chemical Properties,Usage,Production

Synthesis

Part A. Synthesis of 4-cyanobenzoic acid hydrazide A mixture of methyl 4-cyanobenzoate (10.8 g, 67 mmol) and hydrazine monohydrate (18.6 g, 371 mmol) in anhydrous ethanol (70 mL) was heated to reflux for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature. The solid product formed was collected by filtration and washed with cold ethanol (20 mL). Subsequently, the product was dried to give 4-cyanobenzoylhydrazine (8.7 g, 81% yield). The melting point of the product was 201 °C. 1H NMR (300 MHz, CDCl3) δ 4.14 (s, 2H), 7.40 (s, 1H), 7.76 (d, J = 8 Hz, 2H), 7.88 (d, J = 8 Hz, 2H); MS (NH3-Cl) calculated value (M + 1)+: 162, measured value: 162.

References

[1] Bollettino Chimico Farmaceutico, 1999, vol. 138, # 8, p. 432 - 436
[2] Patent: US5668159, 1997, A
[3] Patent: WO2012/76898, 2012, A1. Location in patent: Page/Page column 71
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3012 - 3023
[5] Patent: WO2010/139966, 2010, A1. Location in patent: Page/Page column 123